As filed with the Securities and Exchange Commission on September 28, 2004

                                                   Registration No. 333-_____
                                                   Registration No. 333-_____-01
================================================================================
                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549
                                ________________

                                    FORM S-3
                             REGISTRATION STATEMENT
                        Under the Securities Act of 1933
                                ________________




                                                                                                
                  WINTRUST FINANCIAL CORPORATION                                      WINTRUST CAPITAL TRUST VI
    (Exact name of co-registrant as specified in its charter)        (Exact name of co-registrant as specified in its certificate
                                                                                                of trust)
            ILLINOIS                        36-3873352
 (State or other jurisdiction of         (I.R.S. Employer                     DELAWARE                        APPLIED FOR
 incorporation or organization)       Identification Number)       (State or other jurisdiction of         (I.R.S. Employer
                                                                    incorporation or organization)       Identification Number)


                                ________________

                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096

          (Address, including zip code, and telephone number, including
           area code, of co-registrants' principal executive offices)

                                DAVID A. DYKSTRA
                SENIOR VICE PRESIDENT AND CHIEF OPERATING OFFICER
                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096

                (Name, address, including zip code, and telephone
                    number, including area code, of agent for
                           service for co-registrants)

                                   Copies to:

        John R. Obiala, Esq.                      Timothy J. Melton, Esq.
Vedder, Price, Kaufman & Kammholz, P.C.                Jones Day
 222 North LaSalle Street, Suite 2600         77 West Wacker Drive, Suite 3500
       Chicago, Illinois 60601                    Chicago, Illinois 60601
           (312) 609-7500                            (312) 782-3939

                                ________________

         APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: FROM
TIME TO TIME AFTER THIS REGISTRATION STATEMENT BECOMES EFFECTIVE.
         If the only securities being registered on this form are being offered
pursuant to dividend or interest reinvestment plans, please check the following
box. / /
         If any of the securities being registered on this form are to be
offered on a delayed or continuous basis pursuant to Rule 415 under the
Securities Act of 1933, other than securities offered only in connection with
dividend or reinvestment plans, check the following box. /X/
         If this form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following box
and list the Securities Act registration statement number of the earlier
effective registration statement for the same offering. / /
         If this form is a post-effective amendment filed pursuant to Rule
462(c) under the Securities Act, check the following box and list the Securities
Act registration statement number of the earlier effective registration
statement for the same offering. / /
         If delivery of the prospectus is expected to be made under Rule 434,
please check the following box. / /






                         CALCULATION OF REGISTRATION FEE
-------------------------------------------------------------------------------------------------------------------------------
                                                                                                     PROPOSED
                                                                                                     MAXIMUM
                                                                               PROPOSED MAXIMUM      AGGREGATE      AMOUNT OF
                    TITLE OF EACH CLASS OF                       AMOUNT TO BE  OFFERING PRICE PER    OFFERING      REGISTRATION
                 SECURITIES TO BE REGISTERED                  REGISTERED(1)(2) UNIT OR SHARE(3)     PRICE(1)(2)(3)      FEE
-------------------------------------------------------------------------------------------------------------------------------
                                                                                                       
Debt Securities of Wintrust Financial Corporation(4).......           --               --                  --            --
Preferred Stock, no par value, of Wintrust Financial
   Corporation(5) (6).......... ...........................           --               --                  --            --
Common Stock, no par value, of Wintrust Financial
   Corporation(7)..........................................           --               --                  --            --
Warrants of Wintrust Financial Corporation(8)..............           --               --                  --            --
Trust Preferred Securities of Wintrust Capital Trust VI....           --               --                  --            --
Junior Subordinated Debentures of Wintrust Financial
   Corporation(9)(10)......................................           --               --                  --            --
Purchase Contracts of Wintrust Financial Corporation(11)...           --               --                  --            --
Units of Wintrust Financial Corporation(12)................           --               --                  --            --
Guarantee of Trust Preferred Securities(9)(13).............           --               --                  --            --
Total(4)...................................................   $200,000,000            100%       $200,000,000       $25,340
=================================================================================================================================

(1)      Pursuant to Rule 457(o) under the Securities Act of 1933, which permits
         the registration fee to be calculated on the basis of the maximum
         offering price of all securities listed, the table does not specify
         information as to the amount of any particular security to be
         registered.
(2)      There are being registered hereunder such indeterminate number of
         shares of common stock and such indeterminate principal amount of trust
         preferred securities as may be offered from time to time, with an
         aggregate initial offering price not to exceed $200,000,000.
(3)      The proposed maximum aggregate offering price per class of security and
         per unit or share will be determined from time to time by the
         Registrant in connection with the issuance by the Registrant of the
         securities registered hereunder and is not specified as to each class
         of security pursuant to General Instruction II.D. of Form S-3 under the
         Securities Act of 1933.
(4)      Shares of Preferred Stock or Common Stock may be issuable upon
         conversion of Debt Securities registered hereunder. No separate
         consideration will be received for such Preferred Stock, Depositary
         Shares or Common Stock.
(5)      In the event that the Company elects to offer to the public fractional
         interests in shares of Preferred Stock registered hereunder, Depositary
         Shares, evidenced by depositary receipts issued pursuant to a deposit
         agreement, will be distributed to those persons purchasing such
         fractional interests, and the shares of Preferred Stock will be issued
         to the depositary under any such agreement.
(6)      Shares of Common Stock may be issuable upon conversion of shares of
         Preferred Stock registered hereunder. No separate consideration will be
         received for such shares of Common Stock.
(7)      Each share of Common Stock issued hereunder, including those issuable
         upon conversion of other securities registered hereunder, includes
         Preferred Stock Purchase Rights. Prior to the occurrence of certain
         events, these Rights will not be exercisable or evidenced separately
         from the Common Stock.
(8)      Warrants may be sold separately or together with Debt Securities,
         Preferred Stock, Common Stock, Depositary Shares or Trust Preferred
         Securities. Includes an indeterminate number of Debt Securities, shares
         of Preferred Stock, shares of Common Stock or Depositary Shares to be
         issuable upon the exercise of Warrants for such securities.
(9)      This Registration Statement is deemed to cover the Junior Subordinated
         Debentures of Wintrust Financial Corporation, the rights of holders
         thereof under the Indenture, and the rights of holders of the trust
         preferred securities under the Trust Agreement, the Guarantee and the
         Expense Agreement entered into by Wintrust Financial Corporation.
(10)     The Junior Subordinated Debentures will be purchased by Wintrust
         Capital Trust VI with the proceeds of the sale of the trust preferred
         securities. These securities may later be distributed for no additional
         consideration to the holders of the trust preferred securities upon
         dissolution of the trust and the distribution of its assets.
(11)     The Purchase Contracts may require the holder thereof to purchase or
         sell Debt Securities, Preferred Stock, Depositary Shares or Common
         Stock.
(12)     The Units to be offered hereunder will consist of one or more
         securities described in this prospectus.
(13)     No separate consideration will be received for the Guarantee.



                                ________________

         THE REGISTRANTS HEREBY AMEND THIS REGISTRATION STATEMENT ON SUCH DATE
OR DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE TIME UNTIL THE REGISTRANTS
SHALL FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(a) OF
THE SECURITIES ACT OF 1933 OR UNTIL THE REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTION 8(a),
MAY DETERMINE.



THE INFORMATION IN THIS PROSPECTUS IS NOT COMPLETE, AND IT MAY CHANGE. THIS
PROSPECTUS IS INCLUDED IN A REGISTRATION STATEMENT THAT WE FILED WITH THE
SECURITIES AND EXCHANGE COMMISSION. WE CANNOT SELL THESE SECURITIES UNTIL THAT
REGISTRATION STATEMENT BECOMES EFFECTIVE. THIS PROSPECTUS IS NOT AN OFFER TO
SELL THESE SECURITIES OR THE SOLICITATION OF AN OFFER TO BUY THESE SECURITIES IN
ANY JURISDICTION WHERE AN OFFER TO BUY IS NOT PERMITTED.

               SUBJECT TO COMPLETION, DATED SEPTEMBER 28, 2004

PROSPECTUS

                                  $200,000,000
                      WINTRUST FINANCIAL CORPORATION [LOGO]
                                 DEBT SECURITIES
                                      UNITS
                                    WARRANTS
                               PURCHASE CONTRACTS
                                 PREFERRED STOCK
                                  COMMON STOCK


                            WINTRUST CAPITAL TRUST VI
                           TRUST PREFERRED SECURITIES
         (FULLY AND UNCONDITIONALLY GUARANTEED ON A SUBORDINATED BASIS,
                             AS DESCRIBED HEREIN, BY

                         WINTRUST FINANCIAL CORPORATION)
                               __________________

         Wintrust Financial Corporation may offer from time to time debt
securities, units, warrants, preferred stock and common stock, and Wintrust
Capital Trust VI may offer from time to time trust preferred securities. This
prospectus describes the general terms of these securities and the general
manner in which we will offer the securities. The specific terms of any
securities we offer will be included in a supplement to this prospectus. The
prospectus supplement will also describe the specific manner in which we will
offer the securities.

         You should read this prospectus and any prospectus supplement carefully
before you purchase any of our securities.

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC".

                               __________________

         INVESTING IN OUR SECURITIES INVOLVES RISKS. SEE "RISK FACTORS"
BEGINNING ON PAGE 4.

                               __________________

         NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
REGULATORS HAS APPROVED OR DISAPPROVED THESE SECURITIES OR DETERMINED IF THIS
PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.

         THESE SECURITIES ARE NOT DEPOSITS OR SAVINGS ACCOUNTS BUT ARE UNSECURED
OBLIGATIONS OF WINTRUST FINANCIAL CORPORATION. THESE SECURITIES ARE NOT ISSUED
BY THE FEDERAL DEPOSIT INSURANCE CORPORATION OR ANY OTHER GOVERNMENTAL AGENCY OR
INSTRUMENTALITY.

                               __________________

__________, 2004






                                TABLE OF CONTENTS
                                                                                                               PAGE
                                                                                                            
Important Notice to Readers.....................................................................................ii
Special Note Regarding Forward-Looking Statements...............................................................ii
Prospectus Summary...............................................................................................1
Risk Factors.....................................................................................................4
Use of Proceeds..................................................................................................9
Ratios of Earnings to Fixed Charges..............................................................................9
Description of Debt Securities...................................................................................9
Description of Purchase Contracts...............................................................................17
Description of Units............................................................................................18
Description of Warrants.........................................................................................19
Description of Capital Stock....................................................................................21
Global Securities...............................................................................................29
Description of the Trust........................................................................................31
Description of the Trust Preferred Securities...................................................................32
Description of the Junior Subordinated Debentures...............................................................44
Description of the Guarantee....................................................................................50
Relationship Among the Trust Preferred Securities, the Debentures and the Guarantee.............................53
Book-Entry Issuance.............................................................................................55
Plan of Distribution............................................................................................56
Legal Matters...................................................................................................59
Experts  .......................................................................................................59
Where You Can Find More Information.............................................................................59
Documents Incorporated by Reference.............................................................................60


                                       i



                           IMPORTANT NOTICE TO READERS

         This prospectus is part of a registration statement we filed with the
Securities and Exchange Commission, or SEC, using a "shelf" registration
process. Under the shelf registration process, using this prospectus, together
with a prospectus supplement, we may sell, from time to time, in one or more
offerings, any combination of the securities described in this prospectus in a
dollar amount that does not exceed $200,000,000, in the aggregate. This
prospectus provides you with a general description of the securities we may
offer. Each time we offer securities, we will provide a prospectus supplement
that will contain specific information about the terms of that offering. The
prospectus supplement may also add, update or change information contained in
this prospectus. You should read this prospectus, the applicable prospectus
supplement and the information incorporated by reference in this prospectus
before making an investment in our securities. See "Where You Can Find More
Information" for more information.

         You should rely only on the information contained in or incorporated by
reference in this prospectus or supplement to this prospectus. We have not
authorized anyone to provide you with different information. This document may
be used only in jurisdictions where offers and sales of these securities is
permitted. You should not assume that information contained in this prospectus,
in any supplement to this prospectus, or in any document incorporated by
reference is accurate as of any date other than the date on the front page of
the document that contains the information, regardless of when this prospectus
is delivered or when any sale of our securities occurs.

                                ________________

         In this prospectus, we use the terms "we," "us" and "our" to refer to
Wintrust Financial Corporation and the trusts. We use the term "Wintrust" to
refer to Wintrust Financial Corporation and, unless the context indicates
otherwise, we use the term "trusts" to refer to Wintrust Capital Trust VI.

                SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

         We make certain forward-looking statements in this prospectus and in
the documents incorporated by reference into this prospectus that are based upon
our current expectations and projections about current events. We intend these
forward-looking statements to be covered by the safe harbor provisions for
forward-looking statements contained in the Private Securities Litigation Reform
Act of 1995, and we are including this statement for purposes of these safe
harbor provisions. You can identify these statements from our use of the words
"may," "will," "should," "could," "would," "plan," "potential," "estimate,"
"project," "believe," "intend," "anticipate," "expect," "target" and similar
expressions. These forward-looking statements may include, among
other things, statements relating to our projected growth, anticipated
improvements in financial performance, and management's long-term performance
goals, as well as statements relating to the anticipated effects on results of
operations and financial condition from expected developments or events, our
business and growth strategies, including anticipated internal growth, plans to
form additional de novo banks and to open new branch offices, and to pursue
additional potential development or acquisition of banks, wealth management
entities, specialty finance businesses or fee-related business.

         These forward-looking statements are subject to significant risks,
assumptions and uncertainties, including among other things, changes in general
economic and business conditions and the risks and other factors set forth in
the "Risk Factors" section beginning on page 4 and in a supplemental prospectus.

         Because of these and other uncertainties, our actual future results,
performance or achievements, or industry results, may be materially different
from the results indicated by these forward-looking

                                       ii



statements. In addition, our past results of operations do not necessarily
indicate our future results. You should not place undue reliance on any
forward-looking statement, which speak only as of the date they were made. We do
not intend to update these forward-looking statements, even though our situation
may change in the future, unless we are obligated to do so under the federal
securities laws. We qualify all of our forward-looking statements by these
cautionary statements.


                                      iii



                               PROSPECTUS SUMMARY

         This summary highlights selected information about our company and a
general description of the securities we may offer. This summary is not complete
and does not contain all of the information that may be important to you. For a
more complete understanding of us and the terms of the securities we will offer,
you should read carefully this entire prospectus, including the "Risk Factors"
section, the applicable prospectus supplement for the securities and the other
documents we refer to and incorporate by reference. In particular, we
incorporate important business and financial information into this prospectus by
reference.

ABOUT WINTRUST FINANCIAL CORPORATION

         We are a financial holding company headquartered in Lake Forest,
Illinois, with total assets of approximately $5.33 billion at June 30, 2004. We
currently operate ten community banks, all located in the Chicago metropolitan
area. These banks provide community-oriented, personal and commercial banking
services primarily to individuals and small to mid-size businesses through 42
banking facilities as of June 30, 2004. Each of our banks provides a full
complement of commercial and consumer loan and deposit products and services. We
provide wealth management services through our trust company, investment adviser
and broker-dealer subsidiaries to customers primarily located in the Midwest, as
well as to customers of our banks. In addition, we are involved in specialty
lending through operating subsidiaries or divisions of certain of our banks. Our
specialty lending niches include commercial insurance premium finance; accounts
receivable financing and administrative services to the temporary staffing
industry; and indirect auto lending in which we purchase loans through
Chicago-area automobile dealerships. Our common stock trades on the Nasdaq
National Market under the symbol "WTFC".

         Our principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045-1951, and our telephone number is (847) 615-4096.
Our website address is www.wintrust.com. Information in our website is not a
prospectus and does not constitute a part of this prospectus.

THE SECURITIES WE MAY OFFER

         We may use this prospectus to offer up to $200,000,000 aggregate amount
of securities in one or more offerings. A prospectus supplement, which we will
provide each time we offer securities, will describe the amounts, prices and
detailed terms of the securities and may describe risks associated with an
investment in the securities in addition to those described in "Risk Factors".
We will also include in the prospectus supplement, where applicable, information
about material United States federal income tax considerations relating to the
securities. Terms used in this prospectus will have the meanings described in
this prospectus unless otherwise specified.

         We may sell the securities to or through underwriters, dealers or
agents or directly to purchasers. We, as well as any agents acting on our
behalf, reserve the sole right to accept and to reject in whole or in part any
proposed purchase of our securities. Each prospectus supplement will set forth
the names of any underwriters, dealers or agents involved in the sale of our
securities described in that prospectus supplement and any applicable fee,
commission or discount arrangements with them.

DEBT SECURITIES

         Our debt securities may be senior or subordinated in priority of
payment. We will provide a prospectus supplement that describes the ranking,
whether senior or subordinated, the specific designation, the aggregate
principal amount, the purchase price, the maturity, the redemption terms, the
interest rate or manner of calculating the interest rate, the time of payment of
interest, if any, the terms for



any conversion or exchange, including the terms relating to the adjustment of
any conversion or exchange mechanism, the listing, if any, on a securities
exchange and any other specific terms of the debt securities.

         The debt securities will be issued under an indenture between us and a
Delaware banking institution as trustee. We have summarized the general features
of the indenture under the heading "Description of Debt Securities." We
encourage you to read the indenture, a form which is an exhibit to our
registration statement.

UNITS

         We may sell any combination of one or more of the other securities
described in this prospectus, together as units. In a prospectus supplement, we
will describe the particular combination of securities constituting any units
and any other specific terms of the units.

WARRANTS

         We may sell warrants to purchase our debt securities, shares of
preferred stock or shares of our common stock. In a prospectus supplement, we
will inform you of the exercise price and other specific terms of the warrants,
including whether our or your obligations, if any, under any warrants may be
satisfied by delivering or purchasing the underlying securities or their cash
value.

PREFERRED STOCK

         We may sell our preferred stock, no par value per share, in one or more
series. In a prospectus supplement, we will describe the specific designation,
the aggregate number of shares offered, the dividend rate or manner of
calculating the dividend rate, the dividend periods or manner of calculating the
dividend periods, the stated value of the shares of the series, the voting
rights of the shares of the series, whether or not and on what terms the shares
of the series will be convertible or exchangeable, whether and on what terms we
can redeem the shares of the series, whether we will offer depositary shares
representing shares of the series and if so, the fraction or multiple of a share
of preferred stock represented by each depositary share, whether we will list
the preferred stock or depositary shares on a securities exchange and any other
specific terms of the series of preferred stock.

COMMON STOCK

         We may sell our common stock, no par value per share, and the
associated preferred stock purchase rights. In a prospectus supplement, we will
describe the aggregate number of shares offered and the offering price or prices
of the shares.

ABOUT WINTRUST CAPITAL TRUST VI

         The trust is a newly formed financing subsidiary of Wintrust. Upon
issuance of trust preferred securities, the purchasers will own all of the
issued and outstanding trust preferred securities of the trust. In exchange for
our capital contribution to the trust, we will own all of the common securities
of the trust. The trust exists exclusively for the following purposes:

         o        issuing the trust preferred securities to the public for cash;

         o        issuing the common securities to us;

         o        investing the proceeds from the sale of its preferred and
                  common securities in an equivalent amount of junior
                  subordinated debentures to be issued by us; and

                                       2



         o        engaging in activities that are incidental to those listed
                  above, such as receiving payments on the debentures and making
                  distributions to security holders, furnishing notices and
                  other administrative tasks.

         A detailed description of the general terms of the trust preferred
securities is set forth in "Description of the Trust Preferred Securities" and
the applicable prospectus supplement will set forth the specific terms of any
trust preferred securities.

                                       3



                                  RISK FACTORS

         You should carefully consider the risks described below, as well as the
other information included or incorporated by reference in this prospectus,
before you decide to buy our securities. Additional risks, including those that
relate to any particular offering, will be included in the applicable prospectus
supplement. Our business, financial condition or results of operations could be
materially adversely affected by any of these risks. In addition, please read
"Special Note About Forward-Looking Statements" in this prospectus, where we
describe additional uncertainties associated with our business and the
forward-looking statements included or incorporated by reference in this
prospectus.

         DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY.

         Our financial results have been and will continue to be impacted by our
strategy of de novo bank formations and branch openings. We have employed this
strategy to build an infrastructure that management believes can support
additional internal growth in our banks' respective markets. We opened our
eighth de novo bank in April 2004, and expect to undertake additional de novo
bank formations or branch openings as we expand into additional communities in
and around Chicago and Southeast Wisconsin. Based on our experience, management
believes that it generally takes from 13 to 24 months for new banks to first
achieve operational profitability, depending on the number of branch facilities
opened, the impact of organizational and overhead expenses, the start-up phase
of generating deposits and the time lag typically involved in redeploying
deposits into attractively priced loans and other higher yielding earning
assets. However, it may take longer than expected or than the amount of time we
have historically experienced for new banks and/or branch facilities to reach
profitability, and there can be no guarantee that these new banks or branches
will ever be profitable. To the extent we undertake additional de novo bank,
branch and business formations, our level of reported net income, return on
average equity and return on average assets will be impacted by start-up costs
associated with such operations, and we are likely to continue to experience the
effects of higher expenses relative to operating income from the new operations.
These expenses may be higher than we expected or than our experience has shown.

         WE COULD ENCOUNTER DIFFICULTIES OR UNEXPECTED DEVELOPMENTS RELATED TO
OUR RECENT AND ANY FUTURE ACQUISITIONS.

         We recently completed our acquisition of WestAmerica and Guardian, and
are currently in the process of integrating that business into our organization.
While we expect this process will go smoothly, to the extent we experience any
significant difficulties or challenges with this integration, our business may
be adversely impacted.

         Our pending acquisitions of Northview Financial and Town Bankshares are
currently expected to close by the end of 2004. We have received shareholder and
Federal regulatory approval for the Northview acquisition, and expect to
receive state regulatory approval the week of September 27, 2004. The Town
Bankshares acquisition has received both Federal and state regulatory approvals
and we expect to receive approval by the Town Bankshares shareholders at a
special meeting to be held on October 12, 2004. There can be no assurances that
Wintrust will receive such approvals or as to timing of these approvals. We may
not be successful in completing the acquisitions as planned if, for example, all
of the closing conditions are not met. If we do complete the acquisitions, we
may be adversely impacted if we have difficulty integrating the banks into our
organization or if the composition or quality of the banks' assets or
liabilities that we acquire differ significantly from our expectations. In
addition, our net income and earnings per share could be adversely impacted if
we incur greater than anticipated costs associated with operating these banks,
if we have difficulty retaining key personnel at the banks, or if we are unable
to grow the businesses of the banks as contemplated.

                                       4



         We plan to continue to pursue potential acquisitions of other
community-oriented banks as well as additional specialty lending and related
financial services businesses which could also present challenges relating to
the integration of the operations of acquired businesses into our organization.
To the extent acquisitions divert a significant amount of management time and
attention, our business could be disrupted.

         WE DEPEND ON OUR ABILITY TO ATTRACT AND RETAIN KEY PERSONNEL; WE RELY
HEAVILY ON OUR MANAGEMENT TEAM, AND THE UNEXPECTED LOSS OF KEY MANAGERS MAY
ADVERSELY AFFECT OUR OPERATIONS.

         Our success to date has been influenced strongly by our ability to
attract and to retain senior management experienced in banking and financial
services. Retention of senior managers and appropriate succession planning will
continue to be critical to the successful implementation of our strategies. We
have entered into more than 70 employment contracts with our executive officers
and certain senior officers who we consider to be key employees. It is also
important as we grow to be able to attract and retain additional qualified
senior and middle management. We maintain a limited number of key-man life
insurance policies and maintain bank-owned life insurance policies on most of
our executive and senior officers to offset liabilities under employment
contracts. The unexpected loss of services of any key management personnel, or
the inability to recruit and retain qualified personnel in the future, could
have an adverse effect on our business and financial results.

         OUR ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB
LOSSES THAT MAY OCCUR IN OUR LOAN PORTFOLIO.

         Our allowance for loan losses is established in consultation with
management of our operating subsidiaries and is maintained at a level considered
adequate by management to absorb loan and lease losses that are inherent in the
portfolios. At June 30, 2004, our allowance for loan losses was 191.34% of total
non-performing loans and 0.76% of total loans. The amount of future losses is
susceptible to changes in economic, operating and other conditions, including
changes in interest rates, that may be beyond our control, and such losses may
exceed current estimates. Rapidly growing and de novo bank loan portfolios are,
by their nature, unseasoned. As a result, estimating loan loss allowances for
our newer banks is more difficult, and therefore the banks may be more
susceptible to changes in loss estimates, and to losses exceeding estimates,
than banks with more seasoned loan portfolios. Although management believes that
the allowance for loan losses is adequate to absorb losses that may develop in
our existing portfolios of loans and leases, there can be no assurance that the
allowance will prove sufficient to cover actual loan or lease losses in the
future.

         OUR PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND
COULD EXPOSE US TO SIGNIFICANT LOSSES.

         Of our total loans at June 30, 2004, 21%, or $790.9 million, were
comprised of commercial insurance premium finance receivables that we generated
through First Insurance. These loans, intended to enhance the average yield of
earning assets of our banks, involve a different, and possibly higher, level of
risk of delinquency or collection than generally associated with loan portfolios
of more traditional community banks. First Insurance also faces unique
operational and internal control challenges due to the relatively rapid turnover
of the premium finance loan portfolio and high volume of new loan originations.
The average term to maturity of these loans is less than 12 months, and the
average loan size when originated is approximately $30,000.

         Because we conduct lending in this segment primarily through
relationships with a large number of unaffiliated insurance agents and because
the borrowers are located nationwide, risk management and general supervisory
oversight may be more difficult than in our banks. We may also be more
susceptible to third party fraud. Acts of fraud are difficult to detect and
deter, and we cannot assure investors that our

                                       5



risk management procedures and controls will prevent losses from fraudulent
activity. For example, in the third quarter of 2000, we recorded a non-recurring
after-tax charge of $2.6 million in connection with a series of fraudulent loan
transactions perpetrated against First Insurance by one independent insurance
agency located in Florida. Although we have since enhanced our internal control
system at First Insurance, we may continue to be exposed to the risk of
significant loss in our premium finance business.

         Due to continued growth in origination volume of premium finance
receivables, since the second quarter of 1999, we have been selling some of the
loans First Insurance originates to an unrelated third party. We have recognized
gains on the sales of the receivables, and the proceeds of sales have provided
us with additional liquidity. Consistent with our strategy to be asset driven,
we expect to pursue similar sales of premium finance receivables in the future;
however, we cannot assure you that there will continue to be a market for sale
of these loans and the extent of our future sales of these loans will depend on
the level of new volume growth in relation to our capacity to retain the loans
within our subsidiary banks' loan portfolios. Because we have a recourse
obligation to the purchaser of premium finance loans that we sell, we could
incur losses in connection with the loans sold if collections on the underlying
loans prove to be insufficient to repay to the purchaser the principal amount of
the loans sold plus interest at the negotiated buy-rate and if the collection
shortfall on the loans sold exceeds our estimate of losses at the time of sale.

         OUR STRATEGY OF PURSUING SPECIALTY LENDING NICHES MAY EXPOSE US TO
CREDIT RISKS THAT ARE UNIQUE FOR A COMMUNITY BANKING ORGANIZATION OF OUR SIZE.

         At June 30, 2004, 32% of our total loan portfolio consisted of loans we
make in what we consider to be specialty lending niches. In addition to our
premium finance loans, we engage in indirect auto lending, accounts receivable
financing, mortgage broker warehouse lending, loans to condominium, homeowner
and community associations, and to a much lesser extent, medical and municipal
equipment leasing and small aircraft lending.

         Our portfolio of automobile loans are originated indirectly through
unaffiliated automobile dealers located throughout the Chicago metropolitan
area. At June 30, 2004, our indirect auto loans were $179.8 million and
comprised approximately 5% of our loan portfolio. Because we are lending through
third-party originators, our indirect auto portfolio may be relatively riskier
than direct consumer lending. Because the indirect auto loan industry is highly
competitive, the cost of collection and repossession of the underlying
collateral may significantly reduce the profitability of this portfolio,
particularly in a recessionary environment.

         Through Tricom, we finance payrolls of companies engaged in the
temporary staffing business. At June 30, 2004, these finance receivables totaled
$28.4 million and represented approximately 1% of our loan portfolio. The
principal source of repayments on the loans we make in this niche are payments
to our borrowers from their customers who are located throughout the United
States. While we employ lockboxes and other cash management techniques to
protect our interests, to the extent third parties fail to pay or fraudulently
engage in the conversion of funds through misuse or nonuse of the lockbox or the
creation of ghost payrolls, we may suffer losses.

         Our lease financing niche may involve a higher degree of credit risk
than mortgage or consumer lending due primarily to the potential for relatively
rapid depreciation of medical equipment and other assets securing leases.
Similarly, in the event of a default of loans originated in our aircraft lending
program, the marketability of the collateral may make it more difficult to
convert this collateral to cash, especially in an adverse economic environment.
In our condominium and homeowner association lending niche, we may face
difficulties in securing repayment from our association borrowers to the extent
they are unable to collect assessments from their members, and we may suffer
losses if we are unable to enforce liens against homeowner properties.

                                       6



         OUR WEALTH MANAGEMENT BUSINESSES ARE VULNERABLE TO FLUCTUATIONS IN THE
TRADING VOLUME AND PRICE LEVELS OF SECURITIES; WE FACE STRONG COMPETITION FOR
NEW BROKERS WE SEEK TO HIRE.

         The results of our wealth management subsidiaries depend heavily on
conditions in the financial markets and on economic conditions generally, both
domestically and abroad. Because currently a significant portion of our revenue
in these businesses is derived from commissions, margin interest revenue and
principal transactions, declines in stock prices, trading volumes or liquidity
could result in the failure of buyers and sellers of securities to fulfill their
settlement obligations, and in the failure of our brokerage clients to fulfill
their credit obligations, which could adversely affect our results.

         The success of the strategy we are pursuing to grow our wealth
management business is largely dependent on our ability to identify, hire and
retain talented securities brokers with investment services experience. We face
strong competition for qualified brokers, and many potential candidates are
subject to restrictive covenants with existing employers. If we are unable to
significantly increase the size of our investment services sales force as
planned, we may have difficulty attracting new accounts and increasing assets
under management and may be unable to improve the profitability of this segment
of our business.

         WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

         Our interest income and interest expense are affected by general
economic conditions and by the policies of regulatory authorities, including the
monetary policies of the Federal Reserve. Changes in interest rates may
influence the growth rate of loans and deposits, the quality of the loan
portfolio, loan and deposit pricing, the volume of loan originations in our
mortgage banking business and the value that we can recognize on the sale of
mortgage loans in the secondary market. We expect the results of WestAmerica,
our newly acquired mortgage banking business, in selling loans into the
secondary market will be impacted during periods of rising interest rates. While
we have taken measures intended to manage the risks of operating in a changing
interest rate environment, there can be no assurance that such measures will be
effective in avoiding undue interest rate risk. If market interest rates should
move contrary to our "gap" position on interest earning assets and interest
bearing liabilities, the "gap" will work against us and our net interest income
may be negatively affected.

         The success of our covered call option program, which we have used in
effect to hedge our interest rate risk, may also be affected by changes in
interest rates. With the relatively low interest rates that prevailed over the
last three years, we have been able to augment the total return of our
investment securities portfolio by selling call options on fixed-income
securities we own. We recorded fee income of $7.9 million during 2003, compared
to $6.0 million in 2002 from premiums earned on these covered call option
transactions. During the first six months of 2004, we recorded fee income of
$4.6 million on these transactions. In a rising interest rate environment,
particularly if interest rates continue to increase, the amount of premium
income we earn on these transactions will likely decline. Our opportunities to
sell covered call options may be limited in the future if rates continue to
rise.

         OUR FUTURE SUCCESS IS DEPENDENT ON OUR ABILITY TO COMPETE EFFECTIVELY
IN THE HIGHLY COMPETITIVE BANKING INDUSTRY.

         The financial services business is highly competitive, and we encounter
strong direct competition for deposits, loans and other financial services in
all of our market areas. In recent years, several major bank holding companies
have entered or expanded into the Chicago metropolitan market, and are pursuing
aggressive branching initiatives in the area. Generally, these financial
institutions are significantly larger than we are and have greater access to
capital and other resources. Our ability to compete effectively in the
marketplace is also dependent on our ability to adapt successfully to
technological changes within the banking and financial services industries.

                                       7



         OUR BUSINESS MAY BE ADVERSELY AFFECTED BY THE HIGHLY REGULATED
ENVIRONMENT IN WHICH WE OPERATE.

         We are subject to extensive federal and state legislation, regulation
and supervision. The burden of regulatory compliance has increased under current
legislation and banking regulations and is likely to continue to have or may
have a significant impact on the financial services industry. Recent legislative
and regulatory changes, as well as changes in regulatory enforcement policies
and capital adequacy guidelines, are increasing our costs of doing business and,
as a result, may create an advantage for our competitors who may not be subject
to similar legislative and regulatory requirements. In addition, future
regulatory changes, including changes to regulatory capital requirements, could
have an adverse impact on our future results. Self regulatory organizations,
such as the New York Stock Exchange and the National Association of Securities
Dealers, require our securities brokerage subsidiaries to comply with extensive
rules and regulations, and we could be adversely affected by applicable changes
in these regulations.

         SINCE OUR BUSINESS IS CONCENTRATED IN THE CHICAGO METROPOLITAN AREA, A
DOWNTURN IN THE CHICAGO ECONOMY MAY ADVERSELY AFFECT OUR BUSINESS.

         Currently, our lending and deposit gathering activities are
concentrated primarily in the greater Chicago metropolitan area. Our success
depends on the general economic condition of Chicago and its surrounding areas.
Declining economic conditions could reduce our growth rate, impair our ability
to collect loans, and generally affect our financial condition and results of
operations.

         OUR SHAREHOLDER RIGHTS PLAN AND PROVISIONS IN OUR ARTICLES OF
INCORPORATION AND OUR BY-LAWS MAY DELAY OR PREVENT AN ACQUISITION OF US BY A
THIRD PARTY.

         Our board of directors has implemented a shareholder rights plan. The
rights, which are attached to our shares of common stock and trade together with
our common stock, have certain anti-takeover effects. The plan may discourage or
make it more difficult for another party to complete a merger or tender offer
for our shares without negotiating with our board of directors or to launch a
proxy contest or to acquire control of a larger block of our shares. If
triggered, the rights will cause substantial dilution to a person or group that
attempts to acquire us without approval of our board of directors, and under
certain circumstances, the rights beneficially owned by the person or group may
become void. The plan also may have the effect of limiting shareholder
participation in certain transactions such as mergers or tender offers whether
or not such transactions are favored by incumbent directors and key management.
In addition, our executive officers may be more likely to retain their positions
with us as a result of the plan, even if their removal would be beneficial to
shareholders generally.

         Our articles of incorporation and by-laws contain provisions, including
a staggered board provision, that make it more difficult for a third party to
gain control or acquire us without the consent of our board of directors. These
provisions also could discourage proxy contests and may make it more difficult
for dissident shareholders to elect representatives as directors and take other
corporate actions.

         These provisions of our governing documents may have the effect of
delaying, deferring or preventing a transaction or a change in control that
might be in the best interest of our shareholders.

                                       8



                                 USE OF PROCEEDS

         Except as otherwise described in the applicable prospectus supplement,
we intend to use the net proceeds from any sale of the securities offered
hereunder to increase the capital at our banks, to pursue further growth
opportunities, including though acquisitions, and for general corporate
purposes.

                       RATIOS OF EARNINGS TO FIXED CHARGES

         The following table sets forth our consolidated ratios of earnings to
fixed charges for the periods indicated:




                                            (UNAUDITED)
                                         SIX MONTHS ENDED                           FISCAL YEAR
                                         ----------------       --------------------------------------------------
                                         JUNE 30,   JUNE 30,
                                         2004        2003       2003        2002       2001        2000       1999
                                         ----        ----       ----        ----       ----        ----       ----
                                                                                         
Ratio of earnings to fixed charges:(1)
   Including deposit interest......      1.82       1.65        1.71        1.51       1.32        1.19       1.23
   Excluding deposit interest......      5.12       4.60        4.82        4.03       4.26        2.93       3.54

________________

(1)      Currently, we have no shares of preferred stock outstanding and have
         not paid any dividends on preferred stock in the periods presented.
         Therefore, the ratio of earnings to combined fixed charges and
         preferred stock dividends is not different from the ratio of earnings
         to fixed charges.



         For purposes of calculating the ratio of earnings to fixed charges,
earnings are the sum of:

         o        income before income taxes and losses from unconsolidated
                  investees; and

         o        fixed charges.

         For purposes of calculating the ratio, fixed charges are the sum of:

         o        interest cost, including interest on deposits; and

         o        that portion of rent expense estimated to be representative of
                  the interest factor.

                         DESCRIPTION OF DEBT SECURITIES

DEBT MAY BE SENIOR OR SUBORDINATED

         We may issue senior or subordinated debt securities. The senior debt
securities and, in the case of debt securities in bearer form, any coupons to
these securities, will constitute part of our senior debt and, except as
otherwise included in the applicable prospectus supplement, will rank on a
parity with all of our other unsecured and unsubordinated debt. The subordinated
debt securities and any coupons will constitute part of our subordinated debt
and will be subordinate and junior in right of payment to all of our "senior
indebtedness," which will be defined in the applicable prospectus supplement. If
this prospectus is being delivered in connection with a series of subordinated
debt securities, the accompanying prospectus supplement or the information we
incorporate in this prospectus by reference will indicate the approximate amount
of senior indebtedness outstanding as of the end of the most recent fiscal
quarter. Our debt securities will be issued under an indenture, the form of
which is included as an exhibit to the registration statement of which this
prospectus is a part.

                                       9



         We have summarized below the material provisions of the indenture and
the debt securities, or indicated which material provisions will be described in
the related prospectus supplement. These descriptions are only summaries, and
each investor should refer to the indenture, including the applicable supplement
thereto, which describes completely the terms and definitions summarized below
and contains additional information regarding the debt securities.

PAYMENTS

         We may issue debt securities from time to time in one or more series.
The provisions of each indenture allow us to "reopen" a previous issue of a
series of debt securities and issue additional debt securities of that issue.
The debt securities may be denominated and payable in U.S. dollars.

         Debt securities may bear interest at a fixed rate or a floating rate,
which, in either case, may be zero, or at a rate that varies during the lifetime
of the debt security. Debt securities may be sold at a discount below their
stated principal amount.

TERMS SPECIFIED IN PROSPECTUS SUPPLEMENT

         The prospectus supplement will contain, where applicable, the following
terms of and other information relating to any offered debt securities:

         o        classification as senior or subordinated debt securities and
                  the specific designation;

         o        aggregate principal amount, purchase price and denomination;

         o        currency in which the debt securities are denominated and/or
                  in which principal, and premium, if any, and/or interest, if
                  any, is payable;

         o        date of maturity;

         o        the interest rate or rates or the method by which the
                  calculation agent will determine the interest rate or rates,
                  if any;

         o        the interest payment dates, if any;

         o        the place or places for payment of the principal of and any
                  premium and/or interest on the debt securities;

         o        any repayment, redemption, prepayment or sinking fund
                  provisions, including any redemption notice provisions;

         o        whether we will issue the debt securities in registered form
                  or bearer form or both and, if we are offering debt securities
                  in bearer form, any restrictions applicable to the exchange of
                  one form for another and to the offer, sale and delivery of
                  those debt securities in bearer form;

         o        whether we will issue the debt securities in definitive form
                  and under what terms and conditions;

         o        the terms on which holders of the debt securities may convert
                  or exchange these securities into or for common or preferred
                  stock or other securities of ours offered hereby, into or for
                  common or preferred stock or other securities of an entity
                  affiliated with us or debt or equity or other securities of an
                  entity not affiliated with us, or for the cash value of our
                  stock or any of the above securities, the terms on which
                  conversion or exchange may occur, including
                                       10



                  whether conversion or exchange is mandatory, at the option of
                  the holder or at our option, the period during which
                  conversion or exchange may occur, the initial conversion or
                  exchange price or rate and the circumstances or manner in
                  which the amount of common or preferred stock or other
                  securities issuable upon conversion or exchange may be
                  adjusted;

         o        information as to the methods for determining the amount of
                  principal or interest payable on any date and/or the
                  currencies, securities or baskets of securities, commodities
                  or indices to which the amount payable on that date is linked;

         o        any agents for the debt securities, including trustees,
                  depositories, authenticating or paying agents, transfer agents
                  or registrars;

         o        any applicable United States federal income tax consequences,
                  including:

                  o        whether and under what circumstances we will pay
                           additional amounts on debt securities held by a
                           person who is not a U.S. person for any tax,
                           assessment or governmental charge withheld or
                           deducted and, if so, whether we will have the option
                           to redeem those debt securities rather than pay the
                           additional amounts;

                  o        tax considerations applicable to any discounted debt
                           securities or to debt securities issued at par that
                           are treated as having been issued at a discount for
                           United States federal income tax purposes; and

                  o        tax considerations applicable to any debt securities
                           denominated and payable in foreign currencies; and

         o        any other specific terms of the debt securities, including any
                  additional events of default or covenants, and any terms
                  required by or advisable under applicable laws or regulations.

REGISTRATION AND TRANSFER OF DEBT SECURITIES

         Holders may present debt securities for exchange, and holders of
registered debt securities may present these securities for transfer, in the
manner, at the places and subject to the restrictions stated in the debt
securities and described in the applicable prospectus supplement. We will
provide these services without charge except for any tax or other governmental
charge payable in connection with these services and subject to any limitations
provided in the applicable indenture.

         If any of the securities are held in global form, the procedures for
transfer of interests in those securities will depend upon the procedures of the
depositary for those global securities. See "Global Securities."

SUBORDINATION PROVISIONS

         Subordinated debt securities will be subordinate and junior in right of
payment, to the extent and in the manner stated in the applicable prospectus
supplement, to all of our senior indebtedness.

         Unless all principal of and any premium or interest on the senior
indebtedness has been paid in full, or provision has been made to make these
payments in full, no payment of principal of, or any premium or interest on, any
subordinated debt securities may be made in the event:

         o        of any insolvency or bankruptcy proceedings, or any
                  receivership, liquidation, reorganization or other similar
                  proceedings involving us or a substantial part of our
                  property;

                                       11



         o        that (a) a default has occurred in the payment of principal,
                  any premium, interest or other monetary amounts due and
                  payable on any senior indebtedness or (b) there has occurred
                  any other event of default concerning senior indebtedness that
                  permits the holder or holders of the senior indebtedness to
                  accelerate the maturity of the senior indebtedness, with
                  notice or passage of time, or both, and that event of default
                  has continued beyond the applicable grace period, if any, and
                  that default or event of default has not been cured or waived
                  or has not ceased to exist; or

         o        that the principal of and accrued interest on any subordinated
                  debt securities have been declared due and payable upon an
                  event of default and that declaration has not been rescinded
                  and annulled as provided under the applicable supplemental
                  indenture.

COVENANTS RESTRICTING PLEDGES, MERGERS AND OTHER SIGNIFICANT CORPORATE ACTIONS

         Negative Pledge. The supplemental indenture relating to any senior debt
securities will provide that we will not, and will not permit any subsidiary to,
create, assume, incur or guarantee any indebtedness for borrowed money that is
secured by a pledge, lien or other encumbrance except for liens specifically
permitted by the indenture on:

         o        the voting securities of Wintrust or any subsidiary succeeding
                  to any substantial part of the business now conducted by
                  Wintrust or any such subsidiary, which we refer to
                  collectively as the "principal subsidiaries," or

         o        the voting securities of a subsidiary that owns, directly or
                  indirectly, the voting securities of any of the principal
                  subsidiaries,

without making effective provisions so that the senior debt securities issued
under the indenture will be secured equally and ratably with indebtedness so
secured.

         Merger, Consolidation, Sale, Lease or Conveyance. The indenture
provides that we will not merge or consolidate with any other person and will
not sell, lease or convey all or substantially all of our assets to any other
person, unless:

         o        we will be the continuing corporation; or

         o        the successor corporation or person that acquires all or
                  substantially all of our assets:

                  o        will be a corporation organized under the laws of the
                           United States, a state of the United States or the
                           District of Columbia; and

                  o        will expressly assume all of our obligations under
                           the indenture and the debt securities issued under
                           the indenture; and

         o        immediately after the merger, consolidation, sale, lease or
                  conveyance, we, that person or that successor corporation will
                  not be in default in the performance of the covenants and
                  conditions of the indenture applicable to us.

         Absence of Protections Against All Potential Actions of Wintrust. There
are no covenants or other provisions in the indenture that would afford holders
of debt securities additional protection in the event of a recapitalization
transaction, a change of control of Wintrust or a highly leveraged transaction.
The merger covenant described above would only apply if the recapitalization
transaction, change of control or highly leveraged transaction were structured
to include a merger or consolidation of Wintrust or a sale,

                                       12



lease or conveyance of all or substantially all of our assets. However, we may
provide specific protections, such as a put right or increased interest, for
particular debt securities, which we would describe in the applicable prospectus
supplement.

EVENTS OF DEFAULT

         The indenture provides holders of debt securities with remedies if we
fail to perform specific obligations, such as making payments on the debt
securities or other indebtedness, or if we become bankrupt. Holders should
review these provisions and understand which of our actions trigger an event of
default and which actions do not. The indenture permits the issuance of debt
securities in one or more series, and, in many cases, whether an event of
default has occurred is determined on a series by series basis.

         An event of default is defined under the indenture, with respect to any
series of debt securities issued under that indenture, as being:

         o        default in payment of any principal of the debt securities of
                  that series, either at maturity or upon any redemption, by
                  declaration or otherwise;

         o        default for 30 days in payment of any interest on any debt
                  securities of that series;

         o        default for 60 days after written notice in the observance or
                  performance of any covenant or agreement in the debt
                  securities of that series or the related indenture (other than
                  a covenant or warranty with respect to the debt securities of
                  that series the breach or nonperformance of which is otherwise
                  included in the definition of "event of default");

         o        specified events of bankruptcy, insolvency or reorganization;

         o        failure to make any payment at maturity, including any
                  applicable grace period, on other indebtedness in an amount in
                  excess of $10,000,000 and continuance of that failure for a
                  period of 30 days after written notice of the failure to us by
                  the applicable trustee, or to us and the applicable trustee by
                  the holders of not less than 25% in principal amount of the
                  outstanding debt securities, treated as one class, issued
                  under the indenture;

         o        default with respect to any other indebtedness, which default
                  results in the acceleration of indebtedness in an amount in
                  excess of $10,000,000 without the indebtedness having been
                  discharged or the acceleration having been cured, waived,
                  rescinded or annulled for a period of 30 days after written
                  notice of the acceleration to us by the applicable trustee, or
                  to us and the applicable trustee by the holders of not less
                  than 25% in principal amount of the outstanding debt
                  securities, treated as one class, issued under the indenture;
                  or

         o        any other event of default provided in the supplemental
                  indenture under which that series of debt securities is
                  issued.

         For purposes of the fifth and sixth clauses above, indebtedness means
obligations of, or guaranteed or assumed by, Wintrust, other than the debt
securities of that series, for borrowed money or evidenced by bonds, debentures,
notes or other similar instruments, but does not include non recourse
obligations. In addition, if a failure, default or acceleration referred to in
the fifth and sixth clauses above ceases or is cured, waived, rescinded or
annulled, then the event of default under the applicable indenture caused by
that failure, default or acceleration will also be considered cured.

         Acceleration of Debt Securities upon an Event of Default. The indenture
provides that:

                                       13



         o        if an event of default due to the default in payment of
                  principal of, or any premium or interest on, any series of
                  debt securities issued under that indenture, or due to the
                  default in the performance or breach of any other covenant or
                  warranty of Wintrust applicable to the debt securities of that
                  series but not applicable to all outstanding debt securities
                  issued under that indenture occurs and is continuing, either
                  the trustee or the holders of not less than 25% in aggregate
                  principal amount of the outstanding debt securities of each
                  affected series, voting as one class, by notice in writing to
                  Wintrust and to the trustee, if given by security holders, may
                  declare the principal of all debt securities of each affected
                  series and interest accrued thereon to be due and payable
                  immediately; and

         o        if an event of default due to a default in the performance of
                  any other covenants or agreements in that indenture applicable
                  to all outstanding debt securities issued under that indenture
                  or due to specified events of bankruptcy, insolvency or
                  reorganization of Wintrust, occurs and is continuing, either
                  the trustee or the holders of not less than 25% in aggregate
                  principal amount of all outstanding debt securities issued
                  under that indenture, voting as one class, by notice in
                  writing to Wintrust and to the trustee, if given by security
                  holders, may declare the principal of all those debt
                  securities, interest accrued thereon to be due and payable
                  immediately.

         Annulment of Acceleration and Waiver of Defaults. In some
circumstances, if any and all events of default under the indenture, other than
the non-payment of the principal of the securities that has become due as a
result of an acceleration, have been cured, waived or otherwise remedied, then
the holders of a majority in aggregate principal amount of all series of
outstanding debt securities affected, voting as one class, may annul past
declarations of acceleration of or waive past defaults of the debt securities.

         Indemnification of Trustee for Actions Taken on Your Behalf. The
indenture contains a provision entitling the trustee, subject to the duty of the
trustee during a default to act with the required standard of care, to be
indemnified by the holders of debt securities issued under the indenture before
proceeding to exercise any trust or power at the request of holders. Subject to
these provisions and some other limitations, the holders of a majority in
aggregate principal amount of each series of outstanding debt securities, voting
as one class, may, with respect to debt securities of that class, direct the
time, method and place of conducting any proceeding for any remedy available to
the applicable trustee, or exercising any trust or power conferred on the
trustee.

         Limitation on Actions by You as an Individual Holder. The indenture
provides that no individual holder of debt securities may institute any action
against us under the indenture, except actions for payment of overdue principal
and interest, unless the following actions have occurred:

         o        the holder must have previously given written notice to the
                  trustee of the continuing default;

         o        the holders of not less than 25% in aggregate principal amount
                  of the outstanding debt securities of each affected series,
                  treated as one class, must have (1) requested the trustee to
                  institute that action and (2) offered the trustee reasonable
                  indemnity;

         o        the trustee must have failed to institute that action within
                  60 days after receipt of the request referred to above; and

         o        the holders of a majority in aggregate principal amount of the
                  outstanding debt securities of each affected series, voting as
                  one class, must not have given directions to the trustee
                  inconsistent with those of the holders referred to above.

                                       14



         Annual Certification. The indenture contains a covenant that we will
file annually with the trustee a certificate of no default or a certificate
specifying any default that exists.

DISCHARGE, DEFEASANCE AND COVENANT DEFEASANCE

         We have the ability to eliminate most or all of our obligations on any
series of debt securities prior to maturity if we comply with the following
provisions.

         Discharge of Indenture. If at any time we have:

         o        paid or caused to be paid the principal of and interest on all
                  of the outstanding debt securities in accordance with their
                  terms;

         o        delivered to the applicable trustee for cancellation all of
                  the outstanding debt securities; or

         o        irrevocably deposited with the applicable trustee cash or, in
                  the case of a series of debt securities payable only in U.S.
                  dollars, U.S. government obligations in trust for the benefit
                  of the holders of any series of debt securities issued under
                  the indenture that have either become due and payable, or are
                  by their terms due and payable within one year or are
                  scheduled for redemption within one year, in an amount
                  certified to be sufficient to pay on each date that they
                  become due and payable, the principal of and interest on, and
                  any mandatory sinking fund payments for, those debt
                  securities;

and if, in any such case, we also pay or cause to be paid all other sums payable
by us under the indenture, then the indenture shall cease to be of further
effect, except as to certain rights and with respect to the transfer and
exchange of securities, rights of the holders to receive payment and certain
other rights and except that the deposit of cash or U.S. government obligations
for the benefit of holders of a series of debt securities that are due and
payable or are due and payable within one year or are scheduled for redemption
within one year will discharge obligations under the relevant indenture relating
only to that series of debt securities.

         Defeasance of a Series of Securities at Any Time. We may also discharge
all of our obligations, other than as to transfers and exchanges, under any
series of debt securities at any time, which we refer to as "defeasance."

         o        We may be released with respect to any outstanding series of
                  debt securities from the obligations imposed by any covenants
                  limiting liens and consolidations, mergers, asset sales and
                  leases, and elect not to comply with those sections without
                  creating an event of default. Discharge under those procedures
                  is called "covenant defeasance."

         Defeasance or covenant defeasance may be effected only if, among other
things:

         o        We irrevocably deposit with the applicable trustee cash or, in
                  the case of debt securities payable only in U.S. dollars, U.S.
                  government obligations, as trust funds in an amount certified
                  to be sufficient to pay on each date that they become due and
                  payable or a combination of the above sufficient to pay the
                  principal of and interest on, and any mandatory sinking fund
                  payments for, all outstanding debt securities of the series
                  being defeased.

         o        We deliver to the applicable trustee an opinion of counsel to
                  the effect that:

                                       15



                  o        the holders of the series of debt securities being
                           defeased will not recognize income, gain or loss for
                           United States federal income tax purposes as a result
                           of the defeasance or covenant defeasance; and

                  o        the defeasance or covenant defeasance will not
                           otherwise alter those holders' United States federal
                           income tax treatment of principal and interest
                           payments on the series of debt securities being
                           defeased.

         In the case of a defeasance, this opinion must be based on a ruling of
the Internal Revenue Service or a change in United States federal income tax law
occurring after the date of this prospectus, since that result would not occur
under current tax law.

         o        In the case of any subordinated debt securities:

                  o        no event or condition will exist that, under the
                           provisions described under "--Subordination
                           Provisions" above, would prevent us from making
                           payments of principal or interest on the subordinated
                           debt securities at the date of the irrevocable
                           deposit referred to above or at any time during the
                           period ending on the 91st day after that deposit
                           date; and

                  o        we deliver to the trustee for the subordinated debt
                           securities an opinion of counsel to the effect that
                           (i) the trust funds will not be subject to any rights
                           of holders of senior indebtedness and (ii) after the
                           91st day following the deposit, the trust funds will
                           not be subject to any applicable bankruptcy,
                           insolvency, reorganization or similar laws affecting
                           creditors' rights generally, except that if a court
                           were to rule under any of those laws in any case or
                           proceeding that the trust funds remained our
                           property, then the applicable trustee and the holders
                           of the subordinated debt securities would be entitled
                           to some enumerated rights as secured creditors in the
                           trust funds.

MODIFICATION OF THE INDENTURE

         Modification Without Consent of Holders. We and the applicable trustee
may enter into supplemental indentures without the consent of the holders of
debt securities issued under a particular indenture to:

         o        secure any debt securities;

         o        evidence the assumption by a successor corporation of our
                  obligations;

         o        add covenants for the protection of the holders of debt
                  securities;

         o        cure any ambiguity or correct any inconsistency;

         o        establish the forms or terms of debt securities of any series;
                  or

         o        evidence the acceptance of appointment by a successor trustee.

         Modification with Consent of Holders. We and the applicable trustee,
with the consent of the holders of not less than a majority in aggregate
principal amount of each affected series of outstanding debt securities, voting
as one class, may add any provisions to, or change in any manner or eliminate
any of the provisions of, the applicable indenture or modify in any manner the
rights of the holders of those debt securities. However, we and the trustee may
not make any of the following changes to any outstanding debt security without
the consent of each holder that would be affected by such change:

                                       16



         o        extend the final maturity of the principal;

         o        reduce the principal amount;

         o        reduce the rate or extend the time of payment of interest;

         o        reduce any amount payable on redemption;

         o        change the currency in which the principal, any amount of
                  original issue discount, or interest thereon is
                  payable;

         o        modify or amend the provisions for conversion of any currency
                  into another currency;

         o        reduce the amount of any original issue discount security
                  payable upon acceleration or provable in bankruptcy;

         o        alter the terms on which holders of the debt securities may
                  convert or exchange debt securities for stock or other
                  securities of Wintrust or of other entities or for other
                  property or the cash value of the property, other than in
                  accordance with the antidilution provisions or other similar
                  adjustment provisions included in the terms of the debt
                  securities;

         o        alter certain provisions of the relevant indenture relating to
                  debt securities not denominated in U.S. dollars;

         o        impair the right of any holder to institute suit for the
                  enforcement of any payment on any debt security when due; or

         o        reduce the percentage of debt securities the consent of whose
                  holders is required for modification of the relevant
                  indenture.

         Modification of Subordination Provisions. We may not amend a
supplemental indenture relating to subordinated debt securities to alter the
subordination of any outstanding subordinated debt securities without the
written consent of each potentially adversely affected holder of senior
indebtedness then outstanding.

GOVERNING LAW

         Unless otherwise specified in a prospectus supplement, the debt
securities and the indenture will be governed by, and construed in accordance
with, the laws of the State of Illinois.

                        DESCRIPTION OF PURCHASE CONTRACTS

         We may issue purchase contracts, including purchase contracts issued as
part of a unit with one or more other securities, for the purchase or sale of
our debt securities, preferred stock, depositary shares or common stock. The
price of our debt securities or price per share of common stock, preferred stock
or depositary shares, as applicable, may be fixed at the time the purchase
contracts are issued or may be determined by reference to a specific formula
contained in the purchase contracts. We may issue purchase contracts in such
amounts and in as many distinct series as we wish.

         The applicable prospectus supplement may contain, where applicable, the
following information about the purchase contracts issued under it:

                                       17



         o        whether the purchase contracts obligate the holder to purchase
                  or sell, or both, our debt securities, common stock, preferred
                  stock or depositary shares, as applicable, and the nature and
                  amount of each of those securities, or method of determining
                  those amounts;

         o        whether the purchase contracts are to be prepaid or not;

         o        whether the purchase contracts are to be settled by delivery,
                  or by reference or linkage to the value, performance or level
                  of our common stock or preferred stock;

         o        any acceleration, cancellation, termination or other
                  provisions relating to the settlement of the purchase
                  contracts;

         o        United States federal income tax considerations relevant to
                  the purchase contracts; and

         o        whether the purchase contracts will be issued in fully
                  registered global form.

         The applicable prospectus supplement will describe the terms of any
purchase contracts. The preceding description and any description of purchase
contracts in the applicable prospectus supplement does not purport to be
complete and is subject to and is qualified in its entirety by reference to the
purchase contract agreement and, if applicable, collateral arrangements and
depositary arrangements relating to such purchase contracts.

                              DESCRIPTION OF UNITS

         Units will consist of any combination of one or more of the other
securities described in this prospectus. The applicable prospectus supplement
will also describe:

         o        the designation and the terms of the units and of any
                  combination of the securities constituting the units,
                  including whether and under what circumstances those
                  securities may be held or traded separately;

         o        any additional terms of the agreement governing the units;

         o        any additional provisions for the issuance, payment,
                  settlement, transfer or exchange of the units or of the
                  securities constituting the units;

         o        any applicable United States federal income tax consequences;
                  and

         o        whether the units will be issued in fully registered form.

         The terms and conditions described under "Description of Debt
Securities," "Description of Warrants," "Description of Capital Stock--Preferred
Stock" and "Description of Capital Stock--Common Stock" will apply to each unit
and to the securities included in each unit, unless otherwise specified in the
applicable prospectus supplement.

         We will issue the units under one or more unit agreements to be entered
into between us and a bank or trust company, as unit agent. We may issue units
in one or more series, which will be described in the applicable prospectus
supplement.

                                       18



                             DESCRIPTION OF WARRANTS

         We may issue warrants for the purchase of debt securities, shares of
preferred stock or common stock. Warrants may be issued independently or
together with any debt securities, shares of preferred stock or common stock
offered by any prospectus supplement and may be attached to or separate from the
debt securities, shares of preferred stock or common stock. The warrants are to
be issued under warrant agreements to be entered into between Wintrust and a
bank or trust company, as warrant agent, as is named in the prospectus
supplement relating to the particular issue of warrants. The warrant agent will
act solely as an agent of Wintrust in connection with the warrants and will not
assume any obligation or relationship of agency or trust for or with any holders
of warrants or beneficial owners of warrants. This section is a summary of the
material terms of the warrant agreement; it does not describe every aspect of
the warrants. We urge you to read the form of warrant agreement attached as an
exhibit to the registration statement because it, and not this description, will
define your rights as a warrant holder.

GENERAL

         If warrants are offered, the prospectus supplement will describe the
terms of the warrants, including the following:

         o        the offering price;

         o        the designation, aggregate principal amount and terms of the
                  debt securities purchasable upon exercise of the debt warrants
                  and the price at which such debt securities may be purchased
                  upon such exercise;

         o        the designation, number of shares and terms of the preferred
                  stock purchasable upon exercise of the preferred stock
                  warrants and the price at which such shares of preferred stock
                  may be purchased upon such exercise;

         o        the designation, number of shares and terms of the common
                  stock purchasable upon exercise of the common stock warrants
                  and the price at which such shares of common stock may be
                  purchased upon such exercise;

         o        if applicable, the designation and terms of the debt
                  securities, preferred stock or common stock with which the
                  warrants are issued and the number of warrants issued with
                  each such debt security or share of preferred stock or common
                  stock;

         o        if applicable, the date on and after which the warrants and
                  the related debt securities, preferred stock or common stock
                  will be separately transferable;

         o        the date on which the right to exercise the warrants shall
                  commence and the date on which such right shall expire;

         o        whether the warrants will be issued in registered or bearer
                  form;

         o        a discussion of certain federal income tax, accounting and
                  other special considerations, procedures and limitations
                  relating to the warrants; and

         o        any other terms of the warrants.

         Warrants may be exchanged for new warrants of different denominations.
If in registered form, warrants may be presented for registration of transfer,
and may be exercised at the corporate trust office of the Warrant Agent or any
other office indicated in the prospectus supplement. Before the exercise of

                                       19



their warrants, holders of warrants will not have any of the rights of holders
of the securities purchasable upon such exercise, including the right to receive
payments of principal of, any premium on, or any interest on, the debt
securities purchasable upon such exercise or to enforce the covenants in the
indenture or to receive payments of dividends, if any, on the preferred stock or
common stock purchasable upon such exercise or to exercise any applicable right
to vote.

EXERCISE OF WARRANTS

         Each warrant will entitle the holder to purchase such principal amount
of debt securities or such number of shares of preferred stock or common stock
at such exercise price as shall in each case be set forth in, or can be
calculated according to information contained in, the prospectus supplement
relating to the warrant. Warrants may be exercised at such times as are set
forth in the prospectus supplement relating to such warrants. After the close of
business on the expiration date of the warrants, or such later date to which
such expiration date may be extended by Wintrust, unexercised warrants will
become void.

         Subject to any restrictions and additional requirements that may be set
forth in the prospectus supplement, warrants may be exercised by delivery to the
warrant agent of the certificate evidencing such warrants properly completed and
duly executed and of payment as provided in the prospectus supplement of the
amount required to purchase the debt securities or shares of preferred stock or
common stock purchasable upon such exercise. The exercise price will be the
price applicable on the date of payment in full, as set forth in the prospectus
supplement relating to the warrants. Upon receipt of such payment and the
certificate representing the warrants to be exercised, properly completed and
duly executed at the corporate trust office of the warrant agent or any other
office indicated in the prospectus supplement, we will, as soon as practicable,
issue and deliver the debt securities or shares of preferred stock or common
stock purchasable upon such exercise. If fewer than all of the warrants
represented by such certificate are exercised, a new certificate will be issued
for the remaining amount of warrants.

ADDITIONAL PROVISIONS

         The exercise price payable and the number of shares of common stock or
preferred stock purchasable upon the exercise of each stock warrant will be
subject to adjustment in certain events, including:

         o        the issuance of the stock dividend to holders of common stock
                  or preferred stock, respectively;

         o        a combination, subdivision or reclassification of common stock
                  or preferred stock, respectively; or

         o        any other event described in the applicable prospectus
                  supplement.

         In lieu of adjusting the number of shares of common stock or preferred
stock purchasable upon exercise of each stock warrant, we may elect to adjust
the number of stock warrants. No adjustment in the number of shares purchasable
upon exercise of the stock warrants will be required until cumulative
adjustments require an adjustment of at least 1% thereof. We may, at our option,
reduce the exercise price at any time. No fractional shares will be issued upon
exercise of stock warrants, but we will pay the cash value of any fractional
shares otherwise issuable. Notwithstanding the foregoing, in case of any
consolidation, merger, or sale or conveyance of the property of Wintrust as an
entirety or substantially as an entirety, the holder of each outstanding stock
warrant shall have the right upon the exercise thereof to the kind and amount of
shares of stock and other securities and property, including cash, receivable by
a holder of the number of shares of common stock or preferred stock into which
such stock warrants were exercisable immediately prior thereto.

                                       20



NO RIGHTS AS STOCKHOLDERS

         Holders of stock warrants will not be entitled, by virtue of being such
holders, to vote, to consent, to receive dividends, to receive notice as
stockholders with respect to any meeting of stockholders for the election of
directors of Wintrust or any other matter, or to exercise any rights whatsoever
as stockholders of Wintrust.

                          DESCRIPTION OF CAPITAL STOCK

AUTHORIZED CAPITALIZATION

         As of the date of this prospectus, our capital structure consists of 30
million authorized shares of common stock, no par value per share, and 20
million shares of undesignated preferred stock, no par value per share. As of
September 27, 2004, 20,568,990 shares of our common stock were issued and
outstanding, and no shares of preferred stock were issued and outstanding.

COMMON STOCK

         The holders of common stock will be entitled to receive and share
equally in such dividends, if any, declared by the board of directors out of
funds legally available therefor. Wintrust may pay dividends if, as and when
declared by its board of directors. The payment of dividends by Wintrust is
subject to limitations imposed by the Illinois Business Corporation Act (the
"IBCA"). If Wintrust issues preferred stock, the holders thereof may have a
priority over the holders of the common stock with respect to dividends.

         The holders of common stock possess voting rights in Wintrust. They
elect Wintrust's board of directors and act on such other matters as are
required to be presented to them under Illinois law or Wintrust's articles of
incorporation or as are otherwise presented to them by the board of directors.
Each holder of common stock is entitled to one vote per share and does not have
any right to cumulate votes in the election of directors. Although there are no
present plans to do so, if the Company issues preferred stock, holders of the
preferred stock may also possess voting rights. Certain matters require an 85%
shareholder vote. See "Certain Anti-takeover Effects of Wintrust's Articles and
By-Laws and Illinois Law" below.

         In the event of any liquidation, dissolution or winding up of Wintrust,
the holders of its common stock would be entitled to receive, after payment or
provision for payment of all debts and liabilities of Wintrust, all assets of
Wintrust available for distribution. If preferred stock is issued, the holders
thereof may have a priority over the holders of the common stock in the event of
any liquidation or dissolution.

         Holders of Wintrust's common stock are not entitled to preemptive
rights with respect to any shares that may be issued in the future. The common
stock is not subject to mandatory redemption by Wintrust.

         Certain Anti-takeover Effects of Wintrust's Articles and By-laws and
Illinois Law. Certain provisions of Wintrust's articles of incorporation,
by-laws and the Illinois Business Corporation Act, or IBCA, may have the effect
of impeding the acquisition of control of Wintrust by means of a tender offer, a
proxy fight, open-market purchases or otherwise in a transaction not approved by
Wintrust's board of directors.

         These provisions may have the effect of discouraging a future takeover
attempt which is not approved by Wintrust's board of directors but which
individual Wintrust shareholders may deem to be in

                                       21



their best interests or in which Wintrust shareholders may receive a substantial
premium for their shares over then-current market prices. As a result,
shareholders who might desire to participate in such a transaction may not have
an opportunity to do so. Such provisions will also render the removal of
Wintrust's current board of directors or management more difficult.

         These provisions of Wintrust's articles of incorporation and by-laws
include the following:

                  (1) Wintrust's board of directors may issue additional
         authorized shares of Wintrust's capital stock to deter future attempts
         to gain control of Wintrust, including the authority to determine the
         terms of any one or more series of preferred stock, such as voting
         rights, conversion rates, and liquidation preferences. As a result of
         the ability to fix voting rights for a series of preferred stock, the
         board has the power, to the extent consistent with its fiduciary duty,
         to issue a series of preferred stock to persons friendly to management
         in order to attempt to block a merger or other transaction by which a
         third party seeks control, and thereby assist the incumbent board of
         directors and management to retain their respective positions;

                  (2) Wintrust's staggered board is intended to provide for
         continuity of its board of directors and to make it more difficult and
         time consuming for a shareholder group to fully use its voting power to
         gain control of the board of directors without the consent of
         Wintrust's incumbent board of directors;

                  (3) Wintrust's articles of incorporation do not provide for
         cumulative voting for any purpose, and its articles of incorporation
         and by-laws also provide that any action required or permitted to be
         taken by its shareholders may be taken only at an annual or special
         meeting and prohibit shareholder action by written consent in lieu of a
         meeting;

                  (4) Wintrust's articles of incorporation expressly elect to be
         governed by the provisions of Section 7.85 of the IBCA, as discussed
         above. Under the IBCA fair price provision and Wintrust's articles of
         incorporation, the approval of at least 80% of its shares is required
         in connection with any transaction involving an Interested Shareholder,
         subject to certain exceptions. Fair price provisions are designed to
         impede a two-step takeover transaction that might otherwise result in
         disparate treatment of Wintrust's shareholders; and

                  (5) Amendment of Wintrust's articles of incorporation must be
         approved by a majority vote of the board of directors and also by a
         two-thirds vote of the outstanding shares of Wintrust common stock,
         provided, however, that an affirmative vote of at least 85% of the
         outstanding voting stock entitled to vote is required to amend or
         repeal certain provisions of the articles of incorporation, including
         provisions (a) prohibiting cumulative voting rights, (b) relating to
         certain business combinations, (c) limiting the shareholders' ability
         to act by written consent, (d) regarding the number, classification of
         directors, filling of board vacancies and newly created directorships,
         (e) indemnification of directors and officers by Wintrust and
         limitation of liability for directors, and (f) regarding amendment of
         the foregoing supermajority provisions of Wintrust's articles of
         incorporation. Wintrust's by-laws may be amended only by the board of
         directors.

         The provisions described above are intended to reduce Wintrust's
vulnerability to takeover attempts and certain other transactions which have not
been negotiated with and approved by members of its board of directors.

         Rights Plan. Wintrust has a shareholders rights plan which could
discourage unsolicited or hostile takeover attempts which are not negotiated
with its board of directors. The plan discourages such attempts by causing
substantial dilution to any person who acquires an amount in excess of a
specified

                                       22



percentage of Wintrust's common stock and by making an acquisition of Wintrust,
without the consent of its board of directors, prohibitively expensive. The
description of the rights plan set forth below does not purport to be complete
and is qualified in its entirety by reference to the description of the rights
plan set forth in Wintrust's Registration Statement on Form 8-A dated August 28,
1998. See "Documents Incorporated by Reference" on page 60.

         Each share of Wintrust common stock has attached to it a stock purchase
right having the terms set forth in a rights agreement between Wintrust and
Illinois Stock Transfer Company, as rights agent. Each right will entitle its
registered holder to purchase from Wintrust one one-hundredth of a share of
Junior Serial Preferred Stock A, without par value, at a price of $85.00 per one
one-hundredth share, subject to certain adjustments. Generally, the rights
become exercisable when any person or group (i) acquires or obtains the right to
acquire 15% or more of Wintrust's common stock, or (ii) commences (or announces
its intention to commence) a tender or exchange offer to acquire 15% or more of
Wintrust's common stock.

         In the event that any person or group becomes the beneficial owner of
15% or more of Wintrust's common stock, rights owned by that person or group
will immediately become null and void. Thereafter, other registered rights
holders will have the right to receive, upon exercise at the then-current
exercise price of the right, Wintrust common stock having a value equal to two
times the exercise price of the right. Additionally, if, after any person or
group has acquired 15% or more Wintrust's common stock, Wintrust is acquired in
a merger or other business combination or 50% or more of Wintrust's assets or
earning power are sold, then each registered right holder will receive the right
to purchase, for the exercise price, common stock of the entity which acquires
or survives Wintrust having a value equal to twice the exercise price of the
right.

         Prior to any person or group acquiring 15% or more of Wintrust's common
stock, Wintrust may redeem the rights in whole, but not in part, at a price of
$0.01 per right, to be paid in cash, shares of Wintrust common stock or other
consideration. In addition, at any time after a person or group acquires 15% of
Wintrust's common stock, but prior to such person or group acquiring 50% or more
of Wintrust's common stock, Wintrust may exchange the rights, in whole or in
part, at an exchange ratio of one share of common stock per right. The rights
will expire on July 31, 2008 unless exercised, redeemed, exchanged or otherwise
cancelled before that date.

         Transfer Agent and Registrar. The transfer agent and registrar for our
common stock is Illinois Stock Transfer Company, 209 W. Jackson Boulevard, Suite
903, Chicago, IL 60606.

PREFERRED STOCK

         Our board of directors has authorized the issuance of one or more
series of preferred stock and has authorized a committee of the board of
directors to establish and designate series and to fix the number of shares and
the relative rights, preferences and limitations of the respective series of the
preferred stock offered by this prospectus and the applicable prospectus
supplement. The shares of preferred stock, when issued and sold, will be fully
paid and nonassessable.

         Terms Specified in Prospectus Supplement. The following description
sets forth some general terms and provisions of the preferred stock. The number
of shares and all of the relative rights, preferences and limitations of the
respective series of preferred stock that the board of directors or the
committee establishes will be described in the applicable prospectus supplement.
The terms of particular series of preferred stock may differ, among other
things, in:

         o        designation;

                                       23



         o        number of shares that constitute the series;

         o        dividend rate, or the method of calculating the dividend rate;

         o        dividend periods, or the method of calculating the dividend
                  periods;

         o        redemption provisions, including whether or not, on what terms
                  and at what prices the shares will be subject to redemption at
                  our option;

         o        voting rights;

         o        preferences and rights upon liquidation or winding up;

         o        whether or not and on what terms the shares will be
                  convertible into or exchangeable for shares of any other
                  class, series or security of ours or any other corporation or
                  any other property;

         o        for preferred stock convertible into common stock, the number
                  of shares of common stock to be reserved in connection with,
                  and issued upon conversion of, the preferred stock;

         o        whether depositary shares representing the preferred stock
                  will be offered and, if so, the fraction or multiple of a
                  share that each depositary share will represent; and

         o        the other rights and privileges and any qualifications,
                  limitations or restrictions of those rights or privileges.

         Rank. Each series of preferred stock will rank, with respect to the
payment of dividends and the distribution of assets upon liquidation,
dissolution or winding up:

         o        junior to any series of our capital stock expressly stated to
                  be senior to that series of preferred stock;

         o        senior to our common stock and any class of our capital stock
                  expressly stated to be junior to that series of preferred
                  stock; and

         o        on a parity with each other series of preferred stock and all
                  other classes of our capital stock.

         Dividends. If described in the applicable prospectus supplement, we
will pay cumulative cash dividends to the holders of preferred stock, when and
as declared by the board of directors or the committee, out of funds legally
available for payment. The prospectus supplement will detail the annual rate of
dividends or the method or formula for determining or calculating them, and the
payment dates and payment periods for dividends. The board of directors or the
committee will fix a record date for the payment of dividends. We will pay
dividends on the preferred stock to the holders of record on that record date.
Dividends will be cumulative from the date of original issue of the series. A
series of preferred stock will be junior as to payment of dividends to any
series of preferred stock that may be issued in the future that is expressly
stated to be senior as to payment of dividends to that series of preferred
stock. If at any time we have failed to pay accrued dividends on any of those
senior shares when payable, we may not pay any dividend on that series of
preferred stock or redeem or otherwise repurchase any shares of that series
until we have paid or set aside for payment the full amount of the accumulated
but unpaid dividends on the senior shares.

                                       24



         We will not declare, pay or set aside for payment any dividends on any
preferred stock ranking on a parity as to payment of dividends with the
preferred stock unless we declare, pay or set aside for payment dividends on all
the outstanding shares of preferred stock for all dividend payment periods
ending on or before the dividend payment date for that parity stock. We must
declare, pay or set aside for payment any amounts on the preferred stock ratably
in proportion to the respective amounts of dividends (1) accumulated and unpaid
or payable on that parity stock, on the one hand, and (2) accumulated and unpaid
or payable through the dividend payment period or periods of the preferred stock
preceding the dividend payment date for that parity stock, on the other hand.

         Except as described above, unless we have paid the full cumulative
dividends on the outstanding shares of preferred stock, we may not take any of
the following actions with respect to our common stock or any other preferred
stock of Wintrust ranking junior or on parity with the preferred stock as to
dividend payments:

         o        declare, pay or set aside for payment any dividends, other
                  than dividends payable in our common stock;

         o        make other distributions;

         o        redeem, purchase or otherwise acquire our common stock or
                  junior preferred stock for any consideration; or

         o        make any payment to or available for a sinking fund for the
                  redemption of our common stock or junior preferred stock.

         Redemption. The prospectus supplement will indicate whether, and on
what terms, shares of any series of preferred stock will be subject to mandatory
redemption or sinking fund provision. The prospectus supplement will also
indicate whether, and on what terms, including the date on or after which
redemption may occur, we may redeem shares of a series of the preferred stock.
We will effect any optional redemption upon not less than 30 days' notice at a
redemption price of not less than the stated value per share of the applicable
series of preferred stock plus accrued and accumulated but unpaid dividends to
but excluding the date fixed for redemption. If we have not paid full cumulative
dividends on all outstanding shares of preferred stock, we may not redeem the
preferred stock in part and we may not purchase or acquire any shares of
preferred stock, otherwise than by a purchase or exchange offer made on the same
terms to all holders of the preferred stock. If fewer than all the outstanding
shares of a series of preferred stock are to be redeemed, we will select those
to be redeemed by lot or a substantially equivalent method.

         Liquidation Rights. In the event of any liquidation, dissolution or
winding up of Wintrust, the holders of shares of preferred stock will be
entitled to receive, out of the assets of Wintrust available for distribution to
stockholders, liquidating distributions in an amount equal to the stated value
per share of preferred stock, as described in the applicable prospectus
supplement, plus accrued and accumulated but unpaid dividends to the date of
final distribution, before any distribution is made to holders of:

         o        any class or series of capital stock ranking junior to the
                  preferred stock as to rights upon liquidation, dissolution or
                  winding up; or

         o        our common stock.

However, holders of the shares of preferred stock will not be entitled to
receive the liquidation price of their shares until we have paid or set aside an
amount sufficient to pay in full the liquidation preference of any class or
series of our capital stock ranking senior as to rights upon liquidation,
dissolution or winding

                                       25



up. Neither a consolidation or merger of Wintrust with or into another
corporation nor a merger of another corporation with or into Wintrust nor a sale
or transfer of all or part of Wintrust's assets for cash or securities will be
considered a liquidation, dissolution or winding up of Wintrust.

         If, upon any liquidation, dissolution or winding up of Wintrust, assets
of Wintrust then distributable are insufficient to pay in full the amounts
payable with respect to the preferred stock and any other preferred stock
ranking on parity with the preferred stock as to rights upon liquidation,
dissolution or winding up, the holders of the preferred stock and of that other
preferred stock will share ratably in any distribution in proportion to the full
respective preferential amounts to which they are entitled. After we have paid
the full amount of the liquidating distribution to which they are entitled, the
holders of the preferred stock will not be entitled to any further participation
in any distribution of assets by Wintrust.

         Voting Rights. Unless otherwise determined by our board of directors
and indicated in the prospectus supplement, holders of the preferred stock will
not have any voting rights except as from time to time required by law.

         So long as any shares of the preferred stock remain outstanding, we
will not, without the consent of the holders of at least two thirds of the
shares of preferred stock outstanding at the time, voting together as one class
with all other series of preferred stock having similar voting rights that have
been conferred and are exercisable:

         o        issue or increase the authorized amount of any class or series
                  of stock ranking prior to the outstanding preferred stock as
                  to dividends or upon liquidation; or

         o        amend, alter or repeal the provisions of our certificate of
                  incorporation or of the resolutions contained in the
                  certificate of designation, whether by merger, consolidation
                  or otherwise, so as to materially and adversely affect any
                  power, preference or special right of the outstanding
                  preferred stock or its holders.

         Agents and Registrar for Preferred Stock. The transfer agent, dividend
disbursing agent and registrar for each series of preferred stock will be the
Illinois Stock Transfer Company.

DEPOSITARY SHARES

         We may, at our option, elect to offer fractional shares or some
multiple of shares of preferred stock, rather than individual shares of
preferred stock. If we choose to do so, we will issue depositary receipts for
depositary shares, each of which will represent a fraction or a multiple of a
share of a particular series of preferred stock as described below.

         The following statements concerning depositary shares, depositary
receipts, and the deposit agreement are not intended to be comprehensive and are
qualified in their entirety by reference to the forms of these documents, which
we have filed as exhibits to the registration statement. Each investor should
refer to the detailed provisions of those documents.

         The shares of any series of preferred stock represented by depositary
shares will be deposited under a deposit agreement among Wintrust, a bank or
trust company we select, with its principal executive office in the United
States and a combined capital and surplus of at least $50,000,000, as
depositary, which we refer to as the Preferred Stock Depositary, and the holders
from time to time of depositary receipts issued under the agreement. Subject to
the terms of the deposit agreement, each holder of a depositary share will be
entitled, in proportion to the fraction or multiple of a share of preferred
stock represented by that depositary share, to all the rights and preferences of
the preferred stock represented by that depositary share, including dividend,
voting and liquidation rights.

                                       26


         The depositary shares will be evidenced by depositary receipts issued
under the deposit agreement. Depositary receipts will be distributed to those
persons purchasing the fractional or multiple shares of the related series of
preferred stock. Immediately following the issuance of shares of a series of
preferred stock, we will deposit those shares with the Preferred Stock
Depositary, which will then issue and deliver the depositary receipts to the
purchasers. Depositary receipts will only be issued evidencing whole depositary
shares. A depositary receipt may evidence any number of whole depositary shares.

         Dividends and Other Distributions. The Preferred Stock Depositary will
distribute all cash dividends or other cash distributions received on the
related series of preferred stock to the record holders of depositary receipts
relating to those series in proportion to the number of the depositary shares
evidenced by depositary receipts those holders own.

         If we make a distribution other than in cash, the Preferred Stock
Depositary will distribute the property it receives to the record holders of
depositary receipts in proportion to the number of depositary shares evidenced
by depositary receipts those holders own, unless the Preferred Stock Depositary
determines that the distribution cannot be made proportionately among those
holders or that it is not feasible to make the distribution. In that event, the
Preferred Stock Depositary may, with our approval, sell the property and
distribute the net proceeds to the holders in proportion to the number of
depositary shares evidenced by depositary receipts they own.

         The amount distributed to holders of depositary shares will be reduced
by any amounts required to be withheld by Wintrust or the Preferred Stock
Depositary on account of taxes or other governmental charges.

         Conversion and Exchange. If any series of preferred stock underlying
the depositary shares is subject to conversion or exchange, the applicable
prospectus supplement will describe the rights or obligations of each record
holder of depositary receipts to convert or exchange the depositary shares.

         Withdrawal of Stock. Upon surrender of the depositary receipts at the
corporate trust office of the Preferred Stock Depositary and upon payment of the
taxes, charges and fees provided for in the deposit agreement and compliance
with any other requirement of the deposit agreement, the holder of the
depositary shares evidenced by those depositary receipts is entitled to delivery
of the number of whole shares of the related series of preferred stock and all
money or other property, if any, represented by those shares. Holders of
depositary receipts representing any number of whole shares of preferred stock
will be entitled to receive whole shares of the related series of preferred
stock, but those holders of whole shares of preferred stock will not thereafter
be entitled to deposit those shares of preferred stock with the Preferred Stock
Depositary or to receive depositary shares therefor. If the depositary receipts
delivered by the holder evidence a number of depositary shares in excess of the
number representing whole shares of the related series of preferred stock to be
withdrawn, the Preferred Stock Depositary will deliver to the holder at the same
time a new depositary receipt evidencing the excess number of depositary shares.

         Voting the Preferred Stock. Upon receiving notice of any meeting at
which the holders of any series of the preferred stock are entitled to vote, the
Preferred Stock Depositary will mail the information contained in the notice of
the meeting to the record holders of the depositary receipts relating to that
series of preferred stock. Each record holder of the depositary receipts on the
record date, which will be the same date as the record date for the related
series of preferred stock, may instruct the Preferred Stock Depositary how to
exercise his or her voting rights. The Preferred Stock Depositary will endeavor,
insofar as practicable, to vote or cause to be voted the maximum number of whole
shares of the preferred stock represented by those depositary shares in
accordance with those instructions received sufficiently in advance of the
meeting, and we will agree to take all reasonable action that may be deemed
necessary by the Preferred Stock Depositary in order to enable the Preferred
Stock Depositary to do so. The Preferred

                                       27



Stock Depositary will abstain from voting shares of the preferred stock for
which it does not receive specific instructions from the holder of the
depositary shares representing them.

         Redemption of Depositary Shares. Depositary shares will be redeemed
from any proceeds received by the Preferred Stock Depositary resulting from the
redemption, in whole or in part, of the series of the preferred stock
represented by those depositary shares. The redemption price per depositary
share will equal the applicable fraction or multiple of the redemption price per
share payable with respect to the series of the preferred stock. If we redeem
shares of a series of preferred stock held by the Preferred Stock Depositary,
the Preferred Stock Depositary will redeem as of the same redemption date the
number of depositary shares representing the shares of preferred stock that we
redeem. If less than all the depositary shares will be redeemed, the depositary
shares to be redeemed will be selected by lot or substantially equivalent method
determined by the Preferred Stock Depositary.

         After the date fixed for redemption, the depositary shares called for
redemption will no longer be deemed to be outstanding, and all rights of the
holders of the depositary shares will cease, except the right to receive the
monies payable and any other property to which the holders were entitled upon
the redemption upon surrender to the Preferred Stock Depositary of the
depositary receipts evidencing the depositary shares. Any funds deposited by us
with the Preferred Stock Depositary for any depositary shares that the holders
fail to redeem will be returned to us after a period of two years from the date
the funds are deposited.

         Amendment and Termination of the Deposit Agreement. We may amend the
form of depositary receipt evidencing the depositary shares and any provision of
the deposit agreement at any time and from time to time by agreement with the
Preferred Stock Depositary. However, any amendment that materially and adversely
alters the rights of the holders of depositary receipts will not be effective
unless it has been approved by the holders of at least a majority of the
depositary shares then outstanding, and no amendment may impair the right of any
holder of any depositary receipts, described above under "--Withdrawal of
Stock," to receive shares of the related series of preferred stock and any money
or other property represented by those depositary shares, except in order to
comply with mandatory provisions of applicable law. We may terminate the deposit
agreement at any time with at least 60 days' prior written notice to the
Preferred Stock Depositary. Within 30 days of the date of the notice, the
Preferred Stock Depositary will deliver or make available for delivery to
holders of depositary receipts, upon surrender of the depositary receipts
evidencing the depositary shares and upon payment of any applicable taxes or
governmental charges to be paid by the holders as described below, the number of
whole shares of the related series of preferred stock as are represented by the
depositary receipts. The deposit agreement will automatically terminate after
there has been a final distribution on the related series of preferred stock in
connection with any liquidation, dissolution or winding up of Wintrust and that
distribution has been made to the holders of depositary shares.

         Charges of Preferred Stock Depositary. We will pay all transfer and
other taxes and governmental charges arising solely from the existence of the
depositary arrangements. We will pay all charges of the Preferred Stock
Depositary in connection with the initial deposit of the related series of
preferred stock, the initial issuance of the depositary shares, all withdrawals
of shares of the related series of preferred stock by holders of depositary
shares and the registration of transfers of title to any depositary shares.
However, holders of depositary shares will pay other transfer and other taxes
and governmental charges and the other charges expressly provided in the deposit
agreement to be for their accounts.

         Corporate Trust Office of Preferred Stock Depositary. The Preferred
Stock Depositary's corporate trust office will be set forth in the applicable
prospectus supplement relating to a series of depositary shares. The Preferred
Stock Depositary will act as transfer agent and registrar for depositary

                                       28



receipts, and, if shares of a series of preferred stock are redeemable, the
Preferred Stock Depositary will act as redemption agent for the corresponding
depositary receipts.

         Resignation and Removal of Preferred Stock Depositary. The Preferred
Stock Depositary may resign at any time by delivering to us written notice of
its election to do so, and we may at any time remove the Preferred Stock
Depositary. Any resignation or removal will take effect upon the appointment of
a successor Preferred Stock Depositary. A successor must be appointed by us
within 60 days after delivery of the notice of resignation or removal and must
be a bank or trust company having its principal office in the United States and
a combined capital and surplus of at least $50,000,000.

         Reports to Holders. We will deliver all required reports and
communications to holders of the preferred stock to the Preferred Stock
Depositary, and it will forward those reports and communications to the holders
of depositary shares.

         Inspection by Holders. Upon request, the Preferred Stock Depositary
will provide for inspection to the holders of depositary shares the transfer
books of the depositary and the list of holders of receipts; provided that any
requesting holder certifies to the Preferred Stock Depositary that such
inspection is for a proper purpose reasonably related to such person's interest
as an owner of depositary shares evidenced by the receipts.

                                GLOBAL SECURITIES

         Registered Global Securities. Unless otherwise indicated in the
applicable prospectus supplement, we may issue the securities other than common
stock in the form of one or more fully registered global securities that will be
deposited with a depositary or its nominee identified in the applicable
prospectus supplement and registered in the name of that depositary or its
nominee. In those cases, one or more registered global securities will be issued
in a denomination or aggregate denominations equal to the portion of the
aggregate principal or face amount of the securities to be represented by
registered global securities. Unless and until it is exchanged in whole for
securities in definitive registered form, a registered global security may not
be transferred except as a whole by and among the depositary for the registered
global security, the nominees of the depositary or any successors of the
depositary or those nominees.

         If not described below, any specific terms of the depositary
arrangement with respect to any securities to be represented by a registered
global security will be described in the prospectus supplement relating to those
securities. We anticipate that the following provisions will apply to all
depositary arrangements.

         Ownership of beneficial interests in a registered global security will
be limited to persons, called participants, that have accounts with the
depositary or persons that may hold interests through participants. Upon the
issuance of a registered global security, the depositary will credit, on its
book-entry registration and transfer system, the participants' accounts with the
respective principal or face amounts of the securities beneficially owned by the
participants. Any dealers, underwriters or agents participating in the
distribution of the securities will designate the accounts to be credited.
Ownership of beneficial interests in a registered global security will be shown
on, and the transfer of ownership interests will be effected only through,
records maintained by the depositary, with respect to interests of participants,
and on the records of participants, with respect to interests of persons holding
through participants. The laws of some states may require that some purchasers
of securities take physical delivery of these securities in definitive form.
These laws may impair your ability to own, transfer or pledge beneficial
interests in registered global securities.

                                       29



         So long as the depositary, or its nominee, is the registered owner of a
registered global security, that depositary or its nominee, as the case may be,
will be considered the sole owner or holder of the securities represented by the
registered global security for all purposes under the applicable indenture,
warrant agreement or unit agreement. Except as described below, owners of
beneficial interests in a registered global security will not be entitled to
have the securities represented by the registered global security registered in
their names, will not receive or be entitled to receive physical delivery of the
securities in definitive form and will not be considered the owners or holders
of the securities under the applicable indenture, warrant agreement or unit
agreement. Accordingly, each person owning a beneficial interest in a registered
global security must rely on the procedures of the depositary for that
registered global security and, if that person is not a participant, on the
procedures of the participant through which the person owns its interest, to
exercise any rights of a holder under the applicable indenture, warrant
agreement or unit agreement. We understand that under existing industry
practices, if we request any action of holders or if an owner of a beneficial
interest in a registered global security desires to give or take any action that
a holder is entitled to give or take under the applicable indenture, warrant
agreement or unit agreement, the depositary for the registered global security
would authorize the participants holding the relevant beneficial interests to
give or take that action, and the participants would authorize beneficial owners
owning through them to give or take that action or would otherwise act upon the
instructions of beneficial owners holding through them.

         Payments of principal of, and premium, if any, and interest on, debt
securities, and any payments to holders with respect to warrants or units,
represented by a registered global security registered in the name of a
depositary or its nominee will be made to the depositary or its nominee, as the
case may be, as the registered owner of the registered global security. None of
Wintrust, the trustees, the warrant agents, the unit agents or any other agent
of Wintrust, agent of the trustees or agent of the warrant agents or unit agents
will have any responsibility or liability for any aspect of the records relating
to payments made on account of beneficial ownership interests in the registered
global security or for maintaining, supervising or reviewing any records
relating to those beneficial ownership interests.

         We expect that the depositary for any of the securities represented by
a registered global security, upon receipt of any payment of principal, premium,
interest or other distribution of underlying securities or other property to
holders on that registered global security, will immediately credit
participants' accounts in amounts proportionate to their respective beneficial
interests in that registered global security as shown on the records of the
depositary. We also expect that payments by participants to owners of beneficial
interests in a registered global security held through participants will be
governed by standing customer instructions and customary practices, as is now
the case with the securities held for the accounts of customers in bearer form
or registered in "street name," and will be the responsibility of those
participants.

         If the depositary for any of these securities represented by a
registered global security is at any time unwilling or unable to continue as
depositary or ceases to be a clearing agency registered under the Exchange Act,
and a successor depositary registered as a clearing agency under the Exchange
Act is not appointed by us within 90 days, we will issue securities in
definitive form in exchange for the registered global security that had been
held by the depositary. In addition, under the terms of the indenture, we may at
any time and in our sole discretion decide not to have any of the securities
represented by one or more registered global securities. We understand, however,
that, under current industry practices, the depositary would notify its
participants of our request, but will only withdraw beneficial interests from a
global security at the request of each participant. We would issue definitive
certificates in exchange for any such interests withdrawn. Any securities issued
in definitive form in exchange for a registered global security will be
registered in the name or names that the depositary gives to the applicable
trustee, warrant agent, unit agent or other relevant agent of ours or theirs. It
is expected that the depositary's instructions

                                       30


will be based upon directions received by the depositary from participants with
respect to ownership of beneficial interests in the registered global security
that had been held by the depositary.

FORM OF SECURITIES INCLUDED IN UNITS

         The form of the warrant included in a unit will correspond to the form
of the unit and of any other security included in that unit.

                            DESCRIPTION OF THE TRUST

         Wintrust Capital Trust VI is a Delaware statutory trust formed pursuant
to the Delaware Statutory Trust Act under a trust agreement executed by us, as
sponsor for the trust, and the trustees, and a certificate of trust has been
filed with the Delaware Secretary of State. The trust agreement will be amended
and restated in its entirety in the form filed as an exhibit to the registration
statement of which this prospectus is a part, as of the date the trust preferred
securities are initially issued. The trust agreement will be qualified under the
Trust Indenture Act of 1939.

         The following discussion contains a description of the material terms
of the trust agreement for the trust and is subject to, and is qualified in its
entirety by reference to, the amended and restated trust agreement.

         The holders of the trust preferred securities issued pursuant to an
offering described in this prospectus and subsequent prospectus supplements will
own all of the issued and outstanding trust preferred securities of the trust
which have certain prior rights over the other securities of the trust in
certain circumstances as specified in this prospectus. We will not initially own
any of the trust preferred securities. We will initially own, directly or
indirectly, all of the issued and outstanding common securities. The common
securities, together with the trust preferred securities, are called the trust
securities.

         The trust exists exclusively for the purposes of:

         o        issuing the trust preferred securities to the public for cash;

         o        issuing its common securities to us in exchange for our
                  capitalization of the trust;

         o        investing the proceeds from the sale of the trust securities
                  in an equivalent amount of debentures; and

         o        engaging in other activities that are incidental to those
                  listed above, such as receiving payments on the debentures and
                  making distributions to security holders, furnishing notices
                  and other administrative tasks.

         The trust will not have any independent business operations or any
assets, revenues or cash flows other than those related to the issuance and
administration of the trust securities.

         The rights of the holders of the trust securities are as set forth in
the trust agreement, the Delaware Statutory Trust Act and the Trust Indenture
Act. The trust agreement does not permit the trust to borrow money or make any
investment other than in the debentures. Other than with respect to payment of
distributions on and the liquidation amount of the trust securities, Wintrust
has agreed to pay for all debts and obligations and all costs and expenses of
the trust, including the fees and expenses of the trustees and any income taxes,
duties and other governmental charges, and all costs and expenses related

                                       31



to these charges, to which the trust may become subject, except for United
States withholding taxes that are properly withheld.

         The number of trustees of the trust will initially be five. Three of
the trustees will be persons who are employees or officers of or who are
affiliated with Wintrust. They are the administrative trustees. The fourth
trustee will be an entity that maintains its principal place of business in the
State of Delaware. It is the Delaware trustee. Initially, Wilmington Trust
Company, a Delaware banking corporation, will act as Delaware trustee. The fifth
trustee, called the property trustee, will also initially be Wilmington Trust
Company. The property trustee is the institutional trustee under the trust
agreement and acts as the indenture trustee called for under the applicable
provisions of the Trust Indenture Act. Also for purposes of compliance with the
Trust Indenture Act, Wilmington Trust Company will act as guarantee trustee and
indenture trustee under the guarantee agreement and the indenture. We, as holder
of all of the common securities, will have the right to appoint or remove any
trustee unless an event of default under the indenture has occurred and is
continuing, in which case only the holders of the trust preferred securities may
remove the Delaware trustee or the property trustee. The trust has a term of
approximately 31 years but may terminate earlier as provided in the trust
agreement.

         The property trustee will hold the debentures for the benefit of the
holders of the trust securities and will have the power to exercise all rights,
powers and privileges under the indenture as the holder of the debentures. In
addition, the property trustee will maintain exclusive control of a segregated
noninterest-bearing "payment account" established with Wilmington Trust Company
to hold all payments made on the debentures for the benefit of the holders of
the trust securities. The property trustee will make payments of distributions
and payments on liquidation, redemption and otherwise to the holders of the
trust securities out of funds from the payment account. The guarantee trustee
will hold the guarantee for the benefit of the holders of the trust preferred
securities. We will pay all fees and expenses related to the trust and the
offering of the trust preferred securities, including the fees and expenses of
the trustees.

                  DESCRIPTION OF THE TRUST PREFERRED SECURITIES

         The trust will issue only one series of trust preferred securities and
one series of common securities. The trust agreement for the trust will be
qualified as an indenture under the Trust Indenture Act of 1939. The trust
preferred securities will have terms and will be subject to conditions as set
forth in the trust agreement or made a part of the trust agreement by the Trust
Indenture Act. This summary of certain provisions of the trust preferred
securities and each trust agreement does not purport to be complete and is
subject to, and qualified in its entirety by reference to, all the provisions of
each trust agreement, including the definitions of certain terms, and those
provisions made part of each trust agreement by the Trust Indenture Act. A form
of the trust agreement to be used in connection with the issuance of the trust
preferred securities and a form of the trust preferred securities are filed as
exhibits to the registration statement that includes this prospectus. Wherever
particular defined terms of a trust agreement are referred to in this
prospectus, those defined terms are incorporated in this prospectus by
reference. A copy of the form of the trust agreement is available upon request
from the property trustee.

GENERAL

         The trust agreement authorizes the administrative trustees, on behalf
of the trust, to issue the trust securities, which are comprised of the trust
preferred securities to be sold to the public and the common securities. We will
own all of the common securities issued by the trust. The trust is not permitted
to issue any securities other than the trust securities or incur any other
indebtedness.

         The trust preferred securities will represent preferred undivided
beneficial interests in the assets of the trust, and the holders of the trust
preferred securities will be entitled to a preference over the

                                       32



common securities upon an event of default with respect to distributions and
amounts payable on redemption or liquidation. The trust preferred securities
will rank equally, and payments on the trust preferred securities will be made
proportionally, with the common securities, except as described under
"--Subordination of Common Securities."

         The property trustee will hold legal title to the debentures in trust
for the benefit of the holders of the trust securities. We will guarantee the
payment of distributions out of money held by the trust, and payments upon
redemption of the trust preferred securities or liquidation of the trust, to the
extent described under "Description of the Guarantee." The guarantee agreement
does not cover the payment of any distribution or the liquidation amount when
the trust does not have sufficient funds available to make these payments.

         The specific terms of the trust preferred securities offered by the
trust will be described in a prospectus supplement, including:

         o        the specific designation, liquidation amount, number to be
                  issued by the trust and purchase price;

         o        the currency or units based on or relating to currencies in
                  which distributions and other payments will or may be payable;

         o        the distribution rates (or the method by which the rates will
                  be determined), if any;

         o        the dates on which any distributions will be payable;

         o        any provisions relating to deferral of distribution payments;

         o        the places where distributions and other amounts payable on
                  the trust preferred securities will be payable;

         o        any repayment, redemption, prepayment or sinking fund
                  provisions;

         o        any conversion or exchange provisions;

         o        the voting rights, if any, of holders of the capital
                  securities;

         o        the terms and conditions, if any, upon which the assets of the
                  trust may be distributed to holders of the trust preferred
                  securities;

         o        any applicable United States federal income tax consequences;
                  and

         o        any other specific terms of the trust preferred securities.

         If indicated in the applicable prospectus supplement, the terms of the
trust agreement for, and capital securities offered by, the trust may differ
from the terms summarized in this prospectus.

DISTRIBUTIONS

         Source of Distributions. The funds of the trust available for
distribution to holders of the trust preferred securities will be limited to
payments made under the debentures, which the trust will purchase with the
proceeds from the sale of the trust securities. Distributions will be paid
through the property trustee, which will hold the amounts received from our
interest payments on the debentures in the payment account for the benefit of
the holders of the trust securities. If we do not make interest payments

                                       33



on the debentures, the property trustee will not have funds available to pay
distributions on the trust preferred securities.

         Distributions will accumulate from the date of issuance, will be
cumulative and will be computed on the basis of a 360-day year of twelve 30-day
months. If the distribution date is not a business day, then payment of the
distributions will be made on the next day that is a business day, without any
additional interest or other payment for the delay. However, if the next
business day is in the next calendar year, payment of the distribution will be
made on the business day immediately preceding the scheduled distribution date.

         Extension Period. As long as no event of default under the indenture
has occurred and is continuing, we have the right to defer the payment of
interest on the debentures at any time for a period not exceeding 20 consecutive
quarters. We refer to this period of deferral as an "extension period." No
extension period may extend beyond the maturity date or end on a date other than
an interest payment date, which dates are the same as the distribution dates. If
we defer the payment of interest, quarterly distributions on the trust preferred
securities will also be deferred during any such extension period. Any deferred
distributions under the trust preferred securities will accumulate additional
amounts at an annual rate compounded quarterly from the relevant distribution
date. The term "distributions" as used in this prospectus includes those
accumulated amounts.

         During an extension period, we may not:

         o        declare or pay any dividends or distributions on, or redeem,
                  purchase, acquire or make a liquidation payment with respect
                  to, any of our capital stock (other than stock dividends,
                  non-cash dividends in connection with the implementation of a
                  shareholder rights plan, purchases of common stock in
                  connection with employee benefit plans or in connection with
                  the reclassification of any class of our capital stock into
                  another class of capital stock);

         o        make any payment of principal, interest or premium on or
                  repay, repurchase or redeem any debt securities that rank
                  equally with (including the debentures issued to our other
                  affiliated Delaware trusts), or junior in interest to, the
                  debentures;

         o        make any guarantee payments with respect to any other
                  guarantee by us of any other debt securities of any of our
                  subsidiaries if the guarantee ranks equally with or junior to
                  the debentures (other than payments under the guarantee for
                  the trust preferred securities); or

         o        redeem, purchase or acquire less than all of the debentures or
                  any of the trust preferred securities.

         After the termination of any extension period and the payment of all
amounts due, we may elect to begin a new extension period, subject to the above
requirements.

         We do not currently intend to exercise our right to defer distributions
on the trust preferred securities by deferring the payment of interest on the
debentures.

REDEMPTION OR EXCHANGE

         General. Subject to the prior approval of the Federal Reserve, if
required, we will have the right to redeem the debentures:

         o        in whole at any time, or in part from time to time, on or
                  after the date set forth in the applicable prospectus
                  supplement;

                                       34



         o        at any time, in whole, within 180 days following the
                  occurrence of a Tax Event, an Investment Company Event or a
                  Capital Treatment Event, which terms we define below; or

         o        at any time, and from time to time, to the extent of any trust
                  preferred securities we purchase, plus a proportionate amount
                  of the common securities we hold.

         Mandatory Redemption. Upon our repayment or redemption, in whole or in
part, of any debentures, whether on the date set forth in the applicable
prospectus supplement or earlier, the property trustee will apply the proceeds
to redeem the same amount of the trust securities, upon not less than 30 days'
nor more than 60 days' notice, at the redemption price. The redemption price
will equal 100% of the aggregate liquidation amount of the trust securities plus
accumulated but unpaid distributions to the date of redemption. If less than all
of the debentures are to be repaid or redeemed on a date of redemption, then the
proceeds from such repayment or redemption will be allocated to redemption of
trust preferred securities and common securities proportionately.

         Distribution of Debentures in Exchange for Trust Preferred Securities.
Upon prior approval of the Federal Reserve, if required by law or regulation, we
will have the right at any time to dissolve, wind-up or terminate the trust and,
after satisfaction of the liabilities of creditors of the trust as provided by
applicable law, including, without limitation, amounts due and owing the
trustees of the trust, cause the debentures to be distributed directly to the
holders of trust securities in liquidation of the trust. See "--Liquidation
Distribution Upon Termination."

         After the liquidation date fixed for any distribution of debentures in
exchange for trust preferred securities:

         o        those trust securities will no longer be deemed to be
                  outstanding;

         o        certificates representing debentures in a principal amount
                  equal to the liquidation amount of those trust preferred
                  securities will be issued in exchange for the trust preferred
                  securities;

         o        we will use our best efforts to list the debentures on the
                  Nasdaq National Market or similar national exchange or
                  automated quotation system;

         o        any certificates representing trust securities that are not
                  surrendered for exchange will be deemed to represent
                  debentures with a principal amount equal to the liquidation
                  amount of those trust preferred securities, accruing interest
                  at the rate provided for in the debentures from the last
                  distribution date on the trust preferred securities; and

         o        all rights of the trust securityholders other than the right
                  to receive debentures upon surrender of a certificate
                  representing trust securities will terminate.

         We cannot assure you that the market prices for the trust preferred
securities or the debentures that may be distributed if a dissolution and
liquidation of the trust were to occur would be favorable. The trust preferred
securities that an investor may purchase, or the debentures that an investor may
receive on dissolution and liquidation of the trust, may trade at a discount to
the price that the investor paid to purchase the trust preferred securities.

         Redemption upon a Tax Event, Investment Company Event or Capital
Treatment Event. If a Tax Event, an Investment Company Event or a Capital
Treatment Event occurs, we will have the right to redeem the debentures in
whole, but not in part, and thereby cause a mandatory redemption of all of the
trust securities at the redemption price described above. If one of these events
occurs and we do not elect to redeem the debentures, or to dissolve the trust
and cause the debentures to be distributed to holders of

                                       35



the trust securities, then the trust preferred securities will remain
outstanding and additional interest may be payable on the debentures.

         "Tax Event" means the receipt by the trust and us of an opinion of
counsel experienced in such matters stating that, as a result of any change or
prospective change in the laws or regulations of the United States or any
political subdivision or taxing authority of the United States, or as a result
of any official administrative pronouncement or judicial decision interpreting
or applying the tax laws or regulations, there is more than an insubstantial
risk that:

         o        interest payable by us on the debentures is not, or within 90
                  days of the date of the opinion will not be, deductible by us,
                  in whole or in part, for federal income tax purposes;

         o        the trust is, or will be within 90 days after the date of the
                  opinion, subject to federal income tax with respect to income
                  received or accrued on the debentures; or

         o        the trust is, or will be within 90 days after the date of
                  opinion, subject to more than an immaterial amount of other
                  taxes, duties, assessments or other governmental charges.

         "Investment Company Event" means the receipt by the trust and us of an
opinion of counsel experienced in such matters to the effect that the trust is
or will be considered an "investment company" that is required to be registered
under the Investment Company Act, as a result of a change in law or regulation
or a change in interpretation or application of law or regulation.

         "Capital Treatment Event" means the receipt by the trust and us of an
opinion of counsel experienced in such matters to the effect that there is more
than an insubstantial risk of impairment of our ability to treat the trust
preferred securities as Tier 1 capital for purposes of the current capital
adequacy guidelines of the Federal Reserve, as a result of any amendment to any
laws or any regulations.

         For all of the events described above, we or the trust must request and
receive an opinion with regard to the event within a reasonable period of time
after we become aware of the possible occurrence of an event of this kind.

         Redemption of Debentures in Exchange for Trust Preferred Securities We
Purchase. Upon prior approval of the Federal Reserve, if required by law or
regulation, we will also have the right at any time, and from time to time, to
redeem debentures in exchange for any trust preferred securities we may have
purchased in the market. If we elect to surrender any trust preferred securities
beneficially owned by us in exchange for redemption of a like amount of
debentures, we will also surrender a proportionate amount of common securities
in exchange for debentures. Trust preferred securities owned by other holders
will not be called for redemption at any time when we elect to exchange trust
securities we own for debentures.

         The common securities we surrender will be in the same proportion to
the trust preferred securities we surrender as is the ratio of common securities
purchased by us to the trust preferred securities issued by the trust. In
exchange for the trust securities surrendered by us, the property trustee will
cause to be released to us for cancellation debentures with a principal amount
equal to the liquidation amount of the trust securities, plus any accumulated
but unpaid distributions, if any, then held by the property trustee allocable to
those trust securities. After the date of redemption involving an exchange by
us, the trust securities we surrender will no longer be deemed outstanding and
the debentures redeemed in exchange will be cancelled.

                                       36



REDEMPTION PROCEDURES

         Trust preferred securities will be redeemed at the redemption price
with the applicable proceeds from our contemporaneous redemption of the
debentures. Redemptions of the trust preferred securities will be made, and the
redemption price will be payable, on each redemption date only to the extent
that the trust has funds available for the payment of the redemption price.

         Notice of any redemption will be mailed at least 30 days but not more
than 60 days before the date of redemption to each holder of trust securities to
be redeemed at its registered address. Unless we default in payment of the
redemption price on the debentures, interest will cease to accumulate on the
debentures called for redemption on and after the date of redemption.

         If the trust gives notice of redemption of its trust securities, then
the property trustee, to the extent funds are available, will irrevocably
deposit with the depositary for the trust securities funds sufficient to pay the
aggregate redemption price and will give the depositary for the trust securities
irrevocable instructions and authority to pay the redemption price to the
holders of the trust securities. If the trust preferred securities are no longer
in book-entry only form, the property trustee, to the extent funds are
available, will deposit with the designated paying agent for such trust
preferred securities funds sufficient to pay the aggregate redemption price and
will give the paying agent irrevocable instructions and authority to pay the
redemption price to the holders upon surrender of their certificates evidencing
the trust preferred securities. Notwithstanding the foregoing, distributions
payable on or prior to the date of redemption for any trust securities called
for redemption will be payable to the holders of the trust securities on the
relevant record dates for the related distribution dates.

         If notice of redemption has been given and we have deposited funds as
required, then on the date of the deposit all rights of the holders of the trust
securities called for redemption will cease, except the right to receive the
redemption price, but without interest on such redemption price after the date
of redemption. The trust securities will also cease to be outstanding on the
date of the deposit. If any date fixed for redemption of trust securities is not
a business day, then payment of the redemption price payable on that date will
be made on the next day that is a business day without any additional interest
or other payment in respect of the delay. However, if the next business day is
in the next succeeding calendar year, payment of the interest will be made on
the immediately preceding business day.

         If payment of the redemption price in respect of trust securities
called for redemption is improperly withheld or refused and not paid by the
trust, or by us pursuant to the guarantee, distributions on the trust securities
will continue to accumulate at the applicable rate from the date of redemption
originally established by the trust for the trust securities to the date the
redemption price is actually paid. In this case, the actual payment date will be
considered the date fixed for redemption for purposes of calculating the
redemption price.

         Payment of the redemption price on the trust preferred securities and
any distribution of debentures to holders of trust preferred securities will be
made to the applicable recordholders as they appear on the register for the
trust preferred securities on the relevant record date. As long as the trust
preferred securities are represented by a global security, the record date will
be the business day immediately preceding the date of redemption or liquidation
date, as applicable.

         If less than all of the trust securities are to be redeemed, then the
aggregate liquidation amount of the trust securities to be redeemed will be
allocated proportionately to those trust securities based upon the relative
liquidation amounts. The particular trust preferred securities to be redeemed
will be selected by the property trustee from the outstanding trust preferred
securities not previously called for redemption by a method the property trustee
deems fair and appropriate. The property trustee will promptly notify the
registrar for the trust preferred securities in writing of the trust preferred
securities selected for

                                       37



redemption and, in the case of any trust preferred securities selected for
partial redemption, the liquidation amount to be redeemed. If the redemption
relates to trust preferred securities purchased by us and being exchanged for a
like amount of debentures, then the trust preferred securities we own will be
the ones selected for redemption.

         Subject to applicable law, and if we are not exercising our right to
defer interest payments on the debentures, we may, at any time, purchase
outstanding trust preferred securities.

SUBORDINATION OF COMMON SECURITIES

         Payment of distributions on, and the redemption price of, the trust
preferred securities and common securities will be made based on the liquidation
amount of these securities. However, if an event of default under the indenture
has occurred and is continuing, no distributions on or redemption of the common
securities may be made unless payment in full in cash of all accumulated and
unpaid distributions on all of the outstanding trust preferred securities for
all distribution periods terminating on or before that time, or in the case of
payment of the redemption price, payment of the full amount of the redemption
price on all of the outstanding trust preferred securities then called for
redemption, has been made or provided for. All funds available to the property
trustee will first be applied to the payment in full in cash of all
distributions on, or the redemption price of, the trust preferred securities
then due and payable.

         In the case of the occurrence and continuance of any event of default
under the trust agreement resulting from an event of default under the
indenture, we, as holder of the common securities, will be deemed to have waived
any right to act with respect to that event of default under the trust agreement
until the effect of the event of default has been cured, waived or otherwise
eliminated. Until the event of default under the trust agreement has been so
cured, waived or otherwise eliminated, the property trustee will act solely on
behalf of the holders of the trust preferred securities and not on our behalf,
and only the holders of the trust preferred securities will have the right to
direct the property trustee to act on their behalf.

LIQUIDATION DISTRIBUTION UPON TERMINATION

         We will have the right at any time to dissolve, wind-up or terminate
the trust and cause debentures to be distributed to the holders of the trust
preferred securities. This right is subject, however, to us receiving approval
of the Federal Reserve, if required by law or regulation.

         In addition, the trust will automatically terminate upon expiration of
its term and will terminate earlier on the first to occur of:

         o        our bankruptcy, dissolution or liquidation;

         o        the distribution of a like amount of the debentures to the
                  holders of trust securities, if we have given written
                  direction to the property trustee to terminate the trust;

         o        redemption of all of the trust preferred securities as
                  described under "--Redemption or Exchange--Mandatory
                  Redemption"; or

         o        the entry of a court order for the dissolution of the trust.

         With the exception of a redemption as described under "--Redemption or
Exchange--Mandatory Redemption," if an early termination of the trust occurs,
the trust will be liquidated by the administrative trustees as expeditiously as
they determine to be possible. After satisfaction of liabilities to creditors of

                                       38



the trust as provided by applicable law, the trustees will distribute to the
holders of trust securities, debentures:

         o        in an aggregate stated principal amount equal to the aggregate
                  stated liquidation amount of the trust securities;

         o        with an interest rate identical to the distribution rate on
                  the trust securities; and

         o        with accrued and unpaid interest equal to accumulated and
                  unpaid distributions on the trust securities.

         However, if the property trustee determines that the distribution is
not practical, then the holders of trust securities will be entitled to receive,
instead of debentures, a proportionate amount of the liquidation distribution.
The liquidation distribution will be the amount equal to the aggregate of the
liquidation amount plus accumulated and unpaid distributions to the date of
payment. If the liquidation distribution can be paid only in part because the
trust has insufficient assets available to pay in full the aggregate liquidation
distribution, then the amounts payable directly by the trust on the trust
securities will be paid on a proportional basis, based on liquidation amounts,
to us, as the holder of the common securities, and to the holders of the trust
preferred securities. However, if an event of default under the indenture has
occurred and is continuing, the trust preferred securities will have a priority
over the common securities. See "--Subordination of Common Securities."

         Under current United States federal income tax law and interpretations
and assuming that the trust is treated as a grantor trust, as is expected, a
distribution of the debentures should not be a taxable event to holders of the
trust preferred securities. Should there be a change in law, a change in legal
interpretation, a Tax Event or another circumstance, however, the distribution
could be a taxable event to holders of the trust preferred securities. The
applicable prospectus supplement will contain a detailed description of these
tax consequences.

         If we do not elect to redeem the debentures prior to maturity or to
liquidate the trust and distribute the debentures to holders of the trust
preferred securities, the trust preferred securities will remain outstanding
until the repayment of the debentures. If we elect to dissolve the trust and
thus cause the debentures to be distributed to holders of the trust securities
in liquidation of the trust, we will continue to have the right to shorten the
maturity of the debentures.

EVENTS OF DEFAULT; NOTICE

         Any one of the following events constitutes an event of default under
the trust agreement with respect to the trust preferred securities:

         o        the occurrence of an event of default under the indenture;

         o        a default by the trust in the payment of any distribution when
                  it becomes due and payable, and continuation of the default
                  for a period of 30 days;

         o        a default by the trust in the payment of any redemption price
                  of any of the trust securities when it becomes due and
                  payable;

         o        a default in the performance, or breach, in any material
                  respect, of any covenant or warranty of the trustees in the
                  trust agreement, other than those defaults covered in the
                  previous two points, and continuation of the default or breach
                  for a period of 60 days after there has been given, by
                  registered or certified mail, to the trustee(s) by the holders
                  of at least 25% in

                                       39



                  aggregate liquidation amount of the outstanding trust
                  preferred securities, a written notice specifying the default
                  or breach and requiring it to be remedied and stating that the
                  notice is a "Notice of Default" under the trust agreement; or

         o        the occurrence of events of bankruptcy or insolvency with
                  respect to the property trustee and our failure to appoint a
                  successor property trustee within 60 days.

         Within five business days after the occurrence of any event of default
actually known to the property trustee, the property trustee will transmit
notice of the event of default to the holders of the trust preferred securities,
the administrative trustees and to us, unless the event of default has been
cured or waived. Wintrust and the administrative trustees are required to file
annually with the property trustee a certificate as to whether or not they are
in compliance with all the conditions and covenants applicable to them under the
trust agreement.

         If an event of default under the indenture has occurred and is
continuing, the trust preferred securities will have preference over the common
securities upon termination of the trust. The existence of an event of default
under the trust agreement does not entitle the holders of trust preferred
securities to accelerate the maturity thereof, unless the event of default is
caused by the occurrence of an event of default under the indenture and both the
indenture trustee and holders of at least 25% in principal amount of the
debentures fail to accelerate the maturity thereof.

REMOVAL OF THE TRUSTEES

         Unless an event of default under the indenture has occurred and is
continuing, we may remove any trustee at any time. If an event of default under
the indenture has occurred and is continuing, only the holders of a majority in
liquidation amount of the outstanding trust preferred securities may remove the
property trustee or the Delaware trustee. The holders of the trust preferred
securities have no right to vote to appoint, remove or replace the
administrative trustees. These rights are vested exclusively with us as the
holder of the common securities. No resignation or removal of a trustee and no
appointment of a successor trustee will be effective until the successor trustee
accepts the appointment in accordance with the trust agreement.

CO-TRUSTEES AND SEPARATE PROPERTY TRUSTEE

         Unless an event of default under the indenture has occurred and is
continuing, for the purpose of meeting the legal requirements of the Trust
Indenture Act or of any jurisdiction in which any part of the trust property may
at the time be located, we will have the power to appoint at any time or times,
and upon written request of the property trustee will appoint, one or more
persons or entities either (1) to act as a co-trustee, jointly with the property
trustee, of all or any part of the trust property, or (2) to act as separate
trustee of any trust property. In either case these trustees will have the
powers that may be provided in the instrument of appointment, and will have
vested in them any property, title, right or power deemed necessary or
desirable, subject to the provisions of the trust agreement. In case an event of
default under the indenture has occurred and is continuing, the property trustee
alone will have power to make the appointment.

MERGER OR CONSOLIDATION OF TRUSTEES

         Generally, any person or successor to any of the trustees may be a
successor trustee to any of the trustees, including a successor resulting from a
merger or consolidation. However, any successor trustee must meet all of the
qualifications and eligibility standards to act as a trustee.

                                       40



MERGERS, CONSOLIDATIONS, AMALGAMATIONS OR REPLACEMENTS OF THE TRUST

         The trust may not merge with or into, convert into, consolidate,
amalgamate, or be replaced by, or convey, transfer or lease its properties and
assets substantially as an entirety to any corporation or other person, except
as described below. For these purposes, if we consolidate or merge with another
entity, or transfer or sell substantially all of our assets to another entity,
in some cases that transaction may be considered to involve a replacement of the
trust, and the conditions set forth below would apply to such transaction. The
trust may, at our request, with the consent of the administrative trustees and
without the consent of the holders of the trust preferred securities, the
property trustee or the Delaware trustee, undertake a transaction listed above
if the following conditions are met:

         o        the successor entity either (a) expressly assumes all of the
                  obligations of the trust with respect to the trust preferred
                  securities, or (b) substitutes for the trust preferred
                  securities other securities having substantially the same
                  terms as the trust preferred securities (referred to as
                  "successor securities") so long as the successor securities
                  rank the same in priority as the trust preferred securities
                  with respect to distributions and payments upon liquidation,
                  redemption and otherwise;

         o        we appoint a trustee of the successor entity possessing
                  substantially the same powers and duties as the property
                  trustee in its capacity as the holder of the debentures;

         o        the successor securities are listed or traded or will be
                  listed or traded on any national securities exchange or other
                  organization on which the trust preferred securities are then
                  listed, if any;

         o        the merger, consolidation, amalgamation, replacement,
                  conveyance, transfer or lease does not adversely affect the
                  rights, preferences and privileges of the holders of the trust
                  preferred securities (including any successor securities) in
                  any material respect;

         o        the successor entity has a purpose substantially identical to
                  that of the trust;

         o        prior to the merger, conversion, consolidation, amalgamation,
                  replacement, conveyance, transfer or lease, we have received
                  an opinion from independent counsel that (a) any transaction
                  of this kind does not adversely affect the rights, preferences
                  and privileges of the holders of the trust preferred
                  securities (including any successor securities) in any
                  material respect, and (b) following the transaction, neither
                  the trust nor the successor entity will be required to
                  register as an "investment company" under the Investment
                  Company Act; and

         o        we own all of the common securities of the successor entity
                  and guarantee the obligations of the successor entity under
                  the successor securities at least to the extent provided by
                  the guarantee, the debentures, the trust agreement and the
                  expense agreement.

Notwithstanding the foregoing, the trust may not, except with the consent of
every holder of the trust preferred securities, enter into any transaction of
this kind if the transaction would cause the trust or the successor entity not
to be classified as a grantor trust for federal income tax purposes.

VOTING RIGHTS; AMENDMENT OF TRUST AGREEMENT

         Except as described below and under "Description of the
Guarantee--Amendments" and as otherwise required by the Trust Indenture Act and
the trust agreement, the holders of the trust preferred securities will have no
voting rights.


                                       41



         The trust agreement may be amended from time to time by us and the
trustees, without the consent of the holders of the trust preferred securities,
in the following circumstances:

         o        with respect to acceptance of appointment by a successor
                  trustee;

         o        to cure any ambiguity, correct or supplement any provisions in
                  the trust agreement that may be inconsistent with any other
                  provision, or to make any other provisions with respect to
                  matters or questions arising under the trust agreement, as
                  long as the amendment is not inconsistent with the other
                  provisions of the trust agreement and does not have a material
                  adverse effect on the interests of any holder of trust
                  securities; or

         o        to modify, eliminate or add to any provisions of the trust
                  agreement if necessary to ensure that the trust will be
                  classified for federal income tax purposes as a grantor trust
                  at all times that any trust securities are outstanding or to
                  ensure that the trust will not be required to register as an
                  "investment company" under the Investment Company Act.

         With the consent of the holders of a majority of the aggregate
liquidation amount of the outstanding trust securities, we and the trustees may
amend the trust agreement if the trustees receive an opinion of counsel to the
effect that the amendment or the exercise of any power granted to the trustees
in accordance with the amendment will not affect the trust's status as a grantor
trust for federal income tax purposes or the trust's exemption from status as an
"investment company" under the Investment Company Act. However, without the
consent of each holder of trust securities, the trust agreement may not be
amended to (a) change the amount or timing of any distribution on the trust
securities or otherwise adversely affect the amount of any distribution required
to be made in respect of the trust securities as of a specified date, or (b)
restrict the right of a holder of trust securities to institute suit for the
enforcement of the payment on or after that date.

         As long as the property trustee holds any debentures, the trustees will
not, without obtaining the prior approval of the holders of a majority in
aggregate liquidation amount of all outstanding trust preferred securities:

         o        direct the time, method and place of conducting any proceeding
                  for any remedy available to the indenture trustee, or
                  executing any trust or power conferred on the property trustee
                  with respect to the debentures;

         o        waive any past default that is waivable under the indenture;

         o        exercise any right to rescind or annul a declaration that the
                  principal of all the debentures will be due and payable; or

         o        consent to any amendment or termination of the indenture or
                  the debentures, where the property trustee's consent is
                  required. However, where a consent under the indenture
                  requires the consent of each holder of the affected
                  debentures, no consent will be given by the property trustee
                  without the prior consent of each holder of the trust
                  preferred securities.

The trustees may not revoke any action previously authorized or approved by a
vote of the holders of the trust preferred securities except by subsequent vote
of the holders of the trust preferred securities. The property trustee will
notify each holder of trust preferred securities of any notice of default with
respect to the debentures. In addition to obtaining the foregoing approvals of
the holders of the trust preferred securities, prior to taking any of the
foregoing actions, the trustees must obtain an opinion of counsel experienced in
these matters to the effect that the trust will not be classified as an
association taxable as a corporation for federal income tax purposes on account
of the action.

                                       42



         Any required approval of holders of trust securities may be given at a
meeting or by written consent. The property trustee will cause a notice of any
meeting at which holders of the trust securities are entitled to vote, or of any
matter upon which action by written consent of the holders is to be taken, to be
given to each holder of record of trust securities.

         No vote or consent of the holders of trust preferred securities will be
required for the trust to redeem and cancel its trust preferred securities in
accordance with the trust agreement.

         Notwithstanding the fact that holders of trust preferred securities are
entitled to vote or consent under any of the circumstances described above, any
of the trust preferred securities that are owned by Wintrust, the trustees or
any affiliate of Wintrust or any trustee, will, for purposes of the vote or
consent, be treated as if they were not outstanding.

PAYMENT AND PAYING AGENCY

         Payments in respect of the trust preferred securities will be made to
The Depository Trust Company, or DTC, which will credit the relevant accounts of
participants on the applicable distribution dates, or, if any of the trust
preferred securities are not held by DTC, the payments will be made by check
mailed to the address of the holder as listed on the register of holders of the
trust preferred securities. The paying agent for the trust preferred securities
will initially be the property trustee and any co-paying agent chosen by the
property trustee and acceptable to us and the administrative trustees. The
paying agent for the trust preferred securities may resign as paying agent upon
30 days' written notice to the administrative trustees, the property trustee and
us. If the property trustee no longer is the paying agent for the trust
preferred securities, the administrative trustees will appoint a successor to
act as paying agent. The successor must be a bank or trust company acceptable to
us and the property trustee.

REGISTRAR AND TRANSFER AGENT

         The property trustee will act as the registrar and the transfer agent
for the trust preferred securities. Registration of transfers of trust preferred
securities will be effected without charge by or on behalf of the trust, but
upon payment of any tax or other governmental charges that may be imposed in
connection with any transfer or exchange. The trust and its registrar and
transfer agent will not be required to register or cause to be registered the
transfer of trust preferred securities after they have been called for
redemption.

INFORMATION CONCERNING THE PROPERTY TRUSTEE

         The property trustee undertakes to perform only the duties set forth in
the trust agreement. After the occurrence of an event of default that is
continuing, the property trustee must exercise the same degree of care and skill
as a prudent person exercises or uses in the conduct of its own affairs. The
property trustee is under no obligation to exercise any of the powers vested in
it by the trust agreement at the request of any holder of trust preferred
securities unless it is offered reasonable indemnity against the costs, expenses
and liabilities that might be incurred. If no event of default under the trust
agreement has occurred and is continuing and the property trustee is required to
decide between alternative causes of action, construe ambiguous or inconsistent
provisions in the trust agreement or is unsure of the application of any
provision of the trust agreement, and the matter is not one on which holders of
trust preferred securities are entitled to vote upon, then the property trustee
will take the action directed in writing by us. If the property trustee is not
so directed, then it will take the action it deems advisable and in the best
interests of the holders of the trust securities and will have no liability
except for its own bad faith, negligence or willful misconduct.


                                       43



MISCELLANEOUS

         The administrative trustees are authorized and directed to conduct the
affairs of and to operate the trust in such a way that:

         o        the trust will not be deemed to be an "investment company"
                  required to be registered under the Investment Company Act;

         o        the trust will not be classified as an association taxable as
                  a corporation for federal income tax purposes; and

         o        the debentures will be treated as indebtedness of Wintrust for
                  federal income tax purposes.

In this regard, we and the administrative trustees are authorized to take any
action not inconsistent with applicable law, the certificate of trust or the
trust agreement, that we and the administrative trustees determine to be
necessary or desirable for these purposes.

         We are required to use our best efforts to maintain the listing of the
trust preferred securities on the Nasdaq National Market or a similar national
securities exchange or automated quotation system, but this requirement will not
prevent us from redeeming all or a portion of the trust preferred securities in
accordance with the trust agreement.

         Holders of the trust preferred securities have no preemptive or similar
rights. The trust agreement and the trust securities will be governed by
Delaware law.

                DESCRIPTION OF THE JUNIOR SUBORDINATED DEBENTURES

         Concurrently with the issuance of the trust preferred securities, the
trust will invest the proceeds from the sale of the trust preferred securities
in the debentures issued by us. The debentures will be issued as unsecured debt
under the indenture between us and an indenture trustee. The indenture will be
qualified under the Trust Indenture Act. When used in this section, indenture
refers only to the indenture for the junior subordinated debentures of Wintrust,
and not the indenture for the debt securities of Wintrust.

         The following discussion contains a description of the material
provisions of the indenture and is subject to, and is qualified in its entirety
by reference to, the indenture and to the Trust Indenture Act. We urge
prospective investors to read the form of the indenture, which is filed as an
exhibit to the registration statement of which this prospectus forms a part. If
indicated in the prospectus supplement, the terms of any series may differ from
the terms summarized below.

GENERAL

         The debentures will be unsecured and will rank junior to all of our
senior and subordinated debt, including indebtedness we may incur in the future.
Because we are a holding company, our right to participate in any distribution
of assets of any of our subsidiaries, upon any subsidiary's liquidation or
reorganization or otherwise, and thus the ability of holders of the debentures
to benefit indirectly from any distribution by a subsidiary, is subject to the
prior claim of creditors of the subsidiary, except to the extent that we may be
recognized as a creditor of the subsidiary. The debentures will, therefore, be
effectively subordinated to all existing and future liabilities of our
subsidiaries, and holders of debentures should look only to our assets for
payment. Except as otherwise provided in the applicable prospectus

                                       44



supplement, the indenture does not limit our ability to incur or issue secured
or unsecured senior and junior debt. See "--Subordination" and
"--Miscellaneous."

         The indenture does not contain provisions that afford holders of the
debentures protection in the event of a highly leveraged transaction or other
similar transaction involving us, nor does it require us to maintain or achieve
any financial performance levels or to obtain or maintain any credit rating on
the debentures.

         The applicable prospectus supplement will contain, where applicable,
the following terms of and other information relating to any offered junior
subordinated debentures:

         o        the title of the junior subordinated debentures;

         o        any limit upon the aggregate principal amount of the junior
                  subordinated debentures;

         o        the date or dates on which the principal of the junior
                  subordinated debentures is payable or the method of
                  determination thereof, including the right, if any, of
                  Wintrust to shorten or extend the stated maturity date in
                  certain circumstances;

         o        the rate or rates, if any, at which the junior subordinated
                  debentures will bear interest, the dates on which that
                  interest will be payable, our right, if any, to defer or
                  extend an interest payment date and the record dates for any
                  interest payable on any interest payment date or the method by
                  which any of the foregoing will be determined;

         o        the place or places where the principal of and premium, if
                  any, and interest on the junior subordinated debentures will
                  be payable and where, subject to the terms of the indenture as
                  described below under "--Registration and Transfer of Junior
                  Subordinated Debentures," the junior subordinated debentures
                  may be presented for registration of transfer or exchange and
                  the place or places where notices and demands to or upon us in
                  respect of the junior subordinated debentures and the
                  indenture may be made;

         o        any period or periods within which, or date or dates on which,
                  the price or prices at which and the terms and conditions upon
                  which junior subordinated debentures may be redeemed, in whole
                  or in part, at our option or at the option of a holder of
                  junior subordinated debentures;

         o        our obligation, if any, to redeem, purchase or repay the
                  junior subordinated debentures and the period or periods
                  within which, the price or prices at which, and the other
                  terms and conditions upon which the junior subordinated
                  debentures will be redeemed, repaid or purchased, in whole or
                  in part, pursuant to that obligation;

         o        the denominations in which any junior subordinated debentures
                  will be issuable;

         o        if other than in U.S. dollars, in which the principal of (and
                  premium, if any) and interest, if any, on the junior
                  subordinated debentures will be payable, or in which the
                  junior subordinated debentures will be denominated;

         o        any additions, modifications or deletions in the events of
                  default under the indenture or covenants of Wintrust specified
                  in the indenture with respect to the junior subordinated
                  debentures;

                                       45



         o        if other than the principal amount, the portion of the
                  principal amount of junior subordinated debentures that will
                  be payable upon declaration of acceleration of maturity;

         o        any index or indices used to determine the amount of payments
                  of principal of and premium, if any, and interest on the
                  junior subordinated debentures and the manner in which those
                  amounts will be determined;

         o        whether the junior subordinated debentures will be issuable in
                  registered form or bearer form or both and, if bearer
                  securities are issuable, any restrictions applicable to the
                  exchange of one form for another and to the offer, sale and
                  delivery of the bearer securities;

         o        any additions or changes to the indenture with respect to a
                  series of junior subordinated debentures as will be necessary
                  to permit or facilitate the issuance of that series in bearer
                  form, registrable or not registrable as to principal, and with
                  or without interest coupons;

         o        the appointment of any trustees, depositaries, authenticating
                  or paying agents, transfer agents or registrars or other
                  agents;

         o        whether the junior subordinated debentures will be convertible
                  or exchangeable for other securities or property and, if so,
                  the terms of any conversion or exchange and the terms of the
                  other securities; and

         o        any other terms of the junior subordinated debentures not
                  inconsistent with the provisions of the indenture.

REGISTRATION AND TRANSFER OF JUNIOR SUBORDINATED DEBENTURES

         Holders may present junior subordinated debentures for exchange, and
holders of registered junior subordinated debentures may present these
securities for transfer, in the manner, at the places and subject to the
restrictions stated in the junior subordinated debentures and described in the
applicable prospectus supplement. We will provide these services without charge
except for any tax or other governmental charge payable in connection with these
services and subject to any limitations provided in the indenture.

         Holders may transfer junior subordinated debentures in bearer form and
the related coupons, if any, by delivery to the transferee. If any of the
securities are held in global form, the procedures for transfer of interests in
those securities will depend upon the procedures of the depositary for those
global securities.

SUBORDINATION

         The debentures are subordinated and junior in right of payment to all
of our senior and subordinated debt, as defined in the applicable prospectus
supplement. Upon any payment or distribution of assets to creditors upon any
liquidation, dissolution, winding up or reorganization of Wintrust, whether
voluntary or involuntary in bankruptcy, insolvency, receivership or other
proceedings in connection with any insolvency or bankruptcy proceedings, the
holders of our senior and subordinated debt will first be entitled to receive
payment in full of principal and interest before the holders of debentures will
be entitled to receive or retain any payment in respect of the debentures.

         If the maturity of any debentures is accelerated, the holders of all of
our senior and subordinated debt outstanding at the time of the acceleration
will also be entitled to first receive payment in full of all

                                       46



amounts due to them, including any amounts due upon acceleration, before the
holders of the debentures will be entitled to receive or retain any principal or
interest payments on the debentures.

         No payments of principal or interest on the debentures may be made if
there has occurred and is continuing a default in any payment with respect to
any of our senior or subordinated debt or an event of default with respect to
any of our senior or subordinated debt resulting in the acceleration of the
maturity of the senior or subordinated debt, or if any judicial proceeding is
pending with respect to any default.

PAYMENT AND PAYING AGENT

         Generally, payment of principal of and interest on the debentures will
be made at the office of the indenture trustee. However, we have the option to
make payment of any interest by (a) check mailed to the address of the person
entitled to payment at the address listed in the register of holders of the
debentures, or (b) wire transfer to an account maintained by the person entitled
thereto as specified in the register of holders of the debentures, provided that
proper transfer instructions have been received by the applicable record date.
Payment of any interest on debentures will be made to the person in whose name
the debenture is registered at the close of business on the regular record date
for the interest payment, except in the case of defaulted interest.

         Any moneys deposited with the indenture trustee or any paying agent for
the debentures, or then held by us in trust, for the payment of the principal of
or interest on the debentures and remaining unclaimed for two years after the
principal or interest has become due and payable, will be repaid to us on
September 30 of each year. If we hold any of this money in trust, then it will
be discharged from the trust to us and the holder of the debenture will
thereafter look, as a general unsecured creditor, only to us for payment.

REGISTRAR AND TRANSFER AGENT

         The indenture trustee will act as the registrar and the transfer agent
for the debentures. Debentures may be presented for registration of transfer,
with the form of transfer endorsed thereon, or a satisfactory written instrument
of transfer, duly executed, at the office of the registrar. Provided that we
maintain a transfer agent in Wilmington, Delaware, we may rescind the
designation of any transfer agent or approve a change in the location through
which any transfer agent acts. We may at any time designate additional transfer
agents with respect to the debentures.

         If we redeem any of the debentures, neither we nor the indenture
trustee will be required to (a) issue, register the transfer of or exchange any
debentures during a period beginning at the opening of business 15 days before
the day of the mailing of and ending at the close of business on the day of the
mailing of the relevant notice of redemption, or (b) transfer or exchange any
debentures so selected for redemption, except, in the case of any debentures
being redeemed in part, any portion not to be redeemed.

MODIFICATION OF INDENTURE

         We and the indenture trustee may, from time to time without the consent
of the holders of the debentures, amend, waive our rights under or supplement
the indenture for purposes which do not materially adversely affect the rights
of the holders of the debentures. Other changes may be made by us and the
indenture trustee with the consent of the holders of a majority in principal
amount of the outstanding debentures. However, without the consent of the holder
of each outstanding debenture affected by the proposed modification, no
modification may:

         o        extend the maturity date of the debentures;

                                       47



         o        reduce the principal amount or the rate or extend the time of
                  payment of interest; or

         o        reduce the percentage of principal amount of debentures
                  required to amend the indenture.

As long as any of the trust preferred securities remain outstanding, no
modification of the indenture may be made that requires the consent of the
holders of the debentures, no termination of the indenture may occur, and no
waiver of any event of default under the indenture may be effective, without the
prior consent of the holders of a majority of the aggregate liquidation amount
of the trust preferred securities.

DEBENTURE EVENTS OF DEFAULT

         The indenture provides that any one or more of the following events
with respect to the debentures that has occurred and is continuing constitutes
an event of default under the indenture:

         o        our failure to pay any interest on the debentures for 30 days
                  after the due date, except where we have properly deferred the
                  interest payment;

         o        our failure to pay any principal on the debentures when due
                  whether at maturity, upon redemption or otherwise;

         o        our failure to observe or perform in any material respect any
                  other covenants or agreements contained in the indenture for
                  90 days after written notice to us from the indenture trustee
                  or the holders of at least 25% in aggregate outstanding
                  principal amount of the debentures; or

         o        our bankruptcy, insolvency or reorganization or dissolution of
                  the trust other than in connection with a distribution of the
                  debentures in connection with such dissolution, redemption of
                  the trust securities or certain transactions permitted under
                  the trust agreement.

         The holders of a majority of the aggregate outstanding principal amount
of the debentures have the right to direct the time, method and place of
conducting any proceeding for any remedy available to the indenture trustee. The
indenture trustee, or the holders of at least 25% in aggregate outstanding
principal amount of the debentures, may declare the principal due and payable
immediately upon an event of default under the indenture. The holders of a
majority of the outstanding principal amount of the debentures may rescind and
annul the declaration if the default has been cured and a sum sufficient to pay
all matured installments of interest and principal due otherwise than by
acceleration has been deposited with the indenture trustee and any and all
events of default have been remedied or waived by the holders of a majority of
the outstanding principal amount of the debentures. The holders may not annul
the declaration and waive a default if the default is the non-payment of the
principal of the debentures which has become due solely by the acceleration.

         So long as the property trustee is the holder of the debentures, an
event of default under the indenture has occurred and is continuing, the
property trustee will have the right to declare the principal of and the
interest on the debentures, and any other amounts payable under the indenture,
to be immediately due and payable and to enforce its other rights as a creditor
with respect to the debentures.

         We are required to file annually with the indenture trustee a
certificate as to whether or not we are in compliance with all of the conditions
and covenants applicable to us under the indenture.

ENFORCEMENT OF CERTAIN RIGHTS BY HOLDERS OF THE TRUST PREFERRED SECURITIES

         If an event of default under the indenture has occurred and is
continuing and the event is attributable to the failure by us to pay interest on
or principal of the debentures on the date on which the

                                       48



payment is due and payable, then a holder of trust preferred securities may
institute a direct action against us to compel us to make the payment. We may
not amend the indenture to remove the foregoing right to bring a direct action
without the prior written consent of all of the holders of the trust preferred
securities. If the right to bring a direct action is removed, the trust may
become subject to the reporting obligations under the Securities Exchange Act of
1934.

         The holders of the trust preferred securities will not be able to
exercise directly any remedies, other than those set forth in the preceding
paragraph, available to the holders of the debentures unless there has been an
event of default under the trust agreement.

CONSOLIDATION, MERGER, SALE OF ASSETS AND OTHER TRANSACTIONS

         We may not consolidate with or merge into any other entity or convey or
transfer our properties and assets substantially as an entirety to any entity,
and no entity may be consolidated with or merged into us or sell, convey,
transfer or otherwise dispose of its properties and assets substantially as an
entirety to us, unless:

         o        if we consolidate with or merge into another person or convey
                  or transfer our properties and assets substantially as an
                  entirety to any person, the successor person is organized
                  under the laws of the United States or any state or the
                  District of Columbia, and the successor person expressly
                  assumes by supplemental indenture our obligations on the
                  debentures, and the ultimate parent entity of the successor
                  entity expressly assumes our obligations under the guarantee,
                  to the extent the trust preferred securities are then
                  outstanding;

         o        immediately after the transaction, no event of default under
                  the indenture, and no event which, after notice or lapse of
                  time, or both, would become an event of default under the
                  indenture, has occurred and is continuing; and

         o        other conditions as prescribed in the indenture are met.

         Under certain circumstances, if we consolidate or merge with another
entity, or transfer or sell substantially all of our assets to another entity,
such transaction may be considered to involve a replacement of the trust, and
the provisions of the trust agreement relating to a replacement of the trust
would apply to such transaction. See "Description of the Trust Preferred
Securities-- Mergers, Consolidations, Amalgamations or Replacements of the
Trust" on page 41.

SATISFACTION AND DISCHARGE

         The indenture will cease to be of further effect and we will be deemed
to have satisfied and discharged our obligations under the indenture when all
debentures not previously delivered to the indenture trustee for cancellation:

         o        have become due and payable; and

         o        will become due and payable at their stated maturity within
                  one year or are to be called for redemption within one year,
                  and we deposit or cause to be deposited with the indenture
                  trustee funds, in trust, for the purpose and in an amount
                  sufficient to pay and discharge the entire indebtedness on the
                  debentures not previously delivered to the indenture trustee
                  for cancellation, for the principal and interest due to the
                  date of the deposit or to the stated maturity or redemption
                  date, as the case may be.

                                       49



         We may still be required to provide officers' certificates, opinions of
counsel and pay fees and expenses due after these events occur.

GOVERNING LAW

         Unless otherwise specified in a prospectus supplement, the indenture
and the debentures will be governed by and construed in accordance with Illinois
law.

INFORMATION CONCERNING THE INDENTURE TRUSTEE

         The indenture trustee is subject to all the duties and responsibilities
specified with respect to an indenture trustee under the Trust Indenture Act.
Subject to these provisions, the indenture trustee is under no obligation to
exercise any of the powers vested in it by the indenture at the request of any
holder of debentures, unless offered reasonable security or indemnity by the
holder against the costs, expenses and liabilities which might be incurred. The
indenture trustee is not required to expend or risk its own funds or otherwise
incur personal financial liability in the performance of its duties if the
indenture trustee reasonably believes that repayment or adequate indemnity is
not reasonably assured to it.

MISCELLANEOUS

         We have agreed, pursuant to the indenture, for so long as trust
preferred securities remain outstanding:

         o        to maintain directly or indirectly 100% ownership of the
                  common securities of the trust, except that certain successors
                  that are permitted pursuant to the indenture may succeed to
                  our ownership of the common securities;

         o        not to voluntarily terminate, wind up or liquidate the trust
                  without prior approval of the Federal Reserve, if required by
                  law or regulation;

         o        to use our reasonable efforts to cause the trust (a) to remain
                  a Delaware statutory trust (and to avoid involuntary
                  termination, winding up or liquidation), except in connection
                  with a distribution of debentures, the redemption of all of
                  the trust securities of the trust or mergers, consolidations
                  or amalgamations, each as permitted by the trust agreement;
                  and (b) to otherwise continue not to be treated as an
                  association taxable as a corporation or partnership for
                  federal income tax purposes; and

         o        to use our reasonable efforts to cause each holder of trust
                  securities to be treated as owning an individual beneficial
                  interest in the debentures.

                          DESCRIPTION OF THE GUARANTEE

         The trust preferred securities guarantee agreement will be executed and
delivered by us concurrently with the issuance of the trust preferred securities
for the benefit of the holders of the trust preferred securities. The guarantee
agreement will be qualified as an indenture under the Trust Indenture Act. The
guarantee trustee will act as trustee for purposes of complying with the
provisions of the Trust Indenture Act, and will also hold each guarantee for the
benefit of the holders of the trust preferred securities. The following
discussion contains a description of the material provisions of the guarantee
and is qualified in its entirety by reference to the guarantee agreement and the
Trust Indenture Act. Prospective investors are urged to read the form of the
guarantee agreement, which has been filed as an exhibit to the registration
statement of which this prospectus forms a part. Specific terms of a guarantee

                                       50



will be described in the prospectus supplement relating to the applicable trust
preferred securities. If indicated in the applicable prospectus supplement, the
terms of a particular guarantee may differ from the terms discussed below.

GENERAL

         We agree to pay in full on a subordinated basis, to the extent
described in the guarantee agreement, the guarantee payments (as defined below)
to the holders of the trust preferred securities as and when due, regardless of
any defense, right of set-off or counterclaim that the trust may have or assert
other than the defense of payment.

         The following payments with respect to the trust preferred securities
are called the "guarantee payments" and, to the extent not paid or made by the
trust and to the extent that the trust has funds available for those
distributions, will be subject to the guarantee:

         o        any accumulated and unpaid distributions required to be paid
                  on the trust preferred securities;

         o        with respect to any trust preferred securities called for
                  redemption, the redemption price; and

         o        upon a voluntary or involuntary dissolution, winding up or
                  termination of the trust (other than in connection with the
                  distribution of debentures to the holders of trust preferred
                  securities in exchange for trust preferred securities), the
                  lesser of:

                  (a)      the amount of the liquidation distribution; and

                  (b)      the amount of assets of the trust remaining available
                           for distribution to holders of trust preferred
                           securities in liquidation of the trust.

         We may satisfy our obligations to make a guarantee payment by making a
direct payment of the required amounts to the holders of the trust preferred
securities or by causing the trust to pay the amounts to the holders.

         The guarantee agreement is a guarantee, on a subordinated basis, of the
guarantee payments, but the guarantee only applies to the extent the trust has
funds available for those distributions. If we do not make interest payments on
the debentures purchased by the trust, the trust will not have funds available
to make the distributions and will not pay distributions on the trust preferred
securities.

STATUS OF THE GUARANTEE

         The guarantee constitutes our unsecured obligation that ranks
subordinate and junior in right of payment to all of our senior and subordinated
debt in the same manner as the debentures. We expect to incur additional
indebtedness in the future, although we have no specific plans in this regard
presently, and neither of the indenture nor the trust agreement limits the
amounts of the obligations that we may incur.

         The guarantee constitutes a guarantee of payment and not of collection.
If we fail to make guarantee payments when required, holders of trust preferred
securities may institute a legal proceeding directly against us to enforce their
rights under the guarantee without first instituting a legal proceeding against
any other person or entity.

         The guarantee will not be discharged except by payment of the guarantee
payments in full to the extent not paid by the trust or upon distribution of the
debentures to the holders of the trust preferred securities. Because we are a
bank holding company, our right to participate in any distribution of assets

                                       51



of any subsidiary upon the subsidiary's liquidation or reorganization or
otherwise is subject to the prior claims of creditors of that subsidiary, except
to the extent we may be recognized as a creditor of that subsidiary. Our
obligations under the guarantee, therefore, will be effectively subordinated to
all existing and future liabilities of our subsidiaries, and claimants should
look only to our assets for payments under the guarantee.

AMENDMENTS

         Except with respect to any changes that do not materially adversely
affect the rights of holders of the trust preferred securities, in which case no
vote will be required, the guarantee may not be amended without the prior
approval of the holders of a majority of the aggregate liquidation amount of the
outstanding trust preferred securities.

EVENTS OF DEFAULT; REMEDIES

         An event of default under the guarantee agreement will occur upon our
failure to make any required guarantee payments or to perform any other
obligations under the guarantee. If the guarantee trustee has actual knowledge
that an event of default has occurred and is continuing, the guarantee trustee
must enforce the guarantee for the benefit of the holders of the trust preferred
securities. The holders of a majority in aggregate liquidation amount of the
trust preferred securities will have the right to direct the time, method and
place of conducting any proceeding for any remedy available to the guarantee
trustee in respect of the guarantee and may direct the exercise of any power
conferred upon the guarantee trustee under the guarantee agreement.

         Any holder of trust preferred securities may institute and prosecute a
legal proceeding directly against us to enforce its rights under the guarantee
without first instituting a legal proceeding against the trust, the guarantee
trustee or any other person or entity.

         We are required to provide to the guarantee trustee annually a
certificate as to whether or not we are in compliance with all of the conditions
and covenants applicable to us under the guarantee agreement.

TERMINATION OF THE GUARANTEE

         The guarantee will terminate and be of no further force and effect
upon:

         o        full payment of the redemption price of the trust preferred
                  securities;

         o        full payment of the amounts payable upon liquidation of the
                  trust; or

         o        distribution of the debentures to the holders of the trust
                  preferred securities.

         If at any time any holder of the trust preferred securities must
restore payment of any sums paid under the trust preferred securities or the
guarantee, the guarantee will continue to be effective or will be reinstated
with respect to such amounts.

INFORMATION CONCERNING THE GUARANTEE TRUSTEE

         The guarantee trustee, other than during the occurrence and continuance
of our default in performance of the guarantee, undertakes to perform only those
duties as are specifically set forth in the guarantee. When an event of default
has occurred and is continuing, the guarantee trustee must exercise the same
degree of care and skill as a prudent person would exercise or use in the
conduct of his or her own affairs. Subject to those provisions, the guarantee
trustee is under no obligation to exercise any of

                                       52



the powers vested in it by the guarantee at the request of any holder of any
trust preferred securities, unless it is offered reasonable security and
indemnity against the costs, expenses and liabilities that might be incurred
thereby; but this does not relieve the guarantee trustee of its obligation to
exercise the rights and powers under the guarantee in the event of a default.

EXPENSE AGREEMENT

         We will, pursuant to the separate Agreement as to Expenses and
Liabilities entered into by us and the trust under the trust agreement,
irrevocably and unconditionally guarantee to each person or entity to whom the
trust becomes indebted or liable, the full payment of any costs, expenses or
liabilities of the trust, other than obligations of the trust to pay to the
holders of the trust preferred securities or other similar interests in the
trust of the amounts due to the holders pursuant to the terms of the trust
preferred securities or other similar interests, as the case may be. Third party
creditors of the trust may proceed directly against us under the expense
agreement, regardless of whether they had notice of the expense agreement.

GOVERNING LAW

         Unless otherwise specified in a prospectus supplement, the guarantee
will be governed by Illinois law.

             RELATIONSHIP AMONG THE TRUST PREFERRED SECURITIES, THE
                          DEBENTURES AND THE GUARANTEE

FULL AND UNCONDITIONAL GUARANTEE

         We will irrevocably guarantee, as and to the extent described in this
prospectus, payments of distributions and other amounts due on the trust
preferred securities, to the extent the trust has funds available for the
payment of these amounts. We and the trust believe that, taken together, our
obligations under the debentures, the indenture, the trust agreement, the
expense agreement and the guarantee agreement will provide, in the aggregate, a
full, irrevocable and unconditional guarantee, on a subordinated basis, of
payment of distributions and other amounts due on the trust preferred
securities. No single document standing alone or operating in conjunction with
fewer than all of the other documents constitutes a guarantee. It is only the
combined operation of these documents that has the effect of providing a full,
irrevocable and unconditional guarantee of the obligations of the trust under
the trust preferred securities.

         If and to the extent that we do not make payments on the debentures,
the trust will not pay distributions or other amounts due on the trust preferred
securities. The guarantee does not cover payment of distributions when the trust
does not have sufficient funds to pay the distributions. In this event, the
remedy of a holder of trust preferred securities is to institute a legal
proceeding directly against us for enforcement of payment of the distributions
to the holder. Our obligations under the guarantee are subordinated and junior
in right of payment to all of our other indebtedness.

SUFFICIENCY OF PAYMENTS

         As long as payments of interest and other payments are made when due on
the debentures, these payments will be sufficient to cover distributions and
other payments due on the trust preferred securities, primarily because:

                                       53



         o        the aggregate principal amount of the debentures will be equal
                  to the sum of the aggregate stated liquidation amount of the
                  trust securities;

         o        the interest rate and interest and other payment dates on the
                  debentures will match the distribution rate and distribution
                  and other payment dates for the trust preferred securities;

         o        we will pay for any and all costs, expenses and liabilities of
                  the trust, except the obligations of the trust to pay to
                  holders of the trust preferred securities the amounts due to
                  the holders pursuant to the terms of the trust preferred
                  securities; and

         o        the trust will not engage in any activity that is not
                  consistent with the limited purposes of the trust.

ENFORCEMENT RIGHTS OF HOLDERS OF TRUST PREFERRED SECURITIES

         A holder of any preferred security may institute a legal proceeding
directly against us to enforce its rights under the guarantee without first
instituting a legal proceeding against the guarantee trustee, the trust or any
other person. A default or event of default under any of our senior or
subordinated debt would not constitute a default or event of default under the
trust agreement. In the event, however, of payment defaults under, or
acceleration of, our senior or subordinated debt, the subordination provisions
of the indenture provides that no payments may be made in respect of the
debentures, until the obligations have been paid in full or any payment default
has been cured or waived. Failure to make required payments on the debentures
would constitute an event of default under the trust agreement.

LIMITED PURPOSE OF THE TRUST

         The trust preferred securities evidence preferred undivided beneficial
interests in the assets of the trust. The trust exists for the exclusive
purposes of issuing the trust securities, investing the proceeds thereof in
debentures, and engaging in only those other activities necessary, advisable or
incidental thereto. A principal difference between the rights of a holder of a
preferred security and the rights of a holder of a debenture is that a holder of
a debenture is entitled to receive from us the principal amount of, and interest
accrued on, debentures held, while a holder of trust preferred securities is
entitled to receive distributions from the trust (or from us under the
guarantee) if and to the extent the trust has funds available for the payment of
the distributions.

RIGHTS UPON TERMINATION

         Upon any voluntary or involuntary termination, winding-up or
liquidation of the trust involving the liquidation of the debentures, the
holders of the trust preferred securities will be entitled to receive, out of
assets held by the trust, the liquidation distribution in cash. See "Description
of the Trust Preferred Securities-- Liquidation Distribution Upon Termination"
on page 38.

         Upon our voluntary or involuntary liquidation or bankruptcy, the
property trustee, as holder of the debentures, would be a subordinated creditor
of ours. Therefore, the property trustee would be subordinated in right of
payment to all of our senior and subordinated debt, but is entitled to receive
payment in full of principal and interest before any of our shareholders receive
payments or distributions. Since we are the guarantor under the guarantee and
have agreed to pay for all costs, expenses and liabilities of the trust other
than the obligations of the trust to pay to holders of the trust preferred
securities the amounts due to the holders pursuant to the terms of the trust
preferred securities, the positions of a holder of the trust preferred
securities and a holder of the debentures relative to our other creditors and to
our shareholders in the event of liquidation or bankruptcy are expected to be
substantially the same.

                                       54



                               BOOK-ENTRY ISSUANCE

GENERAL

         The Depository Trust Company ("DTC") will act as securities depositary
for each of the trust preferred securities and may act as securities depositary
for all of the debentures in the event of the distribution of the debentures to
the holders of trust preferred securities. Except as described below, the trust
preferred securities will be issued only as registered securities in the name of
Cede & Co. (DTC's partnership nominee) or such other name as may be requested by
DTC. One or more global trust preferred securities will be issued for the trust
preferred securities and will be deposited with DTC.

         DTC, the world's largest depository, is a limited-purpose trust company
organized under the New York Banking Law, a "banking organization" within the
meaning of the New York Banking Law, a member of the Federal Reserve System, a
"clearing corporation" within the meaning of the New York Uniform Commercial
Code, and a "clearing agency" registered pursuant to Section 17A of the
Securities Exchange Act of 1934. DTC holds securities that its participants
deposit with DTC. DTC also facilitates the settlement among participants of
securities transactions, such as transfers and pledges, in deposited securities
through electronic computerized book-entry changes in participants' accounts,
thereby eliminating the need for physical movement of securities certificates.
Direct participants include securities brokers and dealers, banks, trust
companies, clearing corporations and certain other organizations. DTC is a
wholly-owned subsidiary of the Depository Trust & Clearing Corporation ("DTCC").
DTCC, in turn, is owned by a number of its direct participants and members of
the National Securities Clearing Corporation, Government Securities Clearing
Corporation, MBS Clearing Corporation and Emerging Markets Clearing Corporation,
as well as by the New York Stock Exchange, the American Stock Exchange and the
National Association of Securities Dealers, Inc. Access to the DTC system is
also available to indirect participants, such as securities brokers and dealers,
banks and trust companies that clear through or maintain custodial relationships
with direct participants, either directly or indirectly. The rules applicable to
DTC and its participants are on file with the SEC.

         Purchases of trust preferred securities under the DTC system must be
made by or through direct participants, which will receive a credit for the
trust preferred securities on DTC's records. The ownership interest of each
actual purchaser of each preferred security ("beneficial owner") is in turn to
be recorded on the direct and indirect participants' records. Beneficial owners
will not receive written confirmation from DTC of their purchases, but
beneficial owners are expected to receive written confirmations providing
details of the transactions, as well as periodic statements of their holdings,
from the direct or indirect participants through which the beneficial owners
purchased trust preferred securities. Transfers of ownership interests in the
trust preferred securities are to be accomplished by entries made on the books
of participants acting on behalf of beneficial owners. Beneficial owners will
not receive certificates representing their ownership interest in trust
preferred securities except if use of the book-entry-only system for the trust
preferred securities is discontinued.

         The deposit of trust preferred securities with DTC and their
registration in the name of Cede & Co. or such other nominee will not effect any
change in beneficial ownership. DTC will have no knowledge of the actual
beneficial owners of the trust preferred securities; DTC's records reflect only
the identity of the direct participants to whose accounts the trust preferred
securities are credited, which may or may not be the beneficial owners. The
participants will remain responsible for keeping account of their holdings on
behalf of their customers.

         The information in this section concerning DTC and DTC's book-entry
system has been obtained from sources that we believe to be reliable, but we and
the trust assume no responsibility for the accuracy thereof. Neither we nor the
trust have any responsibility for the performance by DTC or its participants

                                       55



of their respective obligations as described in this prospectus or under the
rules and procedures governing their respective operations.

NOTICES AND VOTING

         Conveyance of notices and other communications by DTC to direct
participants, by direct participants to indirect participants, and by direct and
indirect participants to beneficial owners will be governed by arrangements
among them, subject to any statutory or regulatory requirements as may be in
effect from time to time.

         Redemption notices will be sent to Cede & Co. as the registered holder
of the trust preferred securities. If less than all of the trust preferred
securities are being redeemed, the amount to be redeemed will be determined in
accordance with the trust agreement.

         Although voting with respect to the trust preferred securities is
limited to the holders of record of the trust preferred securities, in those
instances in which a vote is required, neither DTC nor Cede & Co. will itself
consent or vote with respect to trust preferred securities. Under its usual
procedures, DTC would mail an omnibus proxy to the property trustee as soon as
possible after the record date. The omnibus proxy assigns Cede & Co.'s
consenting or voting rights to those direct participants to whose accounts the
trust preferred securities are credited on the record date.

DISTRIBUTION OF FUNDS

         The property trustee will make distribution payments on the trust
preferred securities to DTC. DTC's practice is to credit direct participants'
accounts on the relevant payment date in accordance with their respective
holdings shown on DTC's records unless DTC has reason to believe that it will
not receive payments on the payment date. Payments by participants to beneficial
owners will be governed by standing instructions and customary practices and
will be the responsibility of the participant and not of DTC, the property
trustee, the trust or us, subject to any statutory or regulatory requirements as
may be in effect from time to time. Payment of distributions to DTC is the
responsibility of the property trustee, disbursement of the payments to direct
participants is the responsibility of DTC, and disbursements of the payments to
the beneficial owners is the responsibility of direct and indirect participants.

SUCCESSOR DEPOSITARIES AND TERMINATION OF BOOK-ENTRY SYSTEM

         DTC may discontinue providing its services with respect to any of the
trust preferred securities at any time by giving reasonable notice to the
property trustee or us. If no successor securities depositary is obtained,
definitive certificates representing the trust preferred securities are required
to be printed and delivered. We also have the option to discontinue use of the
system of book-entry transfers through DTC (or a successor depositary). After an
event of default under the indenture, the holders of a majority in liquidation
amount of trust preferred securities may determine to discontinue the system of
book-entry transfers through DTC. In these events, definitive certificates for
the trust preferred securities will be printed and delivered.

                              PLAN OF DISTRIBUTION

         We may sell the securities being offered hereby in one or more of the
following ways from time to time:

         o        through agents to the public or to investors;

                                       56



         o        to underwriters for resale to the public or to investors;

         o        directly to investors; or

         o        through a combination of any of these methods of sale.

         We will set forth in a prospectus supplement the terms of that
particular offering of securities, including:

         o        the name or names of any agents or underwriters;

         o        the purchase price of the securities being offered and the
                  proceeds we will receive from the sale;

         o        any over-allotment options under which underwriters may
                  purchase additional securities from us;

         o        any agency fees or underwriting discounts and other items
                  constituting agents' or underwriters' compensation;

         o        any initial public offering price;

         o        any discounts or concessions allowed or reallowed or paid to
                  dealers; and

         o        any securities exchanges or markets on which such securities
                  may be listed.

AGENTS

         If the applicable prospectus supplement indicates, we will authorize
dealers or our agents to solicit offers by various institutions to purchase
offered securities from us pursuant to contracts that provide for payment and
delivery on a future date. We must approve all institutions, but they may
include, among others:

         o        commercial and savings banks;

         o        insurance companies;

         o        pension funds;

         o        investment companies; and

         o        educational and charitable institutions.

         The institutional purchaser's obligations under a contract will be
subject only to the condition that the purchase of the offered securities at the
time of delivery is allowed by any laws applicable to the purchaser. The dealers
and our agents will not be responsible for the validity or performance of the
contracts.

UNDERWRITERS

         If we use underwriters for a sale of securities, the underwriters will
acquire the securities for their own account. The underwriters may resell the
securities in one or more transactions, including negotiated transactions, at a
fixed public offering price or at varying prices determined at the time of sale.
The

                                       57



underwriters may sell the securities directly or through underwriting syndicates
by managing underwriters. We may designate agents who agree to use their
reasonable efforts to solicit purchases of our securities for the period of
their appointment or to sell our securities on a continuing basis. The
obligations of the underwriters to purchase the securities will be subject to
the conditions set forth in the applicable underwriting agreement. The
underwriters will be obligated to purchase all the securities of the series
offered if they purchase any of the securities of that series. We may change
from time to time any initial public offering price and any discounts or
concessions the underwriters allow or reallow or pay to dealers. We may use
underwriters with whom we have a material relationship. We will describe the
nature of any such relationship in any prospectus supplement naming any such
underwriter.

DIRECT SALES

         We may also sell securities directly to one or more purchasers without
using underwriters or agents. Underwriters, dealers and agents that participate
in the distribution of the securities may be underwriters as defined in the
Securities Act, and any discounts or commissions they receive from us and any
profit on their resale of the securities may be treated as underwriting
discounts and commissions under the Securities Act. We will identify in the
applicable prospectus supplement any underwriters, dealers or agents and will
describe their compensation. We may have agreements with the underwriters,
dealers and agents to indemnify them against various civil liabilities,
including liabilities under the Securities Act, or to contribute payments that
the agents, underwriters, dealers and remarketing firms may be required to make
as a result of those civil liabilities. Underwriters, dealers and agents and
their affiliates may be customers of, engage in transactions with, or perform
services for us or our subsidiary companies in the ordinary course of their
businesses. In connection with the distribution of the securities, we may enter
into swap or other hedging transactions with, or arranged by, underwriters or
agents or their affiliates. These underwriters or agents or their affiliates may
receive compensation, trading gain or other benefits from these transactions.

TRADING MARKETS AND LISTING OF SECURITIES

         Unless otherwise specified in the applicable prospectus supplement,
each class or series of securities will be a new issue with no established
trading market, other than our common stock, which is listed on The Nasdaq
National Market. We may elect to list any other class or series of securities on
any additional exchange or market, but we are not obligated to do so unless
stated otherwise in a prospectus supplement. It is possible that one or more
underwriters may make a market in a class or series of securities, but the
underwriters will not be obligated to do so and may discontinue any market
making at any time without notice. We cannot give any assurance as to the
liquidity of the trading market for any of the securities.

STABILIZATION ACTIVITIES

         Any underwriter may engage in overallotment, stabilizing transactions,
short covering transactions and penalty bids in accordance with Regulation M
under the Exchange Act. Overallotment involves sales in excess of the offering
size, which create a short position. Stabilizing transactions permit bids to
purchase the underlying security so long as the stabilizing bids do not exceed a
specified maximum. Short covering transactions involve purchases of the
securities in the open market after the distribution is completed to cover short
positions. Penalty bids permit the underwriters to reclaim a selling concession
from a dealer when the securities originally sold by the dealer are purchased in
a covering transaction to cover short positions. Those activities may cause the
price of the securities to be higher than it would otherwise be. If commenced,
the underwriters may discontinue any of these activities at any time.

                                       58



PASSIVE MARKET MARKING

         Any underwriters who are qualified market markers on The Nasdaq
National Market may engage in passive market making transactions in the
securities on The Nasdaq National Market in accordance with Rule 103 of
Regulation M, during the business day prior to the pricing of the offering,
before the commencement of offers or sales of the securities. Passive market
makers must comply with applicable volume and price limitations and must be
identified as passive market makers. In general, a passive market maker must
display its bid at a price not in excess of the highest independent bid for such
security. If all independent bids are lowered below the passive market maker's
bid, however, the passive market maker's bid must then be lowered when certain
purchase limits are exceeded.

GENERAL INFORMATION

         The securities may also be offered and sold, if so indicated in the
applicable prospectus supplement, in connection with a remarketing upon their
purchase, in accordance with a redemption or repayment pursuant to their terms,
or otherwise, by one or more remarketing firms, acting as principals for their
own accounts or as agents for us. Any remarking firm will be identified and
terms of its agreement, if any, with us, and its compensation will be described
in the applicable prospectus supplement. Remarketing firms may be deemed to be
underwriters, as that term is defined in the Securities Act, in connection with
the securities remarketed thereby.

                                  LEGAL MATTERS

         Unless otherwise indicated in a prospectus supplement, the validity of
the securities to be offered by this prospectus will be passed upon for us by
Vedder, Price, Kaufman & Kammholz, P.C., Chicago, Illinois. Unless otherwise
indicated in a prospectus supplement, in the event the securities are offered
through one or more underwriters, certain legal matters will be passed upon for
the underwriters by Jones Day, Chicago, Illinois.

                                     EXPERTS

         The consolidated financial statements and schedule of Wintrust
Financial Corporation at December 31, 2003 and 2002, and for each of the three
years in the period ended December 31, 2003, appearing in Wintrust Financial
Corporation's Annual Report on Form 10-K for the year ended December 31, 2003,
have been audited by Ernst & Young LLP, an independent registered public
accounting firm, as set forth in their report thereon included therein and
incorporated herein by reference. Such consolidated financial statements and
schedule are incorporated herein by reference in reliance upon such reports
given on the authority of such firm as experts in accounting and auditing.

                       WHERE YOU CAN FIND MORE INFORMATION

         This prospectus is a part of a Registration Statement on Form S-3 that
we filed with the SEC under the Securities Act. This prospectus does not contain
all the information set forth in the registration statement, certain parts of
which are omitted in accordance with the rules and regulations of the SEC. For
further information with respect to us and the securities offered by this
prospectus, reference is made to the registration statement, including the
exhibits to the registration statement and the documents incorporated by
reference.

                                       59



         We file annual, quarterly and special reports, proxy statements and
other information with the SEC. Our filings are available to the public over the
Internet at the SEC's web site at http://www.sec.gov. You may also read and copy
any document we file with the SEC at its public reference facilities at 450
Fifth Street, N.W., Washington, D.C. 20549. You can also obtain copies of the
documents at prescribed rates by writing to the Public Reference Section of the
SEC at 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at
1-800-SEC-0330 for further information on the operation of the public reference
facilities. Our SEC filings are also available on our web site at
http://www.wintrust.com, and at the office of the Nasdaq National Market. For
further information on obtaining copies of our public filings at the Nasdaq
National Market, you should call (212) 656-5060.

                       DOCUMENTS INCORPORATED BY REFERENCE

         We "incorporate by reference" into this prospectus the information we
file with the SEC, which means that we can disclose important information to you
by referring you to those documents. The information incorporated by reference
is an important part of this prospectus.

         Some information contained in this prospectus updates and supersedes
the information incorporated by reference and some information that we file
subsequently with the SEC will automatically update this prospectus. We
incorporate by reference the documents listed below:

         o        our Annual Report on Form 10-K for the fiscal year ended
                  December 31, 2003, filed with the SEC on March 15, 2004 (File
                  No. 0-21923);

         o        our Quarterly Report on Form 10-Q for the quarter ended March
                  31, 2004, filed with the SEC on May 10, 2004 (File No.
                  0-21923);

         o        our Quarterly Report on Form 10-Q for the quarter ended June
                  30, 2004, filed with the SEC on August 9, 2004 (File No.
                  0-21923);

         o        our Current Report on Form 8-K filed with the SEC on January
                  21, 2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on April 20,
                  2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 11,
                  2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on July 20,
                  2004 (File No. 0-21923); and

         o        the descriptions of (a) our Common Stock contained in our
                  Registration Statement on Form 8-A dated January 3, 1997 (File
                  No. 0-21923), and (b) the associated preferred stock purchase
                  rights contained in our Registration Statement on Form 8-A
                  dated August 28, 1998 (File No. 0-21923).

         We also incorporate by reference any filings we make with the SEC under
Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934 after
the initial filing of the registration statement that contains this prospectus
and before the time that all of the shares offered by this prospectus are sold.

         Any statement contained in a document incorporated by reference in this
prospectus shall be deemed to be modified or superseded for purposes of this
prospectus to the extent that a statement contained in this prospectus, or in
any other document filed later which is also incorporated in this prospectus by
reference, modifies or supersedes the statement. Any statement so modified or
superseded shall not be deemed to constitute a part of this prospectus except as
so modified or superseded. The

                                       60



information contained in this prospectus should be read together with the
information in the documents incorporated in this prospectus by reference.

         You may obtain any of these incorporated documents from us without
charge, excluding any exhibits to these documents unless the exhibit is
specifically incorporated by reference in such document, by requesting them from
us in writing or by telephone at the following address:

                         Wintrust Financial Corporation
                               727 North Bank Lane
                           Lake Forest, Illinois 60045
                           Attention: Legal Department
                                 (847) 615-4096

         Documents may also be available on our website at www.wintrust.com.
Information contained on our website is not a prospectus and does not constitute
part of this prospectus.

                                       61



                                     PART II
                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14. OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

         The following table sets forth the various expenses payable by the
registrants in connection with the distribution of the securities being
registered. All of the amounts shown are estimated except the Securities and
Exchange Commission registration fee.

SEC registration fee.................................          $ 25,340
Printing and engraving expenses......................            15,000
Blue sky fees and expenses...........................            20,000
Trustees' and depositary's fees and expenses.........            10,000
Legal fees and expenses..............................            40,000
Accounting fees and expenses.........................            10,000
Miscellaneous fees and expenses......................             4,660
                                                               --------
   Total.............................................          $125,000
                                                               ========

ITEM 15. INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         In accordance with the Illinois Business Corporation Act (being Chapter
805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of
Wintrust's Articles of Incorporation provide as follows:

         ARTICLE EIGHT: No director of the corporation shall be liable to the
corporation or its shareholders for monetary damages for breach of fiduciary
duty as a director except for liability (a) for any breach of the director's
duty of loyalty to the corporation or its shareholders, (b) for acts or
omissions not in good faith or that involve intentional misconduct of a knowing
violation of law, (c) under Section 8.65 of the BCA, as the same exists or
hereafter may be amended, or (d) for any transaction from which the director
derived an improper personal benefit.

         ARTICLE NINE, PARAGRAPH 1: The corporation shall indemnify, to the full
extent that it shall have power under applicable law to do so and in a manner
permitted by such law, any person made or threatened to be made a party to any
threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative, by reason of the fact that he or she
is or was a director, officer, employee or agent of the corporation, or who is
or was serving at the request of the corporation as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust or
other enterprise against liabilities and expenses reasonably incurred or paid by
such person in connection with such action, suit or proceeding. The corporation
may indemnify, to the full extent that it shall have power under applicable law
to do so and in a manner permitted by such law, any person made or threatened to
be made a party to any threatened, pending or completed action, suit or
proceeding, whether civil, criminal, administrative or investigative, by reason
of the fact that he or she is or was a director, officer, employee or agent of
the corporation, or is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise against liabilities and expenses reasonably
incurred or paid by such person in connection with such action, suit or
proceeding. The words "liabilities" and "expenses" shall include, without
limitation: liabilities, losses, damages, judgments, fines, penalties, amounts
paid in settlement, expenses, attorneys' fees and costs. Expenses incurred in
defending a civil, criminal, administrative, investigative or other action, suit
or proceeding may be paid by the corporation in advance of the final disposition
of such action, suit or proceeding in accordance with the provisions of Section
8.75 of the BCA.

         The indemnification and advancement of expenses provided by this
Article shall not be deemed exclusive of any other rights to which any person
indemnified may be entitled under any statute, by-law,

                                      II-1



agreement, vote of shareholders, or disinterested directors or otherwise, both
as to action in his official capacity and as to action in any other capacity
while holding such office, and shall continue as to a person who has ceased to
be such director, officer, employee or agent and shall inure to the benefit of
the heirs, executors and administrators of such person.

         PARAGRAPH 2: The corporation may purchase and maintain insurance on
behalf of any person referred to in the preceding paragraph against any
liability asserted against him or her and incurred by him or her in any such
capacity, or arising out of his or her status as such, whether or not the
corporation would have the power to indemnify him or her against such liability
under the provisions of this Article or otherwise.

         PARAGRAPH 3: For purposes of this Article, references to "the
corporation" shall include, in addition to the resulting corporation, any
constituent corporation (including any constituent of a constituent) absorbed in
a consolidation or merger which, if its separate existence had continued, would
have had power and authority to indemnify its directors, officers, employees or
agents, so that any person who is or was a director, officer, employee or agent
of such constituent corporation, or is or was serving at the request of such
constituent corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise, shall stand
in the same position under the provisions of this Article with respect to the
resulting or surviving corporation as he or she would have with respect to such
constituent corporation if its separate existence had continued.

         PARAGRAPH 4: The provisions of this Article shall be deemed to be a
contract between the corporation and each director or officer who serves in any
such capacity at any time while this Article and the relevant provisions of the
BCA, or other applicable law, if any, are in effect, and any repeal or
modification of any such law or of this Article shall not affect any rights or
obligations then existing with respect to any state of facts then or theretofore
existing or any action, suit or proceeding theretofore or thereafter brought or
threatened based in whole or in part upon any such state of facts.

         PARAGRAPH 5: For purposes of this Article, references to "other
enterprises" shall include employee benefit plans; references to "fines" shall
include any excise taxes assessed on a person with respect to any employee
benefit plan; and references to "serving at the request of the corporation"
shall include any service as a director, officer, employee or agent of the
corporation which imposes duties on, or involves services by, such director,
officer, employee or agent with respect to any employee benefit plan, its
participants, or beneficiaries; and a person who acted in good faith and in a
manner he or she reasonably believed to be in the interest of the participants
and beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner not opposed to the best interests of the corporation.

         Section 6.3 of the Registrant's By-laws provides as follows:

         SECTION 6.3. MANDATORY INDEMNIFICATION. To the extent that a director,
officer, employee or agent of a corporation, or any subsidiary or subsidiaries,
as the case may be, has been successful on the merits or otherwise in defense of
any action, suit or proceeding referred to in Sections 6.1 and 6.2, or in
defense of any claim, issue or matter therein, such person shall be indemnified
against expenses (including attorneys' fees) actually and reasonably incurred by
him or her in connection therewith.

         The Illinois Business Corporation Act provides for indemnification of
officers, directors, employees and agents as follows:

         5/8.75 INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS;
INSURANCE. (a) A corporation may indemnify any person who was or is a party, or
is threatened to be made a party to any threatened, pending or completed action,
suit or proceeding, whether
                                      II-2



civil, criminal, administrative or investigative (other than an action by or in
the right of the corporation) by reason of the fact that he or she is or was a
director, officer, employee or agent of the corporation, or who is or was
serving at the request of the corporation as a director, officer, employee or
agent of another corporation, partnership, joint venture, trust or other
enterprise, against expenses (including attorneys' fees), judgments, fines and
amounts paid in settlement actually and reasonably incurred by such person in
connection with such action, suit or proceeding, if such person acted in good
faith and in a manner he or she reasonably believed to be in, or not opposed to
the best interests of the corporation, and, with respect to any criminal action
or proceeding, had no reasonable cause to believe his or her conduct was
unlawful. The termination of any action, suit or proceeding by judgment, order,
settlement, conviction, or upon a plea of nolo contendere or its equivalent,
shall not, of itself, create a presumption that the person did not act in good
faith and in a manner which he or she reasonably believed to be in or not
opposed to the best interests of the corporation or, with respect to any
criminal action or proceeding, that the person had reasonable cause to believe
that his or her conduct was unlawful.

         (b)      A corporation may indemnify any person who was or is a party,
or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in
its favor by reason of the fact that such person is or was a director, officer,
employee or agent of the corporation, or is or was serving at the request of the
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees) actually and reasonably incurred by such person in
connection with the defense or settlement of such action or suit, if such person
acted in good faith and in a manner he or she reasonably believed to be in, or
not opposed to, the best interests of the corporation, provided that no
indemnification shall be made with respect to any claim, issue, or matter as to
which such person has been adjudged to have been liable to the corporation,
unless, and only to the extent that the court in which such action or suit was
brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, such person is
fairly and reasonably entitled to indemnity for such expenses as the court shall
deem proper.

         (c)      To the extent that a present or former director, officer or
employee of a corporation has been successful, on the merits or otherwise, in
the defense of any action, suit or proceeding referred to in subsections (a) and
(b), or in defense of any claim, issue or matter therein, such person shall be
indemnified against expenses (including attorneys' fees) actually and reasonably
incurred by such person in connection therewith if the person acted in good
faith and in a manner he or she reasonably believed to be in, or not opposed to,
the best interests of the corporation.

         (d)      Any indemnification under subsections (a) and (b) (unless
ordered by a court) shall be made by the corporation only as authorized in the
specific case, upon a determination that indemnification of the present or
former director, officer, employee or agent is proper in the circumstances
because he or she has met the applicable standard of conduct set forth in
subsections (a) or (b). Such determination shall be made with respect to a
person who is a director or officer at the time of the determination: (1) by the
majority vote of the directors who are not parties to such action, suit or
proceeding, even though less than a quorum, (2) by a committee of the directors
designated by a majority vote of the directors, even though less than a quorum,
(3) if there are no such directors, or if the directors so direct, by
independent legal counsel in a written opinion, or (4) by the shareholders.

         (e)      Expenses (including attorneys' fees) incurred by an officer or
director in defending a civil or criminal action, suit or proceeding may be paid
by the corporation in advance of the final disposition of such action, suit or
proceeding upon receipt of an undertaking by or on behalf of the director or
officer to repay such amount if it shall ultimately be determined that such
person is not entitled to be indemnified by the corporation as authorized in
this Section.  Such expenses (including attorneys' fees) incurred by

                                      II-3



former directors and officers or other employees and agents may be so paid on
such terms and conditions, if any, as the corporation deems appropriate.

         (f)      The indemnification and advancement of expenses provided by or
granted under the other subsections of this Section shall not be deemed
exclusive of any other rights to which those seeking indemnification or
advancement of expenses may be entitled under any by-law, agreement, vote of
shareholders or disinterested directors, or otherwise, both as to action in his
or her official capacity and as to action in another capacity while holding such
office.

         (g)      A corporation may purchase and maintain insurance on behalf of
any person who is or was a director, officer, employee or agent of the
corporation, or who is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise, against any liability asserted against such
person and incurred by such person in any such capacity, or arising out of his
or her status as such, whether or not the corporation would have the power to
indemnify such person against such liability under the provisions of this
Section.

         (h)      If a corporation indemnifies or advances expenses to a
director or officer under subsection (b) of this Section, the corporation shall
report the indemnification or advance in writing to the shareholders with or
before the notice of the next shareholders meeting.

         (i)      For purposes of this Section, references to "the corporation"
shall include, in addition to the surviving corporation, any merging corporation
(including any corporation having merged with a merging corporation) absorbed in
a merger which, if its separate existence had continued, would have had the
power and authority to indemnify its directors, officers, and employees or
agents, so that any person who was a director, officer, employee or agent of
such merging corporation, or was serving at the request of such merging
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, shall stand in the same
position under the provisions of this Section with respect to the surviving
corporation as such person would have with respect to such merging corporation
if its separate existence had continued.

         (j)      For purposes of this Section, reference to "other enterprises"
shall include employee benefit plans; references to "fines" shall include any
excise taxes assessed on a person with respect to an employee benefit plan; and
references to "serving at the request of the corporation" shall include any
service as a director, officer, employee or agent of the corporation which
imposes duties on, or involves services by such director, officer, employee, or
agent with respect to an employee benefit plan, its participants, or
beneficiaries. A person who acted in good faith and in a manner he or she
reasonably believed to be in the best interests of the participants and
beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner "not opposed to the best interest of the corporation" as referred to in
this Section.

         (k)      The indemnification and advancement of expenses provided by or
granted under this Section shall, unless otherwise provided when authorized or
ratified, continue as to a person who has ceased to be a director, officer,
employee, or agent and shall inure to the benefit of the heirs, executors, and
administrators of that person.

         (l)      The changes to this Section made by this amendatory Act of
the 92nd General Assembly apply only to actions commenced on or after the
effective date of this amendatory Act of the 92nd General Assembly. (Last
amended by P.A. 92-0033, L. '01, eff. 7-1-01.)

         Wintrust has purchased $30 million of insurance policies which insure
Wintrust's directors and officers against liability which they may incur as a
result of actions taken in such capacities. In addition,

                                      II-4



Wintrust maintains fiduciary liability coverage up to a $5 million limit and
trust errors and omissions coverage up to a limit of $15 million.

         The Amended and Restated Trust Agreement will provide for
indemnification of the Delaware trustee and each of the administrative trustees
by Wintrust against any loss, damage, claims, liability, penalty or expense of
any kind incurred by the trustees in connection with the performance of their
duties or powers under the agreement in a manner reasonably believed by the
trustee to be within the scope of its authority under the agreement, except that
none of these trustees will be so indemnified for any loss, damage or claim
incurred by reason of such trustee's gross negligence, bad faith or willful
misconduct. Similarly, the agreement provides for indemnification of the
property trustee except that the property trustee is not indemnified from
liability for its own negligent action, negligent failure to act or willful
misconduct. Under the agreement, Wintrust agrees to advance those expenses
incurred by any trustee in defending any such claim, demand, action, suit or
proceeding.

ITEM 16. EXHIBITS AND FINANCIAL STATEMENT SCHEDULES.

         (a)      Exhibits.

The following exhibits are filed herewith or incorporated by reference.

Exhibit
Number   Exhibit Description
------   -------------------

1.1      Form of Underwriting Agreement.*

4.1      Form of Debt Securities Indenture.**

4.2      Form of Junior Subordinated Debentures Indenture.**

4.3      Certificate of Trust.

4.4      Trust Agreement.

4.5      Form of Amended and Restated Trust Agreement.**

4.6      Form of Debt Security (included in Exhibit 4.1).**

4.7      Form of Depositary Agreement.*

4.8      Form of Purchase Contract Agreement.*

4.9      Form of Pledge Agreement.*

4.10     Form of Purchase Contract Agreement.*

4.11     Form of Warrant Agreement.*

4.12     Form of Trust Preferred Securities Certificate.**

4.13     Form of Trust Preferred Securities Guarantee Agreement.**


                                      II-5



4.14     Form of Trust Common Stock Certificate.**

4.15     Form of Preferred Stock Certificate of Wintrust.*

4.16     Form of Common Stock Certificate of Wintrust.*

4.17     Form of Agreement as to Expenses and Liabilities.*

4.18     Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of Wintrust's Form
         8-A Registration Statement (No. 000-21923) filed with the Securities
         and Exchange Commission on August 28, 1998).

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. **

5.2      Opinion of Richards, Layton & Finger, P.A.**

12.1     Computation of Ratio of Earnings to Fixed Charges.**

23.1     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in Exhibit
         5.1).**

23.2     Consent of Richards, Layton & Finger, P.A. (included in Exhibit 5.2).**

23.3     Consent of Ernst & Young LLP.

24.1     Powers of Attorney (included on the signature page).

25.1     Statement of Eligibility on Form T-1 of the trustee under the Indenture
         for the Debt Securities.**

25.2     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Indenture for the Junior Subordinated
         Debentures.**

25.3     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Amended and Restated Trust Agreement.**

25.4     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Guarantee Agreement.**

------------------
*        To be filed by post-effective amendment or Current Report on Form 8-K.
**       To be filed by pre-effective amendment.

ITEM 17. UNDERTAKINGS.

         (a)      The undersigned registrants hereby undertake:

                  (1)      To file, during any period in which offers or sales
                           are being made, a post-effective amendment to this
                           registration statement:

                           (i)      To include any prospectus required by
                                    Section 10(a)(3) of the Securities Act of
                                    1933;


                                      II-6



(ii)     To reflect in the prospectus any facts or events arising after the
         effective date of the registration statement (or the most recent
         post-effective amendment thereof) which, individually or in the
         aggregate, represent a fundamental change in the information set forth
         in the registration statement. Notwithstanding the foregoing, any
         increase or decrease in volume of securities offered (if the total
         dollar value of securities offered would not exceed that which was
         registered) and any deviation from the low or high end of the estimated
         maximum offering range may be reflected in the form of prospectus filed
         with the Commission pursuant to Rule 424(b) if, in the aggregate, the
         changes in volume and price represent no more than a 20% change in the
         maximum aggregate offering price set forth in the "Calculation of
         Registration Fee" table in the effective registration statement; and

                  (iii)    To include any material information with respect to
                           the plan of distribution not previously disclosed in
                           the registration statement or any material change to
                           such information in the registration statement;

                  provided, however, that paragraphs (a)(1)(i) and (a)(1)(ii) do
                  not apply if the registration statement is on Form S-3, Form
                  S-8 or Form F-3, and the information required to be included
                  in a post-effective amendment by those paragraphs is contained
                  in periodic reports filed by the registrant pursuant to
                  Section 13 or Section 15(d) of the Securities Exchange Act of
                  1934 that are incorporated by reference in the registration
                  statement.

                  (2)      That, for the purpose of determining any liability
                           under the Securities Act of 1933, each such
                           post-effective amendment shall be deemed to be a new
                           registration statement relating to the securities
                           offered therein, and the offering of such securities
                           at that time shall be deemed to be the initial bona
                           fide offering thereof.

                  (3)      To remove from registration by means of a
                           post-effective amendment any of the securities being
                           registered which remain unsold at the termination of
                           the offering.

         (b)      The undersigned registrants hereby undertake that, for
                  purposes of determining any liability under the Securities Act
                  of 1933, each filing of the registrant's annual report
                  pursuant to Section 13(a) or Section 15(d) of the Securities
                  Exchange Act of 1934 (and, where applicable, each filing of an
                  employee benefit plan's annual report pursuant to Section
                  15(d) of the Securities Exchange Act of 1934) that is
                  incorporated by reference in the registration statement shall
                  be deemed to be a new registration statement relating to the
                  securities offered therein, and the offering of such
                  securities at that time shall be deemed to be the initial bona
                  fide offering thereof.

         (c)      Insofar as indemnification for liabilities arising under the
                  Securities Act of 1933 may be permitted to directors, officers
                  and controlling persons of registrants pursuant to the
                  foregoing provisions, or otherwise, the registrants have been
                  advised that in the opinion of the Securities and Exchange
                  Commission such indemnification is against public policy as
                  expressed in the Act and is, therefore, unenforceable. In the
                  event that a claim for indemnification against such
                  liabilities (other than the payment by the registrants of
                  expenses incurred or paid by a director, officer or
                  controlling person of the registrants in the successful
                  defense of any action, suit or proceeding) is asserted by such
                  director, officer or controlling person in connection with the
                  securities being registered, the

                                      II-7



                  registrants will, unless in the opinion of their counsel the
                  matter has been settled by controlling precedent, submit to a
                  court of appropriate jurisdiction the question of whether such
                  indemnification by them is against public policy as expressed
                  in the Act and will be governed by the final adjudication of
                  such issue.

         (d)      The undersigned registrants further undertake that for the
                  purposes of determining any liability under the Securities Act
                  of 1933:

                  (i)      The information omitted from the form of prospectus
                           filed as part of this registration statement in
                           reliance upon Rule 430A and contained in the form of
                           prospectus filed by the registrants pursuant to Rule
                           424(b)(1) or (4) or 497(h) under the Securities Act
                           shall be deemed to be part of this registration
                           statement as of the time it was declared effective.

                  (ii)     Each post-effective amendment that contains a form of
                           prospectus shall be deemed to be a new registration
                           statement relating to the securities offered therein,
                           and the offering of such securities at that time
                           shall be deemed to be the initial bona fide offering
                           thereof.

         (e)      The undersigned registrants hereby undertake to file an
                  application for the purpose of determining the eligibility of
                  the trustee to act under subsection (a) of Section 310 of the
                  Trust Indenture Act in accordance with the rules and
                  regulations prescribed by the Commission under Section
                  305(b)(2) of the Act.

                                      II-8



                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, Wintrust
Capital Trust VI certifies that it has reasonable grounds to believe that it
meets all of the requirements for filing on Form S-3 and has duly caused this
registration statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Lake Forest, State of Illinois, on September 28,
2004.

                                    WINTRUST CAPITAL TRUST VI


                                    By:  Wintrust Financial Corporation,
                                         as Depositor


                                    By:/s/ David A. Dykstra
                                       _________________________________________
                                           David A. Dykstra
                                           Senior Executive Vice President and
                                           Chief Operating Officer

         Pursuant to the requirements of the Securities Act of 1933, Wintrust
Financial Corporation certifies that it has reasonable grounds to believe that
it meets all of the requirements for filing on Form S-3 and has duly caused this
registration statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Lake Forest, State of Illinois, on September 28,
2004.

                                    WINTRUST FINANCIAL CORPORATION


                                    By:/s/ David A. Dykstra
                                       _________________________________________
                                           David A. Dykstra
                                           Senior Executive Vice President and
                                           Chief Operating Officer

                                POWER OF ATTORNEY

         KNOW ALL MEN BY THESE PRESENTS, that each person whose signature
appears below hereby constitutes and appoints Edward J. Wehmer and David A.
Dykstra, and each or either of them, his or her true and lawful attorney-in-fact
and agent, with full power of substitution and resubstitution, for him or her
and in his or her name, place and stead, in any and all capacities, to sign any
and all amendments (including post-effective amendments) to this registration
statement on Form S-3 and to file same, with all exhibits thereto and, other
documents in connection therewith, with the Securities and Exchange Commission,
granting unto each said attorney-in-fact and agent full power and authority to
do and perform each and every act and thing requisite and necessary to be done
in and about the foregoing, as fully to all intents and purposes as he or she
might or could do in person, hereby ratifying and confirming all that said
attorney-in-fact and agent or either of them, or their or his or her substitute
or substitutes, may lawfully do or cause to be done by virtue hereof.



         Pursuant to the requirements of the Securities Act of 1933, this
registration statement has been signed by the following persons in the
capacities and on the dates indicated.




                    Name                                    Title                                 Date
                    ----                                    -----                                 ----
                                                                                    
/s/ Edward J. Wehmer                              President, Chief Executive              September 28, 2004
___________________________________                  Officer and Director
    Edward J. Wehmer

/s/ David L. Stoehr                            Executive Vice President and Chief         September 28, 2004
___________________________________              Financial Officer (Principal
    David L. Stoehr                            Financial and Accounting Officer)

/s/ John S. Lillard
___________________________________                  Chairman and Director                September 28, 2004
John S. Lillard

/s/ Peter D. Crist
___________________________________                       Director                        September 28, 2004
Peter D. Crist

___________________________________                       Director
Bruce K. Crowther

/s/ Bert A. Getz, Jr.
___________________________________                       Director                        September 28, 2004
Bert A. Getz, Jr.

___________________________________                       Director
Paul J. Liska

/s/ Philip W. Hummer
___________________________________                       Director                        September 28, 2004
Philip W. Hummer

/s/ James B. McCarthy
___________________________________                       Director                        September 28, 2004
James B. McCarthy

___________________________________                       Director
Albin F. Moschner

/s/ Thomas J. Neis
___________________________________                       Director                        September 28, 2004
Thomas J. Neis

/s/ Hollis W. Rademacher
___________________________________                       Director                        September 28, 2004
Hollis W. Rademacher

/s/ J. Christopher Reyes
___________________________________                       Director                        September 28, 2004
J. Christopher Reyes

___________________________________                       Director
John J. Schornack

___________________________________                       Director
Ingrid S. Stafford




                                  EXHIBIT INDEX

Exhibit
Number         Exhibit Description
------         -------------------

1.1      Form of Underwriting Agreement.*

4.1      Form of Debt Securities Indenture.**

4.2      Form of Junior Subordinated Debentures Indenture.**

4.3      Certificate of Trust.

4.4      Trust Agreement.

4.5      Form of Amended and Restated Trust Agreement.**

4.6      Form of Debt Security (included in Exhibit 4.1).**

4.7      Form of Depositary Agreement.*

4.8      Form of Purchase Contract Agreement.*

4.9      Form of Pledge Agreement.*

4.10     Form of Purchase Contract Agreement.*

4.11     Form of Warrant Agreement.*

4.12     Form of Trust Preferred Securities Certificate.**

4.13     Form of Trust Preferred Securities Guarantee Agreement.**

4.14     Form of Trust Common Stock Certificate.**

4.15     Form of Preferred Stock Certificate of Wintrust.*

4.16     Form of Common Stock Certificate of Wintrust.*

4.17     Form of Agreement as to Expenses and Liabilities.*

4.18     Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of Wintrust's
         Form 8-A Registration Statement (No. 000-21923) filed with the
         Securities and Exchange Commission on August 28, 1998).

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. **

5.2      Opinion of Richards, Layton & Finger, P.A.**

12.1     Computation of Ratio of Earnings to Fixed Charges.**



23.1     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in Exhibit
         5.1).**

23.2     Consent of Richards, Layton & Finger, P.A. (included in Exhibit 5.2).**

23.3     Consent of Ernst & Young LLP.

24.1     Powers of Attorney (included on the signature page).

25.1     Statement of Eligibility on Form T-1 of the trustee under the Indenture
         for the Debt Securities.**

25.2     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Indenture for the Junior Subordinated
         Debentures.**

25.3     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Amended and Restated Trust Agreement.**

25.4     Statement of Eligibility of Wilmington Trust Company on Form T-1, as
         Trustee under the Guarantee Agreement.**

------------------
*        To be filed by post-effective amendment or Current Report on Form 8-K.
**       To be filed by pre-effective amendment.