As filed with the Securities and Exchange Commission on May 7, 2002

                                                      Registration No. 333-84188
================================================================================

                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                AMENDMENT NO. 1
                                       TO
                                    FORM S-3

                             REGISTRATION STATEMENT
                                      UNDER
                           THE SECURITIES ACT OF 1933
                         WINTRUST FINANCIAL CORPORATION
             (Exact Name of Registrant as Specified in Its Charter)

            ILLINOIS                                        36-3873352
  (State or Other Jurisdiction                            (IRS Employer
of 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 Registrant's Principal Executive Offices)

                                DAVID A. DYKSTRA
            SENIOR EXECUTIVE VICE PRESIDENT, CHIEF OPERATING OFFICER
                           AND CHIEF FINANCIAL 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)

      The Commission is requested to send copies of all communications to:
                             JENNIFER R. EVANS, ESQ.
                        VEDDER, PRICE, KAUFMAN & KAMMHOLZ
                            222 NORTH LASALLE STREET
                          CHICAGO, ILLINOIS 60601-1003
                                 (312) 609-7500

         Approximate date of commencement of proposed sale to the public: As
soon as practicable after the effectiveness of this Registration Statement.
         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 interest 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, 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 pursuant to Rule
434, please check the following box. [ ]
         The registrant hereby amends this Registration Statement on such date
or dates as may be necessary to delay its effective date until the registrant
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.
                              ____________________
                        CALCULATION OF REGISTRATION FEE



=================================================================================================================================
  TITLE OF EACH CLASS OF           AMOUNT TO BE     PROPOSED MAXIMUM OFFERING        PROPOSED MAXIMUM              AMOUNT OF
SECURITIES TO BE REGISTERED         REGISTERED         PRICE PER SHARE(1)       AGGREGATE OFFERING PRICE(1)   REGISTRATION FEE(2)
---------------------------------------------------------------------------------------------------------------------------------
                                                                                                        
Common Stock, without par value*      912,734               $21.60                      $19,715,055                 $1,815
=================================================================================================================================

*        Including the preferred share purchase rights associated therewith.
(1)      Estimated solely for the purpose of determining the registration fee
         pursuant to Rule 457(c), based on the average of the high and low sales
         prices on March 11, 2002, as reported on the Nasdaq National Market, of
         $21.7656 and $21.4375, respectively, as adjusted to give effect to the
         3-for-2 stock split on March 14, 2002.
(2)      Previously paid on March 12, 2002.








THE INFORMATION IN THIS PROSPECTUS IS NOT COMPLETE AND MAY BE CHANGED. WE MAY
NOT SELL THESE SECURITIES UNTIL THE REGISTRATION STATEMENT FILED WITH THE
SECURITIES AND EXCHANGE COMMISSION IS EFFECTIVE. THIS PROSPECTUS IS NOT AN OFFER
TO SELL THESE SECURITIES AND IT IS NOT SOLICITING AN OFFER TO BUY THESE
SECURITIES IN ANY STATE WHERE THE OFFER OR SALE IS NOT PERMITTED.



                   Subject to Completion, Dated May 7, 2002



PROSPECTUS


                         WINTRUST FINANCIAL CORPORATION

                         912,734 SHARES OF COMMON STOCK

         Certain shareholders of Wintrust Financial Corporation are offering for
sale from time to time up to 912,734 shares of our common stock under this
prospectus. The selling shareholders may offer the shares:


         o    to or through one or more underwriters,

         o    directly to purchasers,

         o    on the Nasdaq National Market in typical brokerage transactions,

         o    in negotiated transactions, or otherwise.

         The selling shareholders may sell the shares of common stock covered by
this prospectus:

         o    at market prices prevailing at the time of sale,

         o    at prices related to the then-prevailing market price, or

         o    at negotiated prices.

         We will not receive any proceeds from the sale of the shares of common
stock by the selling shareholders. No minimum purchase is required and no
arrangement has been made to have funds received by the selling shareholders
and/or any registered representatives placed in an escrow, trust or similar
account or arrangement.


         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC." On May 3, 2002, the closing price of our common stock as
reported on Nasdaq was $25.84 per share.

         YOU SHOULD CONSIDER, AMONG OTHER THINGS, THE INFORMATION SET FORTH IN
"RISK FACTORS" BEGINNING ON PAGE 7 OF THIS PROSPECTUS.


         THE SHARES OF COMMON STOCK THAT ARE BEING OFFERED ARE NOT SAVINGS
ACCOUNTS OR DEPOSITS OR OTHER OBLIGATIONS OF A BANK AND ARE NOT INSURED BY THE
BANK INSURANCE FUND OR THE FEDERAL DEPOSIT INSURANCE CORPORATION OR ANY
GOVERNMENTAL AGENCY.

         NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
COMMISSION HAS APPROVED OF ANYONE'S INVESTMENT IN THESE SECURITIES OR DETERMINED
IF THIS PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY
IS A CRIMINAL OFFENSE.


                  THE DATE OF THIS PROSPECTUS IS MAY ___, 2002.






                                TABLE OF CONTENTS

                                                                            PAGE
                                                                            ----


Summary Information............................................................1
Risk Factors.................................................................. 7
Use of Proceeds...............................................................12
Price Range of Common Stock and Dividend Policy...............................12
Selling Shareholders..........................................................13
Plan of Distribution..........................................................15
Transfer Agent................................................................16
Legal Matters.................................................................16
Experts  .....................................................................16
Where You Can Find More Information...........................................16
Documents Incorporated By Reference...........................................17


                            ------------------------

         You should rely only on the information contained in this prospectus.
We have not authorized any other person to provide you with different
information. This prospectus is not an offer to sell, nor is it seeking an offer
to buy, these securities in any state where the offer or sale is not permitted.
The information in this prospectus is complete and accurate as of the date on
the front cover, but the information may have changed since that date.

                SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

         We make certain forward-looking statements in 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 include statements
relating to:

         o    our goals, intentions and expectations;

         o    our business plans and growth strategies; and

         o    estimates of our risks and future costs and benefits.


         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
"Risk Factors" beginning on page 7.


         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 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 statements, which speak
only as of the date they were made. We will not update these forward-looking
statements, even though our situation may change in the future, unless we are
obligated to do so under federal securities laws. We qualify all of our
forward-looking statements by these cautionary statements.


                                       i




                               SUMMARY INFORMATION

         This summary highlights information about Wintrust and our business and
should be read in conjunction with the documents incorporated by reference into
this prospectus. Because this is a summary, it may not contain all of the
information that is important to you. Therefore, you should also read the more
detailed information that is included in the documents incorporated by
reference, including our financial statements included in our Form 10-K report
for the year ended December 31, 2001, as well as the "Risk Factors" section of
this prospectus beginning on page 7, before making a decision to invest in our
common stock.

         This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 912,734 shares of common
stock. We newly issued 762,734 of these shares to the selling shareholders in
February 2002 in connection with our acquisition of the Wayne Hummer Companies.
We paid $28 million for the Wayne Hummer Companies, consisting of $8 million in
cash, 762,734 shares of common stock (then valued at $15 million) and $5 million
of deferred cash payments to be made over a three-year period subsequent to the
closing date. We also agreed to pay additional consideration contingent upon the
attainment of certain performance measures over the next five years. This
prospectus also covers up to a total of 150,000 additional shares that we may
issue to the selling shareholders if they are eligible to receive these
additional purchase price amounts. Because the issuance of the shares in that
transaction was not registered with the SEC, the selling shareholders have
"restricted stock." All of the selling shareholders were former owners of the
Wayne Hummer Companies and each of them, other than Messrs. Kahlfeldt and
Rogers, is currently employed by us, pursuant to an employment agreement entered
into in connection with the transaction, as part of our asset management and
brokerage subsidiaries. We are registering the shares to enable the selling
shareholders to resell the shares in the public market from time to time or on a
delayed basis and to permit secondary trading of the shares after they are sold
by the selling shareholders.

ABOUT WINTRUST FINANCIAL


         We are a bank holding company headquartered in Lake Forest, Illinois,
with total assets of approximately $2.7 billion at December 31, 2001. We operate
seven community banks, all in affluent suburbs of Chicago, which provide
community-oriented, personal and commercial banking services primarily to
individuals and small to mid-size businesses through 30 banking facilities. Each
of our banks provides a full complement of commercial and consumer loan and
deposit products and services. Through Wayne Hummer Investments LLC and Wayne
Hummer Management Company, firms we acquired in February 2002 to expand our
asset management business, we now provide brokerage and trust and investment
services to over 35,000 customers, primarily in the Midwest, as well as to
customers of our banks. In addition, we provide specialty lending through
operating subsidiaries or divisions of certain of our banks. Our specialty
lending niches include one of the ten largest, based on management's estimates,
commercial insurance premium finance companies in the United States; a company
which provides accounts receivable financing and administrative services to the
temporary staffing industry; and an indirect auto financing business which
purchases loans through Chicago-area dealerships.


COMMUNITY BANKING

         Each of our banking subsidiaries was founded as a de novo banking
organization (which means started new) within the last approximately ten years.
We have grown from $1.1 billion in assets at December 31, 1997 to $2.7 billion
in assets at December 31, 2001, and our diluted earnings per share have
increased at a compound annual growth rate of 33% over the four-year period
ending December 31, 2001. Our historical financial performance has been affected
by costs associated with growing market share in deposits and loans, opening new
banks and branch facilities, and building an experienced management team. Our
recent financial performance generally reflects the improved profitability of
our





operating subsidiaries as they mature, offset by the costs of opening new banks
and branch offices. Our experience has been that it generally takes from 13 to
24 months for new banks to first achieve operational profitability depending on
the number and timing of branch facilities added.

ASSET MANAGEMENT AND BROKERAGE SERVICES


         Since late 1998, we have offered trust services in the communities
served by our banks through Wintrust Asset Management. We employ experienced
trust personnel and offer a full range of trust and investment services at Lake
Forest Bank, North Shore Community Bank, Hinsdale Bank, Barrington Bank and
Northbrook Bank. Prospective trust and investment customers at our other two
banks are currently being served on an appointment basis.


         To expand our asset management business and to enter into the brokerage
business, on February 20, 2002, we completed our acquisition of Wayne Hummer
Investments, LLC, a registered broker-dealer, Wayne Hummer Management Company, a
registered investment adviser and Focused Investments LLC, a broker-dealer and
wholly-owned subsidiary of Wayne Hummer Investments (collectively referred to in
this prospectus as the Wayne Hummer Companies), each based in Chicago. We intend
to continue to use the Wayne Hummer name in our brokerage and asset management
operations.

         Wayne Hummer Investments, which we will operate as a separate
subsidiary of Wintrust, is a broker-dealer providing a full range of private
client and brokerage services to approximately 35,000 customers, located
primarily in the Midwest, with client assets of approximately $4.1 billion at
December 31, 2001. Focused Investments is a broker-dealer that provides a full
range of investment solutions to clients through a network of community-based
financial institutions throughout the Midwest. Wayne Hummer Management Company
provides money management services and advisory services to individuals and
institutions, municipal and tax-exempt organizations, including the Wayne Hummer
Companies' four proprietary mutual funds. Additionally, WHMC also provides
portfolio management and financial supervision for a wide range of pension and
profit-sharing plans. Individual accounts managed by Wayne Hummer Management
Company totaled approximately $400 million at December 31, 2001, while the four
managed funds had approximately $630 million in total assets at December 31,
2001. Wayne Hummer Management will continue to manage its mutual funds, subject
to approval of the mutual fund shareholders, and the management of its client
accounts, subject to regulatory approval, will be combined with Wintrust Asset
Management Company, which at December 31, 2001, managed approximately $435
million of assets. We believe that the acquisition of the Wayne Hummer Companies
will augment and diversify our revenue stream by adding brokerage services to
our fee-based revenue as well as offering traditional banking products to the
customers of the Wayne Hummer Companies, thereby providing a more comprehensive
menu of financial products and services to our customers and the customers of
the Wayne Hummer Companies.

SPECIALTY LENDING


         We conduct our specialty lending businesses through direct and indirect
non-bank subsidiaries and divisions of our banks.


         Through First Insurance Funding we make loans to businesses to finance
the insurance premiums they pay on their commercial insurance policies on a
national basis. The loans are originated by First Insurance Funding working
through independent medium and large insurance agents and brokers. The insurance
premiums we finance are primarily for commercial customers' purchases of
liability, property and casualty and other commercial insurance. The majority of
these loans are purchased by our banks in order to more fully utilize their
lending capacity. These loans generally provide the banks higher yields than
alternative investments. Since the second quarter of 1999, we have also been
selling some of the


                                       2



loan originations to an unrelated third party with servicing retained. Based on
limited industry data available in certain state regulatory filings and First
Insurance Funding management's experience in and knowledge of the premium
finance industry, management estimates that, ranked by origination volumes,
First Insurance Funding is one of the top five premium finance companies
operating in the United States, with loan origination volume of approximately
$1.3 billion during 2001. Our premium finance loans as of December 31, 2001,
were $348.2 million, or 16.9% of our net loan portfolio.


         Through Tricom, Inc. we provide high-yielding, short-term accounts
receivable financing and value-added, outsourced administrative services, such
as data processing of payrolls, billing and cash management services to the
temporary staffing industry. Tricom's clients, located throughout the United
States, provide staffing services to businesses in diversified industries.
During 2001, Tricom processed payrolls with associated client billings of
approximately $248 million and contributed $7.5 million of revenues, net of
interest expense, to us.

         We engage in other specialty lending through divisions of our banks,
including indirect auto lending which we do through a division of Hinsdale Bank.
The indirect automobile loans are diversified among many individual borrowers,
secured by new and used automobiles and are generated by a large network of
automobile dealers located in the Chicago area with which we have established
relationships. We regard substantially all of these loans as prime quality
loans. Management continually monitors the dealer relationships and the banks
are not dependent on any one dealer as a source of such loans. Like other
consumer loans, the indirect auto loans are subject to the banks' stringent
credit standards. At December 31, 2001, our indirect auto loans were $184.2
million and comprised approximately 8.9% of our net loan portfolio. Management
anticipates that this portfolio will comprise a smaller portion of the net loan
portfolio in the future.


                                       3



OPERATIONAL STRATEGY

         Since our first bank was opened in 1991, we have been committed to the
same fundamental operational strategy, the key elements of which are:


         o        MAINTAINING DECISION-MAKING AUTHORITY LOCALLY WITHIN EACH OF
                  OUR BANKS AND PROVIDING A HIGH LEVEL OF PERSONAL AND
                  PROFESSIONAL SERVICE. Our community banking philosophy is
                  driven by our emphasis on local independence and
                  decision-making authority within each of our banks. While
                  senior management provides expertise to each of our
                  subsidiaries in the areas of capital planning, long-term
                  strategic planning, marketing and advertising, financial
                  management, investment and asset/liability management, and
                  technology, the separate management teams of each of the
                  banks, as well as First Insurance, Wintrust Asset Management,
                  Tricom and the Wayne Hummer Companies, have full managerial
                  responsibilities for customer service and the ongoing
                  day-to-day operations of their respective organizations,
                  subject to the oversight of our Board of Directors and the
                  boards of our subsidiaries. Our banks enjoy the competitive
                  advantages of being able to tailor products and services to
                  meet the differing needs of the customers that they serve, to
                  quickly make decisions affecting customers, and to participate
                  actively in their communities.

         o        EMPLOYING FEWER, BUT HIGHLY QUALIFIED AND PRODUCTIVE
                  INDIVIDUALS AT RELATIVELY HIGH COMPENSATION RATES AND FOCUSING
                  ON LOW NET OVERHEAD RATIOS. Key to our growth and
                  profitability is our management's extensive experience in
                  providing community banking services, and retaining highly
                  qualified managers is critical to our strategy. Our banks'
                  presidents and chief executive officers were selected not only
                  for their years of banking experience but also for their
                  business development skills and their strong ties to the
                  communities they serve. Our practice of employing fewer, but
                  highly qualified and productive individuals at all levels of
                  the organization is key to maintaining a decentralized
                  management structure. Although our management compensation
                  levels may be relatively high, we believe our organizational
                  structure allows us to continue to improve and maintain
                  favorable net overhead ratios as the banks, First Insurance,
                  Wintrust Asset Management and Tricom mature.

         o        MARKETING INNOVATIVE DEPOSIT AND LOAN PRODUCTS. Our banks
                  offer local residents competitive retail products designed to
                  attract customers and to provide the banks with the
                  opportunity to introduce and cross-sell their full range of
                  personalized banking services. While competitive pricing may
                  create pressure on our net interest margin at times, to be
                  more responsive to the needs of consumers in their specific
                  markets, the banks have also introduced a variety of
                  innovative deposit and loan products to appeal to the unique
                  needs of different types of bank customers, such as different
                  age groups and other special segments of the target markets.
                  Each of our banks has developed a strong customer base within
                  its communities through the utilization of innovative
                  community-oriented marketing programs. Our banks market their
                  products aggressively through creative newspaper and other
                  advertising, special promotions and frequently sponsored
                  community events. In addition, each of our banks has a large
                  board of directors comprised of influential business persons
                  and prominent individuals within their respective communities
                  who assist the banking officers with business development.
                  Consequently, we believe substantially all of our deposits are
                  core deposits. We have been successful in growing our deposits
                  at a compound annual growth rate of 26% from December 31, 1997
                  through December 31, 2001.

         o        PURSUING A NUMBER OF SPECIALTY LENDING NICHES. We currently
                  finance loans in several different specialty lending niches to
                  more fully utilize our lending capacity, to diversify our


                                       4



                  loan portfolio, and to enhance the profitability of our banks.
                  In addition to premium finance loans originated by First
                  Insurance, short-term accounts receivables financed by Tricom,
                  and indirect auto loans, we also engage in mortgage warehouse
                  lending, medical and municipal equipment leasing, homeowners
                  and condominium association lending and, more recently, small
                  aircraft lending. Loans in these specialty lending niches tend
                  to be higher yielding than other commercial and consumer loans
                  in our banks' portfolios, but may involve greater credit risks
                  than generally associated with loan portfolios of more
                  traditional community banks.

         o        FOCUS ON GENERATING FEE INCOME TO AUGMENT NET INTEREST INCOME.
                  During 2001, we generated fee income from a variety of sources
                  including the origination and sale of mortgage loans, account
                  service charges, trust and asset management fees, premium
                  income from call option contracts, as well as gains on sales
                  of premium finance receivables and securities. In addition, we
                  earn administrative fees at Tricom related to its payroll
                  processing business. We have further diversified our sources
                  of fee income with the acquisition of the Wayne Hummer
                  Companies which will increase our noninterest income as a
                  percentage of net revenues in 2002. Non-interest income (not
                  including $1.25 million of income from our settlement of a
                  lawsuit) as a percentage of net revenues increased to 34% for
                  the quarter ended March 31, 2002, from 28% for the comparable
                  period in 2001.


GROWTH STRATEGY

         Key elements of our growth strategy are:


         o        INTERNAL GROWTH. Due to our de novo strategy, we believe we
                  have not yet realized the full deposit and asset generation
                  potential in the communities now served by our existing
                  banking facilities. We believe we can leverage our existing
                  infrastructure to support additional business while
                  maintaining a high level of personalized customer service and
                  responsiveness. As consolidation in the financial services
                  industry continues, management expects that more individuals
                  and small businesses will become disenchanted with the
                  perceived lower level of service offered by the larger
                  institutions, providing continuing market share opportunity
                  for Wintrust. Although we will continue to be impacted by
                  start-up costs to the extent we undertake additional de novo
                  bank, branch and business formations, with management's focus
                  on balancing further asset growth with earnings growth, our
                  current strategy is to continue to focus on less aggressive
                  deposit pricing at those banks with significant market share
                  and more established customer bases.

         o        EXPANDING INTO ATTRACTIVE MARKETS WITH LIMITED LOCAL BANKING
                  COMPETITION. We plan to continue our geographic expansion by
                  leveraging our existing banks and opening new branch
                  facilities in nearby communities where management believes
                  targeted customers would be attracted to a community banking
                  alternative. Consistent with this strategy, in 2001 we opened
                  a total of two new locations. In February 2001, we opened a
                  new branch of Crystal Lake Bank in McHenry, Illinois, and in
                  September 2001 we opened Hoffman Estates Community Bank, a
                  branch of Barrington Bank. Additionally, in January 2002, we
                  opened a new branch of Hinsdale Bank in Riverside, Illinois,
                  and in May 2002 we will be opening a permanent facility for
                  our Wauconda, Illinois branch of Libertyville Bank & Trust and
                  a Highland Park branch of Lake Forest Bank. We also intend to
                  continue the formation of additional de novo banks in
                  attractive markets in and around the Chicago metropolitan
                  area. Our seventh separately chartered de novo bank was opened
                  in November 2000 as Northbrook Bank and Trust Company. In
                  addition, we intend to explore and consider potential
                  acquisitions of other community banks that are already
                  operating in desirable markets. We believe some banks may be
                  attracted to our commitment to local operational autonomy and


                                       5



                  may desire to provide their investors the liquidity that could
                  be offered by Wintrust's publicly traded stock.

         o        AUGMENTING THE LOAN PORTFOLIO WITH OUR SPECIALTY LENDING
                  NICHES TO ALLOW THE BANKS TO MORE FULLY UTILIZE THEIR LENDING
                  CAPACITY AND ADDING RELATED FINANCIAL SERVICES BUSINESSES TO
                  INCREASE FEE INCOME. Our specialty lending niches have
                  enhanced the profitability of our community banks by
                  optimizing their earning asset base and allowing them to
                  diversify their loan portfolios. Certain of our related
                  financial services businesses also contribute to higher fee
                  income, such as administrative service fees earned by Tricom
                  for payroll processing. We may pursue acquisitions or
                  development of additional specialty lending businesses engaged
                  in asset generation suitable for bank investment and/or
                  secondary market sales. We may also pursue acquisitions or
                  development of related financial services businesses to
                  augment fee income. Management intends to continue to explore
                  various commercial and consumer finance activities and to seek
                  attractive potential acquisition candidates. Acquisitions, if
                  any, could have a short-term dilutive effect on earnings per
                  share.

         o        GROWTH OF TRUST AND INVESTMENT SERVICES PROVIDED TO SMALL AND
                  MID-SIZED BUSINESSES AND AFFLUENT INDIVIDUALS. With the
                  formation of Wintrust Asset Management, we began to market
                  trust and investment services more aggressively to bank
                  customers in an effort to expand our market share and increase
                  our fee income. Our trust business segment was not yet
                  profitable in 2001, but our recent acquisition of the Wayne
                  Hummer Companies has significantly expanded our investment
                  services customer base and enables us to diversify our revenue
                  stream. We expect that higher brokerage and asset management
                  fees will allow us to increase noninterest income from 28% of
                  total net revenues in 2001 to approximately 40% in 2002. We
                  believe we can further expand our trust and investment
                  services business by marketing our newly expanded base of
                  brokerage and investment management products and services to
                  our banking clients while offering trust services and estate
                  planning products, as well as traditional banking services, to
                  brokerage and asset management clients.

         o        UTILIZING THE INTERNET AS A NEW DISTRIBUTION CHANNEL FOR BOTH
                  EXISTING AND FUTURE BANK PRODUCTS AND SERVICES. We maintain
                  community bank websites and a number of on-line financial
                  services, including on-line banking, bill pay and check
                  register, investment portfolio review, home mortgage
                  applications, a community calendar, links to key sites and
                  wireless access. We anticipate adding new products and
                  services in the future, and expect that the Internet will
                  become an increasingly important distribution channel for our
                  banks.


OFFICE LOCATION

         Our principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045-1951, and our telephone number is (847) 615-4096.


                                       6



                                  RISK FACTORS

         You should carefully consider the following risk factors before you
decide to buy our common stock. You should also consider the other information
in this prospectus, as well as the documents incorporated by reference in this
prospectus.

DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY.

         Our historical results have been 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. To expand into additional communities in and
around Chicago, we may undertake additional de novo bank formations or branch
openings. 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. Wintrust
Asset Management, which we formed on September 30, 1998, is not yet operating
profitably; however, each of our seven chartered banks and all other non-bank
subsidiaries are now 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 expect or than our
experience has shown.

WE MAY NOT BE ABLE TO SUCCESSFULLY IMPLEMENT OUR GROWTH STRATEGY.

         Although we have historically grown primarily through de novo bank
formations and the establishment of new branch offices, our strategic plan also
includes potential acquisitions of other financial institutions in attractive
markets, trust and investment management services companies such as our recent
acquisition of the Wayne Hummer Companies and specialty lending or related
financial services businesses that offer unique earning asset niches or fee
income. We may not be successful in implementing our strategy for any number of
reasons, many beyond our control, including the following:

         o        if we are unable to identify attractive markets, locations or
                  opportunities, including attracting the necessary management,
                  to expand in the future, whether through de novo bank
                  formations, the addition of branch facilities or through
                  acquisitions of other community banks, specialty financial
                  services companies or fee-based businesses;

         o        if potential acquisitions are not available on terms
                  acceptable or favorable to us;

         o        if we are unable to obtain the required regulatory approvals
                  for any proposed acquisitions; or

         o        if we are unable to successfully integrate, operate and manage
                  any business that we acquire, including the Wayne Hummer
                  Companies, so as to maintain or increase profitability.

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. Our ability to retain the executive officers of


                                       7



Wintrust and the current senior management teams of each of our banks, First
Insurance, Tricom, Wintrust Asset Management and the Wayne Hummer Companies,
will continue to be critical to the successful implementation of our strategies.
We have entered into employment contracts with four of our executive officers,
including Edward J. Wehmer, our President and Chief Executive Officer, David A.
Dykstra, our Senior Executive Vice President, Chief Operating Officer and Chief
Financial Officer, Robert F. Key, our Executive Vice President-Marketing, and
Lloyd M. Bowden, our Executive Vice President-Technology, as well as with
approximately 48 of these senior officers who we consider to be key employees.
It is also important as we grow to be able to attract and retain qualified
additional senior and middle management. We do not currently maintain key-man
life insurance policies. 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 losses that are inherent in the portfolio.
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 banks is more difficult, and therefore
the banks may be more susceptible to changes in 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 the existing portfolio 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.

         A significant portion of our assets are comprised of commercial
insurance premium finance receivables that we generate 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.

         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 risk management procedures and
controls will prevent losses from fraudulent activity. For example, in the third
quarter of 2000, we recorded a one-time $2.6 million (after-tax) charge in
connection with a series of fraudulent loan transactions perpetrated against
First Insurance by one independent insurance agency located in Florida. Although
we have recently 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.



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

         A significant portion of our loan portfolio consists of loans we make
in our specialty lending niches. In addition to our premium finance loans, we
engage in indirect auto lending, accounts receivable

                                       8


financing, mortgage broker warehouse lending, loans to condominium, homeowner
and community associations, and small aircraft lending.

         Our portfolio of automobile loans are originated indirectly through
unaffiliated automobile dealers located throughout the Chicago metropolitan
area. Although we actively monitor our dealer relationships and review the
dealers' documentation closely to access the ability of the ultimate borrowers
to repay the loans, because we are lending through third party originators, our
indirect auto portfolio may be relatively riskier than direct consumer lending.
Also, 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. 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
fraudulently engage in the conversion of funds through misuse or nonuse of the
lockbox or the creation of ghost payrolls, we may suffer losses. We are also
exposed to potential credit risk relating to the companies with which Tricom's
customers do business.

         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.


OUR ASSET MANAGEMENT AND BROKER-DEALER BUSINESSES MAY BE AFFECTED BY
FLUCTUATIONS IN THE TRADING VOLUME AND PRICE LEVELS OF SECURITIES AND WE MAY BE
ADVERSELY AFFECTED BY A DOWNTURN IN THE U.S. SECURITIES MARKET.

         The profitability of our brokerage and asset management subsidiaries
depends heavily on conditions in the financial markets and on economic
conditions generally, both domestically and abroad. Because a significant
portion of our revenue in these businesses is derived from commissions, margin
interest revenue and principal transactions, a decline in stock prices, trading
volumes or liquidity could significantly harm our profitability in that the
volume of trades we would execute for our clients and our customer margin
balances may decrease.

         Many factors outside our control may directly affect the securities and
investment management industries, in many cases in an adverse manner. These
include economic and political conditions, broad trends in business and finance,
currency values, market conditions, the availability and cost of short-term or
long-term funding and capital, and the credit capacity or perceived
creditworthiness of the securities industry in the marketplace.

WE ARE EXPOSED TO HEIGHTENED CREDIT RISK IN OUR BROKERAGE BUSINESS DURING MARKET
DOWNTURNS.

         Declines in the market value of securities can 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. We
often permit our brokerage clients to purchase securities on margin or, in other
words, to borrow a portion of the purchase price from us and collateralize the
loan with a set percentage of the securities. During steep declines in
securities prices, the value of the collateral securing margin


                                       9



purchases may drop below the amount of the purchaser's indebtedness. If a client
is unable to provide additional collateral for these loans, we may lose money on
these margin transactions. In addition, particularly during market downturns, we
may face additional expense defending or pursuing claims or litigation.

WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

         Our earnings are derived from the operations of our subsidiaries, and
we are principally dependent on net interest income, calculated as the
difference between interest earned on loans and investments and the interest
expense paid on deposits and other borrowings. Like other banks and financial
institutions, 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 the economic environment
may influence the growth rate of loans and deposits, the quality of the loan
portfolio and loan and deposit pricing. 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.

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. Our principal competitors include other commercial
banks, savings banks, savings and loan associations, mutual funds, money market
funds, finance companies, trust companies, insurers, leasing companies, credit
unions, mortgage companies, private issuers of debt obligations and suppliers of
other investment alternatives, such as securities firms. Many of our non-bank
competitors are not subject to the same degree of regulation as that imposed on
bank holding companies, federally insured banks and national or Illinois
chartered banks. As a result, such non-bank competitors have advantages over us
in providing certain services. In recent years, several major multi-bank holding
companies have entered or expanded in the Chicago metropolitan market.
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.

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. Recently enacted, proposed and future banking legislation and
regulations have had, will continue to have or may have a significant impact on
the financial services industry. Some of the legislative and regulatory changes
may increase our costs of doing business and, as a result, advantage our
competitors. Our asset management and brokerage businesses are also highly
regulated, and we could be adversely affected by applicable changes in
legislation and regulation.

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.
Although currently the economy in the area is favorable, adverse changes in the


                                       10



economy could reduce our growth rate, impair our ability to collect loans, and
generally affect our financial condition and results of operations.

FUTURE SALES OF OUR COMMON STOCK OR OTHER SECURITIES MAY DILUTE THE VALUE OF THE
COMMON STOCK.


         Our board of directors has the authority, without action or vote of the
shareholders, to issue all or part of any authorized but unissued shares of our
common stock, including shares authorized but unissued under our stock option
plan, shares that employees may purchase at their election pursuant to our
Employee Stock Purchase Plan and shares that may be issuable to our directors as
compensation for attendance at Board meetings pursuant to our Directors Deferred
Fee and Stock Plan. In the future, we expect to issue additional securities,
through public or private offerings, in order to raise additional capital to
support our growth. Any such issuance will dilute the percentage of ownership
interest of shareholders and may dilute the per share book value of the common
stock. In addition, option holders may exercise their options at a time when we
would otherwise be able to obtain additional equity capital on more favorable
terms.


OUR ABILITY TO PAY DIVIDENDS ON OUR COMMON STOCK IS LIMITED BY LAW AND CONTRACT.

         Our ability to pay dividends on our common stock largely depends on our
receipt of dividends from our banks. The amount of dividends that our banks may
pay to us is limited by federal and state banking laws and regulations. Because
we became registered as a financial holding company in connection with our
acquisition of the Wayne Hummer Companies, our banks are now required to
maintain capital sufficient to meet the "well-capitalized" standards set by the
regulators and will be able to pay dividends to us only so long as their capital
continues to exceed these levels. We or our banks may decide to limit the
payment of dividends even when we or they have the legal ability to pay them in
order to retain earnings for use in our or our banks' business. We are also
prohibited from paying dividends on our common stock if we have not made
distributions or required payments on our outstanding trust preferred securities
and debt securities.

THERE IS A LIMITED TRADING MARKET FOR OUR COMMON STOCK; YOU MAY NOT BE ABLE TO
RESELL YOUR SHARES AT OR ABOVE THE PRICE YOU PAY FOR THEM.

         The price of our shares of common stock subject to this offering may be
greater than the market price for our common stock following the offering. The
price of our common stock has been, and will likely continue to be, subject to
fluctuations based on, among other things, economic and market conditions for
financial services companies and the stock market in general, as well as changes
in investor perceptions of our company.


         Our common stock is traded on the Nasdaq National Market under the
symbol WTFC. The development and maintenance of an active public trading market
depends, however, upon the existence of willing buyers and sellers, the presence
of which is beyond our control or the control of any market maker. While we are
a publicly traded company, the volume of trading activity in our stock is
relatively limited. Even if a more active market develops, there can be no
assurance that such a market will continue, or that our shareholders will be
able to sell their shares at or above the offering price.



                                       11



                                 USE OF PROCEEDS

         We will not receive any of the proceeds from the sale of the shares of
common stock by the selling shareholders. We expect to incur expenses in
connection with this offering in the amount of approximately $30,000 for
registration, legal, accounting and miscellaneous fees and expenses. We will not
pay for expenses such as commissions and discounts of brokers, dealers or agents
or the fees and expenses of counsel, if any, for the selling shareholders. See
"Selling Shareholders" and "Plan of Distribution."


                 PRICE RANGE OF COMMON STOCK AND DIVIDEND POLICY


         Our common stock is traded on the Nasdaq National Market under the
symbol WTFC. The following table sets forth the high and low sales prices
reported on the Nasdaq National Market for our common stock for the periods
indicated and the semi-annual dividends paid by us during such periods. The
following information gives effect to a 3-for-2 stock split effective as of
March 14, 2002.





                                           HIGH         LOW         DIVIDEND
                                          ------       ------       --------
2002
----
                                                             
First Quarter.......................      $22.99       $18.33         $0.06
Second Quarter (through April 30)...      $26.15       $22.22            --

2001
----
First Quarter.......................      $12.75       $10.54         $0.0467
Second Quarter......................       17.62        11.67            --
Third Quarter.......................       21.41        16.27          0.0467
Fourth Quarter......................       22.13        17.93            --

2000
----
First Quarter.......................      $10.67       $ 8.92         $0.0333
Second Quarter......................       10.83         9.17            --
Third Quarter.......................       11.88        10.17          0.0333
Fourth Quarter......................       11.33        10.25            --




         As of April 30, 2002, there were 1,252 shareholders of record of our
common stock.


DIVIDEND POLICY

         In January 2000, our board of directors approved the payment of our
first semi-annual cash dividend on our common stock. We have continued to pay a
semi-annual cash dividend since that time. The final determination of timing,
amount and payment of dividends on our common stock is at the discretion of our
board of directors and will depend upon our profitability, financial condition,
capital requirements and other relevant factors, including the restrictions
described below.

         Because the principal source of our income at the holding company level
is dividends from our banks, our ability to pay dividends on common stock is
dependent on the banks' ability to pay dividends to us. The payment of dividends
by the banks is subject to certain restrictions imposed by federal and state
banking laws and regulations. During 2001 and 2000, our banks paid us dividends
of $13.5 million and $16.0 million, respectively. During 1999, the banks paid no
dividends. De novo banks are prohibited from paying dividends during the first
three years of operations. Currently, Northbrook Bank which began operations in
November 2000, is our only bank subject to this dividend restriction; this
restriction will lapse in November 2003.


                                       12



         Our ability to pay cash dividends on our common stock is also subject
to statutory restrictions and restrictions arising under the terms of our
outstanding and any future debt securities and trust preferred securities. The
terms of such securities generally restrict payment of dividends on common stock
until required payments and distributions are made on those securities and may
impose additional restrictions in the future. Under applicable corporate law, we
are permitted to pay dividends only to the extent of our shareholders' equity.
Federal regulation of bank holding companies may also impose restrictions on the
ability of a bank holding company to pay dividends. We do not believe that the
terms of our securities, applicable corporate law or applicable banking
regulation will materially inhibit our plans to pay cash dividends on our common
stock in the foreseeable future.


                              SELLING SHAREHOLDERS


         This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 912,734 shares of common
stock. We newly issued 762,734 of these shares to the selling shareholders in
February 2002 in payment of part of the $28 million purchase price in our
acquisition of the Wayne Hummer Companies. This prospectus also covers up to a
total of 150,000 additional shares that may be issuable to the selling
shareholders if they are eligible to receive additional purchase price amounts
that are contingent upon the future financial performance of the businesses
acquired. Because the issuance of the shares in that transaction was not
registered with the SEC, the selling shareholders have "restricted stock." All
of the selling shareholders were former owners of the Wayne Hummer Companies and
each of them, other than Messrs. Kahlfeldt and Rogers, is currently employed by
us, pursuant to an employment agreement entered into in connection with the
transaction, as part of our asset management and brokerage subsidiaries. Mr.
Kratzer, who holds the position of President and Chief Executive Officer of
Wayne Hummer Investments, also now serves as a member of our board of directors.
Messrs. Steven R. Becker, Kratzer and Wholey and Ms. Kogut serve as directors of
Wintrust Asset Management.


         We are registering the shares to enable the selling shareholders to
resell the shares in the public market from time to time or on a delayed basis
and to permit secondary trading of the shares after they are sold by the selling
shareholders. We are paying for the registration of such securities but will not
pay for the fees, commissions, and other similar expenses, if any, of the
selling shareholders, their attorneys or other representatives, as a result of
the sale of such securities by the selling shareholders. See "Use of Proceeds"
and "Plan of Distribution."


                                       13




         The following table sets forth, to the best of our knowledge,
information concerning the selling shareholders, the number of shares to be
offered and sold by the selling shareholders and the amount of common stock that
will be owned by the selling shareholders following the offering (assuming sale
of all shares of common stock being offered hereby).





                            NUMBER OF SHARES                           NUMBER OF SHARES    PERCENTAGE OF SHARES
                             OWNED PRIOR TO      NUMBER OF SHARES     TO BE OWNED AFTER     TO BE OWNED AFTER
 SELLING SHAREHOLDER            OFFERING         TO BE OFFERED(1)          OFFERING              OFFERING
----------------------      ----------------     ----------------    ------------------    --------------------
                                                                                        
H. Flagg Baum.........           27,802               27,802                 --                     *
George T. Becker......           45,618               45,618                 --                     *
Linda C. Becker.......           40,027               40,027                 --                     *
Steven R. Becker......           49,867               49,867                 --                     *
Philip M. Bruno.......           26,908               26,908                 --                     *
W. Douglas Carroll....           50,836               50,836                 --                     *
Peder H. Culver.......           17,143               17,143                 --                     *
Mark H. Dierkes.......            7,453                7,453                 --                     *
Daniel G. Hack........           25,269               25,269                 --                     *
Philip W. Hummer......           48,078               48,078                 --                     *
William B. Hummer.....           41,965               41,965                 --                     *
Laura A. Kogut........           34,138               34,138                 --                     *
Richard J. Kosarek....           34,735               34,735                 --                     *
Raymond L. Kratzer....           51,880               51,880                 --                     *
Philip Scott Park.....           11,181               11,181                 --                     *
Joseph A. Piekarczyk..           39,432               39,432                 --                     *
David P. Poitras......           25,194               25,194                 --                     *
Thomas J. Rowland.....           30,114               30,114                 --                     *
Floyd E. Siegel.......           29,815               29,815                 --                     *
Ronald A. Tyrpin......           25,342               25,342                 --                     *
Laurence H. Weisz.....           23,851               23,851                 --                     *
Richard Wholey, Jr....           39,580               39,580                 --                     *
Jean E. Williams......           19,156               19,156                 --                     *
Robert F. Kahlfeldt...            2,922                2,922                 --                     *
William A. Rogers.....           14,428               14,428                 --                     *
   Total..............          762,734              762,734                 --                     *

-------------------
*        Less than 1%
(1)      This prospectus also covers up to a total of 150,000 additional shares
         that may be issuable to the selling shareholders if they are eligible
         to receive additional purchase price amounts that are contingent upon
         the future financial performance of the businesses acquired.






                                       14



                              PLAN OF DISTRIBUTION

         The common stock offered by this prospectus may be offered and sold
from time to time by the selling shareholders. As used in this prospectus,
"selling shareholders" includes those individuals or entities who may have had
shares of common stock given to them as a gift by a named selling shareholder
after the date of this prospectus and any individuals or entities who may have
shares of common stock pledged to them as collateral by a named selling
shareholder after the date of this prospectus. See "Selling Shareholders." The
shares of common stock covered by this prospectus may be sold, from time to
time, by the selling shareholders in one or more types of transactions (which
may include block transactions) on Nasdaq, in the over-the-counter market, in
negotiated transactions, through put or call options transactions relating to
the shares of common stock, through short sales of shares of common stock, or a
combination of such methods of sale, or otherwise at prices and at terms then
prevailing or at prices related to the then-current market price, or in
negotiated transactions. The shares of common stock may be sold by one or more
of the following methods: (a) a block trade in which the broker or dealer so
engaged will attempt to sell the shares of common stock as agent but may
position and resell a portion of the block as principal in order to facilitate
the transaction; (b) a purchase by a broker or dealer as principal, and the
resale by such broker or dealer for its account pursuant to this prospectus,
including resale to another broker or dealer; or (c) ordinary brokerage
transactions and transactions in which the broker solicits purchasers. Thus, the
period of distribution of these shares of common stock may occur over an
extended period of time.

         The selling shareholders may effect such transactions by selling the
shares of common stock directly to purchasers or to or through a broker or
dealer, who may act as an agent or principal. Such broker or dealer may receive
compensation in the form of discounts, concessions, or commissions from the
selling shareholders and/or the purchasers of shares of common stock for whom
such broker or dealer may act as agent or to whom he sells as principal, or both
(which compensation as to a particular broker or dealer might be in excess of
customary commissions). We know of no existing agreements, understandings or
arrangements between any selling shareholder, broker, dealer, underwriter or
agent relating to the sale or distribution of the shares of common stock.

         The selling shareholders will not pay any of the proceeds from the sale
of the shares of common stock to us. We expect to incur expenses in connection
with this offering in the amount of approximately $30,000 for registration,
legal, accounting and miscellaneous fees and expenses. The selling shareholders
will be solely responsible for commissions and discounts of brokers, dealers or
agents, other selling expenses and the fees and expenses of their own counsel,
if any, none of which will be borne by us.

         In offering the securities, the selling shareholders and any
broker-dealers and any other participating broker-dealers who execute sales for
the selling shareholders may be deemed to be "underwriters" within the meaning
of Section 2(11) of the Securities Act of 1933 in connection with such sales,
and any profits realized by the selling shareholders and the compensation of
such broker-dealers may be deemed to be underwriting discounts and commissions.
In addition, any shares covered by this prospectus which qualify for sale
pursuant to Rule 144 may be sold under Rule 144 rather than pursuant to this
prospectus. Also, if we are notified by a selling shareholder that a donee or
pledgee intends to sell more than 500 shares, a supplement to this prospectus
will be filed naming any donee or pledgee offering the shares before such a sale
is permissible under this prospectus.

         We have informed the selling shareholders that while they are selling
the securities, they (1) are required to comply with Regulation M under the
Securities Exchange Act of 1934 (as described in more detail below), (2) may not
engage in any stabilization activity, except as permitted under the Exchange
Act, (3) are required to furnish each broker-dealer (who may offer this common
stock) copies of this


                                       15



prospectus, and (4) may not bid for or purchase any securities of Wintrust or
attempt to induce any person to purchase any such securities except as permitted
under the Exchange Act.

         Regulation M under the Exchange Act prohibits, with certain exceptions,
participants in a distribution from bidding for or purchasing, for an account in
which the participant has a beneficial interest, any of the securities that are
the subject of the distribution. Regulation M also governs bids and purchases
made in order to stabilize the price of a security in connection with a
distribution of the security.


                                 TRANSFER AGENT

         The transfer agent for our common stock is Illinois Stock Transfer
Company, 209 West Jackson Boulevard, Suite 903, Chicago, Illinois 60606.


                                  LEGAL MATTERS

         Certain legal matters relating to the common stock offered by this
prospectus have been passed upon for us by Vedder, Price, Kaufman & Kammholz,
Chicago, Illinois.


                                     EXPERTS


         Our consolidated financial statements incorporated by reference in our
Annual Report on Form 10-K for the year ended December 31, 2001, have been
audited by Ernst & Young LLP, independent auditors, as set forth in their report
thereon incorporated by reference in our Annual Report and in this prospectus.
These consolidated financial statements are incorporated by reference in this
prospectus in reliance upon the report given on the authority of Ernst & Young
LLP 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.

         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.


                                       16



                       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 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, 2001, filed with the SEC on April 1, 2002 (File
                  No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on February
                  8, 2002 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on February
                  22, 2002 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 3,
                  2002 (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 share 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.


         You may request, either orally or in writing, and we will provide, a
copy of these filings at no cost by contacting David A. Dykstra, our Chief
Financial Officer, at the following address and phone number:


         Wintrust Financial Corporation
         727 North Bank Lane
         Lake Forest, Illinois 60045-1951
         (847) 615-4096


                                       17



                                     PART II
                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION

         The following table sets forth the various expenses payable in
connection with the sale and distribution of the securities being registered,
other than underwriting discounts and commissions. All of the amounts shown are
estimates, except for the SEC registration fee. We do not expect our expenses in
connection with this offering to exceed $30,000.




                                                         
         SEC registration fee...........................    $ 1,815
         Legal fees and expenses........................     15,000
         Accounting fees and expenses...................      7,500
         Miscellaneous..................................      5,685
            Total.......................................    $30,000



ITEM 15.  INDEMNIFICATION OF DIRECTORS AND OFFICERS

         Insofar as indemnification for liabilities arising under the Securities
Act may be permitted to directors, officers, and controlling persons of Wintrust
pursuant to the following provisions, or otherwise, we have been advised that in
the opinion of the Securities and Exchange Commission such indemnification is
against public policy as expressed in the Securities Act and is, therefore,
unenforceable.

         In accordance with the Illinois Business Corporation Act (being Chapter
805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of the
Registrant's Certificate 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


                                      II-1



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, 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:


                                      II-2



         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 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


                                      II-3



         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 attorney's 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 attorney's fees) incurred by 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.


                                      II-4



                  (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 $20 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, Wintrust maintains
fiduciary liability coverage up to a $2 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 16.  EXHIBITS

  3.1    Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

  3.2    Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

  3.3    Amended By-laws of Wintrust Financial Corporation (incorporated by
         reference to Exhibit 3(i) of the Company's Form 10-Q for the quarter
         ended June 30, 1998).

  4.1    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 the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

  4.2    Certain instruments defining the rights of holders of long-term debt of
         the Company and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         the Company and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. The Company hereby agrees to furnish a copy of any
         of these agreements to the Commission upon request.

  5.1    Opinion of Vedder, Price, Kaufman & Kammholz regarding legality.*

  23.1   Consent of Ernst & Young LLP.*

  23.2   Consent of  Vedder, Price, Kaufman & Kammholz (included in opinion
         filed as Exhibit 5.1).

  24.1   Power of Attorney (included on signature page of registration
         statement).

-------------------
*        Filed herewith.

ITEM 17.  UNDERTAKINGS

         (a)      We 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


                                      II-5



Securities Exchange Act of 1934 that is incorporated by reference in this
registration statement shall be deemed to be a new registration statement
relating to the securities offered herein, and the offering of such securities
at that time shall be deemed to be the initial bona fide offering thereof.

         (b)      Insofar as indemnification for liabilities arising under the
Securities Act of 1933 may be permitted to directors, officers and controlling
persons of the registrant pursuant to the foregoing provisions, or otherwise,
the registrant has 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
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant 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 registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Act and will
be governed by the final adjudication of such issue.


                                      II-6



                                   SIGNATURES


         Pursuant to the requirements of the Securities Act of 1933, as amended,
the registrant 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 this 7th day
of May, 2002.


                                       WINTRUST FINANCIAL CORPORATION


                                       By: /s/  Edward J. Wehmer
                                           -------------------------------------
                                           Edward J. Wehmer
                                           President and Chief Executive Officer


          Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons on the 7th day
of May, 2002 in the capacities indicated.



          SIGNATURE                                        TITLE
          ---------                                        -----


/s/ Edward J. Wehmer                            President and Chief Executive
------------------------------                      Officer and Director
       Edward J. Wehmer


/s/ David A. Dykstra                           Senior Executive Vice President
------------------------------                   and Chief Operating Officer;
       David A. Dykstra                            Chief Financial Officer


/s/ Barbara A. Kilian                               Senior Vice President
------------------------------                  (Principal Accounting Officer)
       Barbara A. Kilian


/s/ John S. Lillard*
------------------------------                      Chairman and Director
        John S. Lillard


/s/ Joseph Alaimo*
------------------------------                            Director
         Joseph Alaimo


/s/ Peter D. Crist*
------------------------------                            Director
       Peter D. Crist


/s/ Bruce K. Crowther*
------------------------------                            Director
       Bruce K. Crowther


/s/ Bert A. Getz, Jr.*
------------------------------                            Director
       Bert A. Getz, Jr.


/s/ William C. Graft*
------------------------------                            Director
       William C. Graft


/s/ Kathleen R. Horne*
------------------------------                            Director
       Kathleen R. Horne


                                       S-1



          SIGNATURE                                        TITLE
          ---------                                        -----


/s/ Raymond L. Kratzer*
------------------------------                            Director
       Raymond L. Kratzer


/s/ James B. McCarthy*
------------------------------                            Director
       James B. McCarthy


/s/ Marguerite Savard McKenna*
------------------------------                            Director
   Marguerite Savard McKenna


/s/ Albin F. Moschner*
------------------------------                            Director
      Albin F. Moschner


/s/ Dorothy M. Mueller*
------------------------------                            Director
       Dorothy M. Mueller


/s/ Thomas J. Neis*
------------------------------                            Director
       Thomas J. Neis


/s/ Christopher J. Perry*
------------------------------                            Director
      Christopher J. Perry


/s/ Hollis W. Rademacher*
------------------------------                            Director
     Hollis W. Rademacher



------------------------------                            Director
    Penelope J. Randel


/s/ J. Christopher Reyes*
------------------------------                            Director
    J. Christopher Reyes


/s/ Peter Rusin*
------------------------------                            Director
         Peter Rusin


/s/ John N. Schaper*
------------------------------                            Director
       John N. Schaper


/s/ John J. Schornack*
------------------------------                            Director
       John J. Schornack


/s/ Ingrid S. Stafford*
------------------------------                            Director
      Ingrid S. Stafford


/s/ Katharine V. Sylvester*
------------------------------                            Director
    Katharine V. Sylvester


/s/ Larry Wright*
------------------------------                            Director
        Larry Wright

                                      S-2




*By: /s/ David A. Dykstra
     -------------------------
          David A. Dykstra
          Power of Attorney

                                      S-3







                                  EXHIBIT LIST

  3.1    Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

  3.2    Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

  3.3    Amended By-laws of Wintrust Financial Corporation (incorporated by
         reference to Exhibit 3(i) of the Company's Form 10-Q for the quarter
         ended June 30, 1998).

  4.1    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 the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

  4.2    Certain instruments defining the rights of holders of long-term debt of
         the Company and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         the Company and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. The Company hereby agrees to furnish a copy of any
         of these agreements to the Commission upon request.

  5.1    Opinion of Vedder, Price, Kaufman & Kammholz regarding legality.*

  23.1   Consent of Ernst & Young LLP.*

  23.2   Consent of  Vedder, Price, Kaufman & Kammholz (included in opinion
         filed as Exhibit 5.1).

  24.1   Power of Attorney (included on signature page of registration
         statement).

-------------------
*        Filed herewith.