The Directors and Officers of

Wintrust  Financial  Corporation
cordially invite you to attend our
2002 Annual Meeting of Shareholders
Thursday,  May 23, 2002, 10:00 a.m.
Hyatt-Deerfield
1750 Lake Cook Road
Deerfield, Illinois


   YOU CAN VOTE IN ONE OF THREE WAYS: 1) BY MAIL, 2) BY PHONE, 3) BY INTERNET.
              See the reverse side of this sheet for instructions.


IF YOU ARE NOT VOTING BY TELEPHONE OR BY  INTERNET,  COMPLETE  BOTH SIDES OF THE
           ---
        PROXY CARD, DETACH HERE AND RETURN IN THE ENCLOSED ENVELOPE TO:

                           Illinois Stock Transfer Co.
                      209 West Jackson Boulevard, Suite 903
                             Chicago, Illinois 60606


                                   IMPORTANT
                                   ---------
           Please complete both sides of the PROXY CARD, sign, date,
                  detach and return in the enclosed envelope.

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THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF  DIRECTORS.  IF NOT  OTHERWISE
SPECIFIED ON THE REVERSE SIDE,  THIS PROXY WILL BE VOTED FOR ALL NOMINEES LISTED
AND FOR PROPOSAL 2. THE UNDERSIGNED REVOKES ALL PROXIES HERETOFORE GIVEN TO VOTE
AT SUCH MEETING AND ALL ADJOURNMENTS OR POSTPONEMENTS.






Dated _____________________

___________________________

___________________________
(Please sign here)


Please sign your name as it appears above. If executed by a corporation,  a duly
authorized officer should sign. Executors, administrators,  attorneys, guardians
and trustees  should so indicate  when signing.  If shares are held jointly,  at
least one holder must sign.

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

Wintrust Financial Corporation

If you  personally  plan to attend the Annual  Meeting of  Shareholders,  please
check the box below and list the names of attendees on reverse side.

Return this stub in the enclosed envelope with your completed proxy card.


I/We do plan to attend
the 2002 meeting         ________




                                 TO VOTE BY MAIL

To vote by mail, complete both sides, sign and date the proxy card below. Detach
the card below and return it in the envelope provided.

                              TO VOTE BY TELEPHONE

Your telephone vote is quick, confidential and immediate. Just follow these easy
steps:

1. Read the accompanying Proxy Statement.
2. Using a Touch-Tone  telephone,  call Toll Free  1-800-555-8140 and follow the
instructions.
3. When asked for your Voter Control Number, enter the number printed just above
your name on the front of the proxy card below.  Please note that all votes cast
by telephone must be submitted prior to Monday,  May 20, 2002 at 11:59pm Central
Time.  Your telephone  vote  authorizes the named proxies to vote your shares to
the same extent as if you marked, signed, dated and returned the proxy card.

      If You Vote By TELEPHONE Please Do Not Return Your Proxy Card By Mail

                               TO VOTE BY INTERNET

Your  internet  vote  is  quick,  confidential  and  your  vote  is  immediately
submitted. Just follow the se easy steps:

1. Read the accompanying Proxy Statement.

2. Visit our Internet  voting Site at  HTTP://WWW.EPROXYVOTE.COM/IST-WFCCM/  and
follow the instructions on the screen.

3. When prompted for your Voter Control  Number,  enter the number  printed just
above your name on the front of the proxy card.  Please note that all votes cast
by internet must be submitted  prior to Monday,  May 20, 2002 at 11:59pm Central
Time. Your Internet vote authorizes the named proxies to vote your shares to the
same extent as if you marked, signed, dated and returned the proxy card.

THIS IS A "SECURED" WEB PAGE SITE. YOUR SOFTWARE  AND/OR INTERNET  PROVIDER MUST
BE ENABLED TO ACCESS THIS SITE.  PLEASE CALL YOUR SOFTWARE OR INTERNET  PROVIDER
FOR FURTHER INFORMATION.

      If You Vote By Internet, Please Do Not Return Your Proxy Card By Mail

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Wintrust Financial Corporation
REVOCABLE PROXY

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

The undersigned  hereby appoints John S. Lillard and Edward J. Wehmer and either
of them as Proxies,  each with the power to appoint his  substitute,  and hereby
authorizes  each them to represent  and to vote, as  designated  below,  all the
shares of Common Stock of Wintrust  Financial  Corporation which the undersigned
is entitled to vote at the Annual Meeting of  Shareholders to be held on May 23,
2002 or any  adjournment  thereof.  If any other  business is  presented  at the
Annual Meeting, including whether or not to adjourn the meeting, this proxy will
be voted,  to the extent  legally  permissable,  by those named in this proxy in
their best judgement.

      PROPOSAL 1 -  ELECTION  OF  DIRECTORS  (To  be  designated  as  Class  III
                   Directors with term ending in 2005.)
                   [   ]    FOR ALL NOMINEES LISTED BELOW
                            (Except as marked to the contrary below).

                   [   ]    WITHHOLD AUTHORITY to vote for all nominees below.
                            (INSTRUCTIONS: TO WITHHOLD AUTHORITY TO VOTE FOR
                            ANY INDIVIDUAL NOMINEE, STRIKE A LINE THROUGH THE
                            NOMINEE'S NAME).

        01   Joseph Alaimo                      05   Hollis W. Rademacher
        02   Peter D. Crist                     06   John N. Schaper
        03   Philip W. Hummer                   07   John J. Schornack
        04   John S. Lillard                    08   Larry V. Wright


     PROPOSAL 2 - APPROVAL OF AMENDMENT TO THE 1997 STOCK INCENTIVE PLAN, AS
                  DESCRIBED IN THE PROXY STATEMENT.

                  [   ] FOR   [   ] AGAINST   [   ] ABSTAIN


                        (To be signed on the other side)