Exhibit 5.1

VEDDER PRICE                          VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.
                                      222 NORTH LASALLE STREET
                                      CHICAGO, ILLINOIS 60601
                                      312-609-7500
                                      FACSIMILE: 312-609-5005

                                      OFFICES IN CHICAGO, NEW YORK CITY
                                      AND LIVINGSTON, NEW JERSEY




                                      October 24, 2003



Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, IL  60045

Ladies and Gentlemen:

         Reference is hereby made to the Form S-4 Registration Statement (the
"Registration Statement") being filed by Wintrust Financial Corporation, an
Illinois corporation ("Wintrust"), relating to the registration of up to 360,000
shares of Wintrust common stock, no par value, that may be issued to
stockholders of Village Bancorp, Inc., an Illinois corporation ("Village"). Such
shares are to be issued in exchange for shares of Village common stock, par
value $0.01 per share, pursuant to the proposed merger (the "Merger") of Village
with Wintrust in accordance with the terms and conditions of that certain
Agreement and Plan of Merger dated as of August 7, 2003 by and among Wintrust,
WTFC Merger Co., and Village (the "Merger Agreement").

         In rendering this opinion, we have examined such documents and
materials, including the Amended and Restated Articles of Incorporation and the
Amended and Restated By-laws of Wintrust, and other corporate documents and
records of Wintrust, as we have deemed necessary for the purpose of providing
this opinion.

         On the basis of the foregoing, it is our opinion that such shares of
Wintrust common stock, if and when issued to Village stockholders in accordance
with and pursuant to the Merger Agreement, will be validly issued, fully paid
and nonassessable.

         We hereby consent to the filing of this opinion as part of the
Registration Statement and to the reference of our name under the heading "Legal
Matters" in the proxy statement/prospectus included therein.

                                     Very truly yours,

                                     /s/ VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.