Exhibit 5.1

VEDDER PRICE                             VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.
                                         222 NORTH LASALLE STREET
                                         CHICAGO, ILLINOIS 60601-1003
                                         312-609-7500
                                         FACSIMILE: 312-609-5005


                                         October 26, 2004


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

Ladies and Gentlemen:

         Reference is hereby made to the Registration Statement on Form S-8 (the
"Registration Statement") being filed with the Securities and Exchange
Commission by Wintrust Financial Corporation, an Illinois corporation (the
"Company"), relating to the registration of 94,177 shares of the Company's
common stock, no par value per share (the "Common Stock"), that may be issued
upon exercise of options previously granted by Town Bankshares, Ltd., a
Wisconsin corporation ("Town Bankshares"), to employees or directors pursuant to
the Town Bankshares, Ltd. 1997 Stock Incentive Plan, as amended (the "Town
Bankshares Plan"). Town Bankshares was merged with and into the Company,
effective October 15, 2004. We have acted as counsel for the Company in
connection with this Registration Statement.

         In connection with our opinion, we have examined originals, or copies
certified or otherwise identified to our satisfaction, of (i) the Registration
Statement, (ii) the Amended and Restated Articles of Incorporation of the
Company, (iii) the Amended and Restated Bylaws of the Company, and (iv) such
other corporate records, documents and other papers as we deemed necessary to
examine for purposes of this opinion. We have assumed the authenticity, accuracy
and completeness of all documents submitted to us as originals, the conformity
to authentic original documents of all documents submitted to us as certified,
conformed or photostatic copies and the genuineness of all signatures.

         Based upon the foregoing and the number of shares of Common Stock
issued and outstanding as of the date hereof, it is our opinion that the 94,177
shares of Common Stock of the Company, when issued in accordance with the terms
of the Town Bankshares Plan, will be validly issued, fully paid and
nonassessable.



         The opinion expressed herein is based on the facts in existence and the
laws in effect on the date hereof and is limited to the Federal securities laws
and the laws of the State of Illinois currently in effect.

         We hereby consent to the use of this opinion in connection with said
Registration Statement and to the references to our firm therein.

                                     Very truly yours,

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