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

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


                                      July 29, 2004


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 657,000
shares of Wintrust common stock, no par value, that may be issued to
shareholders of Northview Financial Corporation, an Illinois corporation
("Northview"). Such shares are to be issued in exchange for shares of Northview
common stock, par value $1.00 per share, pursuant to the proposed merger (the
"Merger") of Northview with Wintrust in accordance with the terms and conditions
of that certain Agreement and Plan of Merger dated as of May 10, 2004 by and
between Wintrust and Northview (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 Northview shareholders 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.