St. Louis is nice, smaller than Chicago, but you have all four seasons, a nice mix of restaurants, historic and culture-defined neighborhoods, and wineries 25 minutes away. Good shopping, the loft district, and good sports. Not too much cold/snow in the winter but some, and summers are tolerable. Fall and spring are very well defined. You are also more centralized in the U.S.
Ann Arbor, Mich., looks nice ... but I have never been
http://money.cnn.com/best/bplive/details/ANNAR_MI.html