I think there is a lot of good insight in the replies above. It definitely depends on personal preference, as well as financial availability. I wouldn’t mind living in either Madison or Milwaukee, and of course Minneapolis and Chicago are good nearby options as well. Like someone stated above, IE is a pretty versatile field.
Chicago is my hopeful destination. It has everything I could want. Close enough to Wisco to frequently visit Madison and home. A great food and nightlife scene. Great young professional neighborhoods. It can also be a great place to fast track your career.
Coming from the Midwest I hope to stay in one of the four larger cities around here (Chicago, Milwaukee, Madison, Minneapolis), but it will differ for everybody. The industry you are interested in can have a great influence, as tech, healthcare, manufacturing, etc., may have certain cities with more opportunities. What I have found through searching for opportunities and talking to industry professionals is that most large cities have something to offer for all industries, which is good to hear!