I live in Minnesota, that being said I've spent a great deal of time in Wisconsin and I think the entire northern midwest is a beautiful area to live in, too bad Canada isn't closer! Cheaper, better green The nature and things you can do all season such as going out on the lake soild or liquid, the vast country sides around most cities are amazing.

Madison is a cool little town, but it is as long as it is wide, I've never stayed anywhere outside of girlfriends dorms. Milwaukee is supposed to be pretty chill to and it isn't too far away from Chicago in retrospect either... But you're already leaning towards MA so...