Chicago is pretty fun. When I was there I went to bunch of Jazz Restaurants/Clubs, hung by the Pier, fuck around etc etc . One of the funnest places to go with friends.
As for me I'm planning to go on a cruise but I haven't decided when and where yet. If not I'll probably just stay home the whole time. I've been wanting to go back to SoCal and NY recently though, they're nice places to visit.