Last month Nick and I took a quick trip to Chicago on our way to South Dakota. We had two and a half days to do everything we could.
It snowed for most of our trip, which worked out great since it was empty everywhere we went.
We visited both the Field Museum and the Art Museum (I preferred the Field Museum)
We cocktailed at the John Hancock, went to a Second City Show, walked the Magnificent Mile, rode the Ferris Wheel and managed to eat deep-dish pizza, Chicago dogs, and beef sandwiches! I think a spring or summer trip may be in order in the future!