Hi. I travelled there in the fall, a while back (some years). Chicago is the birth place of the modern skyscraper, and so there is a really good tour of modern architecture that you can do. It's also the hometown of Frank Lloyd Wright, and so you can visit Frank Lloyd Wright house at the Uni. of Chicago campus (a huge neo-gothic campus). Also, deep dish pizza and shopping (USA shopping is always a big draw, as far as I'm concerned!). It's not called "the windy city" for nothing, however! (Bring warm clothes, esp. in November).