Dig Chi Town
Make sure you give yourself enough time in Chicago because there is so much to see and do(and good food to eat) in this town. The Navy Pier was a surprise for me; a real carnival atmosphere without the sleeze. Millennium Park and the Chicago Institute of Art are absolutely brilliant.
Insider Tip:The Ferris Wheel at The Navy Pier is awesome just on sunset; the view of the city (and the odd sailor) is amazing. And the street art in Pilsen is worth the walk/trip on the metro. Avoid the franchise Italian restuarants! There are plenty of groovy little cafes and bars in Chicago.