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Well 1st of all, stop in Madison for Bratfest (its a lot bigger than you'd think... 20,000 people).
After that, Chicago has a lot to offer. Bradford hit on some good ones... here are a few more specifics.
Sears Tower Skydeck (no I don't call it by its new name, nobody in town does)
Art Museum
Field Museum
Shedd Aquarium
Shopping on Michigan Ave.
Second City Theater/Comedy
I highly recommend the Architecture tour on the river, love going on that one.
If you like really expensive views with food try the Signature Room/Lounge on the 95th floor of the Handcock building. If you like the best pizza in the city (besides Lou Malnati's) go to Pizzeria Uno on Ohio, still using the original oven!
If you're driving in the city make sure you do a trip on Lake Shore Drive and also one on Lower Wacker... lots of fun down there, just like in the newer Batman movies.
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