Man.. There's a ton to see. Michigan Ave, the Lakefront, Sears tower, Hancock.. Hit the bars on rush and in Lincoln Park. You might want to head over to Bucktown and see where they filmed the Real World in Chicago. There's the museums, you could check out the house that Jordan built (The United Center on the west side). Soldier Field and definitely Navy Pier...
How long are you going to stay? When are you coming? What sort of hotel budget do you have? What are your interests other than sports? There's a ton to see. Also, It's not cheap to stay right downtown Chicago. You might be better off booking a sleep cheap on the outskirts and then driving in each day. Depends on your budget. Just to let you know, a friend of mine got married recently and his brother came in town and got a room right down in the loop. It was a very nice place, but nothing extravagant. Beautiful view of the mag mile (Michigan Ave). It cost him $250 a night. In your ball park? I don't think you'll be able to touch a room downtown for under $100.
Give me some more information and maybe I can help you out.
BTW.. I used to live in a suburb of Detroit. Actually, I grew up in Plymouth, Michigan. I used to head to Detroit quite a bit because my neighbors had a boat at the DYC. We'd go down for the hydroplane races every year, hit the CART race at Belle Isle and I was even at a few of the GP races back when they had them in Detroit back in the early 80's. Hope that doesn't date me too much. 😉 Going to Trappers Alley was always fun. Been to Cobo for many events including the auto show. Tiger Stadium when they won the World Series in '84. Silverdome in Pontiac for the Bears vs Lions on Tgiving. Don't forget the Pistons winning back to back championships in the late 80's. Mt. Brighton (featured in the movie Aspen Extreme) for weekday skiing and then Boyne and Nubs Knob (nice bumps) for the weekends in the winter. Oh.. There were always those trips over to Windsor Ontario to drink (and bring back) the 6% Canadian beer when we were still under 21. 😉 Memories... 🙂
Anyway... Heh.
Sal