The aquarium is cool (and I think they just expanded it!) - of course you have to go to the cubby bear after the game
Rush street for a night out! (lots and lots of cool places there!)
Blue man group? Very cool - been twice..
Hmmmm, Art museum (see ferris bueller for more info, lol), Michigan avenue (window shopping, lol), the zoo downtown, rent some bikes or rollerblades and go along the lakeshore. Check out Navy Pier, boat cruise around the city...
all kinds of stuff
Lots of cool small restaraunts around!