I've probably posted this stuff before, but here are a few thoughts:
Touristy stuff:
- Navy pier is kind of lame - a big shopping center w/o much to do
- Art Institute is good
- Of the museums, science & industry was my favorite if you can still do the submarine tour
- Field museum is pretty standard
- Shedd Aquarium is good if you've never been to a large aquarium
Nightlife:
- Wrigleyville: young, lots of nightlife near wrigley field
- Lincoln Park: plenty of cool places near Depaul university
- Rush & Division area: less interesting IMO - more touristy
All of these areas areas are a good start because there are dozens of bars nearby which you can wander between.
Food:
- Steak: Chicago Chop House
- Pizza: Giordano's or Lou Malnatis
- Signature Room @ John Hancock for a good view
Summer is a great time there - check out North Beach, etc.
Good resources:
www.metromix.com
www.chicagobarproject.com