Go to Chicago twice a year...Here are my favorites:
Gino's East- The original on Rush. Best pizza in town...hands down!
Go to ESPN zone..Pretty cool spot to check out
Wrigley field is the bomb..but if you can't make the game go to the Cubby Bear...Good times there
Ron of Japan is a great restaurant (Teppan Grill) right of Magnificent Mile (michigan Ave)
Lincoln Park area (college town) lots of bars and drinks....
If you are into Clubbing go to Crobar. They also have a club in South Beach and in New York! All the clubs are great...Really like the one in South Beach!
Red Head Piano Bar is really cool for drinks and a piano bar atmosphere so is Howl on the moon.
Rush and Division is a tourist trap..but they have super good food and beer and music. Any other ???'s just PM.!