Hey, I was just there!
I had a great time in Chicago. If you're looking for a great steakhouse I can highly recommend Gibsons steakhouse.
Gibsons Steakhouse
The food was great and the portions huge. See if you can save room for desert, I'm betting you won't!

The big advantage to Gibsons is it's smackdab downtown on Rush St which is a good street to walk down during the evening.
If you're staying downtown I also recommend jumping in a cab and take a 10 minute ride to VIP's gentlemen's club. Because of the law, they can't have complete nudity where alcohol is served so the dancers come out wearing small pieces of latex taped to their nipples

. They offer $20 lap dances and you can use your corporate credit card to buy VIP dollars. The visa statement says the charge is to Chicago Food & Beverage Company

. Most of the dancers were hot! I would guess that the mileage was low, but didn't really try since I was with coworkers.
If you're a baseball fan, I highly recommend going to Wrigley, especially if it's a day game. The atmosphere is amazing. Get there a couple of hours before the game and take in the bars in the area, like Cubby Bear.
Have a great time, hope this helps a little.
- HAW