Watch Ferris Bueler's Day Off before you go to Chicago - it's a good guide, actually. Every carnivore needs to go to one of Chicago's amazing steakhouses. If you go to the House of Blues, then go to Smith and Wollensky, which is next door. Ask the folks there if you can see the dry-aging room - it really is a spectacle. Gibson's is another great steakhouse. To the person who mentioned Weiners Circle, I think that's a brilliant recommendation - Conne would definitely get a kick out of that place. I second the recommendations of Charlie Trotters and Tru. I would lean towards Trotters for a visitor since it is an American icon of restaurants. For entertainment, I recommend Buddy Guy's Legends and Kingston Mines for music.