Yes, I forgot to add that. Chicago has spectacular public transit. The subway/l-train will take you just about anywhere. You should just be able to leave the car at your hotel/whatnot and walk and take the train everywhere else.
Two more big tourist attractions that are still fun are the Miracle Mile and the Sears Tower. They've put a nice museum type thing on top of the Sears Tower now that has both the history of the building and a little bit about the history of Chicago. If you're not too squeamish about heights, they've recently added glass skyboxes to the top floor. It's literally a little cube of glass that extends about four feet out from the building, glass roof, glass floor, glass walls. It's pretty crazy to stand 1300 feet above the ground with just a glass floor underneath you. If you do that I would suggest going on a clear day, with good visibility you can see for miles and miles and miles. If I recall you can see 5 states from there.
Miracle mile has just about every store you can imagine, it's cool to just walk around. I don't know if you or Matt are into cars much, but Gold Coast Bentley is on the Miracle Mile. They usually have at least one Bugatti Veyron out front, plus a couple dozen Ferraris, Lamborghinis, Bentleys, Porsches, and other exotic cars.
I just called my buddy, and he said he'll have to think about restaurants over the next few days, but off the top of his head, he suggested; Tach Quick Thai, Rico Bene's, Grand Lux Cafe on Michigan Ave, Pizzeria Uno, Pizzeria Due. Those are all pretty much staple restaurants in town, and are really well known. I can also say from experience they're quite tasty
He'll be updating me over the next couple days I'm sure as he thinks of places that are a bit more off the beaten path and whatnot. Suffice to say, you won't be bored