Ditto on Make'n Music.
Glen, this may be your forum, but calling Chicago pizza bad is like calling the Pope'e mother some very bad names and can get you some nasty phone calls at weird times of the night.
That said, Chicago Pizza:
Ginos East good, a tad touristy, but a well known shop. People will tell you "Home Run Inn", stay away.
Look for a Palermo's, Aurelio's, even a Nancy's franchise will run circles around your Uno franchise.
Look for any local place that has the nod from a local guy.
Where are you doing the show? McCormick Place?
If you wanna spend a whole lot on steak and have a story to tell, I suggest either Gibson's Steak house or the Morton's of Chicago here, you won't leave hungry, and you will have portions that make you questioning your sanity for trying to eat that much food.
Music depends on what you wanna see, if you wanna go see a swing band, hit the Green Mill, Blues, Buddy Guys' or I can send you to a place that will scare the hell out of you, but you'll hear a great band.
Right across from Gibson's (btw local celebs frequent there) is Jilly's Piano bar, not a bad lil place to hang out and hear some Sinatra.
HOB is a great venue, also another great steak place is Smith & Wollensky's, best chateaubriand I've ever had.
Sunday out my way is Symphony X at the Pearl Room, I'm there for that show, most def.
use this or Metromix.com to find out the other shows going on if you wanna see a concert or whatever.