If you're staying in the city, I wouldn't bother heading out to Tramonto's out here in Wheeling. There are too many other perfectly wonderful steakhouses downtown to schlep out to the hinterlands.
If you're looking for cuisine that is less widely-available in other cities, I recommend Mexican (which Chicago has a wider variety of than most other large cities), Thai, or Polish, all with a great number of places in the city to choose from. The GNR list posted upthread is a great place to start looking.
Personally, I recommend Podhalanka for a cheap and tasty Polish meal--I had a terrific breakfast there a few months back.