Of the Chicago locations, I've been to three of them. There had been one in Midway Airport (now gone) as well as one in Wrigleyville (again, gone), and each had its own flair. The same can be said for the other three I've dined at.
First is the original restaurant downtown, a few blocks from the nearest Red Line stop. It consists of the fine dining area, a bar area where food is also served, and upstairs is a ballroom where many of the major sports teams will send their premier athletes for a chance for fans to ask questions. A night I was there the line to eat with the Blackhawks stretched down the stairs and out the door. The signature dish is the Chicken Vesuvio (shown below) and it lives up to expectations.
There have been many restaurants in Chicago founded by Chicago's sports personalities, but Harry Caray's has stood the test of time, at the same location and with the same staff.