You might consider the Berghoff Cafe. It's one of the oldest bar/restaurants in Chicago - for a genuine feel for what Chicago was like in its glory days. They have been brewing their own beer (two versions: lager and dark) since long before micro-breweries became the rage. They also make excellent root beer for non-drinkers. It is a large place: one side is a gigantic bar with floor to ceiling dark wood paneling and large photos taken during the prohibition era. The other side is a wonderful restaurant specializing in German fare. Located on 17 West Adams Street.
http://www.berghoff.com/home.php
I live in Chicago - The Berghoff never disappoints out of town guests. No matter where you decide, I'll do what I can to join you.
Jim