David,
You can't go wrong with Mother Hubbard's as a sports bar, but if there is a big game going on, it could be on the loud side . . . I'm not sure if your goal is to stay as close to the downtown area (called "the Loop") or not. There are some great brew pub options a little bit North - probably the best one would be Goose Island Brewery (Goose Island is a Chicago landmark). They have two brew pubs on the North side:
http://www.gooseisland.com/pages/brewpubs/4.php
Jim