Goose Island Brewpub. Not the over-crowded one in wrigleyville... go to the one on Clybourn... it's the original location and it's closing sometime this year. It is not to be missed.
Also, there's Piece brewpub. Never been there. Within 40 miles of downtown you have Three Floyds brewpub. There is also the Flossmor brew pub which is excellent- it's made from an old train station.
Out in the burbs you have 2 brothers brewing, Walter Payton's roundhouse, and Emmit's Ale House (?).
While your there, check out the Map room.
Also, if you can afford it, you might try to make reservations at the Signature room. If you can't afford it, then go up there for an overpriced drink. It's 9/10ths the view that you get from the Sears Tower and you get a good drink instead of buying tickets for an elevator ride- the price is comparable.
If you don't mind getting into sketchier neighborhoods and eating at dives, the best burritos on the planet are at La Pasadita. There's 4 of them, all by the same name, on the same block, so you can't miss them.
