I just got back from Chi-town... Hopleaf is a great beer bar, but The Map room is a classic. We stopped at Goose Island in Wriggleyville before a cubs game, they had some great beers.
As far as Food... Do you ever watch Man vs. Food? It's my favorite show because he goes places that I appreciate. In the Chicago episode he went to:
Al's Italian Beef
Genos East (great Deep Dish Pizza)... We went there, it was fantastic. I'm pretty sure this is near your hotel, but I could be wrong.
Lucky's- This place is near Wrigley Field and is on the same block as a bunch of great bars, not the least of which is Goose Island. They specialize in stuffed sandwhiches, check out the clip: http://www.youtube.com/watch?v=eor2ke62oJU
That's all I got!