re: Spending a long weekend in Chicago near Wrigley, advice on food and stuff?

Absolutely love Chicago. One of my favorite all time American cities. There are already some good recommendations in here so I'll just add one more:

Go catch a show at second city and then head on over to the Old Town Ale House across the street afterwards for a few drinks. The bar is a fantastic beat down old school little place with some great tunes and some truly inspiring "artwork". I always visit at least once when I'm in town.