If you want some deep dish, go here. First, stop in at Beck's next door for a beer. Second, order this at Pequod's: 10" Small Pan Pizza Pan Pizza Modifiers : Well Done, + Spinach, Extra Cheese, Pepperoni
Favorite Wings and Beer Spot
Irish Pub right next door to the Palmer House Hotel. Can't go wrong with a Guinness.
James used to live across from The Hat. Classic Chicago dawgs, gyros, you name it. Get a #5.
The Lakefront absolutely rocks. Walk the trail, stick your toes in the sand, jump in the lake from the concrete beach.
This is a must for anyone in Chicago for the first time. It is not overrated and provides an awesome view and history of Chicago's World Class Architecture. Great way to just sit, relax, and take in the view.
Wrigleyville is a good time, even when the Cubs are out of town (which they are, sadly). Murphy's and Slugger's are classic staples of the experience, but we're also big fans of Sheffield's.