Our favorite place for a burger. If you have at least an hour to kill put your name in with the host and go next door to Lone Wolf for a drink. Remember their single burger is actually two patties and their double is actually three.
Check out where Matt proposed to Christina. This public square right next to Wrigley hosts the Christkindlmarket / ice skating in the winter and morning workouts and markets in the summer. If you head up there we suggest you either get a taco from Big Star or grab a beer at Lucky Dorr.
Our favorite Mexican restaurant in the city. Right down the street from Wrigley, but you'll have an easy time getting in Labor Day weekend b/c the Cubs are on the road. Get either the Michael or anything with the Mole sauce. DISCLAIMER: The margs are strong so one is enough.
Fresh made pasta daily, amazing patio, cocktails. Pretty much a killer trio. If you're looking for Italian in Chicago you can go wrong here.
If you're looking to get out of the city and get more of a suburb feel you can't go wrong with the Half Acre patio. Nestled in the middle of Bowmanville go for a beer or two, stay for their underestimated food menu.
If you're looking for a burger and a bit more of a funky vibe check out The StopAlong for a burger and/or a pizza. The burgers are about as close as we get to an In N Out Double Double Animal Style. This is a neighborhood spot for the kid in all of us furnished with 80s memorabilia and arcade games, but just remember that they back your beers with shots.
Check out these places for all of Chicago's best dishes. Pizza to plantain sandwiches, there's something for everyone.
Checkout what's going on the rest of the weekend if you plan to stay longer in Chicago.