Chicago is an unbeatable food city. Some of our all time favs are Do-Rite or Stan's for donuts, Devil Dawgs for late night, Lou Malnati's if you want deep dish, Al's if you're looking for an Italian beef, Mott St., Au Cheval or Dryhop for burgers, Ramen-San (get the Tonkotsu!), and Sunda or Momotaro for dinners.
Goose Island, Half Acre and Revolution are Derrick's favorites. And if you see 3 Floyds on a menu (especially Gumballhead or Zombie Dust) we highly recommend.
We loved to stroll through Chicago's great neighborhoods with Rodger! Wicker Park, Wrigleyville, Old Town and West Loop are some of our favorites.
You can't go wrong with an architectural tour down the Chicago River. There are a few options, but Wendella was always a favorite of ours, especially the sunset cruise.
Depending on your travel dates, you might be able to catch a Cubs or Sox game.
No trip to Chicago is complete without a stop to take your photo in The Bean! While you're there stroll through Grant Park to see Buckingham Fountain and stop for a drink at Cindy's for iconic rooftop views.
Lincoln Park Zoo is always a fun way to spend an afternoon - plus it's free and has some good photo opps with the city skyline in the background.
If museums are your thing you've got lots of options in the city. Museum Campus not only has the Shedd Aquarium, Adler Planetarium and the Field Museum, it also has some of the best skyline views.
We always loved to window shop down Michigan Ave and Rush Street. There's a Starbucks Roastery on the Mile now too if you need a coffee or espresso martini to fuel your shopping.
Second City, Laugh Factory and Chicago Theater were some of our favs but there's also tons of smaller improv clubs!