Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus.
We got engaged above the Riverwalk! We'd recommend an architecture boat tour if you have time.
Cloud Gate ("The Bean"), Crown Fountain, and Maggie Daley Park.
Established in the 1920s as a movie palace, the theater showcases a variety of concerts, Broadway shows, and comedians.
We picked this place for our last dinner in Chicago before moving to Houston. The restaurant/lounge features creative American dishes and craft cocktails with a ritzy, speakeasy vibe.
In our opinion, the best deep dish around.
One of Chicago's oldest craft breweries produces beloved beers at this facility, which also contains a barrel aging warehouse and a sleek taproom where visitors can grab a drink. Tours are offered Wed-Sun.
Table, Donkey, and Stick; Kuma's; DMK; etc. — Chicago boasts some of the best burger joints around. We think Au Cheval is the best of the best.
Creative Chinese fare from celeb chef Stephanie Izard served in buzzy, ornately decorated surrounds.
An absurd amount of comic talent has come out of Chicago over the last 60 years, and one of the reasons for that is Second City. This fabled comedy club and improv company on Wells Street counts Steve Carell, Bill Murray, Tina Fey, Amy Poehler, Stephen Colbert, Dan Aykroyd, John Belushi, and John Candy among its alumni.
Handcrafted cocktails, a light New American menu, and city views on the Hotel Lincoln's swanky rooftop.
Spanish tapas, paella, and pitchers of sangria fuel a lively scene at this classic Lincoln Park restaurant.
Located on the North Side (5 miles from downtown), Wrigley Field first opened in 1914 and is oozing with baseball history. The iconic ivy walls may not be flush in May, but it's still worth seeing a game. The Cubs play the Diamondbacks at home May 19–22.
In our opinion, the best Chicago dogs. If you are checking out a Cubs game, then stop here!