Need help filling out your Windy City bucket list? As locals (our headquarters are here), we can’t recommend the following things to do in Chicago enough. Just make sure you leave enough time in between these iconic Chicago activities to grab some deep dish. And a hot dog. And an italian beef sandwich.
One of the most fun things to do in Chicago, especially if you have kids, is visit the 25-acre Millennium Park campus. Here, you can snap a selfie of your distorted reflection next to The Bean, catch a summer concert or free movie at the outdoor Jay Pritzker Pavilion, and play in the splashing waters of the interactive Crown Fountain. Nearby Maggie Daley Park is jam-packed with fun family activities, including a climbing wall and large ice-skating ribbon.
Yes, Navy Pier is one of the most popular things to do in Chicago and for good reason—it’s an iconic city landmark dating back to 1916. Since its redevelopment and reopening in 1995, more than 180 million people have visited the Pier, exploring its shops and restaurants, catching shows at Chicago Shakespeare Theater, discovering the Chicago Children’s Museum, and of course, riding the ferris wheel.
American Gothic. Nighthawks, 1942. A Sunday on La Grande Jatte. This world-class art museum is home to these famous works, as well as several Picassos, Monets, O’Keeffes, and Warhols. Kids in particular like seeing the medieval armor in the Arms & Armor section and the dollhouse-esque furniture in the Thorne Miniature Rooms.
One of the best things to do in Chicago? Visit the John Hancock Center. It may not be as tall as the Willis Tower, but its observation deck on the the 94th floor offers some of the best views in the country, according to Travel and Leisure magazine. If you’re especially brave, check out TILT, a movable set of windows that tilt 30 degrees downward for a spine-tingling glimpse of the streets below.
Chicago’s free zoo, an oasis in a bustling city, is a favorite of locals and tourists alike. Visitors can see everything from giraffes to gorillas to African painted dogs at the Lincoln Park Zoo, which has one of the largest zoo-based conservation and science programs in the country. At the Farm in the Zoo, kids can feed the cows and even pet the goats.
Standing at more than 40 feet long and 13 feet tall at the hip is the Field Museum’s prized possession, SUE, the largest, most complete, and best preserved Tyrannosaurus rex specimen. But while she draws the crowds, SUE’s not even the largest dinosaur there. That honor belongs to Máximo, a long-necked, plant-eating titanosaur, whose touchable cast reaches 122 feet across the main floor and stands 28 feet tall at the head. In addition to jaw-dropping dinos, visitors find everything from precious gemstone jewelry to mummies.
At this more than 5-million-gallon aquarium, visitors marvel at 1,500 species of fish and marine mammals. The Shedd is known for its aquatic presentations, during which trainers introduce groups in a water arena to such sea creatures as beluga whales and dolphins. Visitors can even spring for an animal encounter and pet a penguin or get a kiss from a beluga.
There’s really nothing better than Chicago in the summer, especially if you spend a good chunk of the day hanging out at historic Wrigley Field, home to the Chicago Cubs since 1914. The ivy-covered ballpark welcomes fans of all ages for a day filled with hot dogs, cold drinks, and hopefully a win for the Cubbies. If you really want a memorable day, go for the all-inclusive rooftop seats, a big draw for birthday and bachelor/bachelorette parties.
If you think the observation deck at John Hancock Center is high, wait till you see the Skydeck. The Willis Tower’s observation deck is located on the 103rd floor and shows off views spanning up to four states. The bravest visitors can step out onto The Ledge, a glass balcony with a glass floor that overlooks the streets 1,300 feet below.
This ritzy shopping district along Michigan Avenue is packed with more than 460 high-end and mid-range retailers ranging from Gucci and Harry Winston to Sephora and H&M. If shopping’s not your thing, The Mag Mile is still worth a visit as it's home to several architecturally significant buildings, including The Wrigley Building, Tribune Tower, and the old Water Tower, one of the few buildings that survived The Great Chicago Fire of 1871.