1. Snap a pic by Cloud Gate (a.k.a. The Bean)
Plug #Chicago into Instagram and the first image you’ll likely see is “The Bean.” This stunning piece of public art, which was created by Indian-born British artist Sir Anish Kapoor is actually called Cloud Gate, is a must-see for families coming to Chicago. Kids will love making funny faces in the bean’s curvy mirrored surface, and walking underneath it can be an experience in and of itself. The plaza around the bean is open from 6 a.m. to 11 p.m., and it gets pretty busy during the day, so if you’re hoping for a shot sans the crowds (and you happen to have a family full of early risers), it’s best to head out to see it in the morning before 10 a.m.
2. Explore Millennium Park and Maggie Daley Park
Just past The Bean are Millennium and Maggie Daley parks. Millennium Park is home to a large amphitheatre that hosts concerts, workout classes and other special events throughout the year. Check the park’s events calendar beforehand to see what’s happening at the park during your trip. At Maggie Daley Park, you can let your kids explore the large Play Garden, which features six distinct play areas filled with slides, play structures, interactive installations and lots of space to run around. In the colder months, the skating ribbon, an outdoor rink that loops around the park’s rock climbing structure, is a family must-do.
3. Museum hop at Museum Campus
For a full day of activity in one area of the city, Museum Campus is the place. As the name suggests, this area is dedicated to museums and is home to The Field Museum, Shedd Aquarium and the Adler Planetarium (though not technically a museum, Soldier Field Stadium is also close by). Each museum feature changing exhibits that are sure to teach your family something new. Ambitious families planning to hit all three can get access to the trifecta with the Chicago CityPASS, which gives admission to those and other attractions around the city as well, such as the SkyDeck at Willis Tower (more on that below) and the Museum of Science and Industry.
4. Go shopping at American Girl Place
Chicago is home to one of the three American Girl flagship stores in the U.S., and this place is huge. Fans of the popular doll brand will love the beautiful displays and exclusive AG items for sale. However, the American Girl Place is more than just a store—it’s also home to a café, where you can enjoy a nice meal with your AG doll right by your side, and a salon, where both you and your doll can get your hair styled, your nails painted and even your ears pierced! The store also hosts plenty of events including launch parties, cookie decorating, morning yoga sessions and dance classes. Check out the store’s event calendar to see what’s happening during your visit.
5. Experience some live theatre
In 2019, the city designated itself as the Year of Chicago Theatre, so you should probably see at least one show while you’re there. Whether, it’s a play, a musical, an opera or a dance show, there are lots of options for families with older kids. Try to grab tickets to the family-friendly musical sensation Hamilton before the Chicago company closes its doors at the beginning of 2020!
6. Eat everything in sight
If there’s one thing Chicago is known for (other than the Bean), it’s definitely the food. Of course, there’s the world-famous Chicago deep-dish pizza, which you can get at many different places in the city. We suggest checking out Lou Malnati’s where the deep dish pizza is ooey and gooey but sits on top of a sturdy (but fairly thin) crust—it’s delicious! There’s also the Chicago hotdog, which is on menus across the city. We’re partial to the menu at Portillo’s—just don’t ask them for ketchup, it’s blasphemous! For fans of McDonald’s, Chicago’s West Loop is home to the McDonald’s Global HQ, where you can find a rotating menu of items available at McDonald’s locations around the globe like Cyprus, Japan, France and many more.
7. Visit the Ledge at the Willis Tower Skydeck
Willis Tower (formerly known as the Sears Tower) is the eighth-tallest building in the world and the tallest building in the Western Hemisphere. Let your tiny daredevils stand on top of it—well, almost—with a visit up to the Skydeck located on the tower’s 103rd floor. Here, you get an amazing view of the city of Chicago as well as a look a four different states (Illinois, Michigan, Wisconsin and Indiana) spanning across the horizon. And if you’re brave enough, take a step out onto The Ledge, a clear glass balcony that extends four feet away from the building’s exterior, giving you a bird’s eye view from 1,353 feet up in the air. Just don’t look down (or do!).
8. Take a minute to appreciate the architecture
Speaking of tall buildings, did you know that Chicago was home to the world’s first skyscraper? Over the years, the city has built up an impressive resume of tall buildings in a variety of architectural styles, which you can explore at the Chicago Architecture Center. Here, kids can marvel at an interactive scale model of the entire city. Next, head to the Chicago River to catch a ride on an architectural river cruise where docents will give an overview of the buildings that populate Chicago’s skyline as you cruise through the city.
9. Catch a magic show
Chicago is the birthplace of close-up sleight-of-hand magic shows. Chicago magicians are the creme of the crop, and the city has multiple venues solely dedicated to magic and illusions. The Chicago Magic Lounge hosts family matinee shows on Sundays at 3 p.m., which is a great way for kids to get a little taste of the magic. The best part? The entrance to the lounge is through a “laundromat,” so your kids will love looking for the secret door that leads inside.
10. Visit Art on theMART
Walking along the banks of the Chicago River, it’s hard to miss theMART, the largest privately held commercial building in the United States. It’s massive. At night, the building is home to the Art on theMART project, a permanent public art installation that projects art from all over the world onto the building’s 2.5 acre façade. Kids will love watching the colourful digital projections move across the giant wall. The projections are best experienced in the summer, when they run seven nights a week (instead of the usual five).
11. Check out the Chicago Children’s Museum at Navy Pier
Stretching into Lake Michigan just north of the mouth of the Chicago River is Navy Pier, one of the city’s top attractions. It houses the Chicago Children’s Museum, where kids 10 and under can play pretend in Kids Town, build with real tools in the Tinkering Lab and even dig for ancient bones at the Dinosaur Expedition. While you’re at Navy Pier, be sure to also check the Centennial Wheel, the Pier Park, the Funhouse Maze, the Crystal Gardens and the Chicago Shakespeare Theater.
12. Visit the animals at the Lincoln Park Zoo
If you’ve got an animal lover in your family, you can’t miss a visit to the Lincoln Park Zoo. Open 365 days a year and with (the best part!) always free admission, the zoo at Lincoln Park is the perfect way to spend an afternoon. Check out their events calendar for fun family-centred events like Animal Art, Family Nature Days and Breakfast with the Animals. Fun tip: keep an eye on the new arrivals page on the zoo’s site, so you won’t miss a chance to see some adorable baby animals like gorillas, zebras and more!
Some of the writer’s costs were covered by Choose Chicago.
Stay in touch
Subscribe to Today's Parent's daily newsletter for our best parenting news, tips, essays and recipes.