Whether your family loves hands-on museums, outdoor adventures or unforgettable city views, Chicago delivers. As a lifelong Chicagoan and mom of two, I’ve rounded up the attractions, parks, shows and hidden gems I recommend most, making it easy to plan a family trip packed with fun for kids of every age.
Highlights:
- Mix iconic attractions with local favorites. From Millennium Park and Navy Pier to neighborhood gems like Garfield Park Conservatory, Chicago offers experiences that go far beyond the typical sightseeing checklist.
- Find something for every age. Toddlers, tweens and teens can all find activities they’ll love, whether that’s climbing at Maggie Daley Park, meeting penguins at Shedd Aquarium or laughing through an improv comedy show.
- Balance adventure with downtime. Ride bikes along the lakefront, explore world-class museums, enjoy afternoon tea or catch a Broadway show to create a Chicago itinerary that keeps the whole family happy.
Are you ready to explore off the beaten path? Let us inspire you!
See an Improv Comedy Show
Chicago’s improv comedy scene is legendary. Tina Fey, Stephen Colbert, Eugene Levy and literally dozens of other celebrities started their careers on Chicago’s improv stages. See them on stage before they’re famous!
The most famous improv comedy club, Second City, hosts a bunch of shows, most of which are appropriate for older kids. For a G- or PG-rated show, I recommend Comedy Sportz. ComedySportz offers family-friendly improv shows throughout the year. Check the current performance schedule before your visit.
High Tea at the Drake Hotel
A longtime mother-daughter tradition in Chicago is to dress up and have afternoon tea at the iconic Drake Hotel. In the hotel’s luxurious Palm Court room, a live harpist plays as tea is served in china cups along with tiered trays of delicious bite-sized sandwiches and desserts. (Tip: if your child is a picky eater, they’ll bring you a cheeseburger and fries). If you can’t get a reservation here, there are several other lovely afternoon teas throughout the city.
Bike along Lake Michigan
You must go early in the morning because Chicago’s lakefront bike path can get very crowded and treacherous, especially for those not used to urban biking. But you will be rewarded with postcard-like views of Chicago’s skyline all along the lake shore. You’ll bike past things like Buckingham Fountain, Lincoln Park Zoo, Navy Pier, and my kids’ favorite spot, the dog beach at Belmont Harbor.
Garfield Park Conservatory
This massive, gorgeous, 100-year-old garden is one of Chicago’s hidden gems. Greenhouses filled with different types of plants, like cacti or palms, make you feel like you’re walking into different worlds. The 10 acres of outdoor gardens are perfect for lounging, letting the kids run, and soaking in the beautiful flora and fauna.
I recommend driving or Uber-ing there rather than taking the Green Line train from downtown, because the Garfield Park neighborhood can be a little rough. But the conservatory is safe and worth visiting. Admission and parking are free but donations are requested. Another great garden option: Chicago Botanic Garden in the northern suburbs.
High in the Sky
If you’re brave enough, take an elevator to the top of Willis Tower (most locals still call it the Sears Tower) — one of the tallest skyscrapers in the U.S. — and walk out onto the ledge at SkyDeck, the glass boxes that jut out from the 103rd floor.
If you’re REALLY brave, try Tilt at 360Chicago (formerly known as the John Hancock Center). From the iconic skyscraper on Michigan Avenue, you step into a glass box and hold on to the handles as the box slowly tilts face down, 1,000 feet over the Magnificent Mile. It’s impossible not to scream “Whoa!”
Oakbrook Center
If the weather stinks – as it often does in Chicago – this swanky suburban mall has a lot of different fun, indoor activities under one roof (not to mention, great shopping and restaurants).
Located in west suburban Oak Brook, Illinois, the mall includes a high-tech, new indoor mini golf course, Puttshack; a recently opened virtual reality and arcade spot, Immersive Gamebox, where the whole family can play games together; an escape room called Escape the Room; and to wrap up the day or night, there’s an AMC movie theater.
Lincoln Park Zoo
This free, lakefront zoo is charming with hundreds of animals and lovely gardens. Pet animals in a barn, watch apes goof around at the Regenstein Center for African Apes, or see the seals whiz through the water.
The Peggy Notebaert Nature Museum is across the street. It’s a natural history museum aimed at kids that’s operated by the Chicago Academy of Sciences.
During the holidays, the Lincoln Park Zoo’s ZooLights display is outstanding.
Millennium Park
This park in the heart of downtown Chicago is home to some of the city’s most iconic sites: the mirrored sculpture “Cloud Gate” (better known as “The Bean”); the water-spewing Crown Fountain, an excellent stop on a hot day (Bonus: there is lots of seating around the fountains so you can sit while the kids play); Jay Pritzker Pavilion, a free concert venue with a large lawn area; and the playground, play garden and climbing walls at Maggie Daley Park, which has a fun ice skating ribbon in the winter.
Wander just a bit further into Grant Park and you can see Buckingham Fountain, a massive, ornate, century-old fountain along the lakefront.
Navy Pier
Is Navy Pier touristy? Yes. Are things overpriced? Yes. Is it fun? Also yes.
With several rides, including a giant Ferris wheel, plus ice cream shops, restaurants, sightseeing boat rides and the Chicago Children’s Museum, you won’t lack family-friendly activities to do. It’s one of Chicago’s most scenic spots.
My favorite thing to do at Navy Pier is buy a Rainbow Cone (an iconic Chicago brand!) and sit on a bench and eat it while admiring the skyline and watching the boats sail by. Check Navy Pier’s calendar for summer fireworks dates and times.
Slime!
Not my cup of tea, but I’m willing to bet there are parents who read this and think, “My kid will love this!” Sloomoo Institute is dedicated entirely to different ways to play with slime, including a slime waterfall that you need to wear a raincoat for. Nickelodeon fans, rejoice.
Museums, Museums, Museums
Chicago has SO. MANY. MUSEUMS. You can’t make a bad choice, because all of Chicago’s museums are world-class and fabulous. When my kids were younger, the ones they liked best were the Shedd Aquarium (because they loved watching the penguins, sea otters and sharks play around); and the Kenneth C. Griffin Museum of Science and Industry in the Hyde Park neighborhood (because there was lots of interactive stuff to touch and play with).
A fun option for kids ages 5-12 is to do a sleepover at the Shedd Aquarium. You can also splurge on one of the Shedd’s private experiences with penguins, sea otters or beluga whales.
You can’t go wrong with the Adler Planetarium, the Art Institute of Chicago, The Field Museum of Natural History (home to the famous T-Rex dinosaur skeleton, “SUE”), the DuSable Museum of African American History (features virtual reality experiences exploring African American history) and the Peggy Notebaert Nature Museum, where you can walk through a greenhouse with 40 species of free-flying butterflies.
LEGO fans will want to trek out to northwest suburban Schaumburg for the two-story LEGOLAND Discovery Center that includes rides, a 4-D movie and, of course, lots of LEGO play areas.
Children’s museums are always a hit with little ones, and the city and suburbs have several. Our favorites? The Kohl Children’s Museum (in north suburban Glenview) and the Chicago Children’s Museum at Navy Pier.
Teen girls will swoon over WNDR Museum. Rooms full of colorful, interactive, multi-sensory art exhibits will make great Instagram posts.
See a Broadway show
Chicago’s theater offerings are on par with New York’s, and the theaters themselves are gorgeous. While tickets to the most popular shows can be pricey, you can often find deals at HotTix.org. Broadway in Chicago hosts touring productions year-round. Check the current schedule before your trip.
Water Taxi Ride
Don’t have the time, money or attention span for a boat cruise? Take a 10-minute water taxi ride across the city. Chicago Water Taxi’s boats wind through skyscrapers on the Chicago River, and make stops in Chinatown, Michigan Avenue and the Ogilvie train station. All for a few bucks per person.
American Girl Doll Store
There are 11 other stores like this around the U.S., but Chicago’s American Girl Doll shop is a must-see for fans. The two-level store on Michigan Avenue offers lots of experiences, such as girl and doll hair styling, and great shopping.
Maybe your doll needs an ice cream truck, a Harry Potter-themed outfit or canopy bed? It’s all there, and more.
Chicago River Riverwalk
One of the nice free things to do in Chicago on a sunny day is to walk the paved path along the Chicago River. There’s interesting artwork, places to stop and sit, lots of boat docks and restaurants, and at night, you can watch the free Art on the Mart light show on the Merchandise Mart building.
Chicago Magic Lounge
For ages 16 and older (must be accompanied by an adult), this lounge dazzles with cool magic shows and trick demonstrations at your table. Totally unique out for older teens.
Eat!
You’re in Chicago with kids, so you’ll have to eat deep dish pizza, hot dogs (it’s OK for people 18 and younger to put ketchup on their hot dogs — but sacrilege for adults — expect the locals to give you a look if you do!) and Italian beef sandwiches.
FAQs
Some of my favorite free family attractions include Lincoln Park Zoo, Millennium Park, the Chicago Riverwalk and Garfield Park Conservatory (donations are appreciated. In summer, don’t miss Navy Pier’s free fireworks.
I always recommend renting bikes and riding the Lake Michigan lakefront trail early in the morning. You’ll enjoy incredible skyline views while passing landmarks like Buckingham Fountain, Navy Pier, Lincoln Park Zoo and Belmont Harbor.
You really can’t go wrong because Chicago’s museums are outstanding. My family’s favorites are Shedd Aquarium and the Museum of Science and Industry, thanks to their interactive exhibits.
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