Chicago Off the Beaten Path with Kids | Ciao Bambino!

7 Hidden Gems for Families in Chicago

With acres of playground equipment and open green spaces, Maggie Daley Park is a landmark for families in downtown Chicago.
With acres of playground equipment and open green spaces, Maggie Daley Park is a landmark for families in downtown Chicago.

Families can easily spend several full days in Chicago just experiencing the city’s go-to tourist attractions, like the Sky Deck atop the Willis Tower, the Shedd Aquarium, the Navy Pier or the many wonderful and kid-friendly museums. But if your family is seeking out things to do off the beaten path, we’ve got a roundup of lesser-explored but just as fun ideas for your next trip to the Windy City.

It’s easy to get off the beaten path in Chicago and still see all the major highlights, like the Cloud Gate Sculpture in Millennium Park

7 Off-the-Beaten-Path Things to Do in Chicago


There are a select few cities known for their beaches … Barcelona comes to mind, as does Rio de Janeiro. But a landlocked Midwestern city? Yes! Chicago has miles of gorgeous waterfront along Lake Michigan, and portions of this are sandy and call out for a family beach day. Check out the North Avenue, 12th Street, Ohio Street and Oak Street beaches. The beach at 31st Street also has a splash pad. Other stretches of shoreline throughout the city have miles of trails that are great for renting bikes or going for a walk. 

With acres of playground equipment and open green spaces, Maggie Daley Park is a landmark for families in downtown Chicago

Maggie Daley Play Garden

Any visitor to Chicago will wind up at the Cloud Gate Sculpture (aka “The Bean”) in Millennium Park at some point, but smart families know to dedicate at least a half day or more to this area so they can experience the adjacent Maggie Daley Play Garden. I can’t think of another way to describe it than a playground on steroids. This portion of the park complex covers 20 acres, and there are additional things to do all around, like ice skating, mini golf and a concert hall.

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Chicago Children’s Theatre and Emerald City Theatre

Chicago’s nightlife is legendary with jazz clubs, high-end theater, and comedy clubs. But that doesn’t mean families can’t enjoy cultural performances geared more toward children’s enjoyment. The Chicago Children’s Theatre and the Emerald City Theatre are both highly regarded and put on a range of shows each season, from adaptations of classic children’s books to modern, thought-provoking performances.

A family-friendly tour guide can make Chicago’s impressive architecture come to life for kids

Unique Tours

Don’t just gawk at Chicago’s famed skyline from street level — learn more about the city’s fascinating history with a guided tour. If you’re pressed for time, you can cover a lot of ground with the popular river cruise tours that wind their way through downtown. But with a few days in the city, consider a more in-depth yet still kid-friendly walking tour that delves into Chicago’s architecture, art, food scene or key historical moments. You can even hop aboard a fire truck and blaze a trail around the city with a route focused on the Great Chicago Fire, led by a retired firefighter. Our experienced family travel advisors can arrange custom tours of Chicago to best meet your family’s interests.

Oz Park

Tucked away in one of Chicago’s most charming neighborhoods, Lincoln Park, you’ll find an homage to the author of The Wizard of Oz, L. Frank Baum, who hailed from this part of the city. Oz Park is full of whimsical sculptures of the famous characters, as well as playground equipment and open green spaces.

Best Things to Do in Chicago with Kids
Wrigley Field. Photo from

Tour of Wrigley Field

This famous ballpark is quite a draw for fans of the Cubs, or just those who appreciate baseball’s history. While catching a game is always fun, if you’re visiting in the off-season or can’t swing a full nine innings, consider taking a 90-minute tour of Wrigley Field instead. 

TIP: Book your tour for a day when the Cubs aren’t playing so you can go into their dugout. It’s off limits to tours on game days.

Best Things to Do in Chicago with Kids
Kayaking on the Chicago River. “Kayaks on the Chicago River” by Danny Howard is licensed under CC BY-SA 2.0.


Believe it or not, kayaking the waters around Chicago is growing in popularity and there are now many vendors that not only rent kayaks but also do guided experiences through the city. For families, we suggest booking tandem kayaks so kids are with a parent. Avoid kayaking the unpredictable and often choppy waters of Lake Michigan; stick to the Chicago River, where it’s easy to stop for a bite to eat or restroom break as you paddle through the city. Vendors have various age and size requirements, so do some research in advance.

Chicago is a family vacation hot spot for a reason: there are limitless kid-friendly things to do. But with a little imagination and planning, it’s easy to get off the typical tourist path for some creative city fun that kids and parents will both enjoy.

Relevant Links: 

Browse all family-friendly accommodations and activities in Chicago on Ciao Bambino

72 hours in Chicago with kids

Family-friendly hotel bliss at The Langham, Chicago

The Peninsula Chicago takes family amenities to a new level

Best family-friendly activities in Chicago from a local mom

Editor’s Note: Photos by Nicole Wiltrout except where noted.

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