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