Top 5 Family Adventures in Chicago

Planning a family trip to Chicago is always exciting, but finding activities that everyone will enjoy—from the little ones to the adults—can be a bit of a challenge. Luckily, the Windy City is packed with fun experiences for all ages. The secret is knowing where to go—and how to do it without feeling overwhelmed or overspending.

Whether you’re planning a quick weekend trip or an extended city getaway, here is our family’s top 5 favorite family adventures in Chicago, in no particular order!

1. Taste Your Way Through the City on a Guided Food Tour

If you’ve been following along on our Instagram, you know we recently took the Iconic Foods of Chicago Tour with Chicago Food Tours, and it was hands-down one of the highlights of our trip! After how much our family loved their Chinatown Adventure Tour on our last visit, booking this one was an absolute no-brainer. If you’re looking for a small-group, educational, and super unique family travel experience that feels exclusive, this is it. It gets your kids past the standard bucket list so they can experience the city through its real history, hidden neighborhood gems, and iconic flavors!

Over about three hours, you hit five legendary eateries—including Lou Malnati’s for deep dish, Al’s Beef, Portillo’s, Garrett Popcorn, and a stop to sample the original brownie. Did you know the brownie was actually invented right here in Chicago at the Palmer House Hotel back in 1893 for the World’s Columbian Exposition?

Beyond tasting all the classic staples, what makes it an absolute game-changer for families is the VIP no-wait treatment. The tour coordinates directly with the restaurants so your food is fresh and ready the second you sit down. Skipping the crazy long lines—especially when deep-dish pizzas normally take 45–60 minutes to bake—is amazing with hungry kids in tow.

Plus, there is plenty of “sneaky learning” built in along the walk, with your guide sharing fascinating local history, architecture, and fun city facts (like how the Chicago River is the only one in the world that flows backward!). It proved to be the absolute perfect tour to do with kids—especially pre-teens and teenagers, who will gladly walk and soak in the city as long as continuous, delicious food is involved!

2. Take to the Water on an Architecture River Cruise

You can’t visit Chicago without seeing its world-famous skyline from the water. Ashley first experienced an Architecture River Cruise as a little girl when her dad (an architect) took her, so getting to come back years later and experience it all over again with our own kids made it extra special. It was such a fun way to take in the city’s incredible skyline, learn more about its architectural history, and make new memories together as a family!

While we usually visit Chicago during winter for all the holiday magic and sports games, September is hard to beat—green trees, bright blue water, and perfect weather make it our new favorite time to visit. We always try to balance travel adventures with a little learning, and the Chicago’s First Lady architecture cruise hit the sweet spot. Partnered with the Chicago Architecture Center, it allowed us to take in iconic landmarks without walking miles, all while guided by a fantastic docent.

Our guide kept the whole family hooked with incredible trivia from start to finish. We learned that early 1800s builders used horsehair in mortar and plaster, and that Chicago’s unique post-Great Fire alley system keeps trash off the main streets—leaving the city looking remarkably clean compared to other major hubs. We passed the massive Old Post Office—famously featured as a bank in The Dark Knight—and discovered that Skidmore, Owings & Merrill, the firm behind the Willis Tower, also designed the Burj Khalifa in Dubai (one of our other favorite cities!). Frank Lloyd Wright once said that Chicago would eventually become “the most beautiful great city left in the world.” Watching the skyline glide by from the river, it’s hard to argue with him.

3. Hack the Museum Scene (Passes & Pricing Tips!)

Chicago has some of the best museums in the world. Our personal family favorite is the Griffin Museum of Science and Industry—you could easily spend an entire day there exploring the U-505 submarine or the giant tornado simulator. But we also adore the Adler Planetarium, Shedd Aquarium (their marine mammal presentations and aquatic shows are incredible!), The Field Museum, and the Art Institute.

However, admission adds up fast for a big family. Here is how we make it work without breaking the bank:

• Compare Go City vs. CityPASS: Always price out an a la carte day vs. a pass option based on exactly which spots your family wants to hit. Passes often pay for themselves if you’re hitting 3+ major venues.
• The Local Science Center Hack: Check the reciprocity on your home science center’s annual pass! Ours costs $139/year for a family of 6, and thanks to ASTC reciprocity, it gets us free admission to both the Adler Planetarium and the Museum of Science and Industry in Chicago.
• The Local Zoo Hack: If you have a membership with your local zoo, check their AZA reciprocity—it often unlocks discounted admission at the Shedd Aquarium!
• The Lincoln Park Zoo– If your budget does not allow for museum entries, the second oldest zoo in the US is in Chicago, and it’s FREE! They have a lot of big indoor exhibits so it is great even in the winter.

4. Explore Michigan Avenue (With a Few Secret Highlights!)

Walking down the Magnificent Mile is iconic, but there are three specific stops on Michigan Avenue—all housed inside or near Water Tower Place—that make it a total adventure for kids:

• The American Girl Store: Easily the best in the U.S.! If you go, book a table at their Cafe for lunch ($30 per person for a multi-course meal, which is a surprisingly great value for the experience). They provide a tiny clip-on high chair and teacups for your doll—and if you didn’t bring one from home, they’ll even lend your child a doll to eat lunch with! The table conversation starter cards are such a cute touch, too.
• The Harry Potter Store: Grab a chilled Butterbeer at their cafe and step up to put on the Sorting Hat! Fun side note: the hat sorted our daughter into Slytherin. Anyone who knows her knows there has never been a less Slytherin child in the history of the world, but we haven’t stopped giving her a hard time about it since!
• The LEGO Store: Perfect for a quick, creative pitstop. Kids love snapping a photo on the life-sized Friends couch and marveling at the massive LEGO build of the Chicago skyline.

In addition to the great shops, no walk on Michigan Avenue is complete with kids without visiting Maggie Daley Park. This is one of our favorite playgrounds in the world, and we’ve visited A LOT of them in 30+ countries! During winter months, you can also ice skate the ribbon surrounding the playground area. Millennium Park and Grant Park are right by here as well. We ate lunch across the street at the Game Room and played free foosball, pool, shuffleboard, and more!

5. Catch a Chicago Sports Game (or Tour the Fields!)

Honestly, sporting events are often the anchor for why we plan a Chicago trip in the first place!

If you travel in the winter, look for a weekend in December where the Bears, Blackhawks, and Bulls are all playing at home. Catching all three sports in one action-packed weekend is an absolute blast for the kids.

If you’re visiting during baseball season, Wrigley Field is so iconic. Even if you can’t catch a live game, booking a guided tour of Wrigley on an off-day gives you a unique, historic peek behind the scenes—walking through the dugout and stepping onto the field is something your family won’t forget.

Whether you’re heading to the Windy City for the world-class food, the iconic architecture, or a big game weekend, Chicago is bound to leave your family with memories that last far past the trip home.

**This post contains affiliate links.  We are grateful for the opportunity to be hosted by Chicago Food & City Tours and Chicago’s First Lady.  All opinions are our own.

To see all our travel adventures during a year-long trip around the world, head over to our Instagram page.

If you have questions or tips for a trip to Chicago with kids, let us know!  Happy Travels!