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12 Family Reunion Ideas in Chicago That Rock

Boats cruising around through skyscrapers for architecture tour in Chicago

By: Bailey Hill

The Windy City is a great place to host your next family reunion! Chicago is home to awe-inspiring art installations, diverse family-friendly attractions, and some of the most delicious food you won’t find anywhere else. Whether you’re a native Chicagoan or want to explore a brand-new city with the people you love most, there are many ways to make your Chicago family reunion one for the books!

We’ve rounded up some of Chicago’s best tours, activities, and sightseeing opportunities, so you and your crew can take advantage of your time together. Our recommendations are based on personal experiences in Chi-town, local favorites, and the best online reviews. 

Here are 12 of the best family reunion ideas in Chicago!


Chicago sign downtown



       1. Taste River North or Wicker Park on a Sidewalk Food Tour

You can’t visit Chicago without trying some authentic deep-dish pizza, tapas, and doughnuts! Many locations claim to have the best flavors in town, but Sidewalk Food Tours knows which locations mean it. While you savor every bite, your tour guide will point out some iconic landmarks and share little-known stories about their histories.


a close up of a slice of pizza

Chicago-style pizza anyone?


2. Hang Out with Wildlife at Lincoln Park Zoo

Lincoln Park Zoo is home to over 200 species of animals – including some that were once thought to be extinct – and more than 850 different plants! Caretakers invite guests in to watch as they feed and train seals, and you can also see how experts teach intelligent apes cognitive skills. There are also attractions specifically for children if you have many little ones in your group!


a seal sitting on the dock at the zoo

Argh Argh! We can hear them from here.


3. Check Out Free Art and Music at the Chicago Cultural Center

The Chicago Cultural Center spans an entire city block and features the world’s largest Tiffany stained glass dome! But that’s not all – it is also home to art galleries, an interactive learning lab, an art studio, and hundreds of free events year-round. 


Tiffany stained glass dome

Chicago Cultural Center


4. Walk Around Millennium Park

You can’t visit Chicago without snapping a photo in front of the mirrored Bean in Millennium Park! Your family will surely enjoy many other art installations throughout the park, along with free events, a stunning 3.5-acre garden, and plenty of places to run around and release some energy. It’s easy to spend a whole day enjoying yourself here!


The Bean in Chicago

Did you know it way 110 TONS?


5. Catch a Baseball Game at Wrigley Field – or Take a Tour!

If your family loves baseball, a visit to Wrigley Field is a must! If you aren’t in town on a game day, don’t worry. You can tour this historic stadium and hear incredible stories about the people who played and watched baseball over the last 100+ years.


A close up of a hat someone is holding up that says Chicago with Cubs "C" logo in front of their field

Go Cubbies!


6. Walk Along the Chicago River

The Chicago Riverwalk is free and open to the public every day. It’s a 1.25-mile-long path that runs through four Chicago districts: the Confluence, the Arcade, the Civic, and the Esplanade. This is a great way to enjoy a sunny day while sightseeing in the Windy City. Hopefully, it’s not too windy when you visit!


a bridge over a body of water with a city in the background

Chicago Riverwalk


7. View the City from the Top of the Former John Hancock Center

See all of Chi-town in a single glance with 360 Chicago! The top of the former John Hancock Center is 1,000 feet in the sky, providing 360-degree views of the entire city. While you’re there, you can ride Tilt, which gives you a thrilling, unique perspective on the buildings below, and enjoy some cocktails in the sky at CloudBar. 


The view of Chicago from the John Hancock Center

The sweetest 360 of Chicago…


8. Immerse Yourself in Art at the Driehaus Museum

The Richard H. Driehaus Museum is full of architecture and design marvels from the late nineteenth and early twentieth centuries. Explore exciting exhibitions that will make your whole family say “Ooh!” and “Ahh!” in unison!


the interior of a museum with incredible architecture in Chicago

Marvel at the beauty!


       9. Play Mini Golf at Maggie Daley Park

Maggie Daley Park is home to an 18-hole mini golf course located on the south side of the BP Pedestrian Bridge. Your family will have a great time putting their way through replicas of iconic local structures, including a 6-foot-tall Willis Tower and a Plinko-inspired Picasso sculpture.


a close up of a putt putt club and ball

For competitive guests, this may become an intense activity..


10. Uncover Secrets of Science and History at Field Museum

Your family will have a blast exploring ancient Egypt, going on an underground adventure, and gazing upon the bones of dinosaurs that used to roam the planet. The Field Museum also has a 3-D movie experience that family members of all ages will love!


A dinosaur skeleton

Education + entertainment!


11. Shop and Dine Along the Magnificent Mile

The Magnificent Mile is Chicago’s most extensive shopping, retail, restaurant, museum, and hotel district. If you have time to kill during your fun-packed family reunion, this is the perfect spot to grab a bite to eat, shop for souvenirs, or find a pop-up event you didn’t know was happening!


a tall building in Chicago along the Magnificent Mile

Magnificent Mile


     12. Tour Downtown Chicago by Boat

Shoreline Sightseeing offers three unique water tours of the Windy City: the Architecture Tour, the Skyline Lake Tour, and a Fireworks Tour (on Wednesday and Sunday evenings from Memorial Day-Labor Day). This is a great way to rest your feet after a long day of sightseeing without missing out on a moment of fun!


Boats cruising around through skyscrapers for architecture tour in Chicago

See Chicago by boat!


Have the Best Family Reunion in Chicago!

Book your Sidewalk Food Tour in Chicago today to see the best of the best food spots while you’re in Chicago! Paired with any of the above ideas, your family will have incredible memories to look back on fondly until the next reunion.