Show your grandparents how much they mean to you by treating them to one (or all) of these exciting events in Chicago

Is there anything more special than a grandparent? We’re giving that an emphatic no! And is there anything more exciting than experiencing the city with grandparents? With so many accessible, exciting things to do in Chicago, there are plenty of ways to celebrate a visit from such a beloved relative. Spend precious time with your loved ones and make special memories with these attractions, perfect for all generations.

Comb the Orchards for Apples

It's hard to believe, but apple picking season has arrived. Get the grandparents in on the sweet fun by visiting one of Chicagoland's u-pick apple orchards. Be sure to leave time to have chats over an apple cider donut. We recommend a visit to County Line Orchard. Only 45 miles from the city, it's a far easier commute than many farms hours away. Plus, at County Line, you can experience apple picking, train rides, a corn maze, and a kid's farm. Everyone will have a blast!

200 S. County Line Rd.
Hobart, IN

Related: 11 Tips for Grandparents Traveling with Grandkids

Plan a Day Built on Fun at the Morton Arboretum

Sculpture enthusiasts of every age will be dazzled as they search for eight larger-than-life, nature-inspired sculptures throughout the Arboretum's exhibit Human + Nature. Use this map from Morton Arboretum to help you on your hunt and to learn about their names. Be sure to stop by the Children's Garden where kids splash, dig, and play in a kid-safe environment.

4100 Illinois Route 53
Lisle, IL

Related: A Heartfelt Salute to Parents from Grandparents

Geek Out on Architecture

grandparents day
Chicago Architecture Center

It might sound completely touristy, but the 90-minute Architectural Boat Tour is by far one of the best activities for visitors to Chicago. All while cruising the Chicago River, attendees can learn the fascinating stories behind more than 50 buildings and discover how Chicago grew from a small settlement into one of the world's largest cities, as told by an expertly trained volunteer docent. If you can hang, we recommend taking one of the tours that will be cruising when the sun sets—it makes the ride extra magical. 

112 E. Wacker Dr.
Chicago, IL

Put Those Pinkies Up for Tea Party

Sincerely Media on Unsplash

Grandparents deserve white glove service! So, make a reservation for Afternoon Tea at Palm Court in the Drake Hotel. Experience delicious tea, finger sandwiches, cakes, and scones. You and the kiddos will feel like royalty, especially if you book a Prince & Princess Afternoon Tea.

140 E. Walton Place
Chicago, IL

Related: Easy Ways to Stay Connected to Grandparents from a Distance

Take Them to a Show They'll Never Forget

You just can't miss a chance to see a Broadway in Chicago show. You just can't. So, bring Grandma and Grandpa along for a musical theater experience they'll never forget. Anastasia runs Sep. 20-25 and Wicked runs Sep. 28-Dec. 4. 

17 N. State St. Ste. 810
Chicago, IL

Spend a Family Sunday with the Sox

White Sox

Got a south-side baseball lover in the mix? Catch the White Sox play the Tigers at the last Family Sunday Baseball Game of the season, on Sep. 25. The ballpark experience will feature special kid-focused activities and it's guaranteed that you'll have a great time!

333 W. 35th St.
Chicago, IL

Related: The Best Movies to Watch with Grandparents

Have Big Top Fun in the Park 

grandparents day
Midnight Circus in the Parks

Chicago’s offbeat and totally entertaining circus, Midnight Circus in the Parks, takes its act on the road, performing in parks in all corners of the city. It’s all for a good cause, too: The tour raises money to improve the city's many public parks and playgrounds.

1140 W. 84th St.
Chicago, IL

Visit an Old-Fashioned Ice Cream Parlor

Markus Spiske on Unsplash

Is there anything better than ice cream?! Take your grandparent to Homer's Gourmet Ice Cream for a delicious treat and special experience at an old-fashioned ice cream parlor. Apparently, Homer's was a favorite of Al Capone!

1237 Green Bay Rd.
Wilmette, IL

See the Flourish Exhibit at Chicago Botanic Garden

Experience the delightful sights of huge sculptures that show the connection between art and nature at the Chicago Botanic Garden’s Flourish: The Garden. The exhibit features 10 amazing structures created by different artists from Chicago and around the world. The exhibit closes Sep. 25.

1000 Lake Cook Rd.
Glencoe, IL

Related: 10 Lessons I Learned from My Grandparents

Check Out the Scaumburg Park District

grandparents day

The Schaumburg Park District is full of great family-friendly events that would be perfect for the grandparents to join in on throughout the fall season. Enjoy a movie in the park on Sep. 16 or Octoberfest on Oct. 8. You'll find the events listed on page 6 of the Fall Program Guide

505 N. Springinsguth Rd.
Schaumburg, IL

Cruise with Grandma's Pup

Mercury Canine Cruise Chicago

Dogs on boats? Yes! If Grandma has a pooch, bring it along on Mercury's Canine Cruise for quality time cruising on Chicago's waterways. Sit back, relax, and soak in the city as you enjoy a lively narration of Chicago’s rich history and architectural marvels with dog-friendly highlights.

112 E. Wacker Dr.
Chicago, IL



Your daily dose of joy and connection
Get the Tinybeans app