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PIxar Putt is available now through Sept. 10. Photo courtesy of Navy Pier
PIxar Putt is available now through Sept. 10. Photo courtesy of Navy Pier
4/30/23 - By Maureen Wilkey

Looking for things to do with kids in Chicago this May? Here are our favorite kid-friendly things to do in Chicago in May 2023.

Get ready for a lot of pictures of Justin Timberlake on your Facebook feed because It's Gonna Be May! Parades are back and there are two big ones downtown this month: The Polish Constitution Day Parade and the Memorial Day Parade. Has being outside again got you thinking about nature?  Check out environmentally themed fun at Chicago River Day or World Migratory Bird Day. Animal-themed music is also big this month, with a Broadway in Chicago presenting Bluey's Big Play  and Once Upon a Symphony performing Goldilocks and the Three Bears. Festivals celebrating flowers are blooming in Lombard, West Chicago and Oak Park this month as well.

There's still time to book a reservation at one of more than 25 destinations for Mother's Day brunch, or to plan another activity for Mother's Day. Check out one of our favorite tot lots and toddler playgrounds to get your littlest kids out and moving. Or get away from it all with a hike in or around the Windy City.

Here are some of our favorite things to do in May 2024 with kids in Chicago!

 

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May is full of outdoor festivals. Photo by Rene Zepeda courtesy of the Mole de Mayo Festival
May is full of outdoor festivals. Photo by Rene Zepeda courtesy of the Mole de Mayo Festival

Best Things To Do in Chicago in May

Bluey's Big Play The Stage Show

Friday, May 3- Sunday, May 5--Downtown
When Dad feels like a little bit of Sunday afternoon time out, Bluey and Bingo have other plans! Join them as they pull out all of the games and cleverness at their disposal to get Dad off that bean bag. Bluey’s Big Play is a brand-new theatrical adaptation of the Emmy® award-winning children’s television series, with an original story by Bluey creator Joe Brumm, and new music by Bluey composer, Joff Bush. Join the Heelers in their first live theatre show made just for you, featuring brilliantly created puppets, this is Bluey as you’ve never seen it before, brought to real... READ MORE

Mexico Fest at Navy Pier

Friday, May 3-Sunday, May 7—Downtown
Navy Pier is joining forces with the Consulado General de México en Chicago & The Governments of Chihuahua, Nayarit, and Querétaro to host Mexico Fest, a weekend-long event featuring a mercadito of artisans, performances by Mexican musicians and dancers, and workshops for kids. Mariachi and Ballet Folklorico will be featured in the Culture Corner and the Fifth Third Bank Family Pavilion. READ MORE

Polish Constitution Day Parade

Saturday, May 4—Downtown
Chicagoans of all ages are invited to attend the Chicago Polish Constitution Day Parade, in celebration of the Polish Constitution of 1791 and Poland's Independence. The theme for 2024 is “NATO Protects and Unites Us.”   READ MORE

Lilac Time

Saturday, May 4-Sunday, May 19—Lombard
The Village of Lombard celebrates spring and the blooming of the 700 lilacs and 25,000 tulips in Lilacia Park with this annual festival. The festival includes concerts, an arts and crafts fair, botanical tours, a 5K, a parade, and a father-daughter dance. Entry to the park is always free, but some events charge admission. READ MORE

Soap Box Derby 2024 Spring Rally

Saturday, May 4- Sunday, May 5—Naperville
Build your own car or test run a pre-built car at the Greater Chicago Soap Box Derby's track. READ MORE

Go Fly a Kite at Graf Park

May 7—Wheaton
Wheaton Park District invites families to Graf Park for its annual kite fly. Free kites will be available for the first 100 families. Kite performers will show off their tricks near Monroe Middle School, and there will be contests for most unique kite and highest flying kite. READ MORE

World Migratory Bird Day Celebrations

Saturday, May 11—South Holland
The Forest Preserve District of Cook County invites families to celebrate birds at Sand Ridge Nature Center. Kids can enjoy crafts, go on a bird walk, and explore the preserves throughout the day. READ MORE

Chicago River Day

Saturday, May 11—Various locations
Volunteer to help the Friends of the Chicago River create a litter-free environment. Dozens of sites throughout Cook County invite families to come pick up trash, paddle up and down the river, and be inspired by the animals, plants, and people around the river. READ MORE

Mayfest Lincoln Park

Friday, May 17- Sunday, May 19—Lincoln Park
End spring and kick off summer with live music and festival foods in Lincoln Park. Families can check out live music from family friendly entertainers early in the day. READ MORE

Spring Roscoe Village Art and Craft Festival

Saturday, May 18-Sunday, May 19—Roscoe Village
This spring festival on Chicago's North Side includes fabulous paintings, sculptures, fiber pieces, décor, jewelry, and more, all made by local artists. Live music and kids' art activities add to the weekend's fun. Bring your old art to donate to Chicago Furniture Bank. READ MORE

Once Upon a Symphony: Goldilocks and the Three Bears

Saturday, May 18—Downtown
Chicago Symphony Orchestra presents Goldilocks and the Three Bears, a classic story of how young Goldilocks stumbles upon a quaint cottage and goes inside to explore. She has no idea it belongs to three bears who are on their way home! With this classic story as a guide, young audiences are invited to experience the wide and wonderful world of the forest through Goldilocks’ eyes and playfully explore some of the responsibilities that come along with growing older.  READ MORE

Long Grove Chocolate Festival

Friday, May 17- Sunday, May 19—Long Grove
Celebrate chocolate in downtown Long Grove with tastings and pairings, live music, and a carnival. Families can try chocolate donuts, chocolate covered strawberries, chocolate cupcakes, cake pops, cocoa bombs, chocolate truffles, chocolate croissants, chocolate eclairs, chocolate macarons, hand-dipped fine chocolates, chocolate covered funnel cakes, chocolate popcorn, chocolate cotton candy, frozen hot chocolate, and much more. This kicks off the spring festival season in historic Long Grove. READ MORE

Spring Renegade Craft Fair Andersonville

Saturday, May 18- Sunday May 19—Andersonville
Arts and crafts fans can enjoy Renegade's new spring event in Andersonville, featuring incredible makers and designers from all over the US, as well as live entertainment, local DJs, workshops, art installations, food trucks, nonprofits, cocktails, craft beers, and more. READ MORE

Blooming Fest

Saturday, May 18—West Chicago
West Chicagoans are finally celebrating spring at this street festival with more than 80 vendors selling plants, garden decorations, yard art, jewelry, clothing and crafts. The family friendly event also includes a pancake breakfast, live music, and cooking and art demonstrations, and a kids zone. READ MORE

What's Blooming On Harrison

Saturday, May 18—Oak Park
Celebrate spring in Oak Park with an art fair, children's carnival, music stage, food and beer garden and more. READ MORE

Movies at Gallagher Way

Wednesdays, May 15 and 29—Wrigleyville
Visit Gallagher Way near Wrigley Field to see a variety of blockbusters on the big screen. Food trucks from local favorite restaurants like Big Star and West Town Bakery sell their goodies at the park. READ MORE

Parkway Bank Park's "Spring Fun Fest"

Sunday, May 19—Rosemont
Families are invited to visit Parkway Bank Park Saturday, May 13 for a fun-filled day of outdoor festivities at “Spring Fun Fest.” A variety of free activities will be offered from 1 p.m. – 5 p.m. including balloon sculpting, bounce houses, face painting, a petting zoo, and live entertainment from Jeanie B. and the Jelly Beans.  READ MORE

Mole de Mayo

Friday, May 24-Sunday, May 26—Pilsen
Celebrate the Pilsen neighborhood with the country's only outdoor mole cook off. Families can choose their favorite mole while enjoying music, dancing, and the excitement of luche libre wrestling. READ MORE

Chicago Memorial Day Parade

Saturday, May 25—Downtown
Chicagoans of all ages are invited to the annual Memorial Day Parade, in honor of all the men and women who made the ultimate sacrifice in defense of our country. The parade begins at noon, following a wreath laying ceremony at 11am in Daley Plaza, and proceeds from State and Lake to Van Buren Street. READ MORE

Belmont-Sheffield Music Festival

Friday, May 24-Sunday, May 26—Lakeview
Families can kick off summer with music, food, and drinks at this annual Lakeview street festival. READ MORE
The Play Garden at Maggie Daley Park. Photo courtesy of the Chicago Parks Department
The Play Garden at Maggie Daley Park. Photo courtesy of the Chicago Parks Department

More Things To Do in Chicago this Spring

27 of the Best Mother’s Day Brunches in Chicago

Spoil mom with these Mother's Day meals around Chicago. READ MORE

Best Tot Lots and Toddler Playgrounds in Chicago

Check out this list of playgrounds made just for smaller kids. READ MORE

Top 10 Best Hotdogs in Chicago to Try with Kids

There are so many hotdogs for kids to try in Chicago! READ MORE

35 Spring Festivals and Fairs in Chicago for Families

Get ready for spring fun with our roundup of fairs, festivals, and parades around town. READ MORE

Best Places to Hike with Kids Near Chicago

Soak up nature in these forest preserves and parks near the Windy City. READ MORE

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