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Lilac Time in Lombard. Photo credit: Canva
4/28/24 - 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 2024.

Let's be honest. With so many things to do this time of year, how can you possibly decide between them all? This best-of-May guide should do the trick! 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.

 

OUR LATEST VIDEOS

"Bluey's Big Play: The Stage Show." Production photo by Darren Thomas

Best Things To Do in Chicago in May

Bluey's Big Play The Stage Show

Downtown
Friday, May 3-Sunday, May 5
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

Downtown - FREE
Friday, May 3-Sunday, May 7
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

Downtown - FREE
Saturday, May 4
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

Lombard
Saturday, May 4-Sunday, May 19
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

Naperville
Saturday, May 4-Sunday, May 5
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

Wheaton - FREE
May 7
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

Mother's Day Family Fun Festival Bridgeview

Bridgeview
Friday, May 10-Sunday, May 12
Kids and grown-ups can enjoy lots of different activities including a petting zoo, carnival, and magician in Bridgeview. Food and beverages will be available for purchase. READ MORE

World Migratory Bird Day Celebrations

South Holland - FREE
Saturday, May 11
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

Various locations - FREE
Saturday, May 11
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

Lincoln Park
Friday, May 17-Sunday, May 19
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

Roscoe Village - FREE
Saturday, May 18-Sunday, May 19
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

Downtown
Saturday, May 18
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

Long Grove
Friday, May 17-Sunday, May 19
Celebrate chocolate 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

Skokie Festival of Cultures

Skokie - FREE
Saturday, May 18-Sunday, May 19
Celebrate all the cultures of the world in the multi-cultural suburb of Skokie. The event in Oakton Park includes two stages of music and dancing, food and beverage vendors, children's games and activities, interactive cultural booths, and an amazing display of flags. READ MORE

Spring Renegade Craft Fair Andersonville

Andersonville - FREE
Saturday, May 18-Sunday May 19
Arts and crafts fans can enjoy Renegade's new spring event 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

West Chicago - FREE
Saturday, May 18
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

Oak Park - FREE
Saturday, May 18
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

Wrigleyville - FREE
Wednesdays, May 15 and 29
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"

Rosemont - FREE
Sunday, May 19
Families are invited to visit Parkway Bank Park for a fun-filled day of outdoor festivities from 1pm–5pm 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

Pilsen
Friday, May 24-Sunday, May 26
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

Downtown - FREE
Saturday, May 25
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

Lakeview
Friday, May 24-Sunday, May 26
Families can kick off summer with music, food, and drinks at this annual Lakeview street festival. READ MORE

Barrington Art Festival

Barrington - FREE
Saturday, May 25-Sunday, May 26
More than 120 artists fill the streets of downtown Barrington with their wares as restaurants, bars and ice cream shops treat customers to food at this annual festival. Live music and kids' art activities add to the weekend fun. READ MORE

Places featured in this article:

Auditorium Theatre of Roosevelt University