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Best Things to Do in Chicago May 2025 with Kids

Spring Fun Fest. Event photo courtesy of Parkway Bank Park
Spring Fun Fest. Event photo courtesy of Parkway Bank Park
4/27/25 - 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 2025.

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! May in Chicago is all about the outdoors: head to a big downtown parade like The Polish Constitution Day Parade or the Memorial Day Parade. Or, check out environmentally-themed fun at Chicago River Day or World Migratory Bird Day. 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 in one of these Best Places to Hike with Kids.

Here are some of our favorite things to do in May 2025 with kids in Chicago.

 

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Movies at Gallagher Way begin May 21st! Photo courtesy of the event.
Movies at Gallagher Way begin May 21st! Photo courtesy of the event.

Best Things To Do in Chicago in May

Mexico Fest at Navy Pier

Downtown - FREE
Friday, May 2-Sunday, May 4
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 3
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 2025 is "1000 years of the Polish Kingdom."   READ MORE

Lilac Time

Lombard
Saturday, May 3-Sunday, May 18
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 2025 Spring Rally

Naperville
Saturday, May 17-Sunday, May 18
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
Saturday, May 3
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
Saturday, May 10-Sunday, May 11
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: Migration Madness

South Holland - FREE
Saturday, May 10
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 10
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 16-Sunday, May 18
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 17-Sunday, May 18
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: Abiyoyo

Downtown
Saturday, May 10
In this South African folktale adapted by singer-songwriter Pete Seeger, a boy and his father are banished from their town for making mischief. They are welcomed back when they find a way to make a monster named Abiyoyo disappear. This redemptive story features enchanting music performed by members of the CSO. READ MORE

Long Grove Chocolate Festival

Long Grove
Friday, May 16-Sunday, May 18
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 17-Sunday, May 18
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 17-Sunday May 18
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

Switch on Summer with ComEd

Downtown- FREE
Saturday, May 10
The whole family can join ComEd and the Chicago Park District to watch the Buckingham Fountain officially switch on at 12pm and enjoy free family-friendly activities and live entertainment!  READ MORE

What's Blooming On Harrison

Oak Park - FREE
Saturday, May 31
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
Wednesday, May 21
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 17
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

Chicago Memorial Day Parade

Downtown - FREE
Saturday, May 24
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 23-Sunday, May 25
Families can kick off summer with music, food, and drinks at this annual Lakeview street festival. READ MORE

Barrington Art Festival

Barrington - FREE
Sunday, May 25
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

Día de los niños y libros: A Celebration of Children and Books

Downtown - FREE
Saturday, May 10
Join Chicago Public Library and its staff for an open house celebration with play and art activities, music, storytelling, book giveaways and special guests. And meet Daisy from WTTW Kids' Nature Cat!   READ MORE

Vivid Creatures at the Morton Arboretum

Lisle
Opens Saturday, May 17
Vivid Creatures, a new outdoor art exhibition at The Morton Arboretum, is an invitation to explore connections with the natural world through giant, colorful, playful animal sculptures placed outdoors amid towering trees and sweeping green vistas. Each artwork tells a story about the relationships between creatures and the ecosystems where they live. READ MORE

Windy City Hot Dog Fest

Portage Park
Friday, May 30- Sunday, June 1
Taste all the hot dogs Chicago has to offer at this Six Corner festival. In addition to classic Chicago hot dogs from Byron's and Chicago Doghouse, families can taste internationally inspired hot dogs from Baked Cheese Haus, Indian hot dogs from Tikka Masala Dogs, and Asian inspired hot dogs from Lee Concessions. Live music and a hot dog eating contest round out the fun. READ MORE

Maifest Chicago

Lincoln Square
Friday, May 30- Sunday, June 1
Families can don their dirndls and lederhosen and step out to Lincoln Square for German and American food, music, and gemuetlischkeit. The event features carnival games, the crowning of the Maifest Queen and decorating the May Pole. READ MORE

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