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33 Best Things to Do in Chicago May 2023 with Kids

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, World Migratory Bird Day or Cosley Zoo's Party for the Planet. Fairy tales are also a big theme this month, with a Broadway in Chicago's Into the Woods  and Once Upon a Symphony performing The Elves and The Shoemaker. 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 2023 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

Broadway in Chicago "Into the Woods"

Tuesdays through Sundays through May 15—Downtown
Travel through a series of fairy tales with Broadway stars in this much beloved production from Stephen Sondheim and James Lapine. The story follows a Baker and his wife, who wish to have a child; Cinderella, who wishes to attend the King's Festival; and Jack, who wishes his cow would give milk. READ MORE

Mexico Fest at Navy Pier

May 5-7—Downtown
Navy Pier is joining forces with the General Consulate of Mexico in Chicago and the Government of Jalisco 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

Free Comic Book Day 2023

May 6—Locations throughout the city and suburbs
Pow! Crash! Boom!  Getting comic books for free is...super! Free Comic Book Day returns to its usual "first Saturday in May" date. READ MORE

'Go Run

May 6, 13, 20, and 27—Various locations
Kids and grown-ups can try to set new PRs at these weekly free races sponsored by the Chicago Area Runners Association and the Chicago Park District. One mile and 5K courses are featured at a different park throughout the city each week. READ MORE

Naperville Food Truck Festival

May 6—Naperville
Visit more than 25 local food trucks at Naper Settlement. Families can eat tacos, barbecue, Asian cuisine, pizza, empanadas, hot dogs, gourmet grilled cheese, cupcakes, and frozen yogurt. The event also includes live DJ entertainment, a face painter, a bubble artist, and a balloon artist. READ MORE

Polish Constitution Day Parade

May 6—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 2023 is “Polish American Partnership for Peace”   READ MORE

Lilac Time

May 6-21—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 2023 Spring Rally

May 6-7—Naperville
Build your own car or test run a pre-built car at the Greater Chicago Soap Box Derby's track. READ MORE

Roscoe Village Kidical Mass

May 7—Roscoe Village
Join Chicago Family Biking for an easy-going, fun ride around the Roscoe Village neighborhood. Kids can decorate their bikes and take a 3-4 mile ride with their parents around the area. The ride is about 5-6 miles per hour and is designed for kids without training wheels or on their parents bike trailers. READ MORE

Spring Flower Show: Bee's Knees

Daily through May 7—Garfield Park
The Garfield Park Conservatory hosts its spring flower show "Bee's Knees." The show displays the relationship between bees and blooms and includes tulips, daffodils, hyacinth, hydrangeas, delphiniums, azaleas, and more. Empty observation and demo hives are hidden amongst the flowers to give visitors a view from the bees' perspectives. 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

Chicago Dogs 2023 Season Opening Day

May 12—Rosemont
Join the Chicago Dogs at Impact Field for their 2023 season home opener against the Gary Lincoln Saltdogs. Every fan in attendance on opening night will receive a free replica jersey t-shirt and sign a one-day team contract. Fans will be allowed to run the bases after the game. READ MORE

Mayfest Lincoln Park

May 12-14—Lincoln Park
End spring and kick off summer with live music and festival foods in Lincoln Park. Families can check out music from Upbeat Music and Miss Foozie's Pet Parade. READ MORE

World Migratory Bird Day Celebrations

May 13—Cook County Forest Preserves
The Forest Preserve District of Cook County invites families to celebrate birds at Sagawau Nature Center, Little Red Schoolhouse Nature Center, Trailside Museum of Natural History or Crabtree Nature Center. Kids can enjoy crafts, go on a bird walk, and explore the preserves throughout the day. READ MORE

Chicago River Day

May 13—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

Cosley Zoo Conservation Day

May 13—Wheaton
Families can explore various ways to get involved in conservation by visiting with local organizations and businesses. Kids should be on the lookout for the Lorax as they learn how to "spring into action" for the environment. READ MORE

MCA Family Day

May 13—Magnificent Mile
The Chicago Museum of Contemporary Art (MCA) hosts a FREE family day the second Saturday of each month. The event includes free admission to the museum, as well as workshops, open-studio sessions, gallery tours, and performances designed and led by Chicago artists. READ MORE

Spring Roscoe Village Art and Craft Festival

May 13-14—Roscoe Village
This new spring festival on Chicago's North Side includes fabulous paintings, sculptures, and fiber pieces, as well as décor, jewelry and more, all made by local artists. Live music and kids' art activities add to the weekend fun. Bring your old art to donate to Chicago Furniture Bank. READ MORE

Once Upon a Symphony: The Elves and the Shoemaker

May 20—Downtown
Chicago Symphony Orchestra presents The Elves and The Shoemaker, a tale about how we all need help at times and how helping others strengthens our connections with each other. The music of the orchestra is accompanied by an interactive media presentation with vivid storytelling and enchanting visuals for a unique musical experience.  READ MORE

18th Annual Lilac Mutt Strut 5K & 1-Mile

May 20—Lombard
Run or walk with or without your four-legged family member at this annual Lilac Time race. Racers can register for in-person or virtual events. READ MORE

Long Grove Chocolate Festival

May 19-21—Long Grove
Celebrate chocolate in downtown Long Grove with tastings and pairings and live music. 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

The Music of The Beatles for Kids: Mother's Day Celebration

May 13-14—Evanston
The Rock and Roll Playhouse and The Cubby Bear host the Music of the Beatles for Kids! Rock n Roll Playhouse hosts regular concert series for kids, featuring some of the favorite music of their grownups. READ MORE

Spring Renegade Craft Fair Andersonville

May 20-21—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

Mother's Day Jazz Brunch

May 14—West Loop
Enjoy brunchy bites and mom-approved mimosas and spritzes at Time Out Market. Jazz music featuring John Fournier Trio will play from 11 a.m. to 3 p.m. No reservations required. READ MORE

Blooming Fest

May 20—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. READ MORE

What's Blooming On Harrison

May 20—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

May 17 and 31—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

Mole de Mayo

May 26-28—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

Belmont-Sheffield Music Festival

May 27-28—Lakeview
Families can kick off summer with music, food, and drinks at this annual Lakeview street festival. READ MORE

Chicago Memorial Day Parade

May 27—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

Parkway Bank Park's "Spring Fun Fest"

May 13—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

Stars on Ice

May 30—Rosemont
The crowd-pleasing Olympic quality ice show returns for one performance only, bringing a company of world-class champion skaters and ice dancers to strut their icy stuff. Most of this year's US Olympic team are in the cast. READ MORE

Pixar Putt Chicago

PIXAR Putt is 18 holes of fun mini-golf featuring characters and scenes from PIXAR films, including Toy Story, Inside Out, The Incredibles, and more. 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

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

30 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

Best Things To Do in Chicago with Kids this Spring

There's a long list of fun things to do with kids this spring in Chicago. READ MORE

Places featured in this article:

James M. Nederlander Theatre
Various Chicago Parks