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One, two, three, jump into one of these indoor swimming pools in Chicago! The Peninsula—Gold Coast, Chicago
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Best of May: 50 Things To Do in Chicago with Kids for Mother's Day, Memorial Day Weekend, and More

Celebrate Chicago River Day this month! Photo courtesy of the Friends of the Chicago River, Facebook
Celebrate Chicago River Day this month! Photo courtesy of the Friends of the Chicago River, Facebook
5/1/22 - By Maureen Wilkey

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 new presentation of Into the Woods in Des Plaines, Once Upon a Symphony performing Jack and the Beanstalk,  Lookingglass Alice on the Mag Mile, and Alice in Wonderland from the Salt Creek Ballet. If all of that is enough to make you want to go fly a kite, you can do so in Wheaton or Homer Glen.

There's still time to book a reservation at one of our top 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 with kids in Chicago!

While we are trying to promote safer activities that occur outdoors or with social distancing guidelines in place, please keep your family and others safe by always wearing a mask and maintaining an appropriate distance. If you arrive at an event that appears too crowded, try using the “nearby” search feature on our event calendar to find something else to do

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Roscoe Village Kidical Mass photo courtesy of Chicago Family Biking, Facebook
Roscoe Village Kidical Mass photo courtesy of Chicago Family Biking, Facebook

Best Things To Do in Chicago in May

Touch a Truck Festival at Kohl Children's Museum

May 1—Glenview
More than 30 trucks will be available for kids to climb and explore, including the Batmobile, Boilermaker Special train car, the ABC-7 Storm Tracker, and much more. Kids can also enjoy music, balloons, train rides, and food trucks. Sensory friendly no horns hour will take place from 1 p.m. to 2 p.m. READ MORE

Soap Box Derby 2023 Spring Rally

May 1—Naperville
Build your own car or test run a pre-built car at the Greater Chicago Soap Box Derby's track. READ MORE

Lilac Time

May 1-15—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

Hot Wheels Monster Trucks Live Glow Party

May 1—Hoffman Estates
Kids' favorite Hot Wheels Monster Trucks including Mega Wrex™, Tiger Shark™, Boneshaker™, Bigfoot®, and more, plus the all-new Gunkster™ glow in the arena for competitions and battles. All kids will receive a glow stick and a Hot Wheels toy giveaway. READ MORE

Roscoe Village Kidical Mass

May 1—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 9—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

Lookingglass Alice

Tuesdays through Sundays throughout May—Downtown
Take a trip down the rabbit hole with this returning circus inspired performance at the Lookingglass Theater. After touring the country and then taking a seven-year hiatus, the show is back with a fresh coat of magic. READ MORE

Go Fly a Kite at Graf Park

May 7—Wheaton
Wheaton Park District invites families to Graf Park to ring in its hundred and first year with a kite fly. Free kites will be available for the first 100 families. Kite performers will show off their tricks near Monroe Middle School. READ MORE

Derby Day Carousel Races

May 6—Elk Grove Village
Celebrate the Kentucky Derby by racing horses on the Jumps 'n Jiggles Carousel. Participants ride their horses to the finish line to see if they can win a prize. Kids can also play in the play area and enjoy a snack and drink. Cash bar is available for those over 21. READ MORE

'Go Run

May 7, 14, 21, and 28—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

Into the Woods at Prairie Lakes Theater

Fridays through Sundays through May 15—Des Plaines
Big Noise Theater presents the epic Stephen Sondheim fairy tale mashup about wishes, family and choices. Fairy tale characters come together for a timeless modern twist on their old classics. READ MORE

Free Comic Book Day 2023

May 7—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

Once Upon a Symphony: Jack and the Beanstalk

May 7—Downtown
Chicago Symphony Orchestra presents Jack and the Beanstalk, a classic fairy tale about persistence and love for family. The music of the orchestra is accompanied by an interactive media presentation with vivid storytelling, costumes, and sets created by the Chicago Children's Theatre.  READ MORE

Cosley Zoo Party for The Planet

May 7—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

Naperville Food Truck Festival

May 7—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 7—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

MCA Family Day

May 7—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

Mom & Me Golf at Tinley Junction

May 8—Tinley Park
Moms golf for free with a paid round of mini golf at Tinley Junction mini golf. Concession specials are also available. READ MORE

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

May 8—Wrigleyville
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

Mother's Day Jazz Brunch

May 8—West Loop
Enjoy brunchy bites and mom-approved mimosas and spritzes at Time Out Market. Jazz music featuring the Chicago Soul Jazz Collective will play from 1 p.m. to 3 p.m. No reservations required. READ MORE

Mother's Day LUMINARIA

May 8—Glen Ellyn
In honor of Mother's Day empowerHER is releasing custom luminaria honoring women and mothers across Lake Ellyn in Glen Ellyn. Purchase your own luminaria, or watch the display online. READ MORE

Astronomy in the Parks at Park No. 579 (Ridgeway Trailhead)

May 13—Wicker Park
Join Chicago astronomer Joe Guzman to look at the cosmos via telescope. The astronomer and his crew will provide instruction on how to look at the urban night sky. Please follow all current COVID guidelines by wearing masks and social distancing. READ MORE

Movies at Gallagher Way

May 11 and 25—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

Homer Glen Kite Festival

May 14—Homer Glen
Homer Glen celebrates its birthday with professional kite demonstrations, food trucks, a gardening workshop, and giveaways. Lawn games and kites for purchase swill also be on hand. READ MORE

World Migratory Bird Day Celebration

May 14—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 14—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

Sidewalk Art Contest

May 14—Westmont
Join the Westmont Park District at Gregg House Museum to design your own square of sidewalk art. Chalk will be provided and drawings will be judged at 1 p.m. Pre-registration is required to draw, or families can come to view the art at their leisure. READ MORE

17th Annual Lilac Mutt Strut 5K & 1-Mile

May 14—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

Parkway Bank Park's "Spring Fun Fest"

May 14—Rosemont
Families are invited to visit Parkway Bank Park Saturday, May 14 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 ScribbleMonster.  READ MORE

Salt Creek Ballet presents Alice in Wonderland

May 14—Glen Ellyn
Curious and Curiouser… join Salt Creek Ballet for a magical and memorable trip down the rabbit hole. Salt Creek Ballet presents “Alice in Wonderland,” at McAninch Arts Center at The College of DuPage, Glen Ellyn, Saturday, May 14th at 2 p.m. and 5 p.m. Filled with tea parties, colorful characters and superb dancing, this fantastically conceived dance performance is a perennial audience favorite – perfect for young and old alike. Each ticket includes access to a kids' Mad Hatter Tea Party taking place from 3:30-4:30 p.m. (between the 2 p.m. and 5 p.m. shows). This magical production... READ MORE

Stars on Ice

May 14—West Loop
The crowd-pleasing Olympic quality ice show returns for one performance only, bringing a company of world-class champion skaters and ice dancers to Anaheim to strut their icy stuff. Most of this year's US Olympic team are in the cast. READ MORE

Downers Grove Park District 75th Anniversary Celebration

May 14—Downers Grove
Celebrate 75 years with the Downers Grove Park District with a day full of fun activities in McCollum Park. Live entertainment will include DJs and Miss Jamie from the Farm. Kids can also enjoy free mini golf at Miner Mike's, a scavenger hunt, giant yard games, an obstacle course, a parade, and food vendors. READ MORE

Chicago Dogs 2022 Season Opening Day

May 14—Rosemont
Join the Chicago Dogs at Impact Field for their 2022 season home opener against the Gary SouthShore RailCats. In celebration of their fifth season, the Chicago Dogs will debut new jerseys and acclaimed vocalist Wayne Messmer will perform the National Anthem. Every fan in attendance on opening night will receive a free replica jersey t-shirt.  READ MORE

Elmhurst Museum Day

May 15—Elmhurst
Familes can ride the trolley as it rolls through Elmhurst to celebrate Museum Day! Visit the Elmhuirst Art Museum and Elmhurst History Museum. Participate in activities, enjoy refreshments, and enjoy family friendly tours.   READ MORE

Glen Ellyn Carnival

May 18-22—Glen Ellyn
Families can celebrate the end of the school year at the Glen Ellyn Carnival. Wristbands are available for riding unlimited carnival rides, play a variety of carnival games, and taste an array of fair foods in the streets of downtown Glen Ellyn. READ MORE

Bitter Jest Musical Festival

May 20 and May 27—Highland Park
Each week, a different local band and food vendor will team up to entertain Highland Park families. The series finale will feature the best bands of the fest at Navy Pier on Labor Day weekend. READ MORE

Long Grove Chocolate Festival

May 20-22—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

Mayfest Lincoln Park

May 20-22—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

Spring Renegade Craft Fair Andersonville

May 21-22—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

May 21—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 demonstration.s READ MORE

What's Blooming On Harrison

May 21—Oak Park
Celebrate spring in Oak Park with an art fair, children's carnival, music stage, food and beer garden and more. Artists and vendors for 2022 are TBA. READ MORE

Spring Roscoe Village Art and Craft Festival

May 21-22—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

BARK! Walk for a More Humane Chicago

May 21—Musuem Campus
Walk your dog or walk with your family to raise money for Chicago's Anti-Cruelty Society. The 2.5-mile walk starts and ends at Soldier Field, where families can watch dog friendly demonstrations, sample dog related products, enjoy food and beverages (including beer for those over 21) and make a family-friendly craft. READ MORE

Mole de Mayo

May 27-29—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 28-29—Lakeview
Families can kick off summer with music, food, and drinks at this annual Lakeview street festival. READ MORE

North Park Village Nature Center Spring Potluck

May 28—North Park
Visit North Park Village Nature Center for music and dancing outdoors. The SOS Ensemble band will play. Bring family, friends and food to share. The nature center will provide lemonade, iced tea, and some treats. READ MORE

Chicago Memorial Day Parade

May 28—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

Navy Pier Fireworks

May 28—Downtown
Navy Pier celebrates summer with fireworks every Saturday night in May. Families are welcome to sit in Navy Pier's open areas or enjoy the show from nearby parks or beaches. READ MORE

The Dreamer by School of Ballet 5:8

May 28-29—New Lenox
Looking to plan an inspirational affordable and unique family outing? Look no further than the premiere of The Dreamer by choreographer Julianna Rubio Slager. A cast of more than 300 dancers from the School of Ballet 5:8 will enchant audiences through innovative and breathtaking dancing while embodying the powerful story of Joseph from the book of Genesis. The full-length ballet performance poetically retells the life and dreams of Joseph on stage and invites audiences to experience the miraculous way that God turns evil intentions into agents for ultimate good. Come dream with us... READ MORE

Barrington Art Festival

May 28-29—Barrington
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
Photo courtesy of Bigstock
Photo courtesy of Bigstock

Fun Virtual Events for Kids in May

Fast Math Camp Online

Fast math can help kids learn to increase calculation speed and accuracy. In this week-long online camp, children learn tricks and shortcuts to perform better on exams, in competitions, and doing everyday calculations. With these techniques, kids can improve their confidence and concentration. READ MORE

Public Speaking Skills Online Camp for Kids

This valuable, hands-on, and interactive bite-sized workshop is specifically designed for kids to develop public speaking delivery skills, enhance their confidence, and teach essential presentation techniques. READ MORE

Scratch Junior Coding Camp for 4 to 7 Years

Scratch Junior is a visual, block coding language that is perfect for pre-readers. All of the blocks use images for the labels. Each session is only 30 minutes long, so that young students can stay engaged and focused the whole time. READ MORE

Secrets of the Rubik's Cube Online Camp

Join in a fun, five-day online camp to learn the secrets of the world's most popular puzzle toy. Basic and advanced levels are available.  READ MORE
Photo by Lauren LaRoche
Photo by Lauren LaRoche

More Things To Do in Chicago this Spring

25+ Amazing Places for Mother’s Day Brunch and Dinner 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

Best Things to See and Do at the Shedd Aquarium with Kids

Headed to the Shedd? Here's what you can't miss. READ MORE

Best Places to Hike Near Chicago with Kids

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:

Various Chicago Parks
Tinley Junction Mini Golf and Batting Cages
Lake Ellyn Park & Boathouse
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