Things to Do for Kids in Chicago in September 2026
Last Fling (in Naperville)
Naperville - FREE
Friday - Monday, September 4-7, 2026
Naperville's annual end-of-summer festival features live music, food vendors, a carnival, and Family Fun Land. The family area includes sack races, water balloon contests, and eating contests featuring cotton candy, spaghetti, and cupcakes. Music, dancing, stilt walkers, and a real live princess round out the family fun. Website
Taste of Polonia (at Copernicus Center)
Portage Park
Friday - Monday, September 4-7, 2026
The country's largest Polish festival takes place at the Copernicus Center in Chicago on Labor Day weekend. More than 30 bands will play on four stages throughout the weekend, and families can enjoy inflatables, a climbing wall, face painting, clowns, Disney characters, tastings and cooking classes, carnival rides, and games. Website
Elmhurst Touch-a-Truck
Elmhurst - FREE
Saturday, September 5, 2026
Kids can touch and climb into a variety of trucks at Elmhurst's Berens Park during this annual free event. Food trucks will be on hand to complete the truck theme, with Smallcakes, Kona Ice, and Billy Bricks on Wheels serving treats. Website
Frankfort Fall Fest
Roscoe Village - FREE
Friday - Sunday, September 5-7, 2026
Celebrate fall in the southwest suburbs at this annual event featuring concerts, a carnival, food vendors, and more. A parade steps off on Sunday at 1pm, and families can visit the KidWork Children's Museum or Frankfort History Museum nearby. Website
African Festival of the Arts (in Washington Park)
Washington Park
Friday - Sunday, September 5-7, 2026
Washington Park hosts the annual African Festival of the Arts, featuring vibrant drumming, museum-quality and collectible artifacts, colorful and rich handwoven fabric and textile, family-friendly activities, music, and food. Website
Midnight Circus in the Parks
Parks throughout the City
September 5 & 6, 11-13, 19 & 20, and 25-27, 2026
This small, family-run circus is as sweet as they come, bringing the circus to parks all over Chicago for a small, intimate performance! Families can grab a blanket and get cozy in their favorite park to see talented aerialists, gymnasts, tight rope walkers, clowns, and even a dog put on an energetic and awe-inspiring performance. Website
Glow in the Park Lantern Walk (at Lake Ellyn Park)
Glen Ellyn - FREE
Friday, September 11, 2026
Glen Ellyn Park District is partnering with Charlie's Corner Foundation for a lantern walk around Lake Ellyn to benefit Lurie Children's Hospital. The event will include live music, face painting, balloon artists, and a bubble show. Website
German-American Fest (in Lincoln Square)
Lincoln Square - FREE
Friday - Sunday, September 11-13, 2026
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 annual Steuben Parade through North Center and Lincoln Square, and traditional German music and dancing. Website
Throwback Music Fest (at Gladstone Park)
Gladstone Park - FREE
Friday - Sunday, September 11-13, 2026
Introduce kids to the music of the 50s, 60s, 70s, and 80s at this annual northwest-side festival. While grown-ups enjoy tribute bands, a throwback pinup contest, and a classic car show, kids can play games, do crafts, enjoy face painting, and bounce in a bounce house. Website
DuPage Comic Con
Wheaton
Saturday, September 12, 2026
Mighty Con presents the very best new local comic artists along with special guests and deals from comic book and toy vendors at DuPage County Fairgrounds. The legendary cosplay contest starts at 3:30pm. Free comics, free parking, and free admission for kids make this a great day for comic lovers. Website
Bloomingdale Septemberfest
Bloomingdale - FREE
Saturday, September 12, 2026
Celebrate the end of summer and the beginning of fall at this annual event in Bloomingdale. Families can enjoy a parade, live entertainment, carnival rides and games, food and craft vendors, and the Lions Club Beer Tent. Website
Glen Ellyn Backyard BBQ
Glen Ellyn - FREE
Saturday, September 12, 2026
Enter your barbecue recipe, or come taste some of Glen Ellyn's best barbecue while listening to live local bands. Contestants will enter their chicken, ribs, and sauce for judging. Kids' musicians will play at various times throughout the day while kids enjoy Piglet Playland, which features inflatables, arts and crafts, and face painting. Website
Parkway Bank Park's Family Fall Fest
Rosemont - FREE
Saturday, September 12, 2026
Parkway Bank Park entertainment district will kick off the fall season with this annual family-friendly event featuring a variety of free activities including bounce houses, face painting, a petting zoo, balloon sculptors, and more! Website
Printers Row Lit Fest
South Loop - FREE
Saturday & Sunday, September 12 & 13, 2026
Bibliophiles of all ages are welcome at Printers Row Lit Fest, where they can enjoy talks, demonstrations, and workshops with authors of all genres. Kids' authors and books will be featured throughout the fest. Website
El Grito Chicago (in Grant Park)
Grant Park
Saturday & Sunday, September 12 & 13, 2026
El Grito Chicago returns to downtown Chicago’s Grant Park, bringing the heart and soul of Mexican culture to the city. Enjoy live Mariachi bands and traditional ballet folklórico dancers at the Petrillo Bandshell, authentic Mexican cuisine, and kids' activities like inflatables, games, and crafts from local organizations. Website
Taste of Egypt Festival (at St. Mark Coptic Church)
Burr Ridge - FREE
Saturday & Sunday, September 12 & 13, 2026
St. Mark Coptic Church of Burr Ridge invites families to its annual Taste of Egypt Festival! Enjoy camel rides, bouncy houses, inflatables, a petting zoo, church tours, live music, henna tattoos, a craft corner, jewelry, souvenirs, and personalized hieroglyphics. Egyptian food will also be available for purchase, including kufta, grilled chicken, grape leaves, falafel, baklava, Turkish coffee, and Egyptian fruit drinks. Website
Naperville Irish Fest
Naperville
Friday & Saturday, September 18 & 19, 2026
Catch the luck of the Irish at this annual festival at Naperville's Central Park. The event will include cultural activities like singing and dancing, games of hurling, a carnival, food vendors, and more. Kids can have their faces painted, learn an Irish jig, visit faeries, and more. Website
Retro on Roscoe
Roscoe Village
Friday - Sunday, September 18-20, 2026
Artisans, antique vendors, and merchants join three stages of entertainers at this North Side street festival. Local restaurants featuring street fest-friendly foods and classic cars round out the line-up for this old-fashioned family fun event. Website
Old Town Oktoberfest
Old Town
Friday - Sunday, September 18-20, 2026
Celebrate Oktoberfest in Chicago's Old Town neighborhood with live music from brass bands and local cover bands, stein holding contests, and a dog parade. German food vendors will be on hand to serve bratwursts, pretzels and more! Website
Spring Road Fall Fest
Elmhurst - FREE
Saturday, September 19, 2026
Families can enjoy fall-themed entertainment at the intersection of Spring Road and the Prairie Path in Elmhurst. Activities include a petting zoo, pony rides, a moon jump, temporary tattoos, carnival games, and musical entertainment. Kids can also paint pumpkins and enjoy concessions. Website
Migrating Monarchs Celebration (at Sagawau Nature Center)
Lemont - FREE
Saturday, September 19, 2026
Learn how monarchs migrate to Mexico, how researchers tag them to track their movements, and see how they are raised and released. Kids' crafts and educational displays make this event fun for all ages. Website
Oaktoberfest
Oak Park
Friday & Saturday, September 25 & 26, 2026
Oak Park celebrates the changing seasons at Oaktoberfest with music, food from local restaurants, specialty craft beers, and a kids' root beer garden open from noon to 5pm. The pint-sized fun includes zucchini races, a ninja obstacle course, root beer floats, crafts, and other activities sponsored by local businesses. Website
International Festival of Life (in Union Park)
West Loop
Friday - Sunday, September 25-27, 2026
The International Festival Of Life features a very diverse showcase of culture and music from the Caribbean, Africa, Latin America, and United States. The objective of the festival is to bring nations together and live together as one. Website
Long Grove Apple Fest
Long Grove
Friday - Sunday, September 25-27, 2026
How do you like them apples? Long Grove will make them any way you want—baked in pies, dipped in chocolate or caramel, or chopped up in sangria. Families can also enjoy a carnival and live music with their apple treats. Website
World Music Festival
Various Chicago locations - Free
Friday, September 25- Sunday, October 4, 2026
World music fans can enjoy FREE concerts throughout the City of Chicago during the 24th Annual World Music Festival. This city-wide, multi-venue, 10-day festival will include 34 bands representing 22 countries. Experience music from all regions of the world including Brazil, South Korea, and Senegal. Website
Cantigny Fall Fest
Wheaton
Saturday & Sunday, September 26 & 27, 2026
Celebrate the season at Cantigny’s Annual Fall Festival. This family-friendly weekend features a vibrant Fall Market, live music, guided garden tours, and a variety of food trucks offering tasty bites. Kids can enjoy hands-on crafts, bounce houses, and a delightful petting zoo, creating memories for all ages. Website
Meet Me on Milwaukee
Bucktown
Sunday, September 27, 2026
Meet Me On Milwaukee is a pilot series of “pedestrianization” events between Alderman La Spata, the Wicker Park Bucktown Chamber of Commerce (WPBCC), and the Chicago Department of Transportation. For one Sunday in August, September, and October, Milwaukee Avenue between North/Damen and Ashland will be closed to car/bus traffic, replacing the usual traffic, honking, and vehicle emissions with pedestrians, bikes, live music, outdoor dining, exercise classes, sidewalk sales, and more! Website