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31 Best Things To Do in Chicago with Kids September 2025

Printer's Row Lit Fest. Photo by Robert Kusel, courtesy of the event.
Printer's Row Lit Fest. Photo by Robert Kusel, courtesy of the event.
8/29/25 - By Maureen Wilkey

We're headed back to school but there are still plenty of fun things to do in Chicago with kids this September. The last of the summer street festivals are wrapping up on Labor Day weekend, so check out Taste of Polonia or Naperville's Last Fling. Or embrace the feeling of fall with Printers Row Lit Fest, Septemberfest in Bloomingdale, or Oktoberfest in Lakeview. Nostalgia-loving families may enjoy the Throwback Music Fest or a Soap Box Derby in Naperville.

Looking for classes to satisfy kids' interests after school? Our Class Guide has lots of ideas for kids with all kinds of fun hobbies. And don't forget, our family-friendly calendar is filled with plenty of other things to see and do.

Read on to see the best events for kids in Chicago in September 2025.

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Long Grove Apple Fest. Photo courtesy of Enjoy Illinois
Long Grove Apple Fest. Photo courtesy of Enjoy Illinois

Family-Friendly Fun for September 2025

Last Fling

Naperville - FREE
August 29- September 1
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. READ MORE

Taste of Polonia

Portage Park
August 29- September 1
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. READ MORE

African Festival of the Arts

Washington Park
August 30-September 1
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.  READ MORE

German-American Fest

Lincoln Square - FREE
September 5-7
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. READ MORE

Rock the Block Party

Elmhurst - Free
September 5-6
Families can celebrate the end of summer with live entertainment and local food vendors at this annual Elmhurst festival. Kids can enjoy face painting, arts and crafts, games, a photo booth, and a performances from local musicians. Adults can enjoy beverages from the beer and wine tent. READ MORE

Throwback Music Fest

Gladstone Park - FREE
September 5-7
Introduce kids to the music of the '50s, '60s, '70s, and 80's at this annual northwest side festival. While grownups enjoy tribute bands, a throwback pinup contest, and a classic car show, kids can play games, do crafts, enjoy face painting, or bounce in a bounce house.   READ MORE

Printers Row Lit Fest

South Loop - FREE
September 6-7
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. READ MORE

Midnight Circus in the Parks

Parks throughout the City
September 6, 12-14, 20-21, and 26-28
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. READ MORE

Soap Box Derby 2025 September Rally

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

DuPage Comic Con

Wheaton
September 6
Might 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 3:30 p.m. Free comics, free parking and free admission for kids make this a great day for comic lovers. READ MORE

Bloomingdale Septemberfest

Bloomingdale - FREE
September 6
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. READ MORE

Hanover Park Fall Fun Fest Featuring Flavors of Hanover Park

Hanover Park- FREE
September 6
Enjoy all things fall at Hanover Park's annual Fall Fun Fest. Families can go on a hayride, complete an inflatable obstacle course, play BINGO and listen to live music. The event also includes glitter tattoos for kids, food trucks, and fall crafts and games. Families can also taste foods from local restaurants and vendors. READ MORE

Elmhurst Touch-a-Truck

Elmhurst - FREE
September 6
Kids can touch and climb into a variety of trucks at Elmhurst's Beren's Park during this annual free event. Food trucks will be on hand to complete the truck theme, with Smallcakes, Brown's Chicken,and Windy City Ice Cream serving treats. READ MORE

Migrating Monarchs Celebration

River Forest - FREE
September 7
Learn how monarchs migrate to Mexico, how researchers tag them to research their movements, and see how they are raised and released. Kids crafts and educational displays make this event fun for all ages. READ MORE

Retro on Roscoe

Roscoe Village
September 5-7
Roscoe Village is offering up live music, kid's activities, a car and motorcycle show, and much more at this six block street festival for the whole family. READ MORE

Fine Arts Festival - Downers Grove

Downers Grove
September 6
The 48th Annual Downers Grove Fine Arts Festival will be held September 6-7, 2025. The festival features a diverse range of juried artists across various mediums. In addition to the beautiful art, you can enjoy live entertainment, explore unique boutiques, savor delicious offerings at local restaurants, and partake in a children's art activity.  READ MORE

Sundays on State

Downtown- FREE
September 7
Chicago's State Street is closed from Madison to Lake for a block party full of surprises. Families can enjoy art, culture, active recreation, food, and specials from local retailers. READ MORE

Glen Ellyn Backyard BBQ

Glen Ellyn - FREE
September 7
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. READ MORE

Lakeview East Festival of the Arts

Lakeview
September 12-14
Lakeview East Festival of the Arts offers over 150 artists, featuring paintings, sculptures, photography furniture, jewelry, and more. In addition to live music on two stages, the festival includes live demonstrations, family activities and a garden oasis.     READ MORE

Revolutionary War Reenactment

Wheaton
September 13
The 18th century comes alive at Cantigny at this weekend-long battle reenactment. The event will include a fife and drum corp, tomahawk competition, children's games, heritage dance, reenactment of the signing of the Declaration of Independence, and a battle reenactment.  READ MORE

Parkway Bank Park's Family Fall Fest

Rosemont - FREE
September 14
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! READ MORE

Glow in the Park Lantern Walk

Glen Ellyn - FREE
September 12
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. READ MORE

Spring Road Fall Fest

Elmhurst - FREE
September 20
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. READ MORE

Norwood Park Fall Fest

Norwood Park
September 13-14, 2024
Celebrate fall with live entertainment, food and drink vendors, and kids' activities for all ages. Kids can enjoy carnival games, a magic show, tattoos and henna, an inflatable corn maze and kids' music and dance performances. READ MORE

Open House: Merit School of Music – South Shore

South Shore - Free
September 20
Join Merit School of Music’s South Shore Open House on Saturday, September 20! Bring the whole family for a fun, music-filled morning of performances and hands-on activities. Stop by the open house to: Explore an instrument petting zoo Enjoy live performances, including a musical storytime Tour Merit's building Learn about fall programming  and more   READ MORE

Taste of Egypt Festival

Burr Ridge
September 20-21
St. Mark Coptic Church of Burr Ridge invites families for 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.   READ MORE

St. Alphonsus Oktoberfest

Lakeview
September 20-22
Bring your lederhosen and dirndls for some German family fun. Enjoy some bratwurst, some live music, and all things Bavarian, as well as music from favorite Chicago acts. READ MORE

World Music Festival

Various Chicago locations - Free
September 26-October 5
World music fans can enjoy FREE concerts throughout the City of Chicago during the 23rd 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. READ MORE

Lincoln Park Zoo Fall Fest

Lincoln Park - Free
Starts September 26
Families can enjoy a walk through the pumpkin patch, a pumpkin-carving demonstration, and pumpkin-themed treats like a caramel apple station and a s'more station at Lincoln Park Zoo throughout October. READ MORE

Long Grove Apple Fest

Long Grove
September 26-28
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. READ MORE

Leo Lionni's Frederick at Chicago Children's Theatre

West Loop
Opens September 27
While other mice are gathering food for the winter, Frederick daydreams the summer away. But when fall weather comes, it is Frederick who has stored up something special for the long cold winter in a celebration of the idea that there is a place for all of us in this world. Originally a world premiere in CCT’s 10th birthday season, this charming musical based on Leo Lionni’s classic, much-loved Caldecott Award-winning book features a book by Suzanne Maynard Miller and a spirited folk and rock blues music score by Sarah Durkee and Paul Jacobs, performed live, on-stage by a talented cast of... READ MORE

Places featured in this article:

Naperville Central High School
Hanover Park Community Center
Downtown Downers Groveq
State Street from Madison to Lake
Lake Ellyn Park & Boathouse
Merit School of Music – South Shore
Various sites throughout Chicago