35 Fun Things to Do in Chicago in September from a Local

September just might be the best month in Chicago. Summer weather lingers for warm days and comfortably cool nights. The events calendar is still brimming with things to do, and there are fewer tourist crowds to contend with. From festivals and football to concerts and cuisine, September is a great time to explore Chicago. 

I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. September is one of my favorite times in the city. Whether you’re visiting Chicago in September or you live in Chicagoland, here are 30 fun things to do in Chicago in the fall.

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Fun Things to Do in Chicago in September

1. Get Out on one of Chicagoland’s Best Hikes

Chicagoans have access to more than 600 parks in 8,800 acres of the Chicago Park District and nearly 70,000 acres of the Cook County Forest Preserves in and around the city. From Promontory Point and LaBaugh Woods in the city to Matthiessen State Park and Midewin National Tallgrass Prairie, I rounded up my favorite hikes around Chicago.

2. Chicago Jazz Festival – September 3-6, 2026

Chicago is a renowned jazz city, and the Chicago Jazz Fest celebrates this legacy. The free festival in Millennium Park highlights local and international talent like Robert Glasper, the Dee Dee Bridgewater & Bill Charlap Duo, and Paquito D’Rivera.

3. Sound & Gravity Festival – September 3-6, 2026

Sound & Gravity returns to Chicago for its second year of jazz, experimental, and indie music programming. The festival stretches across several venues in the Bricktown neighborhood and features artists like Grouper, Alabaster DePlume, and Hailu Mergia.

4. North Coast Music Festival – September 4-6, 2026

North Coast Music Festival celebrates its 16th anniversary with electronic music talent like Fisher, GRiZ, and Illenium. The beat drops at SeatGeek Stadium in Bridgeview, IL during Labor Day Weekend.

5. ARC Music Festival – September 4-7, 2026

House and techno music fans pack Union Park in the West Loop for ARC Music Festival. The three-day festival includes performances by Anyma, Michael Bibi, Honey Dijon, and Sara Landry.

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

6. Taste of Polonia Festival – September 4-7, 2026

You don’t need to be a member of Chicago’s proud Polish community to enjoy the Taste of Polonia Festival at the Copernicus Center. Stop by Jefferson Park for Polish cuisine, beer, and performances along with a Kids Zone.

7. Deep Dish Cooking Class at Pizzeria Uno

Want to take the taste of Chicago home? Learn how to make your own authentic deep-dish pizza at the place where it was invented. Take a deep dish cooking class at Pizzeria Uno for 90 minutes of fun and flavors.

8. Great American Lobster Fest – September 5-6, 2026

Put on your lobster bib and head to Navy Pier for the Great American Lobster Fest. Crack open fresh Maine lobster and listen to live music as you take in downtown Chicago and Lake Michigan views.

9. African Festival of the Arts – September 5-7, 2026

Ring in Labor Day weekend with Labor Day weekend, with the African Festival of the Arts at the Washington Park Sunken Garden. Purchase a ticket to enjoy art, food, crafts, cultural villages, and live music from across the Diaspora.

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10. Bike the Drive – September 6, 2026

Once a year, Chicagoans have the unique opportunity to ride their bikes on DuSable Lake Shore Drive. Bike the Drive allows you to ride as much of the 30-mile course as you like with views of Lake Michigan and the Chicago skyline.

11. Mandala Makers Festival – September 11-13, 2026

Enjoy music and dance from South Asian performing artists at the Mandala Makers Festival. Performances ranging from folk and classical traditions to an electronic party go down at Comrade Chicago, Epiphany Center for the Arts, and iO Theater.

12. German American Oktoberfest – September 11-13, 2026

Lincoln Square is the place to be in Chicago to honor German traditions like Oktoberfest. German American Oktoberfest includes two tents of beer, food, and music. Don your lederhosen for the parade on Saturday at 2 p.m.

13. Printers Row Lit Fest – September 12-13, 2026

Printer’s Row isn’t home to many printing houses these days, but it still hosts the Midwest’s largest outdoor literary event. Printers Row Lit Fest features row upon row of booksellers and a weekend of author talks for book lovers of all kinds.

14. Evanston Folk Festival – September 12-13, 2026

Just north of Chicago, Evanston Folk Festival put together an all-star lineup of more than 30 musicians including Trampled By Turtles, Indigo Girls, Mdou Moctar and more. The second annual festival goes down on the lakefront at Dawes Park with some performances at Cahn Auditorium.

15. El Grito Chicago – September 12-13, 2026

Celebrate Mexican Independence Day in downtown Chicago at El Grito. The two-day festivities include traditional cuisine, mariachis, ballet folclórico, and more in Grant Park.

16. Ravenswood Art Walk – September 12-13, 2026

Support more than 80 local artists and shop for unique treasures at the Ravenswood Art Walk. Browse pop-ups, go behind-the-scenes at open studios, and enjoy bites from food trucks in this creative community.

17. 26th Street Mexican Independence Day Parade – September 13, 2026

There’s no better place than Little Village to honor Mexican Independence Day with a colorful parade, mariachi music, traditional dance, and more. The 26th Street Mexican Independence Day Parade steps off at the Little Village Arch on 26th Street and Albany from 12-3 p.m.

18. The Bear Private Pedicab Food Tour

Are you a fan of the Bear television show? Do you love food? Book this The Bear Private Pedicab Food Tour to get behind-the-scenes bites featured on the show from beloved Chicago restaurants like Pequod’s pizza and Margie’s Candies while you ride in style in a pedicab.

19. Chicago Exhibition Week – September 14-20, 2026

Explore the city’s vibrant art scene during the fourth annual Chicago Exhibition Week. Gallery hop between 50 participating galleries and creative spaces across the city, highlighting Chicago’s artistic spirit.

20. Englewood Jazz Festival – September 17-19, 2026

Groove along with local musicians at the 27th Englewood Jazz Festival. The free festival at the Hamilton Park & Cultural Center features the Julius Tucker Trio, Dee Alexander, the Jeremiah Hunt Quartet, and more.

21. Reeling: The Chicago LGBTQ+ International Film Festival – September 17-27, 2026

Reeling is the country’s second-oldest LGBTQ+ film festival. Catch nearly 100 screenings at various theaters around Chicago during the diverse festival.

22. Riot Fest – September 18-20, 2026

Mosh with 50,000 fellow music fans in Douglass Park for the return of Riot Fest. Style your tallest mohawk and rock out with headliners like Alanis Morissette, Tool, Twenty One Pilots, Iggy Pop, and more. Don’t miss my tips for attending Riot Fest!

23. Chicago Gypsy Jazz Festival – September 18-19, 2026

Swing to the lively genre known as Gypsy jazz at the Chicago Gypsy Jazz Festival. Shows go down at the Green Mill from 8 p.m. to 12 a.m. and include performers like Andrea Falcone, Dario Napoli, and Alfonso Ponticelli.

24. Retro on Roscoe – September 18-20, 2026

Dig into your old wardrobe and travel back in time for one of Chicago’s favorite street festivals. Retro on Roscoe brings live music, classic cars, and vintage shopping to  Roscoe Village! This throwback extravaganza is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages.

25. World Dumpling Festival – September 19-20, 2026

Taste your way around the globe at World Dumpling Fest in Wrightwood Park . Enjoy music and dance as well as dumplings from more than ten vendors including Cafe Tola and Tandoor Char House.

26. Lakeview East Festival of the Arts – September 19-20, 2026

Come for the art and stay for the live music at the 21st annual Lakeview East Festival of the Arts. Admire work from more than 150 artists, including photography, painting, jewelry, furniture, and more.

27. Tour Chicago’s African American History

From the birthplace of Gospel music to the Obama home, Chicago boasts a proud African American history. The African American Heritage Tour of Chicago guides you through the city’s African American heritage across several neighborhoods from museums to restaurants and more.

28. Chicago Live! – September 19-20, 2026

Navy Pier happens to host the Midwest’s largest free performing arts festival at Chicago Live! More than 100 artists will perform nonstop across multiple stages at this two-day celebration of the arts.

29. Collaborative Works Festival – September 23-26, 2026

Art Song Chicago highlights vocal chamber music throughout the city. Its Collaborative Works Festival explores the theme the Secret Garden through works by Schubert, Brahms, Margaret Bonds, and more at Roosevelt University.

30. Chicago Gourmet – September 24-27, 2026

Chicago is a foodie town, and Chicago Gourmet is one of the best ways to celebrate the city’s cuisine. Enjoy celebrity chef demos, a high-end tasting competition for the best burger on the Harris Theater Rooftop, and around town.

31. Visit the World’s Fair Bison in Humboldt Park

Need some fresh air? Soak up the sun in Humboldt Park, where you can admire sculptures that were created for the 1893 World’s Columbian Exposition. Learn the not-so-straightforward story behind these bison sculptures.

32. African/Caribbean International Festival of Life – September 25-27, 2026

The African/Caribbean International Festival of Life has been celebrating Chicago’s diverse communities for more than 20 years. Don’t miss Afro-Caribbean music, art, and food in Washington Park.

33. World Music Festival – Sept. 25–Oct. 4, 2026

Chicago’s music festival calendar doesn’t slow down come fall. World Music Festival Chicago features artists from around the world playing free performances at venues around the city, from the Cultural  Center to Navy Pier and Millennium Park.

34. Fall Fest – Sept. 25-Nov. 1, 2026

Lincoln Park Zoo’s family-friendly fall celebration is a roaring good time! Enjoy seasonal activities like picking pumpkins, roasting s’mores, and listening to music each weekend in late September and throughout October at Fall Fest.

35. Hyde Park Jazz Fest – September 26-27, 2026

Celebrate Chicago-style jazz at the free Hyde Park Jazz Fest. Venues throughout the neighborhood feature more than 30 artists, including Ben LaMar Gay, the Orbert Davis Sextet, and the Rob Mazurek Prismatic Trio.

Visiting Chicago in September FAQ

Is September a good time to visit Chicago?

Fall is a fantastic time to visit Chicago. It might just be my favorite time of year in the city. September brings the heat and humidity down but still boasts sunny days and temperate evenings. Layer up for unexpected weather while you enjoy a packed calendar of festivals, sports, and cultural events across Chicago. With the crowds of summer break behind us, the city is quiet enough to score cheaper flights and hotel deals than other times of year. Book that buzzy restaurant reservation and visit one of Chicago’s top attractions like the Field Museum, 360 Chicago Observation Deck, or the Art Institute, to skip the lines.

What is Chicago Weather like in September?

September in Chicago is a mix of warm, sunny days and cooler evenings. According to the National Weather Service, the average temperatures in Chicago in September range from a high of 75 degrees to a low of 57 degrees. You might experience rain showers in addition to blue skies and sunshine. The weather can shift rapidly, so be sure to check the forecast before you visit Chicago in the fall so you can pack accordingly.

What Should I Wear to Chicago in September?

If you’re wondering what clothes to wear to Chicago in September, I recommend packing light layers. The days are typically warm and sunny, but you might experience a cool lake breeze off Lake Michigan. Check the weather before you visit Chicago in September so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the fall.

• Chicago is a walking town, so pack comfortable shoes like sneakers or boots.
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. Merino wool makes a great base layer for men and women. You may want to layer with a women’s flannel or a men’s flannel.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• In the fall, I typically layer a lighter trench coat, leather jacket, or bomber jacket over my outfit.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days and a beanie in case it gets chilly at night.

Where to Stay in Chicago in September

Wondering where to stay overnight in Chicago in the fall? I love the views of Grant Park from the Blackstone Hotel and the iconic pool at the InterContinental. The Chicago Athletic Association has great views of Millennium Park and a rooftop fire pit, while the LondonHouse boasts beautiful views of the Chicago River from its rooftop bar.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you prepare to visit Chicago in September

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