30 Fun Things to Do in Chicago in September

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 in the region.

2. Collaborative Works Festival – September 4 and 6, 2025

Art Song Chicago highlights vocal chamber music throughout the city. Its Collaborative Works Festival explores the theme Songs of War and Peace through works by Mahler, Schumann, and more at Roosevelt University.

3. Chicago Gypsy Jazz Festival – September 5-6, 2025

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 Adrien Chevalie, Don Bernardo, and Alfonso Ponticelli & Swing Gitan.

4. Taste of Chicago – September 5-7, 2025

The Taste of Chicago returns to Grant Park in a celebration of the city’s best bites. Chow down on local favorites like Harold’s Chicken, Eli’s Cheesecake, and the Original Rainbow Cone. Lupe Fiasco, Jojo, and Elvis Crespo will get the crowd moving on the music stage.

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!

5. German American Oktoberfest – September 5-7, 2025

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.

6. 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.

7. Retro on Roscoe – September 5-7, 2025

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.

8. Edgewater Music Fest – September 5-7, 2025

Just when you thought you’d seen every Chicago street fest, Edgewater Music Fest brings an incredible lineup to the North Side for its inaugural event. Rock out with Cloud Nothings, Ric Wilson, Foxy Shazam, and more.

9. Mandala Makers Festival – September 5-7, 2025

Enjoy music and dance from South Asian performing artists at the Mandala Makers Festival. Head to the Athenaeum Theatre in Lakeview for performances ranging from folk and classical traditions to an electronic party.

10. Pilsen Mexican Independence Day – September 6, 2025

Pilsen’s 24th annual Mexican Independence Day Parade kicks off at noon on West 18th Street. Celebrate the vibrant holiday with traditional food, clothing, music, and more.

11. Printers Row Lit Fest – September 6-7, 2025

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.

12. Evanston Folk Festival – September 6-7, 2025

Just north of Chicago, Evanston Folk Festival put together an all-star lineup of more than 30 musicians including Iron & Wine, Margo Price, Ani DiFranco, and more. The second annual festival goes down on the lakefront at Dawes Park with some performances at Cahn Auditorium.

13. El Grito Chicago – Postponed

Celebrate Mexican Independence Day in downtown Chicago at El Grito. The two-day festivities include traditional cuisine, mariachis, ballet folclórico, and more. The 2025 festival has been postponed.

14. Ravenswood Art Walk – September 13-14, 2025

Support more than 50 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.

15. Lakeview East Festival of the Arts – September 13-14, 2025

Come for the art and stay for the live music at the 20th annual Lakeview East Festival of the Arts. Admire work from more than 150 artists, including photography, painting, jewelry, furniture, and more.

16. 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.

17. 26th Street Mexican Independence Day Parade – September 14, 2025

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. Englewood Jazz Festival – September 18-20, 2025

Groove along with local musicians at the 25th Englewood Jazz Festival. The free festival at the Hamilton Park & Cultural Center features Ernest Dawkins, Adegoke Steve Colson, Renee Baker, The Young Masters, JoVia Armstrong, Isaiah Spencer, and Dee Alexander.

19. Riot Fest – September 19-21, 2025

Mosh with 50,000 fellow music fans in Douglass Park for the 20th anniversary of Riot Fest. Style your tallest mohawk and rock out with headliners like Green Day, Blink-182, Weezer, Jack White, and “Weird Al” Yankovic. Don’t miss my tips for attending Riot Fest!

20. Chicago Exhibition Weekend – September 19-21, 2025

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

21. Reeling: The Chicago LGBTQ+ International Film Festival – September 19-28, 2025

Reeling is the country’s second-oldest LGBTQ+ film festival. Catch nearly 50 screenings at Landmark’s Century Centre Cinema and Chicago Filmmakers during the diverse festival.

22. 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.

23. Chicago Architecture Biennial – Sept. 19, 2025 – Feb. 28, 2026

The 10th annual Chicago Architecture Biennial kicks off in September and runs through February from the Chicago Cultural Center to locations across the city. The largest architecture and design exhibition in North America is free and features more than 100 projects by global contributors, from installations to lectures.

24. West Loop Music and Art Fest – September 20-21, 2025

Fulton Market transforms into a five-block outdoor art gallery featuring work by 100 artists during the West Loop Music and Art Fest. Come nightfall, the festival explodes with live music on two stages.

25. Chicago Live! – September 20-21, 2025

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

26. 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.

27. Chicago Gourmet – September 25-28, 2025

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.

28. World Music Festival – Sept. 26 – Oct. 5, 2025

Chicago’s music festival calendar doesn’t slow down come fall. World Music Festival Chicago features 31 artists from 16 countries at 11 venues in the city, from the Cultural  Center to Navy Pier and Millennium Park.

29. Fall Fest – September 26-October 26

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.

30. Hyde Park Jazz Fest – September 27-28, 2025

Celebrate Chicago-style jazz at the free Hyde Park Jazz Fest. Venues throughout the neighborhood feature more than 30 artists, including the Isaiah Spencer Quartet, Micah Collier and Proximity, and Fay Victor.

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

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in August
• What to Do in Chicago in October
• Fun Things to Do in Chicago in November
• What to do in Chicago in December