Chicago in September is a very vibrant month, full of can’t-miss events, activities, and plenty of fun fall things to do.
From Taste of Chicago and Riot Fest to the culinary indulgence of Chicago Gourmet, the soulful sounds of the Hyde Park Jazz Festival, and the vibrant celebration of the 26th Street Mexican Independence Day Parade, September in Chicago is all about new beginnings, culture, and connection.
Here is the ultimate guide to events and things to do in September in Chicago.
The Best Things to Do in Chicago This September
Use the navigation below to explore can’t-miss events, recurring city favorites, and editor-curated picks. Bookmark this guide—we’ll be adding new Chicago September festivals, activities, and last-minute finds throughout the month.
Top Events: Must-attend events of the month.
Recurring Chicago Events & Activities: Regular events worth adding to your calendar.
The Curated List: Personal recommendations for unique Chicago experiences.
Top September Festivals & Things to Do in Chicago
Discover the biggest summer festivals and street fairs happening throughout the city.
September Chicago Street Festivals
September is full of exciting summer street and neighborhood festivals. Highlights include:
September 5 – 7, 2025: Retro On Roscoe
September 5 – 7, 2025: Taste of Chicago
September 5 – 7, 2025: Edgewater Music Festival
September 5 – 7, 2025: Throwback Music Festival
September 6, 2025: 79th Street Renaissance Festival
September 6 – 7, 2025: Printer’s Row Lit Fest
September 13 – 14, 2025: Lakeview East Festival of the Arts
September 13 – 14, 2025: El Grito Chicago
September 19 – 21, 2025: Riot Fest & Carnival
September 20 – 21, 2025: West Loop Music and Art Fest
September 25 – 28, 2025: Chicago Gourmet
September 26 – 28, 2025: Oktoberfest Chicago
September 27 – 28, 2025: Hyde Park Jazz Festival
World Music Festival Chicago
September 6–7, 2025 | Citywide, including Chicago Cultural Center
The World Music Festival Chicago celebrates diverse music from nations across the globe. All performances are free, and seating is first-come, first-served. Some venues have limited capacity, so early arrival is encouraged.
Homecoming House Party
September 12, 2025 (6–10 pm) | Chicago
Celebrate community, culture, and connection at Homecoming House Party—an evening honoring the Black collegiate experience and Divine 9 pride. Reunite with friends, enjoy live DJs, sip and stroll, and dance to house music vibes in a one-of-a-kind Chicago experience.
26th Street Mexican Independence Day Parade – “Pride and Power: Our Strength, Our Legacy”
September 14, 2025 (12–3 pm) | Little Village
Experience one of the largest parades in the Midwest, celebrating cultural pride, heritage, and community in Little Village. Enjoy floats, mariachi bands, folkloric dance performances, and more along the bustling two-and-a-half-mile corridor from the Little Village Arch on 26th Street to Kostner Ave.
Hispanic Heritage Month Festival & Art Tours – Chicago Humanities
September 21, 2025 | National Museum of Mexican Art & Pilsen Neighborhood
Celebrate Hispanic Heritage Month with a full day of programs highlighting Latino creativity, culture, and community. Festival Day features talks with artists and chefs, master classes, guided gallery tours, Pilsen mural walks, outdoor pop-ups, hands-on workshops, local vendors, music, and food. Immerse yourself in the rich visual culture, history, and storytelling of Pilsen and the National Museum of Mexican Art.
Midnight Circus in the Parks
September 2025 | Various Chicago Parks
Midnight Circus brings an intimate, world-class circus to neighborhoods across Chicago, offering accessible, affordable, and community-focused performances. Each show features live acrobatics, rescued animal ambassadors, and opportunities for volunteering, fundraising, and local engagement. Since 2007, the circus has raised nearly $2 million for Chicago Park Advisory Councils to support playgrounds, programming, and park improvements.
Chicago SummerDance
September 2025 | Various Locations
Dance under the stars at Chicago SummerDance, a beloved free event series featuring live music and dance lessons in parks across the city. From salsa and swing to line dancing and bachata, each event invites participants of all skill levels to learn a new style and enjoy vibrant community celebrations. Expect themed nights, cultural showcases, and family-friendly activities throughout the summer.
Millennium Park Summer Film Series
September 2025 | Various Locations
Looking for one the best free things to do this summer in Chicago? Watch free outdoor movies all summer long at the iconic Jay Pritzker Pavilion in Millennium Park. Bring a blanket or lawn chair and enjoy a mix of classic and contemporary films shown on a state-of-the-art 40-foot LED screen. A must for anyone looking for free things to do in Chicago in September.
Chicago Farmers Markets
September – October | Various Locations
Now through the fall, you can find fresh fruit, vegetables, flowers, baked goods, and more at various neighborhood farmers’ markets in the city of Chicago.
Maxwell Street Market
September – October | West Maxwell Street &, S Halsted St
On select Sundays, enjoy this free event in Chicago. The Maxwell Street Market will open, featuring an eclectic mix of foods and finds. This year’s edition will also feature live entertainment and programming from cultural partners, incorporating nearby businesses and restaurants, including several “Maxwell Street originals” with longstanding ties to the neighborhood.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Ongoing Things to Experience in Chicago in September
Looking for things to do in Chicago in September that are available all month long? Here’s a round-up of ongoing attractions and seasonal experiences to check out this month.
- Architecture Boat Tour: Experience Chicago’s stunning skyline on a Chicago boat tour, a perfect outdoor activity for warm weather.
- Flyover in Chicago: Marvel at Chicago’s skyline and lakefront from a thrilling 30-minute immersive ride. Located at Navy Pier.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- Chicago Rooftop Pools: Soak up the sun and city views at rooftop pools—perfect for a luxe summer escape.
- 360 CHICAGO Observation Deck Admission: Tower above Chicago from the 94th floor of 875 N. Michigan Avenue, enjoying panoramic views, grab a cocktail at CloudBar, or try the exhilarating TILT experience.
- Museum Free Days: Take advantage of free or discounted admission at museums.
- Interactive Museums: Capture Insta-worthy photos in interactive museums like the Museum of Ice Cream or the colorful Color Factory.
- Weekday Events: Break your routine with free movies in the park, neighborhood festivals, happy hour specials, and concerts happening Monday through Thursday.
The Curated List of Chicago Events in September
Here’s The Haute Seeker’s curated list of the best events, activities, and coolest events to check out during September.
Black & Bronze Festival
What: A cultural celebration rooted in Bronzeville’s legacy of Black excellence, featuring live music, spoken word, and performances that honor the neighborhood’s historic influence on art, culture, and activism. The festival blends history and creativity, uplifting both legendary voices and today’s artists.
When: September 6, 2025 (1–7 p.m.)
Where: Armstrong Park, 4433 S. St. Lawrence Ave.
Link for more information: Black & Bronze Festival
Steppenwolf Theatre 50th Anniversary Season: Mr. Wolf
What: Steppenwolf kicks off its milestone 50th season with the Chicago premiere of Rajiv Joseph’s Mr. Wolf, a gripping family drama directed by ensemble member K. Todd Freeman. Featuring powerhouse performances from Kate Arrington, Tim Hopper, Caroline Neff, and Namir Smallwood, this play explores identity, loss, and belonging.
When: September 11 – November 2, 2025
Where: Steppenwolf’s Downstairs Theater, 1650 N. Halsted St.
Link for more information: Steppenwolf Theatre
23rd Annual Ravenswood ArtWalk: Music, Art & Malt Row Brews
What: Explore 80+ local makers, open studios, live music, food, and craft beer in one of Chicago’s most creative neighborhoods. Highlights include demos at Lillstreet Art Center and a 60-Second Film Festival.
When: September 13–14, 2025
Link for more information: Ravenswood ArtWalk
Move At The Shed
What: A choose-your-own-experience wellness festival featuring yoga, meditation, dance, cardio, and strength classes for all levels. Community Pass holders gain full access to open experiences, lounges, sponsor activation, and movement programming throughout the day.
When: September 21, 2025
Link for more information: Move At The Shed
Clink Festival
What: Curate your own day of tastings, classes, and workshops focused on wine, spirits, and lifestyle experiences. Enjoy a full day exploring lounges, sponsor activations, and live music, or focus on individual classes to build your perfect festival experience. Must be 21+.
When: September 21, 2025
Link for more information: Clink Festival
Chicago Exhibition Weekend(CXW25)
What: This third annual citywide art celebration spans 50 participating galleries and creative spaces, spotlighting Chicago’s dynamic art community with exhibitions, panels, and special programs.
When: September 19–21, 2025
Link for more information: Chicago Exhibition Weekend
Uptown Live Street Fest
What: Uptown’s historic entertainment district hosts a new 3-day fest featuring Joywave, DJ Mark Farina, Liquid Soul, Tortured Soul, and more, alongside food vendors and a family zone.
When: September 19–21, 2025
Link for more information: Uptown Live
TEDxChicago 2025: The Future is Human
What: A daylong conference of talks, performances, and the TEDx Global Idea Search, uniting innovation with humanity’s most pressing challenges.
When: Friday, September 26, 2025
Where: Harris Theater, Millennium Park
Link for more information: TEDxChicago 2025
The Sustainability Market
What: Northcenter’s eco-focused fair features local businesses, artists, and organizations offering sustainable solutions—from composting and e-bikes to zero-waste goods and a Halloween Costume Swap. With food, music, and family activities, it’s both fun and impactful.
When: September 28, 2025 (10 am–4 pm)
Where: Northcenter Town Square, 4100 N. Damen Ave.
Link for more information: The Sustainability Market
September in Chicago: Everything You Need to Know
What’s the Weather Like in Chicago During September?
Is September a good time to visit Chicago?
Is September a good time to visit Chicago?
Absolutely! September is one of the best times to be in the city. If you’re a foodie or a fan of the arts, this month is especially exciting as it marks the beginning of the season for many theaters and major food events. By late September, the city starts to quiet down a bit, but weekends are still booming with cultural festivals, food events, and outdoor activities.
What should I wear in Chicago in September?
What should I wear in Chicago in September?
Pack transitional outfits for your trip. Bring breathable layers like shorts, light dresses, and tees for the day, along with a sweater or jacket for cooler evenings. Comfortable shoes are essential for festivals and the Chicago Riverwalk, open into late fall. Don’t forget sunglasses and sunscreen, as well as a light scarf or jacket for nighttime chill.
What to Look Forward to in September
September is the city’s curtain call before fall fully arrives. Expect neighborhood block parties, art fairs, food festivals, and major music events all month long.
