This month, enjoy live jazz in the heart of downtown, tour a Chicago neighborhood with a friendly local, and browse the city’s longest-running outdoor market — all without spending a dime.
Free things to do in September
What are some free things to do in Chicago this month?
Chicago is bursting with free things to do this September, including free music festivals like the iconic Chicago Jazz Festival, free admission to top Chicago museums, Labor Day festivities, neighborhood Oktoberfests, and so much more. Start planning your budget trip to Chicago with this round-up of the free things to do and see all month long.
1. Check out free jazz festivals
Multiple dates in September
Chicago is the place to be for jazz fans this September. These free music festivals bring unmatched talent and pay homage to Chicago’s deep jazz roots. Don’t miss out on three weekends full of music with these exciting (and wallet-friendly) fests.
- Chicago Jazz Festival (Sept. 3 – 6): Spend Labor Day weekend checking out some of Chicago’s best jazz performances.
- Englewood Jazz Festival (Sept. 17 – 19): This year’s festival celebrates its 27th anniversary, bringing together next-generation musicians and established jazz icons.
- Hyde Park Jazz Fest (Sept. 26 – 27): The 20th annual Hyde Park Jazz festival presents free jazz shows in addition to food and merchant vendors.
Explore more: Check out more music festivals in Chicago.
2. Immerse yourself in culture at Navy Pier
Sept. 19 – 20, 2026
Mark your calendar for the largest free performing arts festival in the Midwest. The annual Chicago Live! festival will bring more than 100 performing arts organizations and artists to the lakefront for two packed days of performances, all free and open to the public.
The extensive lineup showcases Chicago’s rich cultural scene through live music, dance, theatre, and multidisciplinary performances.
3. Attend the Chicago Labor Day parade and festival
Sept. 5, 2026
In the historic Pullman neighborhood, the annual Chicago Labor Day Parade and Eddie Fest brings the community together to celebrate the city’s influential role in labor history.
The parade will march through the 10th Ward, followed by a free festival in Steelworkers Park with music, food, and family fun.
Explore more: Visit the Pullman National Historical Park to discover the area’s fascinating history.
4. Catch the last free summer fireworks
Sept. 2 and 5, 2026
End your summer on a dazzling note with the free fireworks at Navy Pier.
Locals and visitors gather on the lakefront to enjoy iconic skyline views, dazzling pyrotechnic displays, and a classic summertime Chicago experience. Don’t skip your last chance to see this free show before it ends for the season.
Explore more: Find more things to do at Navy Pier, from rides and games to theatre and immersive experiences.
5. Explore Chicago neighborhoods with a local guide
Sept. 10, 2026
Whether you’re a visitor or a local, there’s always something new to discover in Chicago’s vibrant neighborhoods.
International Greeter Day is the perfect opportunity to explore a new neighborhood, with the help of a friendly local guide. Meet in Millennium Park before embarking on a free walk that will delve into a neighborhood’s history, top attractions, and hidden gems.
International Greeter Day in Chicago is brought to you by Chicago Greeter, which pairs visitors and locals for free neighborhood walks year-round.
6. Attend the World Music Festival
Sept. 25 – Oct. 4, 2026
Music from around the world takes over Chicago during the annual World Music Festival, featuring a diverse array of international artists and groups. This free festival showcases genres from around the globe at iconic venues throughout Chicago, including the Chicago Cultural Center.
7. Enjoy free museum days
Multiple dates in September
Stand on the other side of the glass from a beluga whale, explore the depths of the galaxy, or come face-to-face with the most complete T. rex skeleton ever found. Don’t miss what Chicago’s museums have in store on these upcoming free days for Illinois residents:
- Field Museum is free every Wednesday this year
- Art Institute of Chicago is free every Thursday evening through Sept. 17
- Shedd Aquarium is free every Tuesday evening in September
- Chicago History Museum is free Sept. 7 and 24
- Griffin Museum of Science and Industry is free on Sept. 1, 2, 8 – 10, 15, 16, 20 – 23, and 27 – 30
- Adler Planetarium is free on Sept. 8, 9, 10, 14, 15, and 16
- Museum of Contemporary Art is free every Tuesday evening
Explore more: Mark your calendar for free museum days throughout the year.
8. Shop Chicago’s oldest outdoor market
Sept. 13, 2026
Maxwell Street Market is Chicago’s oldest open-air market, dating all the way back to 1847. This seasonal Sunday marketplace includes food, handmade crafts, housewares, clothing, live entertainment, and more.
The September market will be dedicated to kids and families, with young vendors and kid-friendly entertainment for a fun, family-focused experience.
9. Attend a neighborhood festival
Multiple dates in September
If you can count on one thing in Chicago, it’s the abundance of festivals happening around the city every month. Whether you’re in the mood for music, food, art, or culture, there’s a free event for you.
- German-American Oktoberfest (Sept. 11 – 13): Spend an evening indulging in traditional German food, drinks, and dancing to live bands at this Lincoln Square festival.
- Printers Row Lit Fest (Sept. 12 – 13): The Midwest’s largest free outdoor literary festival features authors, exhibitors, and booksellers in the South Loop.
- Lakeview East Art Festival (Sept. 19 – 20): More than 150 artists showcase their unique artwork, alongside entertainment stages and family activities. There is a $5 suggested donation.
Explore more: Browse our complete list of September festivals and find more things to do.
10. Attend open gallery nights
Abel Arciniega :: @tequilagraphics
Sept. 18, 2026
Chicago’s art scene comes to life in our neighborhoods, where local galleries are constantly pushing boundaries and showcasing the latest talent.
Explore the latest and discover up-and-coming artists during these free gallery and open studio nights around Chicago:
- Bronzeville Art District Trolley Tour (Sept. 18): Hop on and off this free trolley that takes art lovers to different galleries throughout the Bronzeville neighborhood.
- 3rd Friday at Bridgeport Art Center (Sept. 18): This vibrant maker space welcomes the public once a month to explore the works of local painters, sculptors, ceramicists, woodworkers, and more.
- 3rd Friday at Zhou B Art Center (Sept. 18): This converted warehouse in the Bridgeport neighborhood has become a leading hub for international and local art.
Looking for more? Check out our guide on free things to do in Chicago all year long.
