10 Free Things to Do in Chicago This September 2025
CHICAGO, IL — September brings cooler weather, changing leaves, and a full calendar of free events across Chicago. From music festivals to cultural showcases, historic walking tours, and museum days, there’s no shortage of ways to experience the city without opening your wallet.
1. Catch Live Jazz at Free Festivals
September is prime time for jazz lovers. The Englewood Jazz Festival (Sept. 18–20) fills Hamilton Park with three days of national and local acts, while the Hyde Park Jazz Festival (Sept. 27–28) spreads performances across the Midway Plaisance and cultural institutions in one of Chicago’s most historic neighborhoods.
Chicago has a deep jazz lineage, stretching back to the 1920s when legends like Louis Armstrong and King Oliver brought New Orleans jazz north during the Great Migration. Hyde Park’s festival reflects this heritage while showcasing contemporary innovators. Englewood’s celebration, founded by saxophonist Ernest Dawkins, highlights both the resilience of the community and the continuing importance of jazz as a voice for the South Side.
2. Explore the Chicago Architecture Biennial
Running Sept. 19, 2025 – Feb. 28, 2026, the Chicago Architecture Biennial is the largest design exhibition in North America. Over 100 projects from architects and artists in 30 countries will be on display at the Chicago Cultural Center and other neighborhood sites — all free to the public.
3. Discover History in Pullman
On Sept. 6, visit Pullman National Historic Park during the Chicago Labor Day Parade and Eddie Fest. The planned 1880s industrial community highlights architecture and labor history, including an exhibit celebrating the centennial of the nation’s first Black labor union.
4. Attend the Taste of Chicago
Back at Grant Park Sept. 5–7, the world-famous Taste of Chicago features more than 40 restaurants and food trucks. Admission is free, with highlights including concerts from Lupe Fiasco, JoJo, and Elvis Crespo, Chicago SummerDance pop-ups, and the cutting of a 1,000-pound Eli’s Cheesecake.
First held in 1980, Taste of Chicago started as a one-day event on Michigan Avenue organized by a group of restaurant owners. With Mayor Jane Byrne’s support, it drew an unexpected 250,000 people. By the mid-1980s, it had moved to Grant Park and evolved into the largest food festival in the world, at one point spanning 10 days and drawing millions annually. Its enduring appeal lies not only in the food but also in its pairing with live music, showcasing Chicago’s reputation as both a culinary and cultural capital.
5. Take a Free Chicago Greeter Tour
Celebrate International Greeter Day on Sept. 6 with free walking tours led by locals. Groups will set off from Millennium Park to explore neighborhoods like Andersonville, Bronzeville, Chinatown, Hyde Park, Pilsen, Uptown, and the Loop.
6. Immerse Yourself in Chicago Live! at Navy Pier
On Sept. 20–21, Navy Pier hosts Chicago Live!, the Midwest’s largest free performing arts festival. Over 100 acts will perform across five stages, including Joffrey Ballet, Black Ensemble Theater, The Second City, Old Town School of Folk Music, and Chicago Shakespeare Theater.
7. Experience the World Music Festival
From Sept. 26 – Oct. 5, the World Music Festival Chicago brings international artists to venues citywide. Highlights include the all-night Ragamala Indian classical music showcase at the Chicago Cultural Center, alongside artists from Brazil, South Korea, Senegal, and more.
8. Enjoy Free Museum Days
Illinois residents can take advantage of multiple free admission days in September:
- Museum of Science and Industry — Sept. 2–4, 7–10, 14–17, 22–24, 29–30
- Chicago History Museum — Sept. 1, 10, 24
- Field Museum — Every Wednesday
- Museum of Contemporary Art — Every Tuesday evening
- Art Institute of Chicago — Every Thursday evening
- Adler Planetarium — Every Wednesday evening
9. Visit Maxwell Street Market
On Sept. 14, browse Chicago’s oldest outdoor market, dating back more than a century. Maxwell Street Market offers everything from homemade crafts to antiques and food, plus free historic walking tours of the storied market district.
The market originated in the late 1800s when Jewish immigrants set up pushcarts in the Maxwell Street neighborhood. Over time, it grew into a vibrant hub for food, trade, and music — especially the birthplace of urban blues. Artists like Muddy Waters and Howlin’ Wolf famously performed there, electrifying Delta blues and creating a sound that would later inspire rock ’n’ roll. Though relocated several times, Maxwell Street Market remains a symbol of Chicago’s immigrant spirit, entrepreneurial grit, and musical legacy.
10. Watch Art on THE MART
Starting Sept. 11, Art on THE MART will showcase new abstract projections in partnership with nonprofit Arts of Life. The nightly 7:30 p.m. shows along the Chicago Riverwalk are one of the city’s most unique public art experiences.
Why These Events Matter
From the smoky jazz clubs that migrated into free outdoor stages, to Grant Park’s Taste of Chicago, to the historic hustle of Maxwell Street, these free September events showcase the soul of Chicago. They reflect the city’s ability to honor its past while continuously reinventing its cultural calendar.
Whether you’re savoring a taste of Eli’s cheesecake, swaying to live jazz under the stars, or exploring the immigrant traditions of Maxwell Street, Chicago offers world-class experiences accessible to everyone.
With its blend of history, music, art, and community, September 2025 proves once again that Chicago’s most memorable moments often come without a price tag. For more cultural highlights and event guides, follow ChicagoMusicGuide.com.