This month, enjoy live jazz at a free music festival, tour a Chicago neighborhood with a friendly local, and attend the largest architecture and design exhibition in North America — all without spending a dime.
Chicago is bursting with free things to do this September, including plenty of live music, free museum days, festivals and parades, cultural happenings, and more. Start planning your budget trip to Chicago with this round-up of the free things to do and see all month long.
1. Catch live jazz at a free festival
Multiple dates this September
September in Chicago is an excellent month for jazz lovers. Check out these signature festivals that bring local, national, and international jazz musicians to Chicago for multiple days of free live music.
- Englewood Jazz Festival (Sept. 18 – 20): Enjoy three days of free music at the 26th annual Englewood Jazz Festival. Shows will take place at Hamilton Park and the adjacent cultural center, featuring local and national acts.
- Hyde Park Jazz Festival (Sept. 27 – 28): This historic neighborhood hosts an annual free jazz festival, with performances at the outdoor Midway Plaisance and throughout the area’s many cultural institutions.
Explore more free music festivals throughout the year in Chicago.
2. Visit the Chicago Architecture Biennial
Sept. 19, 2025 – Feb. 28, 2026
The largest architecture and design exhibition in North America is back in Chicago, featuring projects created by contributors from around the globe at free exhibits and events throughout the city.
The 10th annual Chicago Architecture Biennial opens this month, centered around the Chicago Cultural Center and neighborhood sites with related exhibitions and programming all across the city. This year’s edition will include over 100 projects by architects, artists, and designers from 30 countries — and everything is free and open to the public.
3. Explore Chicago history in Pullman
Sept. 6, 2025
Just a train ride away from downtown Chicago, Pullman National Historic Park is a historic enclave built as a planned industrial community in the 1880s. Today, the site honors the area’s fascinating history, striking architecture, and influential role in the early labor movement.
Visit Pullman during the annual Chicago Labor Day Parade and Eddie Fest on Saturday, Sept. 6 for a day full of fun activities. After, explore on your own or join a tour of the grounds and exhibition center. The Visitors Center is currently hosting an exhibit to celebrate the 100th anniversary of first Black labor union in the country.
4. Attend the iconic Taste of Chicago
Sept. 5 – 7, 2025
One of the largest free admission food festivals in the world, Taste of Chicago takes over lakefront Grant Park for one jam-packed weekend this September.
This year, hungry fest-goers will find more than 40 restaurants and food trucks offering their best bites. While you’ll need to pay for food and drink items from the various vendors, there’s also plenty to do without reaching for your wallet.
- Catch free concerts, with headlining acts on the main stage featuring Lupe Fiasco, JoJo, and Elvis Crespo.
- The Goose Island Stage will also be offering live music all day long by local rising stars.
- Learn some new moves at a Chicago SummerDance pop-up, with live music and dancing across different genres.
- Grab a free slice from the massive 1,000-pound Eli’s Cheesecake during the annual birthday cake-cutting event on Saturday.
5. Discover a new Chicago neighborhood
Sept. 6, 2025
International Greeter Day is an annual event that celebrates the Greeter program, a global initiative that pairs locals and visitors for free walks in more than 140 cities around the world.
This year, Chicago Greeter will be hosting free pop-up walks on Saturday, Sept. 6 all around the city led by friendly and knowledgeable locals. Meet in Millennium Park to head out on walks in the following neighborhoods and downtown spots:
- Andersonville
- Bronzeville
- Chinatown
- Hyde Park
- Millennium Park
- Pilsen
- Uptown
- Loop
- Chicago Riverwalk
Get more details on International Greeter Day 2025.
6. Immerse yourself in culture at Navy Pier
Sept. 20 – 21, 2025
Head to the lakefront for two days of back-to-back performances during Chicago Live!
This free performing arts festival is the largest event of its kind in the Midwest. Hosted at iconic Navy Pier, Chicago Live! showcases more than 100 acts across five stages, including the world premieres of five newly commission works.
This year’s Chicago Live line-up includes local groups like Deeply Rooted Dance Theater, Black Ensemble Theater, Joffrey Ballet, The Second City, Old Town School of Folk Music, Lookingglass Theatre Company, Chicago Shakespeare Theater, and more.
7. Attend the World Music Festival
Sept. 26 – Oct. 5, 2025
The annual World Music Festival is a one-of-a-kind experience that brings hundreds of musicians from all over the world to Chicago for a multi-venue celebration of international music.
Guests can experience the sounds of music from across the globe, with diverse musical acts hailing from Brazil, South Korea, Senegal, and more. Don’t miss top events like Ragamala, an all-night showcase of Indian classical music at the Chicago Cultural Center that’s always a fan favorite.
8. Enjoy a free museum day
Multiple dates in September
Spend an afternoon wandering through a Chicago museum, where you can dive into fascinating history, provocative contemporary art, and galaxies far, far away.
Here are the upcoming free museum days in Chicago this month for Illinois residents:
- Griffin Museum of Science and Industry is free on Sept. 2-4, 7-10, 14-17, 22-24, 29, and 30
- Chicago History Museum is free on Sept. 1, 10, and 24
- Field Museum is free every Wednesday in September
- Museum of Contemporary Art is free every Tuesday evening
- Art Institute of Chicago is free every Thursday evening
- Adler Planetarium is free every Wednesday evening
Explore more: Mark your calendar for free museum days throughout the year.
9. Shop Chicago’s oldest outdoor market
Sept. 14, 2025
Chicago’s oldest market, Maxwell Street Market dates back more than a century. This outdoor bazaar includes homemade items, resale goods, clothes, jewelry, home goods, and beyond. Dive into the history of this storied community market with free historic walking tours on Sunday.
10. Catch a new season of Art on THE MART
Art on THE MART is now showing brand new works along the Chicago Riverwalk. The latest edition of the massive waterfront display kicks off on Sept. 11 with a series of abstract works, created through a collaboration with nonprofit Arts of Life. The new program is on view nightly (7:30 to 8 p.m.) throughout the month.
