The best free things to do in Chicago in September

Chicago may be best known for its blues musicians, but these days it's more of a jazz city. The annual Chicago Jazz Festival celebrates contemporary improvisers and legendary players with free concerts at the Chicago Cultural Center and Millennium Park. This year, the festivities expand to local music venues, where performers will play free shows from August 24 through 29. Headliners include composer, pianist and radio personality Ramsey Lewis; noted jazz vocalists Kurt Elling and Dianne Reeves; and funk legend Maceo Parker.

Hundreds of tricked-out cars and motorcycles line Loomis Street in Pilsen during this annual community festival, where you can take a look under the hood and watch classic rides bouncing around (with some hydraulic assistance). If you can tear yourself away from the automotive display, you can chow down on tasty tacos, shop for goods made by local vendors and listen to live DJs.

Chicago-based artist Brendan Fernandes draws inspiration from the fabricated African masks that were once sold to tourists, exploring how traditional art was modified and commodified. Displayed alongside wooden masks from Burkina Faso, Congo, Cameroon, and Nigeria from DePaul Art Museum’s African collection, Fernandes's striking neon light masks examine the ways in which society claims ownership of artistic ideas.

An album is more than a collection of songs—it can serve as the soundtrack to a pivotal time in your life or the window to a new world of musical discovery. The Liner Notes storytelling series celebrates records that change lives, gathering local musicians, writers and artists to talk about a particularly influential LP. In September, rapper SHOWYOUSUCK discusses Many Facez by Tracey Lee, Chicago Tribune writer Jessi Roti unpacks Fever to Tell by Yeah Yeah Yeahs, Hood Internet producer Steve Reidell professes his love of the soundtrack to Judgement Night and Metro owner Joe Shanahan talks about a mystery album.

Expand your musical tastes at the annual World Music Festival, a series of free concerts at venues throughout the city that feature artists from all corners of the globe, including France, China, Gambia and more. The festival kicks off with the annual Ragamala concert, an overnight concert at the Chicago Cultural Center which features more than 12 hours of classical Indian music. Other highlights of this year's lineup include an El Grito celebration in Millennium Park featuring mariachi bands, an appearance by Morrocan experimental audio-visual artist H.A.T. and a concert held in tandem with World Dumpling Fest in Polk Bros Park.    

That slight chill means it’s time to head to Wicker Park’s gigantic craft fair, where serious crafters from around the country to sell their handmade arts and wares. Browse and buy prints, pottery, jewelry and other handmade goods from makers near and far while enjoying food and drinks being peddled by local businesses and vendors.

Grab a plastic stein and munch on a pretzel at this annual Lincoln Square celebration of Deutschland heritage. The street party takes place under two gigantic tents and features plenty of German food, music and dancing. Make sure to stop by to see the annual Von Steuben Parade march up Lincoln Avenue on Saturday at 2pm.

Celebrate Mexico's independence from Spain with Mexican food, music and dancing in Chicago's Little Village neighborhood. Vendors and carnival rides fill the streets Friday through Sunday, and the 26th Street Mexican Independence Day Parade ends here on Sunday afternoon.

Head to Pilsen to celebrate Mexican Independence Day at this annual processions along 18th Street, which features colorful floats, costumed dancers and local marching bands. The parade steps off at noon from Newberry Avenue and 18th Street and concludes at Wolcott Ave.

Displaying a collection of Chicago-native Ed Paschke’s vibrant paintings, this exhibit connects the artist's experimental images to the tenants he taught his students as a professor at Northwestern University: to learn the rules in order to break them, trust your instincts and get out of your comfort zone. 

Celebrate Hispanic culture outside at the zoo with hands-on art, health, gardening, science and music projects. Plus, the whole family can enjoy cultural dance and music performances.

It's opening night for the new 25-story-tall video installation that will be taking over the side of the Merchandise Mart. Art on theMart harnesses 34 digital projectors to create expansive moving images that will light up the side of the historic building. Art on theMart's first screening will kick off at 7:15pm, showcasing a 35-minute video program followed by a one-minute pyrotechnics show.

In 1989, acclaimed artist Keith Haring came to Chicago to create a gigantic 488-foot-long mural in collaboration with 500 Chicago Public School students. After remaining on display at Midway Airport for several years, 36 panels of the mural will return to the Loop, going on display alongside a selection of Haring's photographs, correspondence, designs and his now-iconic drawings.

Audiences at comedy shows don't get much more supportive than the ones that fill Camp every week in the Village Tap's beer garden. The summer camp-themed showcase gives comedians a place to test out new material and take risks, whether they're developing a new set of jokes or working out the kinks of a wacky character. Hosts Tessa Orzech and Samantha Berkman act as counselors, keeping the evening lively with sketches and unexpected hijinks.

Each Tuesday, the Museum of Contemporary Art hosts a free concert in its Anne and John Kern Terrace Garden—admission to the museum is also free for Illinois residents. The lineup is stacked with notable performers from the Chicago jazz community, including Katie Ernst, Greg Ward and Tomeka Reid. Attendees can order food à la carte from the outdoor grill, which features tacos, beef tenderloin, lobster rolls and BBQ chicken. 

Gallagher Way (the plaza formerly known as the Park at Wrigley) tapped their neighbors at the Music Box to program free outdoor screenings on Wednesday evenings when the Cubs are on the road. The theater selected a series of mostly family-friendly films (all PG-13 or less)—this month, you can see Top Gun and Back to the Future.

Set a new high score at this arcade bar’s quarterly queer night. Guests can take advantage of free pinball (make sure you take a turn on the classic Star Wars and PIN·BOT tables), enjoy bar specials or bust a move in the back room with resident DJ Essential Logic.

This twice-weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours, while the new “Cocktail Hour” Wednesday show is a tight 90 minutes with no intermission.