The best September 2026 events in Chicago

Get ready, punk rockers! Riot Fest is returning to Douglass Park from September 18-20 with a laundry list of rock, punk, metal and emo artists. It's always one of the biggest music fests of the season thanks to a must-see lineup of both legacy acts and emerging newcomers. 

500 swimmers will be making waves in the Chicago River Swim, benefitting ALS research at Northwestern University, youth swim education in underserved communities and programs aimed at closing the racial gap in swim access. Swimmers will launch near the Dearborn Street Bridge and finish at the Clark Street Bridge. Spectators can line the Chicago Riverwalk to cheer them on as participants tackle 1- and 2-mile courses.

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

One of the most unique events of the season is returning this year. The Midway 5K Run & Walk is back to support Special Children’s Charities fund programming for children and adults with disabilities across Chicago. Participants can run or walk the course, which takes place on the airfield at Midway Airport. The main event is followed by a race for kids aged 5-10.

The Lincoln Park Chamber of Commerce hosts the neighborhood's Uncorked Wine Stroll, an evening showcasing Lincoln Park businesses with plenty of vino along the way. With over a dozen stops along Lincoln Avenue, light bites, free pedicab rides and—of course—lots of wine, there’s no better way to get to know the neighborhood. Cobble together a group of five or more to save $5 per ticket.

As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows at Pritzker Pavilion in Millennium Park and the Chicago Cultural Center during this annual festival. Visit the Chicago Jazz Festival webpage for the full lineup and schedule.

For some, Labor Day weekend means cookouts and enjoying some of the final days of summer among family and friends. For others, it means crowding in front of a stage with a bunch of strangers and dancing to the sound of bone-rattling bass drops. North Coast Music Festival brings some of the biggest names in EDM to Bridgeview, Illinois, for three days of beats and pyrotechnics in and around SeatGeek Stadium. The lineup includes big-name acts Fisher, Griz, Gryffin, Illenium and many more. And with multiple stages to explore, you should have no problem finding the house, techno, progressive and trance music that you want to dance to.

More than 70 institutions, galleries and programming partners are coming together this fall for the fourth annual Chicago Exhibition Week. The 7-day event is a celebration of the city's diverse art scene, featuring a lineup of talks, networking events, workshops, performances, activations, parties and more, many of which are free to attend.

Explore notable Impressionist Mary Cassatt's works in the first exhibit in more than 25 years dedicated solely to the American artist at the Art Institute. Known for her works depicting mothers with children and intimate caretaking scenes, Cassatt was the only American to join the French Impressionists. After Impressionism showcases paintings, pastels and prints from the time in her career when she began to take her art in a new direction.

Every local thrifter worth one's salt knows that Vintage House Chicago is a treasure trove holding some of the city's best secondhand scores. The bimonthly vintage and handmade market showcases local makers and curators at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.

The sixth annual ARC Music Festival is scheduled to take over Union Park during Labor Day weekend, celebrating Chicago's house music roots and welcoming an international lineup of dance music artists. Expanding to a four-day sprawl for the first time, the fest features acts including Ben UFO, Honey Dijon, Carl Craig and Hiroko Yamamura. Catch sets at multiple stages spread throughout the park, enjoy food from local chefs and don't skip the ARC After Dark parties at venues like Smartbar and Radius.

If you want to watch people scarf down 10 glizzys in a matter of minutes—without sipping water—then head to Wieners Circle this weekend. The hot dog eating competition, hosted by event company 2 Girls 1 Windy City, will be separated into male- and female-identifying contestants for two rounds of speed eating starting at 2pm.

Gallagher Way hosts a free night market on most Thursdays through September in partnership with Common Goods, featuring dozens of local vintage vendors selling a mix of home goods, clothing, jewelry and more. Grab a glass of wine, browse the market and stick around to catch live music from a host of different artists.

Evanston Folk Festival returns to the lakefront for two days of country, roots and folk music. This year's lineup features acts like Trampled by Turtles, Indigo Girls, Josh Ritter and Mdou Moctar across three stages, alongside talks with Emily Saliers & Amy Ray of Indigo Girls and Ann Powers, Mark Guarino and more.

A celebration of storytelling across mediums comes to life on stage with "live journalism show" Chicago Story Fest at Athenaeum Center in Lakeview. Journalists, comedians, dancers, singers, filmmakers and musicians from Chicago will share their personal stories centered around this year's theme, "Villains: Stories about what we fear, what we misunderstand, and what we become."

From June through September, more than 90 movies will screen in parks across Chicago as part of the Park District's annual Movies in the Parks program. From recent blockbusters like Zootopia 2 and Freakier Friday to classics like Back to the Future and Jumangi, you're sure to find something good to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:45pm, or dusk, each evening. Take a look at the full list of movies and participating parks.

The producers behind South Loop Farmers Market are bringing a new shopping experience to the Water Tower Place. On Thursdays from July 9 through September 24, head to the fourth floor to shop vintage treasures, artisan goods and farmers market finds, and enjoy live music and local food. 

Renegade Craft Fair returns just in time for the holiday shopping sprint, taking over Morgan MFG's industrial digs. Attendees will be able to shop the handmade wares of more than 170 vendor booths, selling everything from candles and screenprints to jewelry and pottery. The fair also boasts food and drink from local restaurants, so you won't have to go hungry (or thirsty) while you shop.

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.

Antique vendors and classic cars fill six blocks of Roscoe Village at this throwback street market, where everything old is new again. The music lineup is usually equally nostalgic, featuring tribute acts that perform hits from the ‘80s and ‘90s.

Navy Pier’s annual performing arts festival welcomes more than 100 local artists for a weekend of music and performances spread across five stages. Featured acts range from Chicago’s world-class stalwarts to many exciting up-and-comers. 

The oldest music festival in North America plays host to more than 90 shows throughout summer, featuring big-name headliners like Paul Simon, Alabama Shakes and Chance the Rapper. Check out the full schedule of artists coming to Highland Park this year, and don't forget to pack a picnic.

Take a car-free ride along DuSable Lake Shore Drive during this annual biking event, which closes down the lakeside thoroughfare to vehicle traffic and allows cyclists to ride through a 30-mile route dotted with rest stops, water and snacks. You'll have to wake up early (the course opens at 6:30am) and enter through one of designated entry points along the road—but the novelty of biking on a stretch of pavement that is decidedly not bike-friendly is worth the hassle. Plus, proceeds from the event support the Active Transportation Alliance, a nonprofit organization working to improve conditions for pedestrians and cyclists throughout Chicago.

Set sail with Chicago Line Cruises for an evening of jazz on the river. On the last Sunday of each month through September, the cruise line is partnering with the Jazz Institute of Chicago for 90-minute cruises featuring live performances, an on-board bar, open-air decks and a prime view of the sunset.

Spin classes and weight lifting can wait for the winter. This summer, jump-start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square on Saturdays from May through August.

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

The newly opened Obama Presidential Center is celebrating the country's 250th anniversary with its inaugural "You Are America" series this summer. The series kicks off on July 4 with The People's Fourth, a free event featuring live music, self-guided tours and other family-friendly activations across the campus. Other series highlights include House Music on the Plaza, Garden Gatherings and an Art in Action talk with Obama Presidential Center-commissioned artist Mark Bradford. Check out the full schedule of You Are America events here.

When Pitchfork Music Festival announced its sudden sunset at the start of 2025, Chicago’s music scene collectively wondered how festival co-founder Mike Reed would fill the sonic void. Turns out, Reed had an ace up his sleeve: Sound & Gravity, a four-day music marathon featuring 40+ performances across six venues in Bricktown and Avondale. Lineup highlights include Grouper, Alabaster DePlume, Walt McClements and more. Read more about Sound & Gravity's inception here.

This 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.

The Chicago Cultural Center is free and open to the public throughout the majority of the year, but if you need an excuse to check out all it has to offer, an Open House should do the trick. This year, the event will feature live music, gallery exhibitions, shopping and more. For a full schedule of activities and to RSVP, visit the official website.

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

During the summer, the Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. During the winter months, the pyrotechnics return for a much-needed encore. If you're feeling weary of crowds, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on Maxwell Street, between South Halsted Street and South Union Avenue on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. 

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Having made its U.S. debut at the Field Museum in May, the immersive exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil-excavation tools and immersive activations throughout.

Mandala South Asian Performing Arts—a bridge connecting audiences to the vibrant colors and rich traditions of South Asian heritage—returns with the annual Mandala Makers Festival. This multidisciplinary platform, which supports a diverse array of South Asian performing artists, kicked off its season on April 15. The festivities continue through October, offering a continuous showcase of immersive music and dance events. Visit the Mandala Makers Festival website for a complete schedule of performances.

Find the perfect vintage piece for your collection at this Andersonville market, where you can shop antiques, home decor, jewelry, clothing and other trinkets from over 30 vendors on six different dates throughout the summer. Participating businesses include Antiqueandmod, J-Bird Clay, Scal's Vintage, The Paper Archive and many more.

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. On the first Friday of every month, galleries and arts-based businesses stay open until 8pm.

Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Center River Cruise takes place aboard a First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline.

Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full lineup and schedule.

Head to Gallagher Way in Wrigleyville on select Monday evenings throughout the summer to join a free Movement Monday class. This year's lineup includes dance classes, self-defense, yoga and more. Classes are free to attend, but you'll need to reserve a spot in advance.

Navy Pier's former Crystal Gardens space transforms into a retro roller skating rink this summer. Grab your skates (or borrow a pair; they're included with your ticket) and hit the rink for old-school fun, plus an arcade, photo booth, drinks and groovy disco tunes. At night, the Skate After Dark party turns up the energy for the 21+ crowd with DJ sets on select nights throughout the summer.

If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

The Budweiser Concert Series is back at Gallagher Way this summer, with three outdoor shows from Guster, Hippo Campus and Ashley McBryde. GA and VIP tickets are available, and $1 from each ticket sold will go to mental health and wellness organization Backline or sustainability organization Reverb.

The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

“Willem de Kooning Drawing” is the first exhibition to explore the full scope of the artist's drawing practice, framing it as the foundation of his boundary-breaking career. Featuring more than 200 artworks—including rarely seen drawings alongside paintings, sculptures and prints—this exhibition offers an unprecedented opportunity to experience seven decades of his graphic production while shedding light on his constant experimentation with various materials, tools and techniques.

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

Looking for free concerts near Chicago? Hop on the Blue Line to Rosemont's Parkway Bank Park for Thursday night performances—with a few holiday and weekend dates sprinkled through the summer—including performances by Atomic Punks, Live the Who and Rhythm of the Rocketman, complete with a fireworks show at the end of the night. Beverage tents will be located on site, but we won't fault you if you prefer to pre-game with a fishbowl-sized spiked punch from nearby Sugar Factory. For a full schedule of shows, visit the Parkway Bank Park website. 

This first-of-its-kind exhibition at the Museum of Contemporary Art Chicago explores the visual, political and spiritual histories of dancehall and reggaetón through contemporary art. Once grassroots scenes, both genres have become globally influential movements tied closely to sexual and political liberation. The show features works by more than 35 artists, including Jean-Michel Basquiat, Edra Soto, supakid and Lee “Scratch” Perry.

Chicago's opulent new magic lounge, The Hand & The Eye, is introducing a limited-edition series dubbed Summer Friday Magic. Through Labor Day, a limited number of guests can enjoy a truncated, 45-minute show in the venue's Vault Theatre without having to commit to the typical full evening of programming.

With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 

Every Wednesday, the Old Town School of Folk Music hosts a showcase of world music and dance. Featuring both local and touring talent, you're sure to hear something new and exciting at this long-running series. Before the show, be sure to peruse the Old Town School of Folk Music Store, where you can rent instruments, learn about lessons and peruse a wide selection of books.

Test your music knowledge on select Tuesday nights with free music bingo at Gallagher Way this summer. Each game covers a different genre, from country and 90s pop to EDM and Broadway. Team sign-up starts at 5:30pm, before the game kicks off at 6pm.

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding.

Find your flow with the whole family in the cozy confines of the Peggy Notebaert Nature Museum at a Brain to Belly Kids Yoga session! This creative class flows through several fun poses, each one complementing the month's children's story. Children (ages two to eight) and their grown-ups will enjoy moving, breathing and connecting together while bringing the story's plot to life. Bonus: Your ticket includes full access to all museum exhibits, so stick around after class!

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

Gallagher Way is showing free outdoor movies on select Wednesday nights through September. From family flicks like Zootopia 2 and High School Musical to classics like How to Lose a Guy in 10 Days and Matilda, there's something for everyone to enjoy. Guests are encouraged to bring a blanket or purchase a VIP or Premier ticket, which includes a reserved seat, snacks and other goodies.

In honor of America's 250th anniversary, the American Writers Museum presents a pop-up exhibition titled "Declarations: 250 Years of Writing Toward Independence." An 1832 William Stone print of the Declaration of Independence, a 1776 British edition of Thomas Paine's Common Sense, which advocated for the independence of U.S. colonies, and more artifacts will be on view. Visitors can also explore works related to the Declaration by Abraham Lincoln, Frederick Douglass and other historical figures, as well as edit the document into their own words through interactive activations.

Highland Park's summertime tradition Food Truck Thursdays is back at the Ravinia District. From June 4 through September 3, more than a dozen local food trucks will set up on Thursday nights on Dean Avenue and at Jens Jensen Park. Bring the whole family (plus your own blankets and lawn chairs), and enjoy food, drinks, live performances and themed events on select nights. 

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.