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. 

Designed as a choose-your-own-adventure experience, the second annual Move at the Shed is your chance to curate your own day of—what else?—movement. You can stretch out with a yoga session, break a sweat at dance cardio or take a ticketed class like Pilates led by Keke Palmer. A free class pass gives you access to a whole gamut of activities, like group runs, cold plunges and photo ops.

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.

Celebrate Mexican Independence Day at the two-day El Grito Fest in Grant Park. Expect to enjoy food and drink offerings from vendors like Xurro, El Campeon, Carnitas Roldan and more, plus mariachi and folkloric dance performances, a Mexican mercadito showcasing local vendors, a kids carnival, art experiences and much more. This year's music lineup includes sets by Adriel Favela, Código FN, Mi Banda El Mexicano and more.

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.

Middle Brow is adding another street fest to the calendar this year with its inaugural Armitage County Fair. The two-day fest features live music across two stages, comedy sets, a petting zoo and county fair-style competitions like greased-watermelon races and giardiniera-eating contests. The food and beverage lineup will exclusively feature local brands like Lonesome Rose, Pretty Cool Ice Cream, Gretel, Marz and Giant.

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

Savor the season with a sip-and-shop wine stroll down Division Street. The route takes you to six participating locations, including Lost Girls Vintage and Makoma House, where you'll be able to fill up on vino along the way. A ticket gets you 12 2-ounce pours and light bites, plus a commemorative tasting glass.

Send summer off with a bang at this indoor/outdoor music and arts festival in suburban Bridgeview (7337 W 100th Pl, Bridgeview, IL, 60456), which has been held on the last Saturday of the summer since its debut in 2024. This year, EDM duo Big Gigantic headlines, alongside Saxsquatch, Henry Fong, The Sponges and more. Check out the full lineup here.

Guinness Open Gate Brewery is hosting a spirited three-day Oktoberfest bash in the West Loop. Expect live polka, oompah and contemporary music, stein-holding contests and Bavarian fare like schnitzel, giant pretzels and sausages. Plus, you can take home your commemorative beer stein for a small fee.

Take a stroll down Ravenswood Avenue to see art, pop-ups, activations and more at this local festival centered around the neighborhood's industrial corridor, showcasing more than 80 artists and local venues including Begyle Brewery, Nudgers Studio, Music House Chicago and more. This year—the festival's 24th—swing by the outdoor beer garden for local brews and food trucks, or listen to some live tunes across two stages.

Explore Chicago's eerie past as you snake down the river aboard the First Lady Creepy Cruise. The 90-minute tour combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.

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.

Celebrate Oktoberfest over the course of three weekends at The Northman Beer & Cider Garden, which is bringing a host of festivities to its Riverwalk digs this September and early October. Expect giant pretzels and German sausages, beer steins and polka music, and scenic waterfront views with a European vibe.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, Drunk Dracula, on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

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.

Sportsman's Club's Sunday BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This year's lineup includes Bar Bambi, Pizz'amici, Milli by Metric, Kimski, Mister Tiger, Diego and more.

They say that there's nothing more American than apple pie, but we're of the opinion that the most patriotic food of all is the chicken wing. Soaked in a variety of different sauces (from classic buffalo to Asian ginger, spicy garlic and honey chili), it's a versatile dish that has become a national staple. WingOut Chicago celebrates the venerable chicken wing, inviting cooks from Jake Melnick's, Smoke Daddy and more to put their spin on the dish. General admission includes entry and access to live entertainment, with the option to purchase à la carte wings and beverages. Opt for VIP tickets for early entry, all-you-can-eat wings and a drink package.

Whether it's on a minibus or on foot, this tour takes you to the locations frequented by some of Chicago's most notorious gangsters and the places that have been haunted by their ghosts. With four tours offered daily, there's always an opportunity to take a step back in time to learn about figures like Al Capone and Chicago's haunted history.

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."

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. 

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.

Get your heart rate up in a mat Pilates class on The St. Regis Chicago's luxe rooftop Terrace. After class, which includes a fitness mat that's yours to take home, guests can enjoy the sprawling 12,000-square-foot wellness floor, complete with an indoor pool, sundeck, sauna, steam room, fitness studios are more.

For this year's edition of Eataly's annual fall fest, the marketplace is transforming its store into an Italian Piazza with 15 drink stations and more than 30 food stations for an all-you-can-eat evening. As always, the fest will also include live music, indoor lawn games, raffles and take-home goodies. Mangia!

Celebrate the arrival of fall in Lincoln Square at the Chicago German-American Oktoberfest, which sets up two gigantic tents in the neighborhood to serve liters of beer, stacks of pretzels and more German delicacies. The weekend also features a parade up Lincoln Avenue, live performances from four German bands and carnival games for the kids.

Grab your dirndls and lederhosens and get ready to party at the second annual Old Town Oktoberfest. The three-day German-inspired fest will have brats, pretzels and German beer, plus live entertainment all weekend. Guests can also participate in stein-holding contests, and dance and sing the night away.

The celebration at the DANK Haus German American Cultural Center in Lincoln Square might be the closest you'll get to the actual Oktoberfest without hopping on a plane. The festive evening will have authentic German food and beer, live music, games, a stein-holding competition, a ceremonial keg tapping and even a yodeling contest. Ticket sales support the non-profit organization's mission to preserve German culture, language and traditions in Chicago.

Chicago's largest Oktoberfest celebration is returning to the heart of Fulton Market. Located just behind Restaurant Row at 171 N. Peoria St., this lively six-week German fest is pouring Hofbräu München beer imported directly from Germany. Guests can also expect Bavarian pretzels, brats, live German music, carnival games and more. 

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.

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. 

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

Taking place in and around Lakeview’s St. Alphonsus Church, this autumn event features the requisite selection of suds, brats, pretzels and two stages of Bavarian music along with sets from local cover bands like Dancing Queen: An ABBA Salute. Activities include a stein-holding contest, polka dancing and a “Kinderfest” for the kiddos on Sunday. 

Brookfield Zoo's Carousel Plaza is transforming into a German-inspired celebration feature family-friendly fun with polka music, dancing, games, giveaways and more. The Oktoberfest event is included with admission and will offer a special seasonal menu with bratwurst, specialty beers, pretzels with cheese and more available for purchase.

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.

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.

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.

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.

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.

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.

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 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.

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.

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.

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.