The best September 2025 events in Chicago

Labor Day weekend may be over, but the Chicago Labor Day Parade & Eddie Fest is keeping the working class spirit alive all month long! Organized by the Chicago Federation of Labor, the event celebrates union pride, solidarity and community togetherness. The parade will step off at 107th Street and head south down Cottage Grove Avenue to 112th Street. Afterwards, stick around for Eddie Fest, featuring live music, food and family-friendly activities. 

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. Running Thursdays through Saturdays beginning at 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

On September 11, ART on THE MART will debut a new sound-and-visual experience: City Circle Heart, a collaboration with local nonprofit Arts of Life, which is celebrating 25 years of supporting artists with intellectual and developmental disabilities.

For one blissful weekend, Fulton Street transforms into an open-air gallery and music venue. Shop more than four blocks of art available for purchase at this family-friendly festival, where you'll also find two days of live music and no shortage of solid dining options nearby.

The annual festival will feature dozens of vendors and food trucks, plus musical performances. This year's special programming includes an Eli's Cheesecake Birthday Celebration, an outdoor "Flag Feast" curated by the Design Museum of Chicago and a headlining set from Lupe Fiasco. And just like last year, the Taste of Chicago will be preceded by a series of day-long fests throughout the summer (at Albany Park, Pullman Park and Marquette Park) before heading to Grant Park for the three-day main event.

Lincoln Park Health & Wellness Weekend is your one-stop shop to refresh and recharge after a whirlwind Chicago summer. Take part in free workout classes, explore interactive demos and enjoy mini-treatments from local businesses. Don’t forget to collect stamps in your Health & Wellness Passport for the chance to snag an exclusive swag bag.

Wrigley Field-adjacent plaza Gallagher Way is once again showing free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available—check out the Gallagher Way website for more details. Gates open at 6pm and the screening kicks off at 7:30pm. This month's movies are a couple of can't-miss classics: Space Jam and Remember the Titans.

With its latest exhibition, the Chicago Botanic Garden showcases the patterns and prints that adorn the natural world. Through meticulously planted gardens and nature-inspired art installations, Patterned by Nature highlights the intersection between graphic design and horticulture. Exhibition highlights include colossal embroidered flowers by Raquel Rodrigo, a collection of upcycled fashion sourced from garden materials by Columbia College Chicago’s School of Fashion and a paisley patterned succulent garden. 

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.

Time to dust off your goggles, Chicagoans—for the first time since the Roaring Twenties, you can legally take a dip in the Chicago River. Chicago River Swim will host 500 swimmers in the Chicago River's green-tinged waters for a race benefitting ALS research at Northwestern University, youth swim education in underserved communities and programs aimed at closing the racial gap in swim access. For spectators, the Riverwalk between Lake and Clark streets will transform into a festive viewing area, with food, drinks and a VIP party for those who prefer a fancier vantage point.

There's a new kid on Chicago's street festival scene, and this one promises to be unlike anything else. Edgewater will be hosting over 35 musical acts—including indie rock mainstays Cloud Nothings, Chicago hip-hop standout Ric Wilson and local drag punk outfit Bev Rage & The Drinks—and 100 vendors for the inaugural Edgewater Music Fest. The fest is open to all ages, with a Kids' Zone activity area for the little ones.

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.

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.

Riot Fest is returning to Douglass Park from September 19-21 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. This year's headliners include Blink-182, Weezer, Jack White and Green Day. And rumor has it—after years of being trolled by the fest—John Stamos may actually be in attendance this year. (Fingers crossed for a Jesse and the Rippers reunion.)

Chicago Gourmet, the annual food festival hosted by the Illinois Restaurant Association, returns this year with a four-day slate of programming and events in celebration of the city's dining scene. Nosh on a variety of delicious bites and sip wines at events like Tacos & Tequila, Hamburger Hop, Grand Cru and the brunch-centric Rise & Shine Gourmet. You can view a full festival schedule on Chicago Gourmet's website, where you can also buy tickets to individual events. 

Celebrate Mexican Independence Day with the inaugural El Grito Fest, which will be the first time in over a decade city-sanctioned festivities take place downtown. Expect to enjoy authentic food and drink offerings, mariachi and folkloric dance performances, a Mexican mercadito showcasing local vendors, a kids carnival, an arts workshop and much more. This year's music lineup includes sets by Oscar Maydon, La Adictiva, Banda Los Recoditos, Selena The Show and more.

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. 

Inspired by the cultural resurgence of Mort Garson’s synth-powered album Mother Earth’s Plantasia, Empty Bottle Presents and Sacred Bones Records have been hosting an annual music festival celebrating plants and people who love them for nearly half a decade. Spread across two days, attendees can enjoy experimental music and on-site activations in the Garfield Park Conservatory's lush confines. This year's Plantasia lineup includes electronic music legend Suzanne Ciani, ambient juggernaut Tim Hecker, Pakistani composer Arooj Aftab and more.

Take a look at art from more than 120 juried artists at this annual event in Lakeview East, where you can also catch live music. Visit a variety of food and drink booths when you get hungry, or head over to the Kidzone to entertain little ones with origami demos, circus performances, live music and other attractions. The fest, which stretches along Broadway from Belmont to Hawthorne, goes until 7pm on Saturday and Sunday—though live music goes into the night.

Learn how to make your own traditional maki rolls with an interactive class at Sunda. Expert chefs will guide you through the process of assembling temaki (hand-rolled sushi), futomaki (fat-rolled sushi) and uramaki (inside-out rolled sushi) using seaweed wraps, rice, spicy tuna and more. Classes are available at the Fulton Market and River North locations.

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.

Looking for some lively fun, laughter, and a way to make lasting memories? You're in luck! Join Time Out Market Chicago for a musical story time with Laura Bityou Beriau, author of You and Me and Animal Who?, and local musician The Mr. Ray Musical Adventure. From story time to singing and dancing, kiddos and adults alike are sure to have a memorable time!

Join the University of Chicago's Smart Museum of Art as they celebrate Unto Thee, Theaster Gates's first solo museum exhibition in his hometown of Chicago. Known for his installations merging sculpture, performance and social practice, Gates has become a driving force in the contemporary art world and beyond. Unto Thee embodies the relationships Gates has fostered throughout Chicago, underpinning Gates' belief that art has the capacity to connect and transform communities. 

Put your thinking caps on and get ready to test your knowledge: Time Out Market is hosting Whaddayaknow Trivia every Wednesday! Whether you're a trivia master or just looking for a good time, this event offers something for anyone and everyone...and it's no coincidence that this evening of brain flexing falls on Wine Wednesday, when Time Out Market offers 50% off all bottles of wine.

Break out those cowboy boots and daisy dukes, because Wrigleyville Country Fest is taking the north side by storm! For one day only, Wrigleyville will transform into Nashville's Music Row, with live music and barbecue abound. Ticket includes a whiskey shot, access to a brunch buffet and, of course, a whole day's worth of live music. 

As if you needed an excuse to spend golden hour at Time Out Market Chicago's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.

For 39 years and counting, the National Museum of Mexican Art has celebrated one of Mexico’s most extraordinary traditions with a multimedia exhibition. This year, Día de Muertos: A Celebration of Remembrance is dedicated to the Texans and New Mexicans who tragically lost their lives in 2025's flash floods. After you've toured the exhibition, make your way to the museum's courtyard space, which will house an installation designed and curated by the youth artists of Yollocalli Arts Reach. End your visit with a moment at the community ofrenda—add a note, drawing or memory to honor someone you’ve lost and be part of this collective tribute. As usual, admission is free—anyone is welcome to stop by the museum and pay their respects to those who are no longer with us.

Don't show up in ye olde jester costume. Here, the word Renaissance signals rebirth. The Auburn Gresham neighborhood is reborn with a showcase of the neighborhood's vendors, artists and performers. The daylong festival is rounded out by a petting zoo, a 60-foot tall Ferris wheel and a headlining set from former Hyde Park resident and “Queen of Funk” Chaka Khan.

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. 

Prost! to Oktoberfest at Brookfield Zoo Chicago, where their Carousel Plaza will feature family-friendly fun with polka music, dancing, games, giveaways and more. This German-style event is included with Zoo admission and will feature a special seasonal menu with bratwurst, specialty beers, pretzels with cheese and more available for purchase.

Kick off the school year in the sweetest way! Time Out Market Chicago residents 2d will be bringing their comic book-inspired flair to a back-to-school donut decorating workshop, complete with vibrant icing and unexpected toppings. Perfect for little ones ages 3 to 12, this hands-on event includes all supplies—and plenty of tasty treats to take home (or eat on the spot!). 

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.

Ever wonder what kind of magic is hiding in the dreamy lofts along Ravenswood Avenue? Now is your chance to find out. Take a stroll down Ravenswood Avenue to see art, live music and theater at this local festival centered around the neighborhood's industrial corridor, showcasing dozens of artists and local venues including Begyle Brewery, Lillstreet Art Center, Koval Distillery, VIN312 Winery and more. This year—the festival's 23rd—swing by the outdoor beer garden for local brews and food trucks, or listen to some live tunes across two stages.

Local no-kill animal shelter PAWS hosts its annual 5K race at Montrose Harbor, where humans and dogs can make their way through a lakefront course while raising money to support the organization's work. Once you cross the finish line, you'll be able to enjoy live entertainment for humans and pups alike, including a dog agility course and a "doggy oasis" outfitted with pools for cooling off. Don't have a four-legged friend to bring along? Not to worry—there will be plenty of good boys and girls for you to pet.

The Hyde Park Jazz Festival returns to venues throughout its namesake neighborhood in September. As always, Hyde Park Jazz Festival's shows are free to attend—for a complete list of performances, visit the festival's website.

The 26th Street Mexican Independence Day Parade returns to Little Village this September, traversing a stretch of 26th Street ahead of Mexican Independence day on September 14. The theme of this year's procession—which includes mariachi bands, colorful floats and folkloric dancing—is “Pride and Power: Our Strength, Our Legacy,” focusing on the heritage and resilience of the Mexican community. The parade runs between Albany and Kostner on 26th Street.

Fall is about more than crisp leaves and pumpkin spice—and Island Party Hut is here to prove it. The Riverwalk tiki bar’s fall fest returns with seasonal cocktails, river hayrides, a pumpkin patch and more. With live music, photo ops and a drink included in your ticket, it’s a celebration guaranteed to get you in the autumn spirit.

On the first Friday of every month in 2025, join Eataly for a culinary adventure. Guests can enjoy five tastings at counters throughout the marketplace, including fresh pasta, Roman-style pizza, housemade pasticcini, artisanal salumi and formaggi, and more.

Chicago's beloved button company Busy Beaver is celebrating 30 years in business with a shindig at Color Club. The event will include live music from Detroit-based garage rock outfit The Henchmen, local lo-fi noisemakers Sharp Pins and more. Attendees can also hop into a Double Dutch match, make their own buttons and sip on signature cocktails from Wilderness Club. Proceeds from the event will benefit the Greater Chicago Food Depository. 

Renegade Craft Fair's flagship event returns to Wicker Park, taking over a stretch of Division Street spanning from Damen to Ashland Avenue. Attendees will be able to shop the handmade wares of more than 400 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.

Designed as a choose-your-own-adventure experience, 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 kick back with live music from Jamila Woods. A class pass fetches you access to a whole gamut of activities, like community walks, special lounge areas and photo ops.

Oktoberfest is coming to the North Side this year thanks to the Chicago Cubs. “Oktoberfest with the Cubs” promises three days' worth of boozy brews, authentic food offerings, carnival attractions (ride tickets required), a stein-holding competition and much more. Pint-sized attendees can enjoy a Kinderfest, complete with kid-friendly crafts, balloon artists and family-friendly competitions.

As folks who do their fair share of smelling and tasting, the folks at All Together Now know how to put together a phenomenal sensory experience. The boutique wine shop and café will be hosting French candlemaker Diptyque for an evening of scents, sips and snacks. During the two-hour experience, guests will move though clusters of wine, snacks and fragrances, transporting them to particular experiences—think dew-dappled hikes and evenings spent next to a roaring fire. A ticket fetches guests a guided wine tasting paired with small bites, a scent lesson and a standard-size Diptyque candle.

Experience the wealth of public art decorating the city through the eyes of an expert. Each walking tour—spanning anywhere from 45 minutes to an hour—is led by a docent and covers a half-mile, beginning outside the Chicago Cultural Center and ending in Millennium Park. Throughout the tour, the docent offers context about each piece and its artist. The tour is free, but keep in mind that advance registration is required.

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world.

Start your Biennial experience at the Chicago Cultural Center, then explore a citywide constellation of exhibitions and public programs hosted by dozens of leading cultural, program, and civic partners throughout Chicago. A full schedule of programming and locations is coming soon. Stay up-to-date by visiting the Chicago Architecture Biennial website.

Sundays on State—which shuts down a strip of State Street spanning from Adams to Lake Streets for activations, performances, food and shopping—brings thousands of visitors downtown to check out everything from outdoor dining and browsing opportunities to pop-up karaoke and barre fitness classes. The event returns on two Sundays this year by popular demand. For a full schedule of vendors and events, check out Chicago Loop Alliance's website.