The best September 2025 events in Chicago

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.

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.

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. 

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. 

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.

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.

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.

The Italian food emporium's wildly popular All You Can Eataly SeptemberFest is back—bigger, bolder and more delicious than ever. The spread will include more than 40 Italian bites and over 30 different kinds of Italian wines, spirits and beers. When you’re not snacking and sipping, you can enjoy in-person demos, live music, performances from famed comedy troupe The Second City and more set throughout the marketplace from 7pm through 11pm.

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.

Mother Monster is officially returning to Chicago. Lady Gaga is bringing her hotly anticipated Mayhem Ball Tour to Chicago in support of her sixth studio album, the synth-happy Mayhem. The Mayhem Ball Tour marks the pop icon's first arena tour since 2018, promising over-the-top theatrics, staggering choreography and deep thematic exploration.

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.

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. 

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.

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.

Prepare to be awed by this one-of-a-kind magic show where kids don't just watch the magic—they help make it happen. Set against the vibrant glow of a mysterious neon portal, this one-magician show is packed with fun for the whole family. Expect jaw-dropping illusions, hilarious moments and interactive surprises.

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.