Chicago’s cultural calendar never takes a break — and September proves it. The city and suburbs are packed with a nonstop lineup of festivals, concerts, theater, and community gatherings that carry us from the last golden days of summer into the first notes of fall. From iconic traditions to fresh debuts, here are the best things to do in Chicago and the suburbs this month.
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Ongoing
Ashland Avenue at Goodman Theatre
Goodman Theatre opens its centennial season with the world premiere of Ashland Avenue, a heartfelt and funny new play by Lee Kirk. Pete’s TV and Video, once a thriving Chicago electronics chain, is down to its final store. Pete (Francis Guinan), a local legend thanks to his commercials, believes the business can be revived, while his daughter Sam (Emmy nominee Jenna Fischer, The Office) dreams of a different path. Directed by Artistic Director Susan V. Booth, the production also stars Will Allan, Cordelia Dewdney, and Chiké Johnson. Runs Sept. 6 – Oct. 5, 2025 in Goodman’s Albert Theatre.
Tiffany Lamps: Beyond the Shade: Driehaus Museum
Driehaus Museum’s Tiffany Lamps: Beyond the Shade (Sept. 12–Mar. 15) casts a new light on one of the Gilded Age’s most recognizable names. The show moves past the familiar glow of Tiffany’s stained-glass shades to reveal the full scope of the studio’s work between the 1890s and 1920s — from bronze boxes and pottery vases to a monumental chandelier rarely seen by the public. With pieces drawn from both the Driehaus collection and the Richard H. Driehaus Art Exhibition Lending Foundation, guest curator Alexandra M. Ruggiero frames the story around the artistry, materials, and influential designers that helped make Tiffany a household name.
Raqib Shaw: Paradise Lost
Epic and intricate, monumental and meticulous—the paintings of Kashmir-raised, London-based artist Raqib Shaw offer fantastical meditations on identity, transformation, and the redemptive power of
beauty. Witness this masterpiece now through January 19, 2026.
MISERY at Citadel Theatre
Romance novelist Paul Sheldon is rescued by obsessed fan Annie Wilkes, who traps him after he kills off her favorite character. Forced to rewrite his novel under her watch, Paul is caught in a tense, life-or-death struggle for survival. This show’s run kicks off on September 12 and ends October 12.
Contemporary Drawings from the Stenn Family Collection
Voraciously curious and contagiously enthusiastic about art, Chicagoan Irving Stenn Jr. has across five decades assembled a spectacular collection of 20th-century art from various movements and across the world. See the exhibit through September 15.
Chicago SummerDance
Enjoy live music and dancing on an open-air dance floor during the annual Chicago SummerDance festival. This summer-long event series brings people together in the city’s scenic parks for evenings filled with music, dance, community, and celebration. Each event features lessons from a professional dance instructor, featuring more than 30 unique dance styles from around the globe. Select dates through September 7.
Gustave Caillebotte: Painting His World
Impressionist artist Gustave Caillebotte (1848–1894) — known and beloved by many Art Institute visitors for his monumental painting Paris Street; Rainy Day — takes center stage in this major exhibition exploring the very personal interests and relationships that shaped his world. Catch it through October 5, details at the Art Institute online.
Pouring Park: A Global Cocktail Journey
From now through the new year, celebrate Park Hyatt’s 45th anniversary with a global cocktail journey—no passport needed. Enjoy iconic drinks from nine destinations, each crafted to reflect its culture. Every 45 days, two new cocktails debut at participating locations, offering a taste of the world, one sip at a time.
ART on the MART
“Superbloom is about radical beauty in the natural world. In a super bloom, wildflower seeds in the desert bloom in high numbers all at the same time. It doesn’t happen often, and a particular set of conditions must be met for the dormant seeds to thrive—rain, wind, cloud coverage, and temperature in the right measure. Carrie Hanson, Artistic Director of The Seldoms, notes ‘A super bloom is demanding and somewhat defiant as it sits outside our attempts to order and harness nature—it is wild in the absolute.'” Catch the show before September 7.
September 5-7: Taste of Chicago
While neighborhoods across the city have had their own pop-up Tastes throughout the summer, none compare to the mother of all foodie festivals, Taste of Chicago — held annually in Grant Park. Since 1980, Chicagoans have been flocking to this fest to sample an array of the best dishes in the city from countless vendors. Summer isn’t over yet, so hit the park to grab a bite and bring a friend or the family while you’re at it. Taste of Chicago online has all the details you need.
September 5-7: Chicago German-American Oktoberfest
Annually in Lincoln Square, the German-American Oktoberfest kicks off the autumn season with delicious food, authentic drinks, and tons of community fun! From live music and dancing to carnival games and beer tents, this festival of German-American culture is a great time for all. Find more information on the Oktoberfest site.
September 6: The Loving Farm Inaugural Gala
The Loving Farm Inaugural Gala: Join us for a memorable night of celebration, community, and compassion to support the lifelong care of rescued, retired, and unwanted horses.
September 6-7: Printers Row Lit Fest Celebrates 40th Anniversary
The Printers Row Lit Fest celebrates its 40th anniversary on Saturday, September 6, and Sunday, September 7. It will feature Sandra Cisneros, author of “House on Mango Street” as the headliner, over 70 live programs, six stages, over 100 booksellers, authors, publishers, storytelling, food vendors and more. Admission is free.
September 7: Sundays on State
The well-loved and well-awarded Sundays on State transforms Chicago’s most iconic street, State Street, into a no-traffic, open air market. The Chicago community and beyond unite for a free, interactive block party, while safely enjoying art, culture, active recreation, food, drinks, shopping, and local attractions in the heart of everyone’s neighborhood—the Loop. Find more details online.
September 10 & 11: Paddle and Plant
Join Friends of the Chicago River and Shedd Aquarium to paddle, explore and volunteer to improve the health of the Chicago-Calumet river system this summer. Volunteer for one of the Paddle and Plant events to put in aquatic plants along the river’s edge, a unique opportunity to put on waders, head out in canoes, park along the banks of the waterway, and install native plants. These plants improve habitat and water quality, in addition to improving our resiliency to climate change.
September 11: Bird Walk: Fall Migration
This fall, take a walk in the Chicago Botanic Garden and learn to identify birds in their sometimes-confusing fall plumage. Earlier bird walks will highlight warblers, vireos, and flycatchers, while later ones will feature ducks, sparrows, and hawks. Please dress for the weather and bring binoculars and a field guide if you have them.
September 12: Homecoming House Party
Celebrate community, culture and connection at Homecoming House Party—an evening that honors the spirit of the Black collegiate experience and Divine 9 pride in the city that built house music. Sport your college gear from any institution: Homecoming House celebrates YOUR unique college experience. Sip, stroll and dance to live DJs spinning house music—this is a night you won’t want to miss!
September 12: Norwood Park Fall Fest
Unsure when to make that transition from summer to fall? Let the Norwood Park Fall Fest help you, with a weekend they describe as a “fall-themed haven” for delicious local food; tasty beer and beverages; live music with a range of genres; a children’s area; and tons of merchandise booths with local goods. Whether or not you’re ready for autumn, come share in this community fun! There is a recommended donation for entry; this is a family-friendly event. More information is available on the Fall Fest site.
September 13: PAWS Chicago 5k
Ready. Set. Bark! Bring your furry friend over to Montrose Harbor for the animal-friendly 25th Annual PAWS Chicago 5k. The race is in support of making Chicago a no-kill city and helping homeless pets get a second chance. After the run, participants — both human and canine — are welcome to share in the lineup of fun for the afternoon, including: giveaways, an interactive dog agility course, raffles and a whole lot more! Specifics about the race and registration are available on the PAWS Chicago website.
September 13-14: Lakeview East Festival of the Arts
All over the city there are art and music festivals, but can you ever really get enough? Head on over to the Lakeview East and check out over 120 juried artists who will be displaying world-class art in a number of mediums, like painting, sculpture, jewelry, photography and more. Additionally, there will be multiple stages with live music, kids activities and, of course, food booths. More information can be found on the Lakeview East Festival Of The Arts website.
September 13-14: Ravenswood ArtWalk (RAW)
In its 23rd year, the Ravenswood ArtWalk (RAW) will be honoring its theme — “Tour of Arts and Industry” — with a weekend-long celebration of the local creative community. Guests can expect to see open studios and galleries; live performances; a pop-up beer garden; and an outdoor arts market with 80+ local makers; live music and dance; food vendors; and more. This family-friendly event is the perfect chance to take in a bit of the culture you may not otherwise have the chance to. Get all info at Ravenswood ArtWalk online.
September 13-14: El Grito Chicago
This month “we’re bringing all the orgullo Mexicano to Grant Park for a full weekend of culture, flavor, and música. Think a taco in one hand, michelada in the other while the banda plays loud and proud with the Chicago skyline in the background.” Check the El Grito Chicago website for all details.
September 14: Music of the Baroque Presents “Orfeo ed Euridice“
Dame Jane Glover leads the Music of the Baroque Chorus, Orchestra, and international stars in our first performances of Gluck’s emotionally charged Orfeo ed Euridice. Follow Orfeo’s desperate journey to the Underworld as he battles fate to rescue his beloved Euridice, armed with nothing but his voice.
September 14: Run for the Parks: 5K Run, Walk or Roll!
Chicago proudly supports its beloved park system, and if you want to be a part of that support too, then check out the upcoming Run for the Parks! 5K. The race — which is sponsored by Chicago Parks Foundation and encourages running, walking or rolling — will take place along the picturesque Lakefront Trail. All are welcome, secure your spot on the Run for the Parks! site.
September 18: After School Matters Annual Gala
The After School Matters Gala will feature an evening of teen showcases, fabulous food and drinks, and networking as we celebrate the 19,000 Chicago teens we serve annually. This cocktail-style event is held from 5:30-8:30 p.m. at 167 Events.
September 19-21: Riot Fest
As always, Riot Fest delivers a powerful lineup — Green Day, Sex Pistols, The Beach Boys, Dropkick Murphys, Jack White, The Pogues, Weezer performing The Blue Album, and Marky Ramone playing The Ramones — capturing decades of rebellious spirit. Beyond the stage, Riot Fest invests year-round in surrounding neighborhoods through its “Beyond the Fest” program, offering paid internships, scholarships, job fairs, vendor workshops, and local artist showcases, all designed to support community growth and opportunity.
September 19-28: Reeling: The Chicago LGBTQ+ International Film Festival
Reeling: The Chicago LGBTQ+ International Film Festival is the second longest-running film festival of its kind, and prides itself on showcasing the best LGBTQ+ films and videos each year. From award-winning international feature films to social documentaries to experimental shorts, Reeling has always presented a range of genres that demonstrate the rich diversity of work being produced. Not only has Reeling become one of the most important cultural events for Chicagoans, it also attracts LGBTQ+ people from throughout the Midwest who consider the festival to be the highlight of their cinematic year.
September 20-21: West Loop Art Fest
Join us for West Loop Music & Art Fest, a two-day celebration of art, music, and community in the heart of Chicago’s near west side. Spanning four blocks of vibrant Fulton Street, this year’s fest brings even more excitement with live music and art activations running all day and into the evening.
September 21: 2025 Walk to End Alzheimer’s
The Walk to End Alzheimer’s is a space carved out for those touched by Alzheimer’s to seek community, raise awareness and funds, and speak out loud about something that effects so many. To join this great cause, visit The Walk to End Alzheimer’s website to register or donate.
September 25-28: Chicago Gourmet
If you, like many other Chicagoans, love the diverse, delicious food our city has to offer then you need to grab your ticket for Chicago Gourmet this month. The multi-day event at various locations features a lineup of curated chefs and their expertly-crafted bites. This event is 21+ and recommended as an outing for friends or couples, but not for kids. Get your ticket while you still can at Chicago Gourmet.
September 26-30: World Music Festival
This free, city-wide festival will feature 30+ artists from 16 countries at multiple venues around Chicago— such as Chicago Cultural Center, Millennium Park, and Navy Pier. This fest continues to bring even more diversity and interest to Chicago’s already rich music festival scene. This free event will run until October 5, 2025.
September 27: AIDS Run & Walk Chicago
Since it began in 2001, thousands of participants have come together for the AIDS Run & Walk Chicago, raising millions of dollars to battle the HIV epidemic. While raising awareness and funds for AIDS Foundation Chicago and partners — with proceeds directly benefiting programs and services that improve people’s lives — the race is also an excellent way to get out and spend time with the community. AIDS Run & Walk Chicago online has all the race details you need as well as virtual registration. Your support could make a difference for countless people near and far!
September 27-28: 19th Annual Hyde Park Jazz Festival
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Well-loved by jazz heads from near and far, the 19th annual Hyde Park Jazz Festival is back for another music-packed year. With so many acts ready to take the stage, attendees who range from jazz lovers to newbies of the genre will find something to love. More information on this celebration of all things jazz can be found on the festival website.
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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.
