By Philip Vidal
September is a month of end-of-summer festivals that are a celebration of all that Chicago offers. Architecture, art, dance, film, food, literature, music, neighborhoods and theater are all featured in festivals both new and old, with a few milestones along the way. September is also the month that many of Chicago’s cultural institutions launch their upcoming seasons.
The world premiere of “Ashland Avenue” kicks off the centennial season for Goodman Theatre, September 6-October 5. Photo by Goodman Theatre.
An electrifying blaze of passion and peril! Liam Scarlett’s “Carmen” is a tale of love, betrayal and defiance. Performances of the Joffrey Ballet’s “Carmen” will be held at the Lyric Opera House, September 18-28. Photo courtesy of Joffrey Ballet and Carolyn McCabe.
The Goodman Theatre launches its centennial season with Lee Kirk’s new play “Ashland Avenue,” about generational tension at a Chicagoland family-run business, September 6-October 5. GRAMMY® Award-winning Third Coast Percussion opens Chicago Chamber Music Society’s 90th season at a private club on Michigan Avenue on September 10. The U.S. premiere of Liam Scarlett’s “Carmen” kicks off the Joffrey Ballet’s 70th season at the Lyric Opera House, September 18-28. Enjoy highlights from both the Joffrey’s upcoming “Carmen” ballet and the Lyric Opera of Chicago’s 2025/2026 season at the Lyric’s annual “Sunday in the Park with Lyric” concert, Jay Pritzker Pavilion, September 7.
Celebrating a 50th anniversary milestone! Northlight Theatre presents James Sherman’s “The First Lady of Television” at the North Shore Center for the Performing Arts. Tickets available for performances September 4-October 5. Photo credit to Greg Inda.
Steppenwolf begins its 50th season with the Chicago premiere of Rajiv Joseph’s “Mr. Wolf, September 11-November 2. Also celebrating its 50th season, Northlight Theatre opens with the world premiere of James Sherman’s “The First Lady of Television,” featuring Cindy Gold as the pioneering actress, producer and screenwriter Gertrude Berg, September 4-October 5 at the North Shore Center for the Performing Arts.
Making its Chicago premiere! “AVA: The Secret Conversations” follows Ava Gardner’s interviews with writer Peter Evans, September 24-October 12 at the Studebaker Theater. Photo credit to Jeff Lorch.
The “Downtown Abbey” TV series and movies featured Evanston-native Elizabeth McGovern as Lady Grantham. She’ll also star in the upcoming film “Downtown Abbey: The Grand Finale,” which arrives in theaters nationwide on September 12. McGovern wrote and stars in “AVA: The Secret Conversations” about film legend Ava Gardner, at the Studebaker Theater, September 24-October 12. Learn more about this Academy Award, Golden Globe, and Emmy Award-nominated actress by attending “Elizabeth McGovern | Life on Stage and Screen: A Conversation with Chicago Tribune Critic Chris Jones” at the Driehaus Museum on September 22. McGovern made her film debut in “Ordinary People” (1980) about a Lake Forest family.
On the film’s 40th anniversary, Universal Pictures will rerelease “The Breakfast Club” (1985) in early September. Filmed at Maine North High School in Des Plaines, the movie stars Brat Pack members Molly Ringwald, Emilio Estevez, Anthony Michael Hall, Judd Nelson, and Ally Sheedy. I remember seeing the movie in a ground floor movie theater at Water Tower Place when it was originally released.
Enjoy 10 days of LGBTQ+ film with Reeling 2025! Tickets are available now for the showings on September 19-28. Artwork by Da-Shuang (Shuang Wu)
The thirty-second edition of the Chicago Underground Film Festival, the longest running underground film festival in the world, runs September 17-21 at the Gene Siskel Film Center and Harper Theater in Hyde Park. The Reeling 2025: The 43rd Chicago LGBTQ+ International Film Festival runs September 19-28 at Chicago Filmmakers and Landmark’s Century Centre Cinema.
American Blues Theater opens its 40th anniversary season with the world premiere of Kristoffer Diaz’ dark comedy “Things with Friends,” August 29-October 4.
Be part of the largest free literary event in the Midwest! Printers Row Lit Fest is fun for the whole family with programs and activities on Saturday September 6 and Sunday September 7. Photo by Printers Row Lit Fest.
The largest free literary event in the Midwest, the 40th annual Printers Row Lit Fest runs September 6-7 on South Dearborn Street. The festival includes a book sale and free literary programming. This year’s headliner is author Sandra Cisneros, who wrote The House on Mango Street.
From film and literature festivals to a food festivals…. The 45th annual Taste of Chicago is September 5-7 in Grant Park. This year’s Chicago Gourmet has a sports theme, “Step up to the Plate,” which celebrates both food and sports, at the Harris Theater Rooftop and other venues from September 25-28.
There are several new festivals this month. The Sound & Gravity Music Festival from Constellation Performing Arts, at seven venues, September 10-14, showcases a wide range of music genres: contemporary classical, jazz, experimental, and indie music. Access Contemporary Music’s CheckOut Opening Festival September 13-28 celebrates the official opening of their new venue and music school, The CheckOut, at 4116 North Clark Street.
The inaugural Edgewater Music Fest takes place along Broadway from Thorndale to Ardmore and features an exceptional music lineup, food and retail vendors the weekend of September 5-7. Photo credit to Michael Courier.
The Edgewater Music Fest has been on hold since 2019, but it’s back on Broadway from Thorndale to Ardmore September 5-7. The 2nd annual Evanston Folk Festival runs September 6-7 with a truly stellar line-up including Ani DiFranco, Loudon Wainright III and Rosanne Cash. Daytime events are held at Dawes Park with Lake Michigan as a backdrop. Ticketed evening performances are at Cahn Auditorium and Evanston Space.
Two events this month celebrate and showcase some of the best of a wide-array of Chicago talent: the fourth edition of the Museum of Contemporary Art’s festival of performance, Chicago Performs, runs September 18-21; and the 5th annual Chicago Live! at Navy Pier, which is billed as the “the Midwest’s largest free performing arts festival in the Midwest,” is September 20.
Celebrate Hispanic Heritage Month by attending the Pilsen/Little Village Day on September 21 at the National Museum of Mexican Art. Photo courtesy of Chicago Humanities.
Since 1989 the Chicago Humanities Festival has always had an outstanding and varied list of presenters. The fall edition of the citywide festival runs September 21-November 13 and includes presentations by chef Rick Bayless, comedians Kate McKinnon and Cheech Marin, authors Margaret Atwood and Salman Rushdie, to name just a few. Co-presented with the National Museum of Mexican Art, the festival also includes an immersive Pilsen/Little Village Day on September 21 celebrating Hispanic Heritage Month, September 15-October 15.
Chicagoland has historically had a large German-American population. Celebrate German heritage at one of the dozens of Oktoberfest events in the Chicago area in September and October. The 102nd Chicago German-American Oktoberfest is September 5-7 at Lincoln Square and includes the 59th annual Steuben German Day Parade, which kicks off from 4100 North Lincoln on September 6. The Chicago Cubs’ inaugural “Oktoberfest with the Cubs,” a Bavarian-style celebration that includes a family-friendly “Kinderfest,” runs September 19-21 in the Toyota Camry Lot at 1126 W. Grace Street.
My grandparents arrived from Germany in the 1920s when Germany was experiencing hyper-inflation. They, and many, many others, visited Chicago’s A Century of Progress fair, which opened in 1933. I know this because I have some of their souvenirs. Revisiting the past, the Elmhurst History Museum presents the exhibition “World of Tomorrow: A Century of Progress,” August 29-January 4, 2026.
View stunning works of art like this at Elmhurst Art Museum’s “Shakkei: Work by Mayumi Lake and Bob Faust.” Mayumi Lake, Unison (Droplets), 2021, courtesy of the artist and Elmhurst Art Museum.
A Century of Progress showcased the latest in architecture and design, which is acknowledged to this day. Celebrating its 10th anniversary, the theme of the sixth edition of the Chicago Architecture Biennial is “Shift: Architecture in Times of Radical Change” and runs September 19-February 28, 2026 at the Chicago Cultural Center and citywide. The Chicago Architecture Biennial (CAB) hosts the largest exhibition of architecture and urbanism in North America. In conjunction with the CAB, the Elmhurst Art Museum presents the work of two Chicago-based artists with “Shakkei: Work by Mayumi Lake and Bob Faust,” September 6-January 5, 2026.
An exhibition illuminating the volume and breadth of Louis C. Tiffany’s vast artistic production! View the stunning range of decorative lighting fixtures on display at the Driehaus Museum’s “Tiffany Lamps: Beyond the Shade” exhibition. Photo courtesy of Driehaus Museum.
The 3rd annual citywide Chicago Exhibition Weekend, CXW25, September 19-21, featuring more than fifty galleries and spaces, showcases Chicago’s diverse and vibrant commercial arts community. The first solo exhibition in his hometown of Chicago, “Theaster Gates: Unto Thee,” at the Smart Museum runs September 23-February 22, 2026. Some of Louis Comfort Tiffany’s designs that his talented artisans brought to life…and light…are featured in the Driehaus Museum’s “Tiffany Lamps: Beyond the Shade” exhibition, September 12-March 15, 2026.
Celebrate architectural achievements at Designight, the architectural awards ceremony hosted by the Chicago Chapter of The American Institute of Architects (AIA Chicago) at the Harris Theater for Music and Dance on September 18. Starchitect Adrian Smith, who designed the world’s tallest building, Burj Khalifa, is the recipient of the 2025 AIA Chicago Lifetime Achievement Award.
An event that I thought I’d never see in my lifetime is the Chicago River Swim. When I was growing up, the river was polluted and devoid of fish. Now it’s much cleaner and full of fish. On September 21, hundreds of swimmers from around the world will participate in this event to raise funds for ALS research and swim lessons for children in underserved local communities. They might be cutting it close because the earliest Chicago snowfall was on September 25 in both 1928 and 1942.
Help the Anti-Cruelty’s mission to help thousands of animals each year by attending their annual “Pour Your Heart Out” fundraising event. Photo courtesy of Anti-Cruelty.
Not only can you swim for a good cause, you can also raise a glass for a good cause. Last year marked Anti-Cruelty’s 125th anniversary as Chicago’s oldest and most comprehensive animal welfare organization. I look forward to attending the Anti-Cruelty’s annual “Pour Your Heart Out” fundraiser with my good friend (and dedicated Anti-Cruelty volunteer) Sarah Ames at Sarabande Chicago on September 25. Pawtenders from across Chicago will pour libations and, of course, there will quality playtime with puppies and kittens.
Dates, times, locations and availability are subject to change.
