Many of Chicago’s cultural institutions launch their upcoming 2026-2027 seasons in September, and Chicago is rightly famous for its many festivals. September’s festivals are a wonderful finale to the end of summer.
Chicago is known for its food-related festivals. September opens with the largest and oldest Polish festival in the country, the Taste of Polonia Festival of Music and Food at the Copernicus Center, September 4-7. El Grito Chicago in Grant Park, September 12-13, celebrates Mexican Independence Day with food, live music and crafts. One of the top food festivals in the country, Chicago Gourmet, runs September 24-27 in Millennium Park and at other venues. For something on a smaller scale, head to one of my favorite street festivals, Retro on Roscoe in Roscoe Village, which features live music, a classic car show, and food of course, September 18-20.
Two festivals this month celebrate and showcase some of the best of a wide array of Chicago talent: the fifth edition of the Museum of Contemporary Art’s “Chicago Performs” runs September 18-20, and the 6th annual Chicago Live Festival at Navy Pier, which is billed as “the Midwest’s largest free performing arts festival,” is September 19-20.
Speaking of local talent, Rockford’s Cheap Trick performs at Aurora’s RiverEdge Park on September 10. Allison Krauss (who was raised in Champaign) and Union Station perform at the Ravinia Festival on September 12. The final concert of Ravinia’s 2026 season is September 23. Liz Phair (who grew up in Winnetka) and Sleater-Kinney perform at the Salt Shed Outdoors (Fairgrounds) on September 17.
An estimated 460,00 people attended the Lollapalooza over its four-day run in Grant Park this summer. That music festival is over, but there are still many music festivals for every taste this month.
If you like jazz, the Chicago Jazz Festival runs September 3-6 citywide, including at the Jay Pritzker Pavilion in Millennium Park, and at the Chicago Cultural Center. Celebrating its 20th anniversary, the Hyde Park Jazz Festival runs September 26-27 at architecturally significant venues in the Hyde Park, Kenwood and Washington Park neighborhoods.
Last year’s inaugural Constellation Performing Arts’ Sound & Gravity Festival, which showcases a wide range of music genres: contemporary, classical, jazz, experimental, and indie, was so successful that it’s back again this year, September 3-6 at multiple venues on the Northwest Side.
The 6th annual ARC Music Fest features house (which was created in Chicago) and electronic music, September 4-7, Union Park.
The Indigo Girls are just one of the headliners at 3rd annual Evanston Folk Festival at Dawes Park, September 12-13.
Just a few of the featured artists at Riot Fest are Alanis Morrisette, Morrissey, Iggy Pop, Elvis Costello and ninety-five-year-old “Star Trek” star William Shatner, who debuts The *uckers, his new heavy metal band, at the festival which features rock, punk, hip-hop, and alternative music, September 18-20, Douglass Park.
The Music Box Theatre’s 17th annual “Noir City: Chicago” film festival has a musical theme this year, “Face the Music,” September 4-10. Reeling 2026: The 44th annual Chicago LGBTQ+ International Film Festival runs September 17-27 at Chicago Filmmakers, Landmark’s Century Centre Cinema, and the Music Box Theatre. The thirty-third edition of the Chicago Underground Film Festival, the longest running underground film festival in the world, runs September 23-27 at the Gene Siskel Film Center and Harper Theater.
Since 1989, the Chicago Humanities Festival has had an outstanding and varied list of programs. The festival’s fall edition runs September 14-November 14 at various venues and includes three Festival Days: Pilsen Day (September 26); Northwestern University Day (October 4); and Hyde Park Day (November 7). Actor Kyle MacLachlan talks about his memoir “Fictional Selves” during a storytelling conversation on September 30 at the Athenaeum Center for Thought and Culture.
Chicago has a rich and long history of journalism and literature. Billed as “one of the largest journalism shows in the country,” the inaugural Chicago Story Fest is September 18 at the Athenaeum Center and features storytelling, short films, dance performances, and live music.
With more than 200 acclaimed authors, journalists, poets, screenwriters, booksellers and storytellers, the largest free literary event in the Midwest, the 41st annual Printers Row Lit Fest, runs September 12-13 in the South Loop.
Chicago-born author, poet, singer and songwriter Patti Smith will receive the 2026 Harold Washington Literary Award at the award dinner at the Union League Club on September 10. The Pattis Family Foundation Chicago Book Award recognizes books that transform public understanding of Chicago, its history, and its people. Dominic A. Pacyga receives this year’s award on September 19 at a ceremony at the Newberry Library for his book “Clout City: The Rise and Fall of the Chicago Political Machine” (University of Chicago Press, 2025), which outlines the beginnings of Chicago’s distinctive political system to its collapse.
Featuring the work of Chicago artists and companies, the 37th Rhinoceros Theater Festival takes place September 25-October 26 at four venues across Chicago.
The world premiere of Jessica Huang’s “The Birth of the Pill,” based on the book by Pulitzer Prize-winning Chicagoan Jonathan Eig, is one of the plays opening the upcoming theater season, at TimeLine Theatre Company, September 2-October 4. Mary Beth Fisher portrays Chicago philanthropist Katherine McCormick (1875-1967), who was instrumental in funding the research to develop the first birth control pill. This is TimeLine’s 30th anniversary season and inaugural season in their new permanent home in Uptown.
The first public performance in Northlight Theatre’s new home in Evanston is the world premiere of “The Front Page,” adapted by Jeffrey Chatcher from the original Ben Hecht and Charles MacArthur 1928 play, September 9-October 18. Set in a 1930s Chicago press room, this production stars real-life husband & wife team Kate Fry and Edward Kane. The screenplay for the 1940 screwball comedy “His Girl Friday,” starring Cary Grant and Rosalind Russell, was also adapted from the Hecht and MacArthur play.
After a hiatus, Victory Gardens Theater will return producing shows at their Biograph Theater. The world premiere of Northwestern University professor Zahd Ayers Dohrn’s “The Humanities” runs September 10-October 4 with an all-Chicago ensemble that includes Nora Dunn, a former “Saturday Night Live” cast member. Porchlight Music Theatre moves its upcoming 2026-2027 season to the Victory Gardens Biograph Theater. Their “New Faces Sing Broadway 1976” runs September 14-15.
The Chicago premiere of John Neumeier’s “Liliom” opens Joffrey Ballet’s 71st season at the Lyric Opera House, September 17-27. The production features Michel Legrand’s score performed live by the sixteen-piece Rob Parton’s Jazztech Big Band, joined by the Lyric Opera Orchestra. “Liliom” was inspired by Ferenc Molnár’s 1909 play, which later was the basis for the Rodgers and Hammerstein’s musical adaptation “Carousel.”
Opening the Harris Theater Presents 2026-27 season is the Chicago premiere of “Dancing with Bob: Rauschenberg, Brown, and Cunningham Onstage” on September 17. Trisha Brown Dance Company with the Merce Cunningham Trust celebrate the choreographers’ collaborations with the artist Robert Rauschenberg.
Celebrating contemporary art across Chicago, the 4th annual Chicago Exhibition Week (CXW), September 14-20, brings together more than 70 galleries, artist-run spaces, museums and cultural institutions.
The Tokyo-based international digital-art collective teamLab will transform the Smart Museum of Art’s galleries into immersive spaces for “teamLab: Everything Exists in Infinite Continuity,” running September 22-February 21, 2027.
Marking the centennial of artist Mary Cassatt’s death, the Art Institute of Chicago’s exhibition “Mary Cassatt: After Impressionism” runs September 6-January 3, 2027. Cassatt’s painting, “A Child’s Bath” (1893), is one of the Art Institute’s most familiar and beloved works. Cassat has a history in Chicago: Berthe Honoré Palmer, who was President of the Lady Managers at the 1893 World’s Columbian Exposition, commissioned Cassatt to paint a (now lost) mural for the fair’s Woman’s Building.
Headlined by Chicana musician, composer and feminist music scholar Martha Gonzalez, the Boleros de Noche concert series returns to the Harris Theater on September 25. It’s a great way to celebrate Hispanic Heritage Month, September 15-October 15. You can also head to Chicago’s Little Village neighborhood for the 55th annual 26th Street Mexican Independence Day Parade on September 13. The Chicago Latino Theater Alliance’s citywide Destinos, the 9th Chicago International Latino Theater Festival runs September 14-October 11.
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 United German-American Societies of Greater Chicago host the 104th anniversary celebration of Oktoberfest in Lincoln Square, September 11-13. The world’s biggest beer festival, Oktoberfest Munich, is September 19-October 4. I’m flying to Munich to visit my German relatives just after Munich’s Oktoberfest, so I’ll miss the festivities there.
Dates, times, locations and availability are subject to change.
