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Printers Row Lit Fest
Photograph: Ken Carl

September 2023 events calendar for Chicago

Summer is almost over, but September in Chicago is packed with things to do, including festivals, exhibits and concerts.

Emma Krupp
Edited by
Emma Krupp
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September might be here, but don't despair—summer in Chicago isn't over yet! From Labor Day weekend festivities to summer festivals (including the first-ever Bulls Fest), we've still got plenty of warm weather fun to take advantage of before the leaves start to turn and the temperature drops. Soak up the sun at the best Chicago beaches and rooftop bars, or spend your weekends checking out the end of festival season at events like the Hyde Park Jazz Festival, Printers Row Lit Fest or ARC Music Festival. And if you really can't wait for fall to arrive, might we suggest some early leaf peeping? Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September. 

RECOMMENDED: Events calendar for Chicago in 2022

Featured events in September 2022

  • Comedy
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  • Uptown
This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.
  • Theater
  • Musicals
  • Streeterville
Based on the beloved romantic novel by Nicholas Sparks—which in turn inspired the 2004 movie starring Rachel McAdams and Ryan Gosling—this musical adaptation chronicles the decades-long love story of Allie and Noah with music and lyrics from indie songwriter Ingrid Michaelson. Catch the musical's world premiere at the Chicago Shakespeare Theater, where it will play for a nearly two-month run. 
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  • Comedy
  • Sketch shows
  • price 1 of 4
  • Lake View
Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened a decade ago for a three-week run, then kept getting extended. A cast of four to six performers portray characters at the fictional "Franks Bar," telling stories that explore the city's robust drinking culture. Each show incorporates interactive audience drinking games, allowing you to sip a cocktail or beer while taking cues from the cast. And if you're up for a nightcap after the performance, you can stick around for the official after party and mingle with the cast.
  • Art
  • Sculpture
  • price 1 of 4
  • Suburbs
See eight towering sculptures by South African artist Daniel Popper at the Morton Arboretum's new outdoor exhibition, which spreads the 15- to 26-foot-tall works throughout the natural area. Made of glass-reinforced concrete, wood, fiberglass and steel, the one-of-a-kind pieces in "Human+Nature" depict human figures that evoke the natural landscape they're set amid, including a pair of 36-foot-long hands reaching out from a grove of oak trees and a maternal figure that springs up amid magnolia trees. Access to "Human+Nature" is included as part of timed-entry admission to the Morton Arboretum, and there's a map that will allow you to easily plan your visit and spot all eight  sculptures along the way.
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  • Art
  • Sculpture
  • price 2 of 4
  • Hyde Park
Want to see recreations of Van Gogh's “Starry Night,” Da Vinci's “Mona Lisa” and Michaelangelo's “David”  constructed with Lego bricks? The Museum of Science and Industry's latest exhibition collects the work of Nathan Sawaya, a former lawyer who turned his passion for tiny plastic bricks into contemporary art. “The Art of the Brick” include more than 100 of his creations, include a 20-foot-long T.rex skeleton and a life-sized sculpture of a man pulling his chest apart. The traveling show is the first major museum exhibition to use Lego bricks as its sole medium—and a testiment to the creativity that can be achieved with hundreds of thousands of tiny pieces of plastic. This Museum of Science and Industry exhibit rquires a seperate ticket for entry, in addition to regular museum admission.
  • Music
  • Latin and world
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Explore music from around the globe during this annual festival, now in its 22nd year, which brings a wide array of performers to venues across the city for free musical performances. This year, catch the 10th anniversary edition of Ragamala—the largest all-night-long presentation of Indian classical music in the country—on September from 6pm-8am at the Chicago Cultural Center, plus the return of the annual Global Peace Picnic in Humboldt Park. For a full list of performances, visit the festival's website. 
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  • Art
  • Arts centers
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  • Humboldt Park
Working in partnership with the Museo de Arte de Ponce in Puerto Rico, the National Museum of Puerto Rican Arts & Culture is bringing a stunning selection of paintings to Chicago—some of which have never been shown outside of Puerto Rico—for an exhibition highlighting several of the island's most important artists. Centered around three curatorial themes (“My Home,” “My People” and “My Island”), the works span from the 18th century to the first half of the 20th century, showcasing artists like José Campeche, Francisco Oller, Miguel Pou and Myrna Báez, among others. Tickets to the exhibition are free, but you might consider a small online donation to the Museo de Arte de Ponce, which is still recovering from damage sustained in a 2020 earthquake.  
  • Theater
  • Experimental
  • Lincoln Park
Bedridden and recently widowed, the ailing Martha Washington is attended to by a team of enslaved people—all of whom will be set free as soon as she's dead—in this genre-bending play by the Pulitzer-winning playwright James Ijames. The Chicago premiere production at Steppenwolf's Downstairs Theater stars Steppenwolf ensemble member Celeste M. Cooper alongside Sydney Charles, Carl Clemons-Hopkins, Nikki Crawford, Cindy Gold, Victor Musoni and Donovan Session.
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  • Things to do
  • Loop
Cabaret ZaZou’s premier production Luminaire takes immersive entertainment to a new level on the 14th floor of the Cambria Hotel. Housed in a fantastical Belgian Spiegeltent, Luminaire creates a world of comedy and international cirque performances. Enjoy a four-course meal in cabaret-style seating while you watch the artistry unfold.
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  • Things to do
  • Loop
Dark Testament: A Century of Black Writers on Justice honors the significant contributions of Black writers to American literature and history. In this exhibit, you’ll explore and better understand racial injustice in America by examining the work of Black American writers from the end of the Civil War through the Civil Rights Movement. Featuring original artwork, augmented reality and other interactive elements that enliven and enrich the experience, Dark Testament brings the work of writers past and present to life.
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