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What Plays, Musicals to See in Chicago This Fall

Posted on September 5, 2023   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Lin-Manuel Miranda at the opening night of “Hamilton” at the CIBC Theatre in the Loop in 2016

Lin-Manuel Miranda at the opening night of “Hamilton” at the CIBC Theatre in the Loop in 2016. (Tasos Katopodis / Getty)

After we shared how to see Chicago plays and musicals on a budget, we decided to round up shows we’re most excited to see this season.

Best Chicago Story: ‘Welcome to Matteson’

📍 Northwestern University’s Abbott Hall in Streeterville

🗓️ Sept. 6–Oct. 1

This Congo Square Theatre dark comedy imagines a dinner party between one couple who has long lived in the southwest suburb and another couple who moved from the Cabrini-Green housing complex.

Most-Anticipated Return: ‘Hamilton’

📍 Nederlander Theatre in the Loop

🗓️ Sept. 13–Dec. 30

After running a three-plus-year run in the city, the popular Lin-Manuel Miranda musical is back and so is the $10 digital lottery!

Best Chicago History: ‘Jane’

📍 The Edge Off-Broadway in Edgewater

🗓️ Sept. 14–Oct.15

Based on interviews, the play explores the underground collective of Chicago women who provided safe abortions before Roe v. Wade.

Best Theater Fest: Destinos Festival

📍 Citywide

🗓️ Sept. 28–Nov. 12

The annual fest showcases Latinx theater and companies from Chicago and across the world. Productions will be in Pilsen, Chicago Lawn, Wicker Park, Oak Park, and more.

Best Musical Adaptation: ‘The Color Purple’

📍 The Studebaker Theater in the Loop

🗓️ Sept. 29–Oct. 1

Before the new film comes out, see the musical based on Alice Walker’s Pulitzer Prize-winning novel.

Best Staged Reading: ‘The White City’

📍 Glessner House in South Loop

🗓️ Oct. 6–7

Get into the spooky spirit with this tale of serial killer H. H. Holmes, who murdered more than 20 people during the World’s Fair of 1893.

Best Musical Tribute: ‘A Taste of Soul’

📍 Black Ensemble Theater in Ravenswood

🗓️ Through Oct. 15

Celebrate the genre’s evolution from its gospel roots to today’s pop hits. Songs are from Barry White, Gladys Knight, Peaches & Herb, and more.

Best for Kids: ‘Pinocchio’

📍 Beverly Arts Center

🗓️ Oct. 25–Nov. 22

The one-hour musical invites kids to help Pinocchio become a real boy.

📍 Steppenwolf Theatre in Lincoln Park

🗓️ Oct. 26–Dec. 3

Seven women in the West Wing try to keep a White House PR nightmare from spinning out of control in a play that explores politics, power, and sex.

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