The first Equity national tour of the terrifically creative 2025 Tony nominated musical runs through October 11, 2026

The Operation Mincemeat tour is an absolute smash. I adore this inventive and fun musical. It’s extremely original, and it’s the kind of show that gives me hope for the future of new one-of-a-kind musicals like it. Written by David Cummings, Felix Hagan, Natasha Hodgson, and Zoë Roberts, Operation Mincemeat tells the true story of the MI5 mission to turn the tide of World War II. Members of the British intelligence agency devised a plan to have a corpse wash up on the tides of Spain, outfitted with fictitious documents detailing Britain’s plan to invade Sardinia — diverting Nazi troops away from Sicily.

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Steppenwolf opens its 51st season with a blistering and captivating production of Suzan Lori-Parks’s Topdog/Underdog. This play has long been on my theater bucket list, and it’s absolutely what I think of when I think of a “Steppenwolf play”: A gritty family drama about brothers undergoing hard times, grappling with racial injustice and the fallacy of the American Dream. 

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This reimagining of Twelfth Night using Duke Ellington’s song catalog runs through October 18, 2026

Play On! is a lively retelling of Shakespeare’s Twelfth Night. Conceived by Sheldon Epps (who also directs) and with a book by Cheryl L. West, Play On! transports Shakespeare’s story to Harlem, New York. West’s book skillfully weaves Duke Ellington’s songs into the narrative. 

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TimeLine’s 30th anniversary season opens with the world premiere of Jessica Huang’s play, based on Jonathan Eig’s book, running through October 11, 2026

TimeLine Theatre Company’s The Birth of the Pill takes some big swings…and sometimes misses. Adapted for the stage by Jessica Huang from Jonathan Eig’s book, it’s certainly relevant now. And Huang’s script takes “A People’s History of the United States” approach to storytelling. The play takes a character who refers to herself as a “footnote” in Eig’s original text and places her literally center stage. Ramona Delgado represents an amalgamation of the Puerto Rican women who were the trial subjects for the Pill — often without informed consent, and notably, taking pills with much higher doses of progesterone than the current medication — and sometimes debilitating side effects. 

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The Broadway In Chicago transfer of Kokandy’s Jekyll & Hyde plays the Broadway Playhouse through November 8, 2026

Kokandy Productions’ fun and spooky Jekyll & Hyde returns just in time for autumn, this time in a co-production with Broadway In Chicago at the Broadway Playhouse. The transfer maintains the intimacy and sparseness of Kokandy Artistic Director Derek Van Barham’s original staging with a company of 12 actors and 15 musicians. 

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Now extended through October 11, 2026

The Attic: Things I’ve Seen While Lying On My Back is genuinely a unique experience at the Goodman. The 7 Fingers Co-Founder Shana Carroll wrote, directed, and choreographed this world-premiere autobiographical performance piece that shares vignettes from her life story. An international company of circus artists and acrobats join Chicago actor Tyler Meredith onstage to tell much of the story through movement.

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The remount of Anna Ouyang Moench’s play runs through October 4, 2026

Birds of North America is a touching and supremely well-acted two hander. A Red Orchid Theatre’s return engagement reunites Cassidy Slaughter-Mason and John Judd as father-daughter duo Caitlyn and John, directed by Artistic Diretor Kirsten Fitzgerald. Over the course of roughly 10 years, Caitlyn and John bird from the yard of their family home in Maryland. Through these encounters, playwright Anna Ouyang Moench explores the evolution of this father-daughter relationship. Sometimes, John and Caitlyn appear to be each other’s biggest supporters. But as with many family dynamics, their close relationship also means they have the ability to push one another’s buttons and deliver astounding, painful barbs. 

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This storefront staging of the iconic Sondheim musical runs through November 29, 2026

Sunday in the Park with George is an immense vocal and visual masterpiece from composer/lyricist Stephen Sondheim and librettist James Lapine — and simultaneously an intimate portrait of two artists (both named George), struggling with creation and craft. It was a bold choice for Kokandy’s artistic director Derek Van Barham to stage such a huge musical in the tiny cabaret space at the Chopin Theater. Fortunately, Sondheim’s brilliant score and lyrics are gorgeously delivered in Kokandy’s version. And while most productions of Sunday have large pit orchestras, music director Nick Sula has beautifully arranged this Sunday for only five musicians — and it doesn’t feel like they miss a note. This production preserves the live music so integral to Sunday, and notably, the pattering, dot-like orchestrations in much of the music — a clever and powerful nod to George Seurat’s pointillist painting style. 

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The return engagement of the 2024 Tony Award-winning musical runs through August 16, 2026

The Outsiders remains an exhilarating and inventive musical adaptation of S.E. Hinton’s acclaimed 1967 novel. I enjoyed this tour so much on first viewing that I came back six months later! Director Danya Taymor’s original Broadway staging is faithfully recreated for this tour — with a fantastic ensemble cast that’s certainly Broadway caliber. Jamestown Revival (Jonathan Clay and Zach Chance) and Justin Levine’s score fittingly combines contemporary Broadway and folk rock as it relays the story of 14-year-old narrator Ponyboy Curtis and his fellow Greasers. Adam Rapp and Justin Levine’s book remains economical, capturing some of the most iconic lines from Hinton’s novel while keeping the pacing taut. 

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The Max Martin jukebox musical returns to Chicago — this time featuring Joey Fatone of N*SYNC

On its second Chicago engagement, & Juliet remains a glittering, joyous confection of a jukebox musical — and this time it features iconic boy band member Joey Fatone. While I’m not usually a jukebox fan, it was particularly clever for & Juliet’s writers to bring together one of the most iconic playwrights William Shakespeare — and one of modern pop music’s most iconic songwriters and producers Max Martin. With a book by David West Read and lyrics (of course) by Max Martin and friends, & Juliet reimagines Shakespeare’s iconic play if Juliet lived…and sang various 2000s and 2010s pop bangers. 

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