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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Raven Theatre’s spectacular production of Dave Molloy’s musical transfers to the Goodman’s Owen Theatre

I loved Dave Molloy’s inventive and captivating a cappella musical Octet at Raven Theatre so much that here I am, reviewing it a second time in short succession now that it’s moved to the Goodman’s Owen Theatre. Director Keira Fromm leads an ensemble of eight that shines just as brightly in the Owen as they did at Raven’s more intimate space. Fromm’s staging that plays to three sides of the audience fits naturally in the Owen, which is precisely designed to flank the proscenium from three directions. Milo Bue’s set remains spare, but it doesn’t seem empty at all in the Owen. Instead, it’s a fittingly minimalist design that evokes a church basement — where it’s likely that the internet addicts who call themselves Friends of Saul have gathered.

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The first national tour of Shaina Taub’s Tony winning musical runs through July 19, 2026

Shaina Taub’s new musical Suffs, now making a Chicago stop on its first national tour, has a textbook feel: The lyrics are generic, and the story relies heavily on exposition. I admire Taub’s initiative to take on this musical all by herself (she’s written book, music, and lyrics — and won 2024 Tonys for both). And telling the story of the (white) women’s suffrage movement in the United States is ripe for the musical treatment — and notably, with an entirely female/non-binary cast. Unfortunately, it often plays like a history lesson. Taub seems to have made a major commitment to historical accuracy, which is admirable. But that means the character development suffers. 

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Now with more improv! The Second City e.t.c.’s 50th revue plays an open run. 

The Second City e.t.c.’s 50th revue Reality Detox promises more improv than ever before. While originally billed as an all-improv piece, ensemble members Kennedy Baldwin, Anna Portnick, Chas Lilly, Max Thomas (appearing in his second e.t.c revue), Annie Sullivan, and Riley Woolen haven’t quite made it there. But Reality Detox features substantially more improv than some past revues. The ensemble uses a chalkboard to indicate the line-up of sketches and improv moments of the evening. It appears that the improv slots rotate so audiences also see different sketches each night, making each performance a little different. 

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The hilarious and wacky world-premiere musical comedy featuring Megan Mullally and Nick Offerman runs through August 16, 2026

Iceboy! is an absolute riot. It’s a truly original and genuinely laugh-out-loud story with tight pacing and structure from Erin Quinn Purcell, Jay Reiss, and Mark Hollmann. The plot is entirely far-fetched, but I love that the creators don’t make the show feel absurd: The characters are so totally entrenched in the world of the show, which is core to making it work. 

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Water for Elephants transports audiences to the circus — and has some dazzling aerial tricks up its sleeve. Based on the popular 2006 novel by Sara Gruen, Rick Elice’s book and PigPen Theatre Co.’s score comprise a memory musical: The elderly Mr. Jankowski (Robert Tully) looks back on his days as a member of a traveling circus back in 1931. Young Jacob (Chicago native Zachary Keller), who almost graduated veterinary school, stumbles onto a train…and finds himself among the “kinkers” of the Benzini Brothers’ one-ring circus. The narration switches between the two Jacobs, as he recalls his role of animal caretaker and how he falls for Marlena (Helen Krushinski), the circus’s star act and wife of the cruel and abusive ringmaster August (Connor Sullivan). 

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Untitled Vampire Play — a world premiere from Lookingglass ensemble member Kevin Douglas — is a fun, wacky romp. The play doesn’t take itself seriously, and director Devon de Mayo’s cast has plenty of fun with vampire and human antics alike. Douglas’s script draws on all sorts of vampire lore for his vision and vividly imagines what it might be like if vampires roamed the streets of Chicago. 

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A play as befuddling as its nonsensical title — now playing at Steppenwolf through July 12, 2026

I left Catch as Catch Can at Steppenwolf Theatre Company on Sunday night wondering exactly what I had just seen, and what, if anything, I was meant to take from it. In part, playwright Mia Chung’s play presents as an acting exercise:  It centers on two families —  the working class Lavecchias and Phelans of New England — but only three actors play all the roles. In Amy Morton’s production, ensemble members Gary Cole, Audrey Francis, and Tim Hopper bridge age and gender to play various combinations of parents and children among the two. But to what end? It’s not clear. I thought perhaps Catch As Catch Can would offer some sort of meditation on the parent-child relationship. Perhaps it was meant to explore how children become their parents? It doesn’t.

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Tom Stoppard’s Leopoldstadt follows multiple generations of an Austrian Jewish family from prosperity to despair — spanning over 50 years from 1899 to 1955. Now in its Chicago-area premiere at Writers Theatre, the late Stoppard’s final play includes a cast of 24 actors and many, many characters. Leopoldstadt (named after the Jewish quarter of Vienna) is a sprawling and ambitious work. 

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