Chicago Shakespeare Theater Unveils 40th Anniversary Season, Featuring ILLINOISE Return

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Artistic Director Edward Hall and Executive Director Kimberly Motes lead the Navy Pier theater into its next chapter.

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Chicago Shakespeare Theater has unveiled its 40th Anniversary Season. America's leading Shakespeare Theater curates a season rooted in Shakespeare and Chicago with a complement of world-class contemporary work—emblematic of the Theater's global, yet unmistakably Chicago perspective.

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Celebrating four decades of vivid and entertaining performances that captivate minds, spark conversation, and invite new perspectives, CST now embarks on the Theater's next thrilling chapter.

The 2026/27 Season begins with Play On!, a joyful musical inspired by Shakespeare's Twelfth Night set to the songs of Duke Ellington , directed by Sheldon Epps . Next is an unforgettable theatrical event: The Winter's Tale and A Midsummer Night's Dream, both staged by Artistic Director Edward Hall and performed in repertory by a single company of 14 actors, a first-ever in CST's history.

The winter will feature Romeo y Julieta, a bilingual English and Spanish adaptation of Romeo and Juliet directed by Henry Godinez ; and the return of the Tony Award-winning smash hit Illinoise, based on the Sufjan Stevens album and directed and choreographed by Justin Peck , after a sold-out world premiere at CST in 2024. The season ends with the hilarious whodunnit Reunion in Bartersville directed by Jerry Dixon ; and the world premiere of Heartbreakers, a high-voltage reimagining of Shakespeare's Romeo and Juliet told through the electrifying rock catalog of Grammy-winners Pat Benatar and Neil Giraldo and with book and direction by Bradley Bredeweg . CST continues to deepen its commitment to the next generation of theatergoers through award-winning education programs, annually serving more students and teachers than any theater in the city.

“It is only fitting that this celebratory milestone season brings together the best of Shakespeare and the best of contemporary work,” said Edward Hall , Artistic Director. “We've long believed that plays of the past can illuminate our present—and that the voices of today shine a light on how much we share with one another: past, present, and future. It is my joy to embrace our audiences with distinctly Chicago-style Shakespeare. This upcoming season is a tribute to the artistry, excellence, and ambition that has come to define Chicago Shakespeare Theater.”

“From the moment that the first words ‘O for a Muse of Fire…' were spoken on the roof of the Red Lion Pub in Barbara Gaines ' debut production of Henry V, a destiny for Chicago Shakespeare Theater was born,” shared Kimberly Motes, Executive Director. “Now forty years later, CST has grown beyond what anyone might have imagined—and the sky is the limit as we dream ahead to the Theater's next 40 years and beyond.”

Launching the season in The Yard is Play On! (September 11–October 18, 2026 | The Yard), a joyful musical retelling of Shakespeare's beloved comedy Twelfth Night set to the timeless jazz tunes of quintessential American composer Duke Ellington . Original creator Sheldon Epps returns to the three-time Tony-nominated musical with book by Cheryl L. West for the first time in 20 years to stage Shakespeare's story for a new generation. Aspiring songwriter Vy takes the A-Train to Harlem in the swinging 1930s with big dreams of a career in showbiz, only to find that it's a man's world. She disguises herself to reach the inner circle of renowned band leader, the Duke—but plans backfire when she catches the eye of Lady Liv, the star singer of the Cotton Club, and mistaken identities make way for romance. Music is indeed the food of love with big band pizzazz and Ellington's hit songs “It Don't Mean a Thing,” “Don't Get Around Much Anymore,” “I'm Beginning to the See the Light,” and much more. Play On! is presented in association with MMaxwellMedia, WMK Productions, Alyssa Melani, and The Classical Theatre of Harlem.

“Over the last couple of years, Cheryl and I took a deep dive back into the book of the show,” revealed director Sheldon Epps . “Our credo in all of this has been to enhance and heighten the celebration of Black Excellence, Black Brilliance, and Black JOY. The Excellence being the celebration of the artists who inspired these characters and the actual cast onstage; the Brilliance is that of Mr. Shakespeare and the Duke of Ellington; and the Joy is consistently the experience of the audience that we hope to achieve with each performance. In simple but very effective ways, we have and will continue to focus on the fact that the show is all about the search for LOVE, and removing the masks that we often wear that keep that hoped-for goal from entering our lives fully.”

CST's 40th Anniversary Season continues with an unforgettable theatrical event in the Jentes Family Courtyard Theater: for the first time in CST's history, two plays will be performed in repertory by one masterfully talented Chicago Shakespeare Company of actors. Under the creative leadership of CST Artistic Director Edward Hall and taking its inspiration from Shakespeare's own company and CST's roots as the Shakespeare Repertory, a company of 14 actors perform both The Winter's Tale and A Midsummer Night's Dream, two of Shakespeare's most beguiling fairy tales. This double header of productions makes for a thrilling theatrical experience, with two beautiful plays exploring the formidable power of love, laughter, and forgiveness. Audiences will have the unique opportunity to experience both repertory productions in one day on November 21 & 24 and December 5 & 12.

“Bringing these two plays together with one group of actors is a genuinely exciting prospect,” said Artistic Director Edward Hall . “Audiences will have the rare opportunity of seeing performers switch into completely different roles from one play to another celebrating Chicago's huge well of creative talent. This Chicago Shakespeare Company will have it all: laughter, drama, magic, forgiveness, and love. An unforgettable journey through magic forests and wild seacoasts, with fairies, oracles, bears, kings, and queens. Everything that a good adventure can bring you and all from the safety of your seat!”

The repertory series begins with Shakespeare's The Winter's Tale (October 13–December 12, 2026 | The Jentes Family Courtyard Theater). Once upon a time in a land called Sicilia, King Leontes is infected by an uncontrollable jealousy over his pregnant wife Hermione. Shakespeare's timeless romance takes us on a fairy tale adventure from the drama of Sicilia to the color and music of Bohemia. Shipwrecks, bears, and magic oracles dance across the stage in this story of betrayal, forgiveness, reunion, and reconciliation. Hope and forgiveness sit at the heart of Shakespeare's most magical of fairy stories with an unforgettable ending driven by the power of redemption.

A Midsummer Night's Dream (November 11, 2026–January 3, 2027 | The Jentes Family Courtyard Theater) sparkles with the festive spirit of the holiday season. Shakespeare's magical romantic comedy is a delectable treat for the entire family. A snowy Athens gives way to the warm and colorful dream of a midsummer forest as Shakespeare's best-loved characters are consumed by the absurd chaos of love and the joy of friendship. Young love collides with a fairy feud and an enthusiastic group of amateur theatricals in the most warm-hearted play in the English language. An enchanting story of love, marriage, and magic, this holiday Dream will fill you with happiness and hope.

Next in the Courtyard, Henry Godinez directs Romeo y Julieta (January 26–March 14, 2027 | The Jentes Family Courtyard Theater). Shakespeare's classic tale of star-crossed young lovers from feuding families is transported to Miami in the early 1960s, as an influx of Cuban exiles find their dreams of returning to their homeland at odds with the reality of their new home. As conflict escalates between the Montescos and the Capuletas, the young couple defy the enmity between their families and the prejudices of their community—only to discover that love is the true universal language. This dynamic 90-minute bilingual adaptation from Karen Zacarías and Godinez is performed in both English and Spanish with projected translation. A Havana native, Godinez is a co-founder of Teatro Vista and the Sabl Resident Director at Goodman Theatre, where he most recently directed Inherit the Wind, Fannie, and American Mariachi. He returns to Chicago Shakespeare, where he first appeared thirty-seven years ago in Barbara Gaines ' Cymbeline in 1989, and went on to perform in ten productions as well as to direct 2022's highly acclaimed Measure for Measure.

Director Henry Godinez shared, “My favorite old t-shirt, which I've proudly worn to tatters, is from NYC's Shakespeare in the Park with the words ‘SHAKESPEARE PARA TODOS' emblazoned on the front. I'm sure at some point I wore that shirt to Chicago Shakespeare Theater 18 years ago when Karen Zacarías and I were first developing this bilingual adaptation of Romeo and Juliet. Now, at a time when the Latiné community of Chicago has been horribly villainized and persecuted, made to feel like this country was not our home, the opportunity to present this Romeo y Julieta at one of the great cultural institutions in the heart of our city is a tremendous source of pride and validation. It shows the universality of the greatest writer—and perhaps the greatest story ever written—in the English language. It proves, like my tattered t-shirt says, that ‘SHAKESPEARE IS FOR EVERYONE!'”

The Tony Award-winning phenomenon Illinoise (February 9–March 14, 2027 | The Yard) returns to where it all began. Based on Sufjan Stevens ' landmark album Illinois, this “mysterious, deeply moving and unforgettable dance-musical” (The New York Times) is directed and choreographed by Tony winner Justin Peck (New York City Ballet, Steven Spielberg 's West Side Story). Peck partners with Pulitzer Prize-winning playwright Jackie Sibblies Drury to tell a hauntingly beautiful original story through live music, dance, and theater. After a sold-out world-premiere at Chicago Shakespeare in 2024, Illinoise took Broadway by storm. Now, it returns to its spiritual home at CST.

Director Justin Peck shared, “It is incredibly meaningful to bring Illinoise back as part of CST's 40th Anniversary Season. This show has always been about memory, senses, and the quiet poetry of human connection—ideas that feel deeply aligned with a theater reflecting on its own legacy. At the same time, returning to CST with Illinoise feels less like a revisit and more like a continuation shaped by the artists, audiences, and spirit that make Chicago such a vital creative home. The icing-on-the-cake will be hearing Sufjan Stevens ' hit song 'Chicago' ring out within the very city that inspired it."

Next in The Yard is the hilarious whodunnit Reunion in Bartersville (April 11–May 9, 2027 | The Yard). The surviving members of the Bartersville High class of 1933 gather in their small Texas hometown to celebrate their 50th reunion. Over punch bowls and sandwich platters, a decades-old murder case is thrown wide open when the septuagenarians are confronted by a ghost from their past and they must all face their own scandalous secrets. This irreverent comedy will have audiences dying of laughter. Written by award-winning playwright Celeste Bedford Walker, this quick-witted comedy first premiered at the Billie Holiday Theatre in Brooklyn in 1987. Now, it finds new life in Ch

_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/chicago/article/ILLINOISE-And-More-Set-for-Chicago-Shakespeare-Theater-40th-Anniversary-Season-Lineup-20260515)._