As the crisp winds of November usher in the holiday season, Chicago’s vibrant theater and performing arts scene is abuzz with a lineup of productions. From classic musicals to avant-garde operas and thought-provoking art exhibitions, there’s something for each type of traveler to enjoy in the Windy City this fall.

Broadway In Chicago

Broadway In Chicago has the following shows as part of its new season

• Company (playing October 31 – November 12, 2023, at the Broadway Playhouse Cadillac Palace Theatre), winner of 5 Tony Awards including Best Revival of a Musical, COMPANY features Sondheim’s award-winning songs You Could Drive a Person Crazy, The Ladies Who Lunch, Side by Side by Side, and the iconic Being Alive.
• Beetlejuice (playing November 7-19, 2023, at the Auditorium Theatre) Based on Tim Burton’s dearly beloved film, this musical tells the story of Lydia Deetz, a strange and unusual teenager whose whole life changes when she meets a recently deceased couple and a demon with a thing for stripes.
• BOOP! The Musical (playing November 19, 2023 – December 31, 2023, at the CIBC Theatre) – For almost a century, Betty Boop has won hearts and inspired fans around the world with her trademark looks, voice, and style. Now, in BOOP!, Betty’s dream of an ordinary day off from the super-celebrity in her black-and-white world leads to an extraordinary adventure of color, music, and love in New York City—one that reminds her and the world, “You are capable of amazing things.”
• The Wiz (a pre-Broadway Chicago premiere playing November 28 – December 10, 2023, at the Broadway Playhouse Cadillac Palace Theatre) – This twist on The Wizard of Oz changed the face of Broadway—from its iconic score packed with soul, gospel, rock, and finger-snapping 70s funk to its stirring tale of Dorothy’s journey to find her place in a contemporary world.

Chicago Opera Theater

Chicago Opera Theater will celebrate its 50th anniversary this season with the following productions:

• The Nose (December 8 and 10, 2023, at the Harris Theatre for Music and Dance) – Russian classic The Nose will receive its Chicago premiere this December. With music and libretto by Dimitri Shostakovich based on a short story by Nikolai Gogol, Shostakovich’s absurdist masterpiece follows a bureaucrat named Kovalyov who wakes up one morning to discover his nose has not only taken on a life of its own but is a high-ranking government official.

Chicago Shakespeare Theater

Chicago Shakespeare Theater has the following performances this season.

• Twelfth Night (October 25 – November 26, 2023) at the Courtyard Theater – Shakespeare’s cleverest comedy is brought to vibrant new life as director Tyrone Phillips reimagines Illyria in the Caribbean isles.
• Islander, a co-production from Scotland that is part of Chicago Shakespeare’s WorldStage Series—a landmark commitment to bring the world’s great theaters to Chicago and Chicago Shakespeare to the world, will play November 29 – December 17, 2023, upstairs at Chicago Shakespeare. Staged with a contemporary folk-inspired score and epic storytelling, two performers reveal a world of characters, live-mixing and layering their voices to create a dazzling, unexpected soundscape as dramatic as the Scottish coastline.

Congo Square Theatre

Congo Square Theatre has the following productions scheduled for this season.

• The Blackside: Season Four (October 13 – December 9, 2023) – Congo Square’s popular free online sketch comedy series, The Blackside (formerly Hit ‘em on the Blackside), returns for a fourth season this fall. Audiences can expect more of the witty, pitch-perfect, and timely humor that made sketches from the first three seasons like “Black History Game Show” and “Black Survivalist” so funny and poignant.

Chicago’s Deeply Rooted Dance Theater reimagines and diversifies the aesthetics of contemporary dance by uniting modern, classical, American, and African American traditions in dance and storytelling.

DePaul University School of Music welcomes Third Coast Percussion on December 5, 2023. For over fifteen years, the ensemble has created exciting and unexpected performances that constantly redefine the classical music experience. The concert features a new piece by Michael Burritt that was commissioned to celebrate the 400th anniversary of Zildjian cymbals.

Guarneri Hall has the following performances this season.

• Buster Keaton’s SHERLOCK JR. with original score by Stephen Prutsman (November 15, 2023) – Guarneri Hall will celebrate the legendary silent film star Buster Keaton with a multimedia program dedicated to his work. Pianist and composer Stephen Prutsman will be joined by violinist Steven Copes and members of NEXUS Chamber Music for a screening of Keaton’s classic Sherlock Jr. (1924), with live accompaniment of Prutsman’s original score.
• Alternate Realities: Bartók Quartet Cycle with The Borromeo Quartet (December 4-5, 2023) – Among the most influential achievements of Hungarian composer and ethnomusicologist Béla Bartók’s career are the six string quartets he wrote between 1908 and 1939. One of the earliest and most influential champions of bringing folk music into the concert hall, Bartók’s notoriously challenging quartets synthesize his myriad musical influences from folk songs to romanticism to serialism.
• The Daughter of the Regiment (November 4-25, 2023) – Lyric Opera of Chicago is delighted to bring this production of Donizetti’s The Daughter of the Regiment — bel canto opera’s equivalent of vintage champagne — to the city for the first time. Marie, the lovable, irrepressible spirited heroine — a foundling, raised by soldiers — loves handsome Tonio. Things get complicated when the Marquise carts her off to refine her with a “proper” education.
• Janáček’s Jenůfa (November 12-26, 2023) -Janáček’s Jenůfa is a dark and stunning masterpiece, both musically and dramatically. In this profoundly moving story, the Kostelnička secretly drowns her foster-daughter Jenůfa’s illegitimate child, hoping to save Jenůfa — and herself — from shame and humiliation. When the murder is discovered, the Kostelnička accepts the consequences, but Jenůfa ends the opera with hope for the future.

Wrightwood 659 presents Difference Machines: Technology and Identity in Contemporary Art (October 13 – December 16, 2023), addressing the complex relationship between the technologies we use and the identities we inhabit. This interactive ‘laboratory’ presents the work of seventeen contemporary artists who ask some of the most urgent questions we face today: How is technology changing the way we see ourselves, and each other? In what ways does it contribute to—or allow us to resist—prejudice and systemic forms of oppression? What role should it have in our lives and in our communities?