ADIRONDACK CHAIR CIRCLE & More Lead Chicago's 2026 Holiday Theatre Shows

Adirondack Chair Circle

Steppenwolf's Ensemble Theater - Now through December 06, 2026

A gaggle of suburban moms, armed with pickleball paddles and hard kombucha, are ready to take on the school board in the fight of their lives: attempting to ban the controversial books available to their kids in the school library. But is this trusted inner circle all on the same page? A piercing world premiere from a Chicago playwright, Stephanie Alison Walker’s Adirondack Chair Circle exposes the hilarious hypocrisy of the causes we claim and the company we keep. And has a damn good time doing it.

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A Christmas Carol

Drury Lane Theatre - Now through December 27, 2026

Set in Victorian-era London, Charles Dickens’ A Christmas Carol tells the classic tale of Ebenezer Scrooge and the spirited ghosts that visit him one fateful Christmas Eve hoping to persuade him to change his miserly ways. Complete with falling snow and magical illusions, A Christmas Carol is a visually stunning experience and, at one hour long, perfect for children of all ages. Continue your tradition or start a new one by gathering the whole family for this truly memorable holiday classic.

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Jimmy Buffett’s Escape to Margaritaville

Music Theater Works - Now through November 1, 2026

Music Theater Works is proud to announce the cast and creative team for the third production of its 2026 season, Jimmy Buffett’s Escape to Margaritaville, in the North Theatre, at the North Shore Center for the Performing Arts in Skokie, 9501 Skokie Blvd., Skokie, October 8 - November 1. Escape to Margaritaville has a book by Greg Garcia and Mike O’Malley, with music and lyrics by Jimmy Buffett. Music Theater Works’ production is directed and choreographed by Brenda Didier with co-director Sarafina Vecchio and co-choreographer Clayton Cross and music directed by Linda Madonia.

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KING HEDLEY II

City Lit Theater - Now through November 29, 2026

Revisiting characters established in August Wilson’s SEVEN GUITARS, this play returns to Pittsburgh’s Hill District in 1985. King Hedley, a man recently released from prison, attempts to rebuild his life by selling stolen refrigerators so he can buy a video store. Despite decades of generational trauma, can King break free from the crippling socio-economic struggles that have held him down? Amid the realities of rampant crime and drug use in the neighborhood community, he tries to carve out his own destiny. 

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An Evening with Heather Headley

Mary B. Galvin Recital Hall - November 1, 2026 through November 1, 2026

Experience Tony Award and Grammy Award winner Heather Headley live in an intimate concert! One of Broadway’s most celebrated voices, Headley originated the role of Nala in The Lion King and won the Tony Award for her unforgettable performance in Aida. Don’t miss this rare opportunity to experience her powerhouse voice in the beautiful Mary B. Galvin Recital Hall overlooking Lake Michigan.

Your ticket includes a post-performance celebration featuring cocktails, hors d’oeuvres, and sweeping lakefront views.

Proceeds benefit Over The Rainbow Association and its mission to provide affordable, accessible housing for people with disabilities throughout Chicago and northern Illinois.

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Frozen the Broadway Musical

Marriott Theatre - November 4, 2026 through January 3, 2027

Marriott Theatre, Chicagoland’s longest-running musical theatre, concludes its 2026 mainstage season with Frozen the Broadway Musical, the internationally celebrated stage musical based on Disney’s Academy Award-winning animated film. Nominated for three Tony Awards, including Best Musical, Frozen features beloved songs by Kristen Anderson-Lopez and Robert Lopez from the film, along with new music written specifically for the stage. Previews begin November 4, with a press opening on November 11, and running through January 3. The production is directed by Ashley Rodbro (Broadway: Resident Director of Hamilton, Associate Director of Moulin Rouge! The Musical; Steppenwolf: The Movement You Need), choreographed by Katie Spelman (Broadway: The Notebook; Marriott Theatre: Come From Away, The Music Man), with music direction by Jeff Award winner Ryan T. Nelson. 

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Cut to the Chase

Lookingglass Studio Theatre - November 5, 2026 through November 15, 2026

A staple of Chicago theater for over two decades, CUT TO THE CHASE presents as one fun night of theater a number of new plays chosen from hundreds of submissions by writers from across the country. The plays are performed back-to-back, with the complete program running approximately 80 minutes. CUT TO THE CHASE is a perfect taste of dynamic theater in an intimate space. Ensemble member Annie Hogan will curate the festival, which will be directed and performed by ensemble members and other theatre artists. CUT TO THE CHASE will be performed for two weekends, from November 5 -15, at the Lookingglass Studio Theater, 163 E. Pearson at Michigan Avenue, on Chicago’s Magnificent Mile. Tickets are $25.00 plus fees and are available at https://www.theartistichome.org/cut-to-the-chase-2026-2027.

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Jersey Boys

CIBC Theatre - November 11, 2026 through November 22, 2026

The original Broadway sensation returns to the road! Celebrating 20 years – Jersey style!

They were just four guys from Jersey, until they sang their very first note. They had a sound nobody had ever heard… and the radio just couldn’t get enough of.But while their harmonies were perfect on stage, off stage it was a very different story — a story that has made them an international sensation all over again. The show features all their hits including “Sherry,” “Big Girls Don’t Cry,” “Oh What a Night,” “Walk Like a Man,” “Can’t Take My Eyes Off You,” “Beggin’” and “Working My Way Back to You.”

Go behind the music and inside the story of Frankie Valli and The Four Seasons in the Tony Award®-winning, original Broadway sensation, JERSEY BOYS. From the streets of New Jersey to the Rock and Roll Hall of Fame, this is the musical that’s too good to be true.

Advisories: Flashing probe lights, loud gunfire, theatrical haze, herbal cigarette smoke and authentic, profane Jersey vocabulary are special effects used in this production.

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A Christmas Carol

Paramount Theatre - November 11, 2026 through January 3, 2027

Paramount Theatre presents a world premiere reimagining of Charles Dickens' A Christmas Carol, adapted and directed by Trent Stork. This all-ages production brings a fresh take on the beloved holiday classic to downtown Aurora's historic Paramount Theatre. Running November 11, 2026 through January 3, 2027, it is the second production in Paramount's 15th Broadway Series.

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Irving Berlin's White Christmas

Deerfield Theater - November 13, 2026 through November 22, 2026

Deerfield Theater and the Deerfield Park District announce the cast and production team for their upcoming production of Irving Berlin’s White Christmas. Performances are at Caruso Auditorium, 1801 Montgomery Rd, Deerfield, IL 60015.

Evening performances are November 13, 14, 20, and 21 at 7:30pm, and matinees are November 14, 15, 21, and 22 at 1pm.

Producer Ryan Elliott has assembled an all-star production team led by director Ken Preuss, with music direction by Marty Karlin and choreography by Kristine Burdi-Stickney. With timeless songs, classic tap numbers, and plenty of holiday cheer, this production is the perfect way for the whole family to kick off the season.

Based on the beloved Paramount Pictures film, White Christmas follows Bob Wallace and Phil Davis, two World War II buddies turned song-and-dance stars, who follow a pair of singing sisters to a Vermont inn for the holidays. There they discover the struggling lodge belongs to their former commanding officer, General Henry Waverly. To save it, they set out to put on a show. With a score of Irving Berlin classics including “Blue Skies,” “Sisters,” “Count Your Blessings,” and the iconic title song, White Christmas is a heartwarming celebration of friendship, romance, and the magic of the holidays.

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Annie

Woodstock Opera House - November 13, 2026 through November 29, 2026

Set in Depression-era New York City, Annie follows a spirited young orphan determined to find the family she has always dreamed of. When billionaire Oliver Warbucks invites Annie into his home for the holidays, an unexpected bond forms that changes both of their lives. But with Miss Hannigan and her scheming accomplices looking for an opportunity of their own, Annie’s journey home won’t be easy. Featuring beloved songs including “Tomorrow,” “It’s the Hard Knock Life,” “Maybe,” and “You’re Never Fully Dressed Without a Smile,” Annie is a heartwarming celebration of hope, resilience, and finding family in unexpected places.

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SIX (Boleyn Tour)

Peoria Civic Center - November 17, 2026 through November 19, 2026

Divorced, beheaded, died, divorced, beheaded, survived. From Tudor Queens to Pop Princesses, in SIX the wives of Henry VIII take the mic to reclaim their identities out of the shadow of their infamous spouse-remixing five hundred years of historical heartbreak into a celebration of 21st century girl power. The female cast is backed by an all-female band, the "Ladies in Waiting."

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It’s A Wonderful Life: A Radio Play

Oil Lamp Theater - November 20, 2026 through December 27, 2026

Oil Lamp Theater is proud to announce the cast and creative team for its next production and the final production in its 2026 season, It’s A Wonderful Life: A Live Radio Play, November 20 - December 27, adapted by Joe Landry and directed by Becca Holloway at Oil Lamp Theater, 1723 Glenview Road. 

This heartwarming production is the perfect way to embrace the spirit of the Christmas season. Experience unmatched holiday cheer with Frank Capra's beloved classic, It's a Wonderful Life, reimagined as a captivating Live Radio Play, complete with foley sound effects and set in Oil Lamp Theater’s WBFR radio studio. Audiences are invited to journey to Bedford Falls, where George Bailey's troubles lead him to wish he was never born. Clarence, an angel sent to intervene, steps in to make his wishes come true and George quickly learns just how blessed he is and how many lives he has touched.

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