This holiday season, one of Broadway’s most beloved musicals is headed to Skokie as Music Theater Works brings Annie to the George Van Dusen Theatre at the North Shore Center for the Performing Arts from December 18 through January 4, 2026. Presented by the long-standing North Shore company known for its lush, story-driven productions, this new staging offers Chicago-area audiences a warm, funny, and heartfelt celebration perfectly timed for families and theater lovers looking to wrap up the year with optimism and classic musical theater charm.

Annie presented by Music Theater Works at North Shore Center for the Performing Arts

Annie has been inspiring audiences for generations with the story of a fearless young girl who refuses to give up on the idea that brighter days are ahead. Set against the grit and glamour of New York City, the musical follows Annie’s journey from a rough-and-tumble orphanage to the home of billionaire Oliver “Daddy” Warbucks, where her courage and open-hearted belief in tomorrow change the lives of everyone around her. Featuring music by Charles Strouse, lyrics by Martin Charnin, and a book by Thomas Meehan, the show is packed with songs that have become part of the musical theatre canon, including “Tomorrow,” “NYC,” and “You’re Never Fully Dressed Without a Smile.” Its themes of resilience, generosity, and chosen family make it an especially fitting choice for the holiday season, when audiences come together to share stories that affirm hope.

Music Theater Works, a resident professional company founded in 1980 and now based at the North Shore Center, has built its reputation on honoring the great traditions of musical theatre while breathing fresh life into classic titles. Under the direction of Producing Artistic Director Kyle A. Dougan, this production of Annie is poised to continue that legacy, with choreography by Mollyanne Nunn and music direction by Michael McBride bringing energy, polish, and a sense of playful spectacle to the George Van Dusen Theatre. The intimacy and finely tuned acoustics of the North Shore Center create an ideal setting for audiences to experience both the show’s big ensemble numbers and its tender, character-driven moments.

Leading the company is Elin Joy Seiler as Annie, joined by Michael Metcalf as Oliver Warbucks, Sarah Smith as Miss Hannigan, Desiree Gonzalez as Grace Farrell, David Geinosky as Rooster Hannigan, and Emily Holland as Lily St. Regis, supported by a bustling ensemble of orphans, New Yorkers, and household staff played by performers including Brielle Horwitch, Larrah Lambo, Molly Dibble, Léa Juat, Catharina Araujo, Allison Rose Macknick, Bob Sanders, Callan Roberts, Peter Ruger, and many others. Rounding out the cast in scene-stealing fashion is Teddy as Sandy. Together, this ensemble brings humor, heart, and high-voltage musicality to a story that balances scrappy comedy with genuine emotional punch.

For families across Chicago and the North Shore, this Annie offers an ideal outing: a timeless story told with professional production values, live orchestration, and a cozy yet vibrant theatrical home in Skokie. For longtime fans, it is a chance to rediscover a favorite musical in a fresh staging; for young theatergoers, it may be the production that makes them fall in love with live performance for the first time. With performances scheduled across the holidays and into the new year, Music Theater Works’ Annie promises a feel-good experience that sends audiences back into winter with full hearts, humming “Tomorrow” and reminded that hope can turn any hard-knock year into something brighter.