From SIX to Amadeus, here are the ten productions worth stepping into this season.
Chicago’s winter theatre season delivers a mix of powerhouse musicals, holiday favorites, bold stage drama and family-friendly productions. Broadway In Chicago anchors the lineup with nationally touring spectacles, while Steppenwolf, Goodman, Joffrey, and Chicago’s independent stages round out a diverse cultural calendar. Whether you lean toward big-stage music or intimate character work, these ten productions define the season.
1. SIX — CIBC Theatre (Broadway in Chicago)
December 2 – 14, 2026
SIX opens the list with a vibrant, pop-concert-style retelling of the wives of Henry VIII. The musical’s humor, power vocals and fast pacing make it one of the most energetic winter titles available. Each queen commands the stage with charisma and rhythm, inviting the audience into a modern reinterpretation of history. This is a top pick for winter theatre-goers looking for electricity over tradition.
2. A Magical Cirque Christmas — CIBC Theatre (Broadway in Chicago)
November 25–30, 2025
A holiday spectacular blending acrobatics, music and theatrical play. Designed for families and audiences who enjoy visual entertainment, this show delivers festive energy with circus-style movement and bright seasonal atmosphere. It’s short-run programming with strong appeal — a reliable go-to for a holiday-week outing.
3. The Phantom of the Opera — Cadillac Palace Theatre (Broadway in Chicago)
December 11, 2025 – February 1, 2026
The Phantom returns as a winter mainstage event built on sweeping score, romance and gothic grandeur. The production remains one of theatre’s most recognizable works and a definitive cold-season ticket for Chicago audiences. Delivered with full orchestration and dramatic scale, it stands as a marquee Broadway In Chicago experience.
4. Amadeus — Steppenwolf Theatre Company
November 6, 2025 – January 4, 2026
Steppenwolf enters the winter slate with a character-driven drama built on ego, genius and legacy. Amadeus examines jealousy and brilliance through tense dialogue and ensemble performance. Audiences wanting something powerful, reflective and grounded in acting craft will find it here. A standout non-musical offering with emotional gravity.
5. The Nutcracker — Joffrey Ballet at Lyric Opera House
December 5 – 28, 2025
A Chicago winter tradition featuring lush ballet, Tchaikovsky’s score and visual storytelling. Families, young viewers and longtime patrons return yearly to immerse themselves in the production’s magic. The Nutcracker remains a seasonal anchor rooted in beauty, movement and orchestral depth.
6. A Christmas Carol — Goodman Theatre
November–December 2025
Goodman Theatre’s annual production continues to define Chicago’s holiday theatre identity. Warm, emotional and rooted in story rather than spectacle, this staging delivers heart and generational familiarity. It is one of the most dependable and tradition-rich winter tickets in the city.
7. Mrs. Claus! A Holiday Musical — Beverly Arts Center
December 3 – 23, 2025
Colorful, musical and written for young audiences, this production brings Mrs. Claus and the elves into the spotlight. The show is upbeat, cheerful and ideal for families, school groups and early-theatre introductions. A light and accessible seasonal selection.
8. Rudolph Runs Wild — The Second City
November 28 – December 31, 2025
A comedic holiday show built on improv, music and audience interaction. Designed for laughter and looseness rather than structured story, it provides a holiday experience without sentiment or tradition at the center. Perfect for adults and families wanting a less-formal evening.
9. It’s a Wonderful Life: Live in Chicago! — American Blues Theater
November 21 –December 28, 2025
A radio-theatre reinterpretation of the classic story, complete with Foley sound, live delivery and a nostalgic set. It offers warmth, humanity and familiar storytelling without excess. One of the most heartfelt winter experiences available.
10. Who’s Holiday! — Theater Wit
November 28 – December 28, 2025
A sharp, comedic, adult-leaning holiday play following an older Cindy Lou Who navigating life after Whoville. Irreverent, bold and funny, this production adds edge and humor to the winter lineup for audiences who want something modern and unexpected.