Chicago Theatre & Arts Scene: Must-See Winter Performances

Chicago is home to a legendary theater and arts scene that few American cities can rival. From Broadway shows at the grand stages of the Chicago Loop to improv productions crafted by hard-working local acting troupes in hole-in-the-wall theaters, Chicago lives and breathes the performing arts. Our real estate agents are excited to share some of the shows they're most looking forward to in early 2026. 

Upcoming Theater Events in Chicagoland

Patrons of the theater should mark their calendars for these exciting upcoming productions in January and February. This list includes shows that are part of the venerated Chicago Theatre Week. 

Holiday at Goodman's Albert Theatre - Chicago, IL

Address: 170 N. Dearborn St., Chicago, IL 60601

A 1920s romantic comedy that inspired the beloved film starring Cary Grant and Katharine Hepburn, a new adaptation of Holiday will run from January 31 to March 1, 2026. This fresh take on Philip Barry's classic work is presented by Tony Award winner Richard Greenberg and will be held on the grand main stage at the 850-seat Albert Theater in the Chicago Loop. 

Prospera at Theatre Wit - Chicago, IL

Address: 1229 W. Belmont Ave., Chicago, IL 60657

A new sci-fi retelling of Shakespeare's The Tempest, Prospera made its world debut at Chicago's Theatre Wit and will run through February 8. Produced by the visiting Otherworld Theatre Company, the play promises a fun and exciting experience at this intimate 294-seat venue. 

The Enormous Crocodile at the Fine Arts Building - Chicago, IL

Address: 410 S. Michigan Ave., Chicago, IL 60605

From January 29 to February 21, audiences will be treated to a fun and exciting musical adaptation of Roald Dahl's The Enormous Crocodile. Featuring music by Ahmed Abdullahi Gallab and lyrics by Suhayla El-Bushra, the production showcases astonishing puppetry and costume design to thrill theatergoers of all ages. The musical will take place at the Fine Arts Building across from Grant Park, home to the Studebaker Theater and a haven for Chicago artists since 1898. 

The Dance of Death at the Steppenwolf Theatre - Chicago, IL

Address: 1650 N. Halsted St., Chicago, IL 60614

A fixture of Chicago's theater scene, the Steppenwolf Theatre Company has been putting on legendary performances in the Lincoln Park neighborhood since 1974. As part of the theatre's 50th anniversary season, The Dance of Death will be running from January 29 to March 22. This new take on August Strindberg's wicked tale of marital deceit and sabotage is directed by ensemble member Yasen Peyankov.

Stereophonic at CIBC Theatre - Chicago, IL

Address: 18 W. Monroe St., Chicago, IL 60603

The most Tony-nominated play of all time, Stereophonic, arrives at Chicago's CIBC Theatre on January 27, where it will run for sixteen performances through February 8. It's the story of an up-and-coming rock band in 1976, and the pressures that could either spark their creative breakthrough or lead to their breakup. This acclaimed touring production is presented by Broadway In Chicago and features original songs by Grammy Award-winner Will Butler.

Romeo & Juliet at Drunk Shakespeare - Chicago, IL

Address:182 N. Wabash Ave., Chicago, IL 60601

Held in a speakeasy-style Lion Theatre in the Chicago Loop, The Drunk Shakespeare Society stages the Bard's classic works with a twist. Before each performance, one member of the troupe downs five shots of whiskey, and hilarity and mayhem ensue. Join the crew as they attempt to get through Romeo and Juliet each night starting February 4.

Contact us today to learn more about life in Chicagoland. It's a city with an unrivaled arts culture, and a beautiful place to call home if you love the theater.