February Heats Up With Drama, Music, and History on Chicago Stages

The lights dim at Timeline Theatre Company in Rogers Park, and suddenly the audience is transported to a cramped Kansas boarding house where loneliness hangs as thick as cigarette smoke. William Inge’s “Come Back, Little Sheba” opens February 7th, marking the first major revival of the Pulitzer Prize-winning drama in Chicago in over a decade.

Director Janet Louer has stripped away the typical 1950s suburban veneer to expose the raw desperation beneath Doc and Lola’s failing marriage. “Inge understood that the American Dream could be a prison,” Louer explains. “These characters are suffocating in their own lives, and that feeling resonates just as powerfully today.”

The production features Chicago theater veterans Janet Ulrich Brooks and Sean Fortunato as the troubled couple, their performances already generating buzz among early reviewers. Brooks transforms Lola from a stereotypical nagging housewife into a woman whose childlike optimism masks profound grief over her lost youth and stillborn child.

Meanwhile, across town at the Chicago Theatre District, February showcases the kind of diverse programming that makes the city’s Arts & Culture scene nationally recognized. Court Theatre opens “A.G. Gaston: American Entrepreneur” on February 14th, exploring the life of the Alabama businessman who became one of the wealthiest Black Americans of the 20th century while navigating the Jim Crow South.

Playwright Javon Johnson crafts Gaston’s story as both historical drama and contemporary meditation on wealth, power, and responsibility within Black communities. The production arrives as Chicago grapples with its own questions about economic development and racial equity, making Gaston’s choices—including his controversial cooperation with segregationist policies—particularly relevant.

“Gaston built an empire by playing within a rigged system,” says Court Theatre’s artistic director Charles Newell. “The question the play asks is whether that kind of pragmatism was survival or complicity.”

For those seeking lighter fare, Victory Gardens Theater offers “Songs for a New World” starting February 21st. Jason Robert Brown’s song cycle has become a favorite among Chicago’s musical theater community, and this production promises to showcase why local talent consistently punches above its weight class.

The show features four performers navigating Brown’s emotionally complex score, which jumps from a 1940s jazz club to a contemporary rooftop without traditional narrative structure. Director Erica Daniels has assembled a cast that includes rising star Maria Antoinette and veteran performer Kevin Michael Moore, creating what early rehearsal footage suggests will be a vocal powerhouse.

Chicago Shakespeare Theater rounds out the month with “The Tempest,” opening February 28th. Director Teller—half of the famous Penn & Teller magic duo—brings his background in illusion to Shakespeare’s tale of magic and revenge. The production promises elaborate stage magic that transforms the Navy Pier venue into Prospero’s enchanted island.

The decision to cast deaf actor Troy Kotsur as Prospero adds another layer to the production’s exploration of communication and power. Kotsur, fresh from his Academy Award win for “CODA,” uses American Sign Language alongside spoken dialogue to create what early previews describe as a mesmerizing performance.

Smaller venues are also stepping up their February game. The Den Theatre in Wicker Park presents “Pipeline” by Dominique Morisseau, examining how the school-to-prison pipeline affects one middle-class Black family. The production, directed by local favorite Gabrielle Randle-Bent, promises the kind of intimate, emotionally raw storytelling that smaller theaters do best.

Steppenwolf Theatre Company continues its season with “Mary Page Marlowe,” Tracy Letts’ ambitious drama that follows one woman through fragments of her life presented in non-chronological order. The ensemble piece showcases Steppenwolf’s signature style of fearless, physically committed performances.

What makes February particularly exciting is how these productions reflect Chicago’s ongoing evolution as a theater city. While New York dominates headlines and Los Angeles captures film attention, Chicago has quietly built a theater ecosystem that rivals both coasts. The city’s theaters consistently develop work that moves to Broadway, while nurturing artists who choose to stay and build careers locally.

This month’s offerings also highlight Chicago theater’s commitment to addressing contemporary issues through both classic and new works. Whether examining 1950s domestic despair, 20th-century Black entrepreneurship, or modern educational inequities, these productions use the stage to process the cultural moment.

The timing coincides with the Chicago Theatre’s ongoing centennial celebrations, creating a sense of both looking back at the city’s theatrical legacy and pushing forward into new artistic territory.

Ticket prices vary widely, from Timeline’s $35 student tickets to Chicago Shakespeare’s premium weekend performances at $89. Most venues offer rush tickets and discounted previews, making live theater accessible across income levels. Several theaters have also expanded their digital programming, offering post-show discussions and behind-the-scenes content that extends the theatrical experience.

For theater lovers, February presents the rare opportunity to see both emerging and established artists tackle material that ranges from intimate character studies to spectacular magical realism. Whether seeking the psychological complexity of “Come Back, Little Sheba” or the visual splendor of “The Tempest,” Chicago’s stages offer compelling reasons to bundle up and venture out into the February cold.

The month ahead proves once again that Chicago theater doesn’t just entertain—it challenges, provokes, and occasionally transforms both audiences and artists willing to take the risk.