Best Chicago Plays Running in 2024 and 2025

The Hot Wing King by Katori Hall and directed by Lil-Anne Brown, this Pulitzer Prize winning play runs at the Writers Theatre in 2024. When it comes to wings, Cordell is king! Supported by his beau Dwayne and the best friends who serve as his fry crew, the group embarks on a fun night of pre-competition prep for Memphis’s Annual “Hot Wang Festival.” But when Dwayne’s troubled nephew unexpectedly needs a place to stay, it quickly becomes a recipe for disaster. TheaterMania called it a “charming new dramedy” and “a sensitive portrait of black masculinity.”

Running June 19 – July 21, 2024 at the Writers Theatre.

Little Bear Ridge Road, written by Samuel D. Hunter and directed by Joe Mantello, will star ensemble member Laurie Metcalf in a comic, cosmic and intimate world premiere. In the outer limits of rural Idaho, the last two members of the Fernsby family tree, an estranged aunt and nephew, reunite to sort the mess left behind after a troubled father's passing. They now face an uncomfortable and universal question: how do we deal with other people? And is connection more trouble than it’s worth? As their relationship begins anew, the two reluctant Fernsby's—separated by age and experience—​start to understand the joys and perils of letting someone else into your own story, even if only for a moment.

Running June 13 – August 4, 2024 at Steppenwolf Theatre Company in the Lincoln Park neighborhood.

Dontrell, Who Kissed the Sea, written by Nathan Alan Davis and directed by Ilesa Duncan, plays at Pegasus Theatre Chicago. Pegasus Theatre is pleased to produce Nathan Alan Davis’ Dontrell, Who Kissed The Sea. Blending poetry, humor, wordplay and ritual, Dontrell, Who Kissed the Sea is a  hero’s quest to explore the journey to redeem history’s misdeeds. Eighteen-year-old Dontrell Jones the Third decides his duty and destiny is to venture into the Atlantic Ocean in search of an ancestor lost during the Middle Passage. However, his family is not at all ready to abandon their prized son to the waters of a mysterious and haunting past. 

Dontrell, Who Kissed the Sea plays at Pegasus Theatre from July 11 to August 18, 2024.

Drunk Shakespeare: "Drink sir, is a great provoker..." Macbeth, Act 2, Scene 3

The stage is set in a hidden venue. Five professional actors meet as members of The Drunk Shakespeare Society. One of them has 5 shots of whiskey and then attempts to perform a major role in a Shakespearean play. Hilarity and mayhem ensue while the four sober actors try and keep the script on track. Every show is different depending on who is drinking... and what they're drinking! Craft cocktails are available for purchase throughout the show.

The Second City is an improvisational theater In Chicago famous for how many actors and comedians got their start on its stages. Tina Fey, Chris Farley, Amy Poehler, Bill Murray, Aidy Bryant, Jordan Peele, Gilda Radner, and many, many more have all played at The Second City. There is comedy on every single night – check out the official website to see what’s playing today.

Harry Potter and the Cursed Child, written by Jack Thorne and directed by John Tiffany, begins its National tour in Chicago in September 2024. It’s time to believe in magic again. When Harry Potter’s head-strong son Albus befriends the son of his fiercest rival, Draco Malfoy, it sparks an unbelievable new journey for them all—with the power to change the past and future forever. Prepare for a mind-blowing race through time, spectacular spells, and an epic battle, all brought to life with the most astonishing theatrical magic ever seen on stage.

Running September 10, 2024 – February 25, 2025 at the James M. Nederlander Theatre.

The Audience, written by Peter Morgan (known for The Crown on Netflix), plays at the Drury Lane Theatre. Peek behind closed doors of Buckingham Palace with The Audience, an intimate portrait of Queen Elizabeth II and the pivotal private audiences she held with her prime ministers. The Audience is an enthralling exploration of the delicate balance of power and unspoken rules of engagement that underscore these confidential meetings. Masterfully blending the personal and the political, The Audience gives an extraordinary glimpse into the woman behind the crown and the leaders she outlasted.

The Audience plays at the Drury Lane Theatre from August 28 to October 20, 2024.

Leroy and Lucy, written by Ngozi Anyanwu and directed by Awoye Timpo, runs at Steppenwolf’s Ensemble Theater and features ensemble member Jon Michael Hill. Two lost souls meet at a crossroads, in the dead of night, deep in the Mississippi of it all. With a yearning guitar between them, they tell secrets and conjure a sound once forgotten—a tune pitched with Leroy’s longing and the sweet purr of Lucy’s desires. In this sultry world premiere, a play with music from Ngozi Anyanwu, the Delta Blues fills the air, the future lies just down the road, and we are everywhere and nowhere all at once.

Running October 24 – December 15, 2024 at Steppenwolf Theatre Company.

Fool For Love, written by Sam Shepard and directed by Jeremy Herrin, runs at Steppenwolf’s Downstairs Theatre. In a sweltering motel room in the Mojave Desert, May and Eddie lick their wounds and get ready for another relentless round. This brawl is eternal and infernal. And the Old Man is always watching. Perhaps the sexiest, most haunting play of the 20th century, Fool for Love is a twisted and tequila-soaked love letter from Sam Shepard, one of the greatest American playwrights, indulging the need to get inside someone just to tear them apart. 

Running January 30 – March 16, 2025 at Steppenwolf Theatre Company.

The Book of Grace, written by Suzan-Lori Parks and directed by Steve H. Broadnax III, runs at Steppenwolf’s Ensemble Theatre and features ensemble member Glenn Davis.  Grace looks for the good in everything: in her husband’s rules, in the border he patrols, in the return of his estranged son. But a want for goodness cannot unwind the past, as this taut family reunion explodes in all directions. The Chicago premiere of Suzan Lori-Parks’ The Book of Grace is an incendiary family portrait from the Pulitzer Prize-winning writer of Topdog/Underdog. Witness this startling reminder that the search for common ground can be bloody and brutal, leaving casualties on every side of the divide.

Running March 27 – May 18, 2025 at Steppenwolf Theatre Company.

Noises Off, written by Michael Frayn and directed by Anna D. Shapiro, runs at Steppenwolf in a co-production with Geffen Playhouse. The cast and crew of Nothing On are scrambling to prepare for opening night, but despite their earnest efforts, the production is an absolute mess. Line flubs and lost props and missed cues, oh my! Can this beleaguered ensemble overcome egos and jealousies to pull the show together in time? Onstage antics collide with offstage foibles in Steppenwolf’s production of Noises Off, the classic comedy that writes an ingenious, slapstick and zany tribute to “theatre-people” everywhere. By the end of this dizzying play-within-a-play, you won’t know stage right from left.

Running September 12 – October 27, 2024 at Steppenwolf’s Downstairs Theater.

You Will Get Sick, written by Noah Diaz and directed by Audrey Francis, runs at Steppenwolf’s Downstairs Theater and features ensemble members Cliff Chamberlain, Amy Morton, and Namir Smallwood. A young man with a secret. An older woman who will listen. A predatory flock of birds. An upcoming audition for The Wizard of Oz. Welcome to You Will Get Sick, a wildly imaginative new play that traces the touching, hilarious, heartbreaking saga of one man’s illness and his unlikely caretaker’s pursuit of her dreams. Admired as “lively, surreal and surprising” by The New York Times, Noah Diaz’s Chicago debut is equal parts comedy, form-bending experiment and sober meditation on mortality. Renowned ensemble member Amy Morton (a Tony nominee for August: Osage County and Edward Albee’s Who’s Afraid of Virginia Woolf?) returns to the Steppenwolf stage for the first time in over a decade, making this season finale a must-see experience!

Running June 5 – July 13, 2025 at Steppenwolf Theatre’s Downstairs Theater.