Best Chicago Plays Running During the 2025 Season

James and Lou move from Chicago to London to escape the past… but they soon discover that places aren’t haunted, people are. An original story set in the world of the terrifying Paranormal Activity film franchise, this thrilling new play from celebrated Chicago playwright Levi Holloway (Broadway’s Grey House) and Punchdrunk’s Felix Barrett (Sleep No More) with illusions by Tony Award winner Chris Fisher (Stranger Things: The First Shadow, Harry Potter & The Cursed Child) will haunt you long after you get home. 

Running through November 2, 2025 at Chicago Shakespeare Theater.

Meet Beatrice and Benedick: two ferociously independent individuals who have steadfastly avoided sharing their lives with anyone but themselves… until now. Despite their best efforts to remain single, falling for one another is inevitable in the wittiest and wildest of Shakespeare’s comedies. CST welcomes back acclaimed director Selina Cadell, whose ground-breaking Hamlet starring Eddie Izzard broke box office records at CST and in theaters around the world. Set against the backdrop of romantic Italy, it’s a warm-hearted ode to the power of love and the joy of partnership.

Running November 18 to December 21, 2025 at Chicago Shakespeare Theater.

After three tours in Afghanistan, Jess returns home to a changed world, and body. With dark humor and virtual reality therapy, she begins to rebuild her life one puzzle piece at a time, confronting scars both seen and unseen in this powerful story of how beauty endures beneath the surface.

Running through November 15, 2025 at Theater Wit.

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 Infinite Wrench is a chance to see thirty original plays in just one hour, written and performed by the Neo-Futurist Ensemble. Each play offers something different, be it funny, profound, elegant, disgusting, topical, irreverent, terrifying, or a song; all are truthful and tackle the here-and-now, inspired by the lived experiences of the performers. With new plays every week, THE INFINITE WRENCH is The Neo-Futurists’ ongoing and ever-changing attempt to shift the conventions of live performance and speak to those unreached or unmoved by traditional theater.

Running every Friday and Saturday at 10:30pm and Sundays at 7pm.

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.

If all things end, why begin at all? Intimately staged in the round, Wild Door Theater’s Smokefall is a new take on Noah Haidle's richly funny, deeply vulnerable, and audaciously theatrical play about family, legacy, and the courage it takes to face each new day.

Running November 10 to December 21, 2025 at Theater Wit.

Rediscover Dickens’ classic with an adaptation that “makes you believe kindness can win” (Chicago Tribune). Follow Ebenezer Scrooge, a businessman whose disdain for the holidays is transformed on Christmas Eve. Malkia Stampley takes the reins as director, with Christopher Donahue returning as Scrooge.

Running November 15 to December 31, 2025 at the Goodman Theatre.

In this turn-of-the-century Victorian mystery, strange things start to happen as the seemingly perfect marriage of Jack and Bella devolves into something sinister. Why is the attic door locked? Whose footsteps wander the halls at night? And is that light really flickering… or not? Bella’s reality is twisted into an indistinguishable tangle of truth, manipulation, and her husband’s intentions, where certainty is uncertain for characters and audience alike

Running November 28 to December 28, 2025 at Northlight Theatre.

Our holiday hit returns for the fifth year running — Cindy Lou Who, now 40, holds court from her trailer home, retelling the story of the sordid events after she met the Grinch in this adult romp!

Running November 28 to December 28, 2025 at Theater Wit.

Running at Steppenwolf, Amadeus is set in Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild child. The two artists begin a vicious and thrilling duet, a rivalry that will define their lives and their legacies for years to come. Winner of 5 Tonys and 8 Academy Awards, Amadeus is the ultimate ode to ambition and musical genius, a brilliant requiem for a villain in history—but a hero in his own story. Vi saluto!

Running November 6, 2025 to January 11, 2026 at Steppenwolf Theatre.