Chicago’s theater scene is popping this fall, which is why we narrowed down some of the plays and musicals we’re most looking forward to seeing.
Most-Anticipated Return: ‘Ain’t Too Proud — The Life and Times of The Temptations’
📍 CIBC Theatre in the Loop
🗓️ Sept. 24–29
The hit musical will have you dancing and singing along as you watch how the Detroit group reached the Rock & Roll Hall of Fame.
- 🥈 Runner-up: “Spider-Man: Into the Spider-Verse” at Cadillac Palace Theatre
Best for Being Transported to the South: ‘East Texas Hot Links’
📍 Court Theatre in Hyde Park
🗓️ Through Sept. 29
A mysterious omen disrupts a cafe that has become a haven for regulars in East Texas during the Jim Crow era. Playwright Eugene Lee won a Pulitzer for his play.
- 🥈 Runner-up: “Beneath the Willow Tree” at The Den Theatre
Best for Shakespeareans: ‘Henry V’
📍Chicago Shakespeare Theater at Navy Pier
🗓️ Through Oct. 6
Chock-full of some of Shakespeare’s most famous speeches, “Henry V” follows a young king’s decision to invade France and start war.
- 🥈 Runner-up: “Macbeth” at The Windy City Playhouse
- 🥉 Runner-up: “A Midsummer’s Night Dream” at The Edge Theater
Catch the Founding Fathers in the burbs this fall in “1776.” (Richard Hartog / Los Angeles Times / Getty)
Best ‘Hamilton’ Dupe: ‘1776’
📍 Marriott Theatre in Lincolnshire
🗓️ Through Oct. 13
Head to the north burbs to watch the Founding Fathers try to craft the Declaration of Independence in this show that premiered on Broadway 55 years ago.
Best for Your Inner Theater Kid: ‘Noises Off’
📍 Steppenwolf Theatre in Lincoln Park
🗓️ Through Oct. 27
Theater kids everywhere know how hard it is to put on a show — and all that can go wrong backstage. That’s why this play about a play has been a classic for years and been done at high schools (including mine).
- 🥈 Runner-up: “Into the Woods” at Chopin Theatre
Best Chicago Story: ‘Chicago Lore(s)’
📍 UrbanTheater Company in West Town
🗓️ Sept. 27–Oct. 27
This play follows the life of a co-founder of the Young Lords — including how the Puerto Rican gang created in the ‘60s became a powerful political organization in Chicago.
- 🥈 Runner-up: “Royko: The Toughest Man in Chicago” at Chopin Theatre
Best for Halloween: ‘Dracula’
📍 Brightside Theatre in Naperville
🗓️ Oct. 18–Nov. 3
Forget “Twilight” and “Vampire Diaries” — see the most famous vampire’s story told out in the west burbs 🧛
- 🥈 Runner-up: “The Addams Family” at Beverly Theatre Guild
Best for Kids: ‘Milo Imagines the World’
📍 Chicago Children’s Theatre in West Loop
🗓️ Oct. 12–Nov. 10
The musical adaptation of Matt de la Peña’s book will follow Milo and his colorful imagination as he learns that you can’t judge a book by its cover.
- 🥈 Runner-up: “Harry Potter & the Cursed Child” at Nederlander Theatre
- 🥉 Runner-up: “Dog Man: The Musical” at Fine Arts Building
“Port of Entry” is one of the shows at the Destinos Festival. (Eric Strom, Sarah Joyce / GlitterGuts)
Best Festival: Destinos
📍 Citywide
🗓️ Sept. 30–Nov. 17
The annual fest showcases Latinx theater from Chicago and across the world. Productions will be in Chicago Lawn, Belmont Cragin, and more.
