We're working hard to keep our current and future guests safe. Please read our safety policies and procedures here:

~ Happenings ~

Chicago’s 2020 Theatrical Season

Written By: Jessie White

American actor and producer Michael Douglas once said, “Hollywood is hype. New York is talk. Chicago is work.” The hundreds of performers and thespians that have moved to the city with dreams of gracing the Chicago stages packed in their luggage are going to agree wholeheartedly. If you’re a fan of dinner and a show, you should really be checking out the restaurants in Chicago as the Windy City has performances for everyone. With comedy sets, pre-broadway previews, and national tours making annual rounds: Chicago is rich with artistic indulgences and some of the best performances you’ll see in your lifetime.

The Chicago theatre season is rare to disappoint, with a yearly blend of modern and classical works as well as diverse and alternative stories for audiences. Many shows that are destined for New York City’s Broadway first perform shows in Chicago such as Spamalot, Kinky Boots, Big Fish, The Producers, and more. Not only do the most successful stand up comedians make sure they perform in Chicago, but many of them began their careers in Chicago as well at The Second City, iO, or one of the thousand open mics all over the city.

So if you catch yourself in Chicago this year, check out what’s performing downtown or near your hotel. You’re guaranteed to find a show that you like, simply from the list of musicals that we chose to highlight below. Whether you’re a fan of musicals, improv, or crime dramas you are likely to leave any Chicago theatre happy.

Summer: The Donna Summers Musical

February 12th – 23rd

James Nederlander Theatre

Summer: The Donna Summers Musical tells the origin story of the Bostonian church gospel singer turned pop star sensation. With over 20 of Donna Summer’s best classics, Summer tells a story of battling obstacles and providing inspiration to those who have often felt silenced with a score that will have you playing Donna bops for weeks to come.

Perfect for: Donna Summer fans, Girls Night, Mom and Daughter Date

Purchase tickets here!

My Fair Lady

March 24th – April 12th

Cadillac Palace Theatre

My Fair Lady is the story of everyone’s favorite Cockney flower-seller, Eliza Doolittle as she and her linguist teacher attempt to give Eliza a complete character transformation. One of musical theatre’s most timeless stories with classics like “I Could Have Danced All Night” and “On the Street Where You Live”, you’ll want to see this story before it’s too late.

Perfect for: Lunch Date with Mom or Grandma

Purchase tickets here!

Once Upon a One More Time

April 14th – May 17th

James Nederlander Theatre

This is the Grimm’s Tales like you’ve never seen them before and oh baby, baby, you need to get ready for a “Circus” of a show. Once Upon a One More Time follows everyone’s favorite princess, Cinderella as she goes on a journey to find a new story to follow. The adventure she embarks on is a tale of independence, friendship, and love and it’s all told to the iconic bops of pop sensation Britney Spears. Chicago is “Lucky” to have this amazing show stop through town.

Perfect for: Britney Spears fans, Girls Night, Friendventure

Purchase tickets here!


May 19th – 24th

CIBC Theatre

Waitress tells the story of Jenna, a waitress and baker with her head in the clouds who dreams of finding a way out of her small town and turbulent marriage. With a score composed by 7-time Grammy nominated singer Sara Bareilles, Waitress has been a crowd favorite since it’s first tour in 2015.

Perfect for: Sara Bareilles fans, thespians, the whole family

Purchase tickets here!

Dear Evan Hansen

July 7th – September 27th

CIBC Theatre

Dear Evan Hansen has been a critically-acclaimed sensation since its release in 2016. Evan Hansen is a teenager with social anxiety disorder who struggles to make friends as he navigates the obstacles of high school. Dear Evan Hansen tells a heartbreaking story of love, listening, and finding a voice during a time in life when it’s easiest to feel small. Chicago is all the happier to have the amazing story come to the CIBC theatre this July.

Perfect for: Teens, Date Night, thespians.

Purchase tickets here!

The Devil Wears Prada

July 13th – August 15th

CIBC Theatre

If you are in any way a fan of the 2006 film of the same name, you may want to look into purchasing tickets for The Devil Wears Prada: A New Musical. Making its first rounds in the Windy City, this musical tells the story of a struggling writer in New York City who finds an unlikely home in the office of one of the most prestigious magazines in the country. With a score composed by the amazingly talented Elton John, this musical gives the story a much-needed makeover and a hilariously fun adaptation.

Perfect for: Meryl Streep fans, Lunch Date with Mom

Purchase tickets here!

Jesus Christ Superstar

August 11th – 23rd

Cadillac Palace Theatre

The iconic musical phenomenon that has captured hearts all over the nation, Jesus Christ Superstar will be celebrating its 50th anniversary with a revival like no other. This Andrew Lloyd Webber creation takes place during the last week of Jesus Christ’s life; telling stories to the sounds that defined a generation of the 1970’s. If you’ve never seen this show, you’ll want to make sure you catch it this time around! 

Perfect for: Rock Opera fans, Church Lunch Date

Purchase tickets here!

Moulin Rouge! The Musical

December 17th – January 21st, 2021

James Nederlander Theatre

If you are a fan of Baz Luhrmann’s landmark 2001 film, you better get yourself excited for all of the glitz, glamour, and spectacle of Moulin Rouge! The Musical. This musical adaptation of the fan-favorite tells the story of talent, truth, but more important than anything, love. This jukebox musical has everything from “Diamonds are a Girl’s Best Friend” to “Your Song” and has something for everyone to enjoy before they leave the theatre speechless.

Perfect for: Rock Opera fans, Date Night

Purchase tickets here!

 Need Hotel Accommodations?

The Majestic Hotel

Located in the heart of Wrigleyville, accessible via Red Line train

 The Willows Hotel

Located at the edge of Lakeview and Lincoln Park, accessible via Brown Line train

 The City Suites Hotel

In the heart of Boystown, accessible by the Red Line train

 The Ivy Hotel

Located near the Magnificent Mile in Chicago’s Loop

Like this article?

Share on facebook
Share on Facebook
Share on twitter
Share on Twitter
Share on linkedin
Share on Linkdin
Share on pinterest
Share on Pinterest