7 Best Plays and Musicals in Chicago | Hotel EMC2

7 Best Plays and Musicals in Chicago

If you’re planning an upcoming trip to Chicago, then you probably have created a bucket list of things you want to do before you leave the Windy City. Since Chicago is known for its fantastic theater and arts scene, you’ve most likely included attending a show on your list. 

The city is filled with many different types of performances, including top Broadway musicals and plays. With the end of winter approaching and the arrival of spring, many new shows are coming to Chicago’s Theatre District. Since it might be hard to decide which performances in Chicago you’ll attend when you visit, here’s a list of the best plays and musicals that you won’t want to miss. 

Top plays

graveyard shift

“graveyard shift,” a play centered on the tense relationships between African Americans and police officers, is a fictional account based on an actual event. The main character of the play, Janelle, relocates from Illinois to Texas in order to give love a chance. Meanwhile, a small-town police officer wrestles with the harsh realities of change. When their worlds collide, both are forced to confront the consequences of an imbalance of power. 

This play is currently playing at the Goodman Theatre until March 8

What the Constitution Means to Me 

“What the Constitution Means to Me” is a boundary-breaking play that reflects on the impact of the Constitution and how it will affect the next generation of Americans. The tour stars Tony-nominated actress Maria Dizzia, from “Orange is the New Black,” and features original Broadway cast members Mike Iveson and Rosdely Ciprian. 

You can watch this play at Broadway Playhouse between March 4 and April 12.

Top musicals


Jane Austen’s beloved novel “Emma” is now a musical. Privileged, pampered, and preoccupied with romance, Emma Woodhouse indulges in her pastime of misguided matchmaking, but remains quite clueless when it comes to her own feelings—and a gentleman named Mr. Knightley. Lora Lee Gayer, a renowned Broadway actress, stars in this musical. 

Watch this performance at the Chicago Shakespeare Theater, now until March 15.

My Fair Lady

This classic musical tells the story of Eliza Doolittle, a young Cockney flower seller, and Henry Higgins, a linguistics professor who is determined to transform her into his idea of a “proper lady.” Buy tickets to see the astounding transformation of the main character into a fair lady.

You’ll be able to watch “My Fair Lady” at Cadillac Palace Theatre from March 24 to April 12.

Once Upon a One More Time 

Imagine a musical with a variety of fairytales and music by Britney Spears, and you’ve got “Once Upon a One More Time.” This play centers on a group of fairy tale princesses who gather for a book club where they read from “Grimm’s Fairy Tales.” What’s better than rewritten classic fairy tales and some of Britney Spears’ top hits.

Watch “Once Upon a One More Time” at the James M. Nederlander Theater from April 14 to May 17

The Office! A Musical Parody 

This musical is a treat for anybody who enjoys binge-watching “The Office” on Netflix. “The Office! A Musical Parody” combines the hit TV show, “The Office,” and musical parodies. The musical features songs like “Welcome to Scranton (The Electric City)” and “The Dundies.” 

“The Office! A Musical Parody” will be playing at the Broadway Playhouse from April 28 to May 17.


“Waitress” is a hit Broadway musical that features original music and lyrics from 7-time Grammy nominee Sara Bareilles, including hit songs like “Brave” and “Love Song.” The musical follows Jenna, a waitress and expert pie-maker, who dreams of a way out of her small town and rocky marriage. When a baking contest in a nearby county—and a satisfying encounter with someone new—show Jenna a chance at a fresh start, she must find the courage to seize it. 

“Waitress” will be playing at the CIBC Theatre from May 19 to 24.

Visiting Chicago

Choosing to visit Chicago in the springtime is a unique and thrilling experience. There’s truly something for everyone in Chicago, no matter what your interests are. You can choose to attend a show in Chicago’s Theatre District, shop on Michigan Avenue, visit Navy Pier, walk along the Chicago Riverwalk, take photos of Cloud Gate, and more. Your upcoming trip can be customized to fit your curiosities, with exciting performances, delicious foods, thrilling adventures, and spectacular sights. 

Need a place to stay when visiting Chicago? Book your reservation here.