We know The Windy City is famous for tall skyscrapers and deep-dish pizza. But there is also so much exciting artistic energy in Chicago. Sitting on the banks of the great Lake Michigan, Chicago is the place to be for enjoying the latest Broadway hits, jazz, ballet, speakeasies, and more.
There’s nothing like Chicago theatre. If you love a good show, tasty food, and excellent entertainment – Chicago is the place to be. Use our guide to the city’s arts scene, so you don’t miss a beat on your next trip.
Whether you want to catch an award-winning musical or opt for a more intimate theatre experience, we’re sharing the best of Chicago’s vibrant theater district.
James M. Nederlander Theatre – Since 1926, the James M. Nederlander Theatre (originally named the Oriental Theatre) has been entertaining thousands in the grandiose 2,253-seat theater in a renovated historical cinema. Be sure to soak in the stunning architecture of this Chicago landmark while you’re there!
Cadillac Palace Theatre – The venue is operated by Broadway In Chicago. The theatre has been the home to pre-Broadway hits, including “The Producers—The New Mel Brooks Musical” and “Mamma Mia!” in 2001.
(photo credit: Chicago Transit Guide)
Tip* The Cadillac Palace Theater, James M. Nederlander Theatre, and the CIBC Theatre host behind-the-scenes tours where you can get an intimate look at the city’s most historic theatres.
The Top Speakeasies in Chicago
During Prohibition, Chicago speakeasies popped up to quench the thirst of locals and mobsters alike. Often tucked below restaurants or hidden in a hotel lounge, Chicago still has plenty of speakeasies where you can sip on an expertly crafted cocktail in one of these secret watering holes.
The Violet Hour – Rooted in pre-prohibition style libations, The Violet Hour is known for serving artisanal cocktails in the heart of Wicker Park. Once inside, you’ll have to abide by the “house rules,” which prohibit cell phone use, baseball hats, and reservations. Contraband includes Jager bombs, light beer, Grey Goose, and Cosmopolitans, but don’t worry about the Cosmos; the crew behind the bar will whip you up a cocktail that would make Carrie Bradshaw quiver.
(photo credit: Imbibe Magazine)
The Drifter – You’ll find this authentic 20s-era speakeasy in the basement of the Green Door Tavern. The Drifter is a craft cocktail bar with nightly live entertainment located in Chicago’s oldest bar. When you walk in, you’re stepping on the same floor where drifters have passed through for over a century. The drinks change every day, and the cocktails are just as quirky as the old-school entertainers.
Chicago’s Best Jazz Clubs
If there’s anything you can count on when you visit Chicago, it’s that ultra-crispy pizza crust is a no-go, the Willis Tower will forever remain the ‘Sears Tower’ in local’s minds, and the jazz scene is popping.
(photo credit: See Chicago Dance)
Classical Music in The Windy City
Symphony Center – If you’re a classical music fan, no trip to Chicago will be complete without a visit to Symphony Center to see (and hear) the acclaimed Chicago Symphony Orchestra. Symphony Center was founded in 1891, and the current music director Riccardo Muti has proven to be one of the best.
(photo credit: WTTW News)
Tip* Muti will conclude his directorship of the orchestra at the close of the 2021-2022 season. So get your tickets now, so you don’t miss out!
The Ravinia Festival – Hosted each summer in Ravinia Park, the Ravinia Festival is the oldest outdoor music festival in the United States! Every year from June to September, the festival hosts symphony, jazz, folk, rock, and opera artists.
Acclaimed Ballet in Chicago
When we think of ballet in Chicago, The Joffrey Ballet Dance Company immediately comes to mind.
The Joffrey Ballet – If you’re a dance fan, The Joffrey Ballet is a world-class ballet company presenting classic, cutting-edge, and truly breathtaking performances. The Joffrey regularly performs classical ballets, including Romeo & Juliet, along with modern dance pieces. You can catch the gorgeous dancers in The Joffrey Ballet at the historic Auditorium Theatre in Chicago’s Loop.
Don’t miss out on Joffrey’s annual Nutcracker performance during the holiday season!
Opera involves every aspect of the performing arts. If you’re already a fan, you’ll know a well-performed opera is a treat for the eye and ears. However, when it comes to opera in Chicago, our minds immediately travel to The Lyric Opera House to escape into another world.
The Lyric Opera House – The Lyric Opera House is a well-known opera company famous for its lavish performances in the massive Art Deco Civic Opera House. The 2021/2022 Season is awe-inspiring with Giuseppe Verdi’s Macbeth, Mozart’s The Magic Flute, and so much more.
(photo credit: Timeout)
The Best Way to Get Around Chicago
Chicago Public Transportation (specifically the L train) is easy to navigate, fast, and cost-effective. Cut down on transportation time and make the most of your time. If you have a show at The Lyric at night and a tour of the James M. Nederlander Theatre during the day, you’ll want to take public transportation, so you don’t miss any of the fun.
And there you have it—our guide to the arts in Chicago. Chicago is internationally celebrated for its performing arts scene. There’s so much creativity and culture to discover in this city. Explore what The Windy City has to offer this season.