Top Chicago Shows & Performances

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Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

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The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

4.0

(56)

from $32

Likely to Sell Out

Sit back and take in some magic—and enjoy a one-of-a-kind night on the town—during this engaging Chicago show. Show up a few minutes before curtain time to get the best possible seat and start sipping the drinks you brought. Cups and bottle openers are available for your use. Buying your tickets in advance means less waiting for entry; you'll be sure to get the day and time you that fits your schedule.

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Trickery Chicago Magic Show

1 to 2 hours

4.9

(108)

from $41

Nitti’s Supper Club: Chicago Mobster Speakeasy Dinner Show

Step inside landmark building of Harry Caray's Italian Steakhouse in River North, once owned by infamous Chicago mobster Frank Nitti, and travel back in time for dinner and a show based on the real-life murder of Eddie O'Hare. This irreverent comedy features an ensemble cast of characters, many of whom walked the very halls of 33 W. Kinzie back when Nitti called it home. The immersive experience invites you to step into the role of partygoer at Frank Nitti's birthday, and delve into the unsolved murder of Edward J. "Easy Eddie" O'Hare -- Al Capone's lawyer and father of war hero Butch O'Hare for whom the airport is named. The crime was never solved, but suspects included Frank Nitti, his wife Annette, Al Capone and several others. Can you crack the case? The interactive show is filled with historical anecdotes, laughs, audience interaction and toe-tapping musical productions.

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Nitti’s Supper Club: Chicago Mobster Speakeasy Dinner Show

3 hoursFree Cancellation

5.0

from $88

Sip Happens: Chicago Loop Prohibition Tour

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like Al Capone. This evening tour blends fascinating stories of gangsters and bootleggers with Chicago's vibrant cocktail and beer scene, making it an ideal experience for history lovers and cocktail enthusiasts alike. - Visit intriguing speakeasy-style venues and secret bars in Chicago's Loop - Discover the rich history of Prohibition and its impact on the city - Optional purchase of drinks and food at most stops, with recommendations provided - Perfect for history buffs and those seeking a unique night out in Chicago

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Sip Happens: Chicago Loop Prohibition Tour

1 hour 30 minutes to 2 hoursFree Cancellation

5.0

from $5

Drunk Shakespeare Ticket – Chicago

1 hour 30 minutesFree Cancellation

4.6

(159)

from $29

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this 2-hour experience begins on Lake Michigan, sails through the locks, and navigates the Chicago River, providing breathtaking views and delightful sunsets. On Thursdays, a representative from Phase Three Brewing will be onboard to share insights about their innovative ales and lagers, enhancing your tasting experience. On Fridays, we showcase live music. This cruise is exclusively for adults 21 and older, making it the perfect outing for beer enthusiasts looking to unwind in a vibrant setting. - Enjoy a 2-hour sunset cruise - Cruise through Lake Michigan and downtown Chicago's iconic skyline - Exclusively for adults 21 and over, ensuring a mature atmosphere

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Happy Hour Fireboat Cruise

2 hoursFree Cancellation

5.0

(1)

from $80

Per group

Special Offer

Experience Chicago at its most magical—and admire views that few other visitors get to see—on this evening Segway tour. Visit popular Grant Park and see Buckingham Fountain’s summertime light show, with an illuminated Windy City skyline as the perfect backdrop. Then, glide along the lakefront, and admire Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included.

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Chicago Pier Fireworks Segway Tour

2 hoursFree Cancellation

Come see Chicago's hottest up-and-coming burlesque stars! Experience the next generation of spectacle at Rising Stars, an alluring burlesque and variety revue that honors the Windy City's storied legacy of live entertainment. This high-energy showcase brings together the city's most captivating emerging burlesque dancers and variety entertainment for a night full of fun, whimsy, humor, and seduction. Whether you're a long-time fan of burlesque or a curious newcomer, we invite you to come enjoy Stars & Garters' intimate venue, world-class cocktails, and unforgettable performance artists. Every Rising Stars show features a unique roster of talent, so there's reason to come back again and again. (Follow @starsandgarterstheater on instagram to see when your favorite performers are scheduled for a show.)

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Rising Stars Burlesque Revue Tickets in Chicago

2 to 3 hoursFree Cancellation

5.0

from $30

Peep Show is Chicago's finest burlesque and comedy revue! In 90 minutes, each show features a rotating cast of up to 4 dancers, performing original striptease dances for our audiences! We also add hilarious comedians, mystifying magicians, risque drag performers and our own brand of fantastic hosts to engage in heavy audience interraction! We're perfect for date night, bachelor or bachelorette parties or for adventurous adults looking for a wild night out in Chicago!

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Burlesque Peep Show Ticket in Chicago

2 hoursFree Cancellation

4.8

(9)

from $32

The Infinite Wrench: Experimental theater in Chicago

1 hour 20 minutesFree Cancellation

4.5

from $20

Chicago Local Fashion Designers Shopping Tour with a Stylist

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and take a figurative soft tour outside your comfort zone as your stylist pulls pieces for you to explore and try. Think of it as a mini style consultation followed by recommendations and a hands-on practice session during the shopping tour where you can ask any fashion and style-related questions. Throughout your shopping circuit and neighborhood's discovery, listen to fashion stories as told by your fashion savvy guide, and get a unique insight into the industry. Prior to your shopping tour, you will be sent a little shopping form to help personalize your experience. And following your fashion escapade, you will be sent a personal style summary of recommendations received by your stylist as well as some tour souvenir photos.

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Chicago Local Fashion Designers Shopping Tour with a Stylist

3 hours

from $148

Price varies by group size

Top Attractions in Chicago

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There is something for everyone among Chicago shows and performances, whether intimate magic acts and burlesque revues, or interactive murder mystery dinners and Shakespeare with a twist. Many venues offer BYOB options or full bar service, making it easy to grab a drink while you watch the action unfold. Book ahead to secure the best seats for your night out, whether you’re planning a date, celebrating with friends, or just looking for some grown-up fun in the Windy City.

Top Chicago Shows & Performances

11 results

Top Attractions in Chicago

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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