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Upcoming Chicago Events
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Music & Comedy
Music & Comedy, Theatre & Performing Arts
420 Shakespeare
4 professional actors meet to perform a Shakespeare play… but only after one of them takes at least 20mg of you know what, leading to…
Music & Comedy
LaTrez Anderson at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry PLEASE NOTE: This is a special…
Music & Comedy
The Regulars
A cult favorite candle-lit comedy show soirée! Doors: 8:30 Start: 9:00 SHOW: Enjoy a piece of news roundup in the style of “Weekend Update” that…
Music & Comedy, Theatre & Performing Arts
Voila: The Improvised Musical
iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…
Music & Comedy, Theatre & Performing Arts
Hitch*Cocktails
A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…
Music & Comedy
Laughter Hours: Late Night Jazzy-Themed Comedy Show
A late-night comedy showcase with a jazzy, lounge vibe featuring a live jazz musician and Chicago’s best comedians This is a showcase featuring some of…
Music & Comedy
Stargazers Adventure Club
Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…
Music & Comedy
Sueños Music Festival 2026
The Sueños Music Festival celebrates its fifth anniversary in Grant Park, Chicago, on Saturday, May 23, and Sunday, May 24, 2026. This Memorial Day weekend…
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
Music & Comedy
Hecklers’ Happy Hour Comedy Show
Audiences can unleash their inner “heckler” against some of Chicago’s funniest comics in this chaotic standup showcase Hecklers’ Happy Hour aims to give audiences a…
Music & Comedy, Theatre & Performing Arts
Dinner Detective Murder Mystery Show
The Dinner Detective is an interactive true crime murder mystery show set in the present day and based on real cold cases. Feast on a…
Music & Comedy
Slide Away
The Slide Away 2026 festival will take place in Chicago over two nights, Friday, May 22, and Saturday, May 23, 2026. The festival features a…
Music & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Music & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Music & Comedy, Theatre & Performing Arts
Improvised Jane Austen
Improvised Jane Austen Improvised Jane Austen continues its entirely improvised tales of love and laughter. Audiences will enjoy an evening with wit and heart in…
Music & Comedy
Here for a Fun Time!: A Bubblingly Fun Chicago Comedy Showcase
Here for a Fun Time! is a monthly comedy variety show that features Chicago’s best stand ups, character comedians, drag stars, and more! There’s fun…
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
Music & Comedy
Secret Sketch Show
Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…
Music & Comedy
Prime Time – Chicago’s hottest comedy showcase
If you like, innovative, smart and FUNNY comedy this is the show for you! It has been scientifically proven that 9 o’clock on a Saturday…
Music & Comedy, Theatre & Performing Arts
Best Of Annoyance Sketch
Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…
Music & Comedy
Chicago Comedy Hour
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
Music & Comedy
Sueños Music Festival 2026
The Sueños Music Festival celebrates its fifth anniversary in Grant Park, Chicago, on Saturday, May 23, and Sunday, May 24, 2026. This Memorial Day weekend…
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
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