Upcoming Chicago Events
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Music & Comedy
Music & Comedy
iO Fest 2026
iO Fest 2026 — Chicago’s largest improv festival returns on July 23-26! Featuring over 135 acts and 11 headliners, including: Baby Wants Candy, Improvised Shakespeare…
Music & Comedy
Boleros de Noche Chicago September 25 at the Harris Theater
Boleros De Noche returns to the Windy City following a successful Chicago debut in 2025. Already a beloved tradition in Los Angeles, where the concert…
Music & Comedy
America: Songs and Stories of Protest and Freedom
2026 marks the 250th anniversary of the United States’ Declaration of Independence. America: Songs and Stories of Protest and Freedom is a multi-genre concert of…
Music & Comedy, Theatre & Performing Arts
“Dirty Money” – Dinner Detective Chicago
The Dinner Detective is an interactive true crime mystery show set in the present day and based on real cold cases. Feast on a fantastic…
Music & Comedy, Theatre & Performing Arts
Pandemonium, Please Hold
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
Music & Comedy
Houndmouth – The Lordy Tour
Houndmouth is performing at The Salt Shed in Chicago on Saturday, July 25, 2026.
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
Malik Bazille at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Malik Bazille headlines an evening of…
Music & Comedy, Theatre & Performing Arts
Reality Detox: The Improv Experience
Reality Detox: The Improv Experience is a high-energy night of improvisation from The Second City, with a few sketch surprises mixed in along the way. Built…
Music & Comedy, Theatre & Performing Arts
Hitch*Cocktails: Summer of Suspense
Hitch*Cocktails: The Improvised Thriller / Drinking Show brings audiences another SUMMER OF SUSPENSE! The long-running show kicks off its second special summer series with special…
Music & Comedy
Karol G – Viajando Por El Mundo Tropitour
Karol G is launching her “Viajando Por El Mundo Tropitour” global stadium tour in Chicago with two back-to-back nights at Soldier Field in July 2026.
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…
Festivals, Fairs & Special Events, Music & Comedy
Nelly at Brookfield Zoo Chicago
The ultimate summer evenings await at Roaring Nights, Brookfield Zoo Chicago’s premier summer concert series! Get ready to turn up the volume for unforgettable nights…
Music & Comedy, Theatre & Performing Arts
The Best Musical Ever!
Producers and creators of musical theater are consistently attempting to reinvent or discover the “new era” of musical theater… or whatever generates the most profit.…
Music & Comedy
Buddy Guy – Buddy Guy 90 Tour
Buddy Guy will celebrate his 90th birthday in his home city with a special performance at The Chicago Theatre on Saturday, July 25, 2026.
Music & Comedy
Majah Hype Live!
Majah Hype is performing at Park West in Chicago on Saturday, July 25, 2026.
Music & Comedy, Theatre & Performing Arts
Best of The Second City: Chicago-Style
The Best of The Second City: Chicago-Style is a fast-paced sketch and improv comedy revue from The Second City featuring classic scenes from its legendary…
Music & Comedy
Keyon Harrold Live
Keyon Harrold is a GRAMMY® nominated trumpeter, vocalist, composer, and producer whose music defies boundaries. A genre-fluid innovator, he blends jazz, hip-hop, R&B, blues, and…
Music & Comedy
St. Vincent Live In Concert
St. Vincent is scheduled to perform in Highland Park on Saturday, July 25, 2026, as part of the Ravinia Festival. This performance is a unique…
Music & Comedy
Benson Boone – Wanted Man Tour
Benson Boone is performing in the Chicago area on Saturday, July 25, 2026, at Allstate Arena in Rosemont, IL, as part of his Wanted Man…
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, 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
The Improvised Movie: Summer Blockbusters
Are you ready for a cinematic showdown where your favorite song lyrics inspire completely improvised, never-seen-before, and never-seen-again summer movies? Join us Saturdays in July…
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