Upcoming Chicago Events
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Music & Comedy
Music & Comedy
The Fray & Dashboard Confessional – Summer of Light Tour
The Fray and Dashboard Confessional are scheduled to perform in Chicago on Saturday, August 29, 2026, which is the final stop of their “Summer of…
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
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
Kesha – The Freedom Tour
Kesha is scheduled to perform in Tinley Park on Saturday, August 29, 2026, as part of her “The Freedom Tour”. The tour supports her 2025…
Music & Comedy
Ray LaMontagne – Trouble 20th Anniversary Tour
Ray LaMontagne is scheduled to perform at the Ravinia Festival in Highland Park, IL, on Saturday, August 29, 2026. This concert is part of his…
Museums, Galleries & Exhibitions, Music & Comedy
Heatwave House Party at Shedd Aquarium
Turn up the heat at the first-ever Heatwave House Party! Close out summer in true Chicago style with a night of house music, electric vibes and…
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
T. Murph – Why Am I Raising Adults Tour
T. Murph is performing live in his hometown of Chicago on Saturday, August 29, 2026, as part of his headlining comedy run, the “Why Am…
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
Chayanne – Bailemos Otra Vez Tour
Chayanne is scheduled to perform at the Allstate Arena in Rosemont on Saturday, August 29, 2026, as part of his Bailemos Otra Vez Tour.
Music & Comedy
Jorge Medina – Legendario Tour
Jorge Medina, the acclaimed Mexican regional music artist and former lead singer of La Arrolladora Banda El Limón, will be bringing his Legendario Tour to…
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
Bop to the Top
The Bop to the Top Summer Tour 2026 will be at the Byline Bank Aragon Ballroom in Chicago on Saturday, August 29, 2026. This “biggest…
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…
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, 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
Best of The Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
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, 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, 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
Miranda Lambert Live In Concert
Miranda Lambert is scheduled to perform at the Ravinia Festival in Highland Park, IL, on Sunday, August 30, 2026.
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…
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