Upcoming Chicago Events
Check out what's happening all around Chicago.
Search events category
Music & Comedy
Music & Comedy
Kohl’s Cash: TGIF (That’s Good Improv Friday)
Start your weekend off laughing at one of the hottest improv shows in Chicago! Every Friday at 9:30pm, iO house team Kohl’s Cash presents a…
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Music & Comedy
Best of 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…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
DETROIT ’67
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
Music & Comedy, Theatre & Performing Arts, Tours & Attractions
The Cosmic Underground Show
Step aboard for a one-of-a-kind journey where mind-reading, magic, comedy, and sci-fi collide in ways you won’t find anywhere else in Chicago. Hosted by real-life…
Music & Comedy
Gods of Chaos Halloween: OsamaSon, Waka Flocka Flame & 2slimey
The second annual Gods of Chaos festival will take over the Byline Bank Aragon Ballroom in Chicago on Halloween night—Saturday, October 31, 2026. This high-adrenaline…
Music & Comedy
420 Frankenstein
The creator of 420 Shakespeare is bringing Mary Shelley’s monster to life… with a little help from Mary Jane. On a dark and stormy night,…
Music & Comedy, Theatre & Performing Arts
You Win Some, You Dim Sum: an uplifting comedy show
We don’t celebrate our wins enough — so we made a comedy show where you can watch stand-up, win dim sum treats, and celebrate each…
Music & Comedy
Main Character Syndrome
Main Character Syndrome is a solo character showcase by Chicago’s funniest improvisers presenting original SNL-audition ready character sketches. From Tim Robinson to Cecily Strong, iO…
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
Sergei Putinski at The Comedy Bar
Born beneath the Kremlin and rumoured to be Vladimir Putin’s nephew, Sergei Putinski is a man who has seen things you wouldn’t believe — mostly…
Music & Comedy
Akeem Ali – The Texture Tour
Akeem Ali is performing at the House of Blues Chicago on Saturday, October 31, 2026, for “The Texture Tour.”
Museums, Galleries & Exhibitions, Music & Comedy
Haunted House Party at Shedd Aquarium
Join Shedd Aquarium for a frightfully fun night at Haunted House Party, where house music and Halloween collide. Come dressed in your creepiest, kookiest costumes…
Music & Comedy
Sanctum Dark Music Festival 2026
The Sanctum Dark Music Festival returns to Chicago for Halloween weekend on Friday, October 30, and Saturday, October 31, 2026. The darkwave, industrial, and post-punk…
Music & Comedy
Saturday Night Sketch
Saturday Night Sketch brings Chicago’s best sketch comedy ensembles to the stage for a high-octane evening. From sharp political satire to mind melting absurdity, come…
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Music & Comedy
The Best of IO
Celebrate 45 years of improvisational excellence with the Best of iO Improv. This show brings together two teams of our very best improvisers, each delivering…
Music & Comedy, Theatre & Performing Arts
Brahms Requiem
Brahms once called A German Requiem his “human requiem” — and it fits. The gently powerful score emphasizes consolation for the living rather than fiery judgment, and…
Music & Comedy
Allison Russell – Chicago, IL – The In The Hour of Chaos Tour
Allison Russell will perform live at The Vic Theatre in Chicago, Illinois, on Saturday, October 31, 2026. The Grammy-winning singer-songwriter, poet, and activist is bringing…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
DETROIT ’67
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
Music & Comedy
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
Arcangel – La 8va Maravilla World Tour
Arcángel is performing live in Rosemont on Saturday, October 31, 2026, as part of his “La 8va Maravilla World Tour 20 Aniversario”.
Music & Comedy
Rod Wave – Don’t Look Down Tour
Rod Wave is scheduled to perform live in Chicago, Illinois on Saturday, October 31, 2026, as part of his newly announced Don’t Look Down Tour.…
Music & Comedy
GOOFAZZ Halloween Comedy Show at The Comedy Bar
Stand up comedian, Ohjay Lamont, is a Comedy Bar favorite. Watch his newest special, OHJAY DID IT, dedicated to his late father and filmed live…
Explore Chicago hotels, flights, deals, and more
Plan your trip
