events-cat-music-comedy

Upcoming Chicago Events

Check out what's happening all around Chicago.

October 16, 2026: Oct16
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…
Old Town
Event details
Friday, October 16th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct16
Music & Comedy
Devil’s Daughter
The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Lincoln Park
Event details
Friday, October 16th
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct16
Music & Comedy
Brad Williams: The Tall Tales Tour
Brad Williams will bring the Tall Tales Tour to The Chicago Theatre on Friday, October 16.
Loop
Event details
Friday, October 16th
7:30 p.m. – 9:30 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Oct16
Music & Comedy
Mike D – Chicago – 2026 Tour
Beastie Boys co-founder Michael Diamond, performing under his new project name Mike D, is bringing his newly expanded international tour to Chicago, Illinois on Friday,…
Uptown
Event details
Friday, October 16th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Oct16
Music & Comedy
Devil’s Daughter
The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Lincoln Park
Event details
Friday, October 16th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Oct16
Music & Comedy, Theatre & Performing Arts
Branford Marsalis & Dianne Reeves Celebrate John Coltrane
Jazz would not sound the same today without John Coltrane. Known for dissolving the boundaries of jazz, he could “pull listeners right out of their…
Loop
Event details
Friday, October 16th
8:00 p.m. – 10:00 p.m.

220 S. Michigan Ave.
Oct16
Music & Comedy
Tinashe – Chicago – A Night With A Popstar Tour
Multi-platinum R&B/pop singer, songwriter, and dancer Tinashe is bringing her exclusive fall run, “A Night With A Popstar,” to Chicago, Illinois on Friday, October 16,…
Event details
Friday, October 16th
8:00 p.m. – 11:00 p.m.
The Salt Shed
1357 N Elston
Oct16
Music & Comedy, Theatre & Performing Arts
Honk! A Short Form Improv Show
Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…
Event details
Friday, October 16th
9:00 p.m. – 10:00 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
Oct16
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…
Old Town
Event details
Friday, October 16th
9:30 p.m. – 11:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct16
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…
Old Town
Event details
Friday, October 16th
9:30 p.m. – 11:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct16
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…
Event details
Friday, October 16th
10:00 p.m. – 11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Oct16
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…
Lakeview
Event details
Friday, October 16th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 17, 2026: Oct17
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,…
Event details
Saturday, October 17th
6:00 p.m. – 7:00 p.m.
See all events in series
de Maat Theatre at Second City
230 W North Ave
Oct17
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…
Old Town
Event details
Saturday, October 17th
6:30 p.m. – 8:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct17
Music & Comedy
Knox – Chicago – My Midwest Best World Tour
Rising pop/country singer-songwriter Knox (Knox Morris) will perform live in Chicago on Saturday, October 17, 2026, at the House of Blues Chicago. The concert is…
River North
Event details
Saturday, October 17th
6:30 p.m. – 10:00 p.m.
House of Blues
Oct17
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…
Andersonville
Event details
Saturday, October 17th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct17
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…
Old Town
Event details
Saturday, October 17th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct17
Music & Comedy
Ben Schwartz & Friends
Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
Loop
Event details
Saturday, October 17th
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Oct17
Music & Comedy
Catch Your Breath – Not Broken Enough Tour
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”. Supporting Lineup: This heavy…
Event details
Saturday, October 17th
7:00 p.m. – 10:00 p.m.
The Vic Theatre
3145 N. Sheffield
Oct17
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…
Old Town
Event details
Saturday, October 17th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct17
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…
Old Town
Event details
Saturday, October 17th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St., Theater on the Second Floor
Oct17
Music & Comedy, Theatre & Performing Arts
Guerrero Leads Fandangos & Enigma Variations
Few contemporary violin concertos have made a splash with audiences like Arturo Márquez’s Fandango, which won a 2024 Latin Grammy. Composed for Anne Akiko Meyers, this…
Loop
Event details
Saturday, October 17th
7:30 p.m. – 9:30 p.m.
See all events in series

220 S. Michigan Ave.
Oct17
Music & Comedy
Suki Waterhouse – The Loveland Tour
Suki Waterhouse will conclude her North American tour in Chicago on Saturday, October 17, 2026. This show at the Byline Bank Aragon Ballroom is part…
Uptown
Event details
Saturday, October 17th
7:30 p.m. – 10:30 p.m.
Aragon Ballroom
1106 W. Lawrence Ave., Chicago, IL 60640
Oct17
Music & Comedy
Judah and The Lion – 2026 Tour
Alternative folk-pop band Judah & The Lion will bring their headline tour to Chicago on Saturday, October 17, 2026. The performance is part of their…
Uptown
Event details
Saturday, October 17th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave

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