events-cat-music-comedy

Upcoming Chicago Events

Check out what's happening all around Chicago.

October 23, 2026: Oct23
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 23rd
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,
Oct23
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 23rd
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 24, 2026: Oct24
Music & Comedy
The Wrecks – Finally : OUTSIDE Tour
Alternative rock band The Wrecks will bring their national fall headline run, the “Finally : OUTSIDE Tour,” to the House of Blues Chicago on Saturday,…
River North
Event details
Saturday, October 24th
5:00 p.m. – 9:00 p.m.
House of Blues
Oct24
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 24th
6:00 p.m. – 7:00 p.m.
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de Maat Theatre at Second City
230 W North Ave
Oct24
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 24th
6:30 p.m. – 8:00 p.m.
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The Second City
1616 N. Wells St.
Oct24
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 24th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct24
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 24th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct24
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 24th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Oct24
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 24th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Oct24
Music & Comedy, Theatre & Performing Arts
Sleeping Beauty & Dvořák Cello Concerto
The crown jewel of cello repertoire, Dvořák’s heroic and soulful Cello Concerto marks the return of Jian Wang, a soloist with a lustrous sound and…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 9:30 p.m.
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220 S. Michigan Ave.
Oct24
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
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The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Oct24
Music & Comedy
Blondshell – Scaring Strangers Tour
Blondshell is scheduled to perform live in Chicago, Illinois on Saturday, October 24, 2026, as part of her newly announced “Scaring Strangers Tour”. Supporting Act:…
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct24
Music & Comedy
Edward Scissorhands In Concert
Released in 1990 and directed by Tim Burton (Beetlejuice, Disney Tim Burton’s The Nightmare Before Christmas), the film centers on Edward (Johnny Depp), a gentle…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Oct24
Music & Comedy, Theatre & Performing Arts
Don Giovanni
The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 11:00 p.m.
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Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct24
Music & Comedy
Lupillo Rivera – 90’s CORRIDOS TOUR
Lupillo Rivera is bringing his 90’s CORRIDOS TOUR to the Rosemont Theatre on Saturday, October 24, 2026. This concert features a nostalgic lineup of regional…
Event details
Saturday, October 24th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Oct24
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…
Lincoln Park
Event details
Saturday, October 24th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct24
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…
Lakeview
Event details
Saturday, October 24th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
Oct24
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…
Event details
Saturday, October 24th
9:30 p.m. – 10:30 p.m.
See all events in series
de Maat Theatre at Second City
230 W North Ave
Oct24
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 24th
9:30 p.m. – 11:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct24
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 24th
9:30 p.m. – 11:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
October 25, 2026: Oct25
Music & Comedy, Theatre & Performing Arts
Omar
Where memory is preserved, legacy endures. MacArthur “Genius Grant” recipient Rhiannon Giddens and celebrated co-composer Michael Abels deliver a profoundly moving story about the strength…
Loop
Event details
Sunday, October 25th
2:00 p.m. – 4:30 p.m.
See all events in series
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct25
Music & Comedy, Theatre & Performing Arts
Sleeping Beauty & Dvořák Cello Concerto
The crown jewel of cello repertoire, Dvořák’s heroic and soulful Cello Concerto marks the return of Jian Wang, a soloist with a lustrous sound and…
Loop
Event details
Sunday, October 25th
3:00 p.m. – 5:00 p.m.
See all events in series

220 S. Michigan Ave.
Oct25
Music & Comedy, Theatre & Performing Arts
Malarkey Comedy Expo League
Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…
Event details
Sunday, October 25th
6:00 p.m. – 7:30 p.m.
See all events in series
Malarkey Comedy
1501 N. Kingsbury St.
Oct25
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
Sunday, October 25th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.

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