Upcoming Chicago Events

Name: LET’S PLAY A GAME: Chicago’s scariest short-form show
Start: 2025-10-18T22:00:00-05:00
End: 2025-10-18T23:00:00-05:00
Location: Annoyance Theatre & Bar

Check out what's happening all around Chicago.

October 11, 2025: Oct11
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Saturday, October 11th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct11
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 11th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct11
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 11th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct11
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 11th
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
Oct11
Music & Comedy, Theatre & Performing Arts
Here 4 A Bit *Naughty Improv
Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…
Old Town
Event details
Saturday, October 11th
9:00 p.m. – 10:00 p.m.
See all events in series
The Second City
1616 N. Wells St., Theater on the Second Floor
Oct11
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 11th
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Oct11
Music & Comedy, Theatre & Performing Arts
LET’S PLAY A GAME: Chicago’s scariest short-form show
Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…
Lakeview
Event details
Saturday, October 11th
10:00 p.m. – 11:00 p.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 12, 2025: Oct12
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Sunday, October 12th
5:00 a.m. – 9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
October 14, 2025: Oct14
Music & Comedy
Tuesday Good Show
Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…
Event details
Tuesday, October 14th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
October 15, 2025: Oct15
Music & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Event details
Wednesday, October 15th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
October 16, 2025: Oct16
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Thursday, October 16th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct16
Music & Comedy, Theatre & Performing Arts
Dumb and Drummer
Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…
Event details
Thursday, October 16th
7:30 p.m. – 9:00 p.m.
See all events in series
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
October 17, 2025: Oct17
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Friday, October 17th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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
Friday, 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
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 17th
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,
Oct17
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 17th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 18, 2025: Oct18
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Saturday, October 18th
12:00 p.m. – 3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct18
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Loop
Event details
Saturday, October 18th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct18
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 18th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct18
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 18th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct18
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 18th
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
Oct18
Music & Comedy, Theatre & Performing Arts
Here 4 A Bit *Naughty Improv
Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…
Old Town
Event details
Saturday, October 18th
9:00 p.m. – 10:00 p.m.
See all events in series
The Second City
1616 N. Wells St., Theater on the Second Floor
Oct18
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 18th
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Oct18
Music & Comedy, Theatre & Performing Arts
LET’S PLAY A GAME: Chicago’s scariest short-form show
Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…
Lakeview
Event details
Saturday, October 18th
10:00 p.m. – 11:00 p.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.