Upcoming Chicago Events

Name: Comedy Hour at Annoyance Theatre
Start: 2026-05-29T00:00:00-05:00
End: 2026-05-30T01:00:00-05:00
Location: Annoyance Theatre & Bar

Check out what's happening all around Chicago.

May 17, 2026: May17
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 May 17, 2026
5:00 a.m. – 9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May 20, 2026: May20
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 May 20, 2026
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May 21, 2026: May21
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 May 21, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May21
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 May 21, 2026
7:30 p.m. – 9:00 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May 22, 2026: May22
May23
Theatre & Performing Arts
Comedy Hour at Annoyance Theatre
Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…
Lakeview
Event details
Friday May 22, 2026
12:00 a.m. – Saturday May 23, 2026
1:00 a.m.
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Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May22
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 May 22, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May22
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 May 22, 2026
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May22
Theatre & Performing Arts
The Improvised Shakespeare Company®
The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…
Lincoln Park
Event details
Friday May 22, 2026
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
May22
Music & Comedy, Theatre & Performing Arts
Missed Call Sketch Comedy Show
Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!
Lakeview
Event details
Friday May 22, 2026
8:00 p.m. – 9:00 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May22
Theatre & Performing Arts
The Lincoln Lodge
The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…
Event details
Friday May 22, 2026
8:00 p.m. – 9:30 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May22
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 May 22, 2026
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,
May22
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 May 22, 2026
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May 23, 2026: May23
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 May 23, 2026
12:00 p.m. – 3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May23
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 May 23, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May23
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 May 23, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
May23
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 May 23, 2026
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May23
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 May 23, 2026
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
May23
Theatre & Performing Arts
The Improvised Shakespeare Company®
The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…
Lincoln Park
Event details
Saturday May 23, 2026
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
May23
Theatre & Performing Arts
The Lincoln Lodge
The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…
Event details
Saturday May 23, 2026
8:00 p.m. – 9:30 p.m.
See all events in series
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May23
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 May 23, 2026
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
May 24, 2026: May24
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 May 24, 2026
5:00 a.m. – 9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May 27, 2026: May27
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 May 27, 2026
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May 28, 2026: May28
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 May 28, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
May 29, 2026: May29
May30
Theatre & Performing Arts
Comedy Hour at Annoyance Theatre
Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…
Lakeview
Event details
Friday May 29, 2026
12:00 a.m. – Saturday May 30, 2026
1:00 a.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.