Upcoming Chicago Events

Name: Best Of Annoyance Sketch
Start: 2026-01-10T21:30:00-06:00
End: 2026-01-10T22:30:00-06:00
Location: The Annoyance Theatre

Check out what's happening all around Chicago.

December 31, 2025: Dec31
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, December 31st
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
January 1, 2026: Jan1
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 January 1, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
January 2, 2026: Jan2
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 January 2, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan2
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 January 2, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan2
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 January 2, 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,
Jan2
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 January 2, 2026
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
January 3, 2026: Jan3
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 January 3, 2026
12:00 p.m. – 3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan3
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 January 3, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan3
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 January 3, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan3
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 January 3, 2026
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Jan3
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 January 3, 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
Jan3
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 January 3, 2026
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
January 4, 2026: Jan4
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 January 4, 2026
5:00 a.m. – 9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
January 8, 2026: Jan8
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 January 8, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
January 9, 2026: Jan9
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 January 9, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan9
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 January 9, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan9
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 January 9, 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,
Jan9
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 January 9, 2026
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
January 10, 2026: Jan10
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 January 10, 2026
12:00 p.m. – 3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan10
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 January 10, 2026
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Jan10
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 January 10, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan10
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 January 10, 2026
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Jan10
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 January 10, 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
Jan10
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 January 10, 2026
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.