Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Best Of Annoyance Sketch
Start: 2026-09-26T21:30:00-05:00
End: 2026-09-26T22:30:00-05:00
Location: The Annoyance Theatre

Check out what's happening all around Chicago.

September 18, 2026: Sep18
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, September 18th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Sep18
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, September 18th
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,
Sep18
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, September 18th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
September 19, 2026: Sep19
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, September 19th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sep19
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, September 19th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Sep19
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, September 19th
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
Sep19
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, September 19th
9:00 p.m. – 10:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Sep19
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, September 19th
9:30 p.m. – 10:30 p.m.
See all events in series
The Annoyance Theatre
851 W. Belmont Ave.
September 21, 2026: Sep21
Music & Comedy, Theatre & Performing Arts
Magic Mondays
Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…
Lincoln Park
Event details
Monday, September 21st
7:00 p.m. – 8:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
September 22, 2026: Sep22
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, September 22nd
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Sep22
Music & Comedy
Iron Maiden Live In Chicago – Run For Your Lives Tour 2026
English heavy metal legends Iron Maiden brings the Run For Your Lives 2026 World Tour to Credit Union 1 Amphitheatre in Tinley Park, IL, on…
Event details
Tuesday, September 22nd
7:15 p.m. – 11:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
Sep22
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…
Event details
Tuesday, September 22nd
9:00 p.m. – 10:30 p.m.
See all events in series
The Lincoln Lodge
2040 North Milwaukee Avenue
September 23, 2026: Sep23
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, September 23rd
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
September 25, 2026: Sep25
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, September 25th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sep25
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, September 25th
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Sep25
Music & Comedy
Michael Shannon & Jason Narducy
Michael Shannon & Jason Narducy will perform live at Riviera Theatre on Sep. 25, 2026.
Uptown
Event details
Friday, September 25th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Sep25
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, September 25th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Sep25
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, September 25th
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,
Sep25
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, September 25th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
September 26, 2026: Sep26
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, September 26th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sep26
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, September 26th
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Sep26
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, September 26th
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
Sep26
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, September 26th
9:00 p.m. – 10:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Sep26
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, September 26th
9:30 p.m. – 10:30 p.m.
See all events in series
The Annoyance Theatre
851 W. Belmont Ave.