Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Magic Mondays
Start: 2026-09-21T19:00:00-05:00
End: 2026-09-21T20:30:00-05:00
Location: iO Theater

Check out what's happening all around Chicago.

September 11, 2026: Sep11
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 11, 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,
Sep11
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 11, 2026
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
September 12, 2026: Sep12
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 12, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sep12
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Saturday September 12, 2026
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Sep12
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 12, 2026
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Sep12
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 12, 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
Sep12
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 12, 2026
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
September 13, 2026: Sep13
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Loop
Event details
Sunday September 13, 2026
4:00 p.m. – 7:00 p.m.
See all events in series
Spiegeltent – Cambria Hotel
32 W. Randolph
September 15, 2026: Sep15
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 15, 2026
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
September 16, 2026: Sep16
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 16, 2026
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
September 17, 2026: Sep17
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Thursday September 17, 2026
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Sep17
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 September 17, 2026
7:30 p.m. – 9:00 p.m.
See all events in series
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
September 18, 2026: Sep18
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 18, 2026
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sep18
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Friday September 18, 2026
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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 18, 2026
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 18, 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,
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 18, 2026
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 19, 2026
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
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Saturday September 19, 2026
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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 19, 2026
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 19, 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
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 19, 2026
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
September 20, 2026: Sep20
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Loop
Event details
Sunday September 20, 2026
4:00 p.m. – 7:00 p.m.
See all events in series
Spiegeltent – Cambria Hotel
32 W. Randolph
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 21, 2026
7:00 p.m. – 8:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.