The Orbit
Mar31
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday March 31, 2027
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Mar31
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…

Wednesday March 31, 2027
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
DuSummer Live Music Series
Apr1
Music & Comedy

DuSummer Live Music Series

DuSummer Music Series 2026  Get ready for an unforgettable summer of music at the DuSable Museum Outdoor Courtyard! Join us every other Thursday for some…

Thursday April 1, 2027
6:00 p.m.9:00 p.m.
Dusable Black History Museum and Cultural Centwe
740 East 57th Place
The Infinite Wrench
Apr2
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…

Friday April 2, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Devil’s Daughter
Apr2
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.…

Friday April 2, 2027
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
Apr2
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…

Friday April 2, 2027
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,
Hitch*Cocktails
Apr2
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…

Friday April 2, 2027
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Apr3
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…

Saturday April 3, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Apr3
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…

Saturday April 3, 2027
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Apr3
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…

Saturday April 3, 2027
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Apr3
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…

Saturday April 3, 2027
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Tuesday Good Show
Apr6
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.…

Tuesday April 6, 2027
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The Orbit
Apr7
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday April 7, 2027
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Apr7
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…

Wednesday April 7, 2027
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Infinite Wrench
Apr9
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…

Friday April 9, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Devil’s Daughter
Apr9
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.…

Friday April 9, 2027
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Wine Down Comedy
Apr9
Music & Comedy

Wine Down Comedy

Wine Down Comedy at iO Theater invites you to relax into the weekend with great wine and Chicago’s best stand up comedians. Sip, laugh, and…

Friday April 9, 2027
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
Apr9
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…

Friday April 9, 2027
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,
Hitch*Cocktails
Apr9
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…

Friday April 9, 2027
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Apr10
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…

Saturday April 10, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Apr10
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…

Saturday April 10, 2027
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Apr10
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…

Saturday April 10, 2027
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Apr10
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…

Saturday April 10, 2027
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Nothing But Thieves – The Stray Dogs World Tour
Apr12
Music & Comedy

Nothing But Thieves – The Stray Dogs World Tour

Nothing But Thieves are performing live in Chicago on Monday, April 12, 2027, as part of “The Stray Dogs World Tour”.

Monday April 12, 2027
7:30 p.m.10:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL