Teatro Zinzanni
May10
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…

Sunday May 10, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May10
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…

Sunday May 10, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Wheel of Improv
May10
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday May 10, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
May12
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 May 12, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Rodrigo Y Gabriela – 20th Anniversary Tour
May13
Music & Comedy

Rodrigo Y Gabriela – 20th Anniversary Tour

Rodrigo y Gabriela are scheduled to perform in Chicago, IL, on Wednesday, May 13, 2026, as part of their “20th Anniversary Tour”.

Wednesday May 13, 2026
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Triumph Live In Chicago – 50th Anniversary Tour
May13
Music & Comedy

Triumph Live In Chicago – 50th Anniversary Tour

Canadian rock legends Triumph /w special guests April Wine will perform live at Rosemont Theatre on May 13, 2026.

Wednesday May 13, 2026
8:00 p.m.10:00 p.m.
Rosemont Theatre
Hooch & Holler Comedy Show
May13
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 May 13, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Teatro Zinzanni
May14
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…

Thursday May 14, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Bring Me The Horizon – Ascension Program 2 Tour
May15
Music & Comedy

Bring Me The Horizon – Ascension Program 2 Tour

Bring Me The Horizon is scheduled to perform in Rosemont, IL, on Friday, May 15, 2026, at the Allstate Arena. The concert is part of…

Friday May 15, 2026
6:00 p.m.11:00 p.m.
Allstate Arena
6920 Mannheim Road
The Infinite Wrench
May15
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 May 15, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
May15
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…

Friday May 15, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Devil’s Daughter
May15
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 May 15, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May15
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!

Friday May 15, 2026
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Voila: The Improvised Musical
May15
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 May 15, 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,
Hitch*Cocktails
May15
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 May 15, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Yellowcard – The Up Up Down Down 2026 Tour
May16
Music & Comedy

Yellowcard – The Up Up Down Down 2026 Tour

Alt-rock band Yellowcard will perform live at The Salt Shed Outdoors on May 16, 2026.

Saturday May 16, 2026
6:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
The Infinite Wrench
May16
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 May 16, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Matt McCusker – Healing Frequency 2026 Tour
May16
Music & Comedy

Matt McCusker – Healing Frequency 2026 Tour

Comedian Matt McCusker is scheduled to perform in Chicago, IL, on Saturday, May 16, 2026, as part of his “The Healing Frequency Tour”

Saturday May 16, 2026
7:00 p.m.9:00 p.m.
The Riveria Theater
4746 N Racine Ave
Teatro Zinzanni
May16
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…

Saturday May 16, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
May16
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 May 16, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May16
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 May 16, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
May16
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 May 16, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Teatro Zinzanni
May17
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…

Sunday May 17, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May17
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…

Sunday May 17, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St