Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Best Of Annoyance Sketch
Start: 2026-05-16T21:30:00-05:00
End: 2026-05-16T22:30:00-05:00
Location: The Annoyance Theatre

Check out what's happening all around Chicago.

May 9, 2026: May9
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, May 9th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May 10, 2026: May10
Music & Comedy
Disclosure: Spring 2026 North America Tour
Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.
Event details
Sunday, May 10th
6:30 p.m. – 9:30 p.m.
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The Salt Shed
1357 N Elston Ave, Chicago, IL
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!)…
Old Town
Event details
Sunday, May 10th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May 12, 2026: 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.…
Event details
Tuesday, May 12th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May12
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, May 12th
9:00 p.m. – 10:30 p.m.
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The Lincoln Lodge
2040 North Milwaukee Avenue
May 13, 2026: 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”.
Loop
Event details
Wednesday, May 13th
7:30 p.m. – 10:30 p.m.
The Chicago Theatre
175 N. State
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.
Event details
Wednesday, May 13th
8:00 p.m. – 10:00 p.m.
Rosemont Theatre
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…
Event details
Wednesday, May 13th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May 15, 2026: 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…
Event details
Friday, May 15th
6:00 p.m. – 11:00 p.m.
Allstate Arena
6920 Mannheim Road
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…
Andersonville
Event details
Friday, May 15th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
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.…
Lincoln Park
Event details
Friday, May 15th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
May15
Music & Comedy
Charlie Puth – Whatever’s Clever! World Tour 2026
Grammy-nominated singer-songwriter Charlie Puth is scheduled to perform at Rosemont Theatre on Friday, May 15, 2026, as part of his global “Whatever’s Clever! World Tour”.
Event details
Friday, May 15th
7:30 p.m. – 11:30 p.m.
Rosemont Theatre
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.…
Lincoln Park
Event details
Friday, May 15th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
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!
Lakeview
Event details
Friday, May 15th
8:00 p.m. – 9:00 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
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…
Event details
Friday, May 15th
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,
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…
Lakeview
Event details
Friday, May 15th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May 16, 2026: 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.
Event details
Saturday, May 16th
6:00 p.m. – 10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
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…
Andersonville
Event details
Saturday, May 16th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
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”
Uptown
Event details
Saturday, May 16th
7:00 p.m. – 9:00 p.m.
The Riveria Theater
4746 N Racine Ave
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…
Old Town
Event details
Saturday, May 16th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
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…
Old Town
Event details
Saturday, May 16th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
May16
Music & Comedy
Bruno Mars – The Romantic Tour
16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.
South Loop
Event details
Saturday, May 16th
7:30 p.m. – 11:30 p.m.
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Soldier Field
1410 Special Olympics Drive
May16
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, May 16th
9:00 p.m. – 10:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
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…
Lakeview
Event details
Saturday, May 16th
9:30 p.m. – 10:30 p.m.
See all events in series
The Annoyance Theatre
851 W. Belmont Ave.