Upcoming Chicago Events

Name: Tuesday Good Show
Start: 2026-06-02T19:00:00-05:00
End: 2026-06-02T20:30:00-05:00
Location: The Gallery Cabaret

Check out what's happening all around Chicago.

May 28, 2026: May28
Music & Comedy
Morgan’s Laugh Lounge
Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…
Event details
Thursday, May 28th
7:00 p.m. – 8:30 p.m.
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Morgan’s On Fulton
950 W Fulton Market
May28
Music & Comedy, Theatre & Performing Arts
Dark Side of the Pillow Sketch Comedy Show
The thoughts you have at 2 a.m.? We put them on stage. Looking for a night out that feels unmistakably Chicago? Dark Side of the…
Event details
Thursday, May 28th
7:30 p.m. – 8:30 p.m.
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The De Matt Theater at The Second City
230 W North Ave
May 29, 2026: May29
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 29th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May29
Music & Comedy, Theatre & Performing Arts
The Last Word
The Last Word is the first 4 course craft cocktail progression paired with a screenplay. 6 actors come on stage and read through a high…
Lincoln Park
Event details
Friday, May 29th
7:00 p.m. – 9:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May29
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 29th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
May29
Music & Comedy
Rilo Kiley Live In Concert
Rilo Kiley is scheduled to perform in Chicago, IL, on Friday, May 29, 2026, as part of their reunion tour.
Loop
Event details
Friday, May 29th
7:30 p.m. – 10:30 p.m.
The Chicago Theatre
175 N. State
May29
Music & Comedy
Summer Walker – Still Finally Over It Tour 2026
R&B star Summer Walker is scheduled to perform in Chicago on Friday, May 29, 2026, as part of her first major arena run, the “Still…
West Loop
Event details
Friday, May 29th
7:30 p.m. – 10:30 p.m.
United Center
1901 W Madison St,
May29
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 29th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
May29
Music & Comedy, Theatre & Performing Arts
Honk! A Short Form Improv Show
Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…
Event details
Friday, May 29th
9:00 p.m. – 10:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
May29
Music & Comedy, Theatre & Performing Arts
420 Shakespeare
4 professional actors meet to perform a Shakespeare play… but only after one of them takes at least 20mg of you know what, leading to…
Event details
Friday, May 29th
9:00 p.m. – 10:30 p.m.
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The De Matt Theater at The Second City
230 W North Ave
May29
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 29th
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,
May29
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 29th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May 30, 2026: May30
Music & Comedy
Stargazers Adventure Club
Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…
Event details
Saturday, May 30th
10:00 a.m. – 11:30 a.m.
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Stars & Garters Theater
3914 N. Clark St.
May30
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 30th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May30
Music & Comedy
Bobby Lee – The Finally Tour 2026
Comedian Bobby Lee is bringing his first-ever headline tour, “The Finally Tour 2026,” to Chicago on Saturday, May 30, 2026.
Loop
Event details
Saturday, May 30th
7:00 p.m. – 9:00 p.m.
The Chicago Theatre
175 N. State
May30
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 30th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May30
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 30th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
May30
Music & Comedy
Cody Johnson Live In Chicago
Cody Johnson is scheduled to perform in Rosemont on Saturday, May 30, 2026, at the Allstate Arena.
Event details
Saturday, May 30th
7:30 p.m. – 10:30 p.m.
Allstate Arena
6920 Mannheim Road
May30
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 30th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May30
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 30th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May 31, 2026: May31
Music & Comedy, Theatre & Performing Arts
Malarkey Comedy Expo League
Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…
Event details
Sunday, May 31st
6:00 p.m. – 7:30 p.m.
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Malarkey Comedy
1501 N. Kingsbury St.
May31
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 31st
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May31
Music & Comedy, Theatre & Performing Arts
Improvised DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage with…
Event details
Sunday, May 31st
8:00 p.m. – 9:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
June 2, 2026: Jun2
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, June 2nd
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave