Upcoming Chicago Events

Name: Tuesday Good Show
Start: 2026-05-26T19:00:00-05:00
End: 2026-05-26T20:30:00-05:00
Location: The Gallery Cabaret

Check out what's happening all around Chicago.

Featured Events

Festivals, Fairs & Special Events, Music & Comedy

Windy City Smokeout

United Center Parking Lot

Jul8

May 23, 2026: May23
Music & Comedy
Hecklers’ Happy Hour Comedy Show
Audiences can unleash their inner “heckler” against some of Chicago’s funniest comics in this chaotic standup showcase Hecklers’ Happy Hour aims to give audiences a…
Event details
Saturday, May 23rd
6:00 p.m. – 7:15 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May23
Music & Comedy, Theatre & Performing Arts
Dinner Detective Murder Mystery Show
The Dinner Detective is an interactive true crime murder mystery show set in the present day and based on real cold cases. Feast on a…
Event details
Saturday, May 23rd
6:00 p.m. – 9:00 p.m.
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Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario St
May23
Music & Comedy
Slide Away
The Slide Away 2026 festival will take place in Chicago over two nights, Friday, May 22, and Saturday, May 23, 2026. The festival features a…
Uptown
Event details
Saturday, May 23rd
6:00 p.m. – 11:00 p.m.
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Aragon Ballroom
May23
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 23rd
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May23
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 23rd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May23
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 23rd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
May23
Music & Comedy, Theatre & Performing Arts
Improvised Jane Austen
Improvised Jane Austen Improvised Jane Austen continues its entirely improvised tales of love and laughter. Audiences will enjoy an evening with wit and heart in…
Lincoln Park
Event details
Saturday, May 23rd
7:30 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May23
Music & Comedy
Here for a Fun Time!: A Bubblingly Fun Chicago Comedy Showcase
Here for a Fun Time! is a monthly comedy variety show that features Chicago’s best stand ups, character comedians, drag stars, and more! There’s fun…
Event details
Saturday, May 23rd
7:30 p.m. – 8:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May23
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
Lincoln Park
Event details
Saturday, May 23rd
7:30 p.m. – 10:00 p.m.
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Greenhouse Theater Center
2257 North Lincoln Avenue
May23
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 23rd
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May23
Music & Comedy
Prime Time – Chicago’s hottest comedy showcase
If you like, innovative, smart and FUNNY comedy this is the show for you! It has been scientifically proven that 9 o’clock on a Saturday…
Event details
Saturday, May 23rd
9:00 p.m. – 10:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May23
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 23rd
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May23
Music & Comedy
Chicago Comedy Hour
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
Event details
Saturday, May 23rd
9:30 p.m. – 10:30 p.m.
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The De Matt Theater at The Second City
230 W North Ave
May 24, 2026: May24
Music & Comedy
Sueños Music Festival 2026
The Sueños Music Festival celebrates its fifth anniversary in Grant Park, Chicago, on Saturday, May 23, and Sunday, May 24, 2026. This Memorial Day weekend…
South Loop
Event details
Sunday, May 24th
12:00 p.m. – 11:00 p.m.
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Grant Park
337 E Randolph St
May24
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
Lincoln Park
Event details
Sunday, May 24th
2:30 p.m. – 5:00 p.m.
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Greenhouse Theater Center
2257 North Lincoln Avenue
May24
Music & Comedy, Theatre & Performing Arts
Who’s Waldo?
Ten of Chicago’s best comedians and performers will rapid-fire take the stage as Waldo, and it’s up to the audience to figure out: Who’s Waldo?…
Event details
Sunday, May 24th
5:00 p.m. – 6:30 p.m.
Lincoln Lodge, 2040 N Milwaukee Ave, Chicago, IL 60647
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May24
Music & Comedy
Thornhill – The Mercia Tour
Australian alternative metal band Thornhill is scheduled to perform in Chicago on May 24 as part of The Mercia Tour. Supporting Acts: 156/Silence, Fox Lake,…
Event details
Sunday, May 24th
6:00 p.m. – 11:00 p.m.
The Vic Theatre
3145 N. Sheffield
May24
Music & Comedy
UFO Case Files
Men in Black meets Whose Line Is It Anyways? UFO Case Files is a live improv show in Logan Square where the cast creates a…
Event details
Sunday, May 24th
7:00 p.m. – 8:00 p.m.
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cosmic underground theater
3433 W Fullerton Ave
May24
Music & Comedy
Chicago’s Best Comedy Show at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street,…
River North
Event details
Sunday, May 24th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
May24
Festivals, Fairs & Special Events, Music & Comedy
Rockin’ in the Park 2026 Free Summer Concert Series
Rosemont’s Parkway Bank Park Entertainment District (5501 Park Place, Rosemont) will set the stage for another summer of live music with the return of its “Rockin’ in the…
Event details
Sunday, May 24th
7:00 p.m. – 10:00 p.m.
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Parkway Bank Park Entertainment District
5501 Park Place
May24
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 24th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May 25, 2026: May25
Music & Comedy
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…
River North
Event details
Monday, May 25th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
May25
Music & Comedy, Theatre & Performing Arts
The Oldest Profession: Solo Comedy Show About Sex Worker History | Chicago
The Oldest Profession is a solo comedy show by Kaytlin Bailey — comedian, former sex worker, and host of the acclaimed podcast of the same…
Lakeview
Event details
Monday, May 25th
7:00 p.m. – 9:00 p.m.
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Theater Wit
May 26, 2026: May26
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 26th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave