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Post Malone: The BIG ASS Stadium Tour
May22
Music & Comedy

Post Malone: The BIG ASS Stadium Tour

Post Malone announced his upcoming tour includes a show at Wrigley Field in 2025! His debut performance at the Friendly Confines is scheduled for Thursday,…

Thursday, May 22nd
7:30 p.m.10:30 p.m.
Wrigley Field
1060 West Addison Street
Teatro Zinzanni
May23
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Friday, May 23rd
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
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…

Friday, May 23rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Grossman Ensemble – World Premieres III
May23
Music & Comedy, Theatre & Performing Arts

Grossman Ensemble – World Premieres III

Esteemed conductor Tim Weiss returns to lead the Grossman Ensemble for an eagerly anticipated third collaboration. Composers Christopher Stark, whose music The New York Times has called, “fetching…

Friday, May 23rd
7:30 p.m.9:00 p.m.
Logan Center for the Arts – Performance Hall
915 E. 60th St.
An Evening with Vince Gill
May23
Music & Comedy

An Evening with Vince Gill

Vince Gill will perform at The Chicago Theatre on Friday, May 23.

Friday, May 23rd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Devil’s Daughter
May23
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 23rd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Paul Simon – A Quiet Celebration Tour
May23
Music & Comedy

Paul Simon – A Quiet Celebration Tour

During “A Quiet Celebration Tour,” Paul Simon will present the live-debut performance of his critically acclaimed, Grammy-nominated album Seven Psalms, as well as perform a…

Friday, May 23rd
8:00 p.m.11:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Voila: The Improvised Musical
May23
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 23rd
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
May23
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 23rd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
May24
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday, May 24th
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May24
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday, May 24th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May24
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 24th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
May24
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 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May24
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 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
AC/DC: Power Up Tour with The Pretty Reckless
May24
Music & Comedy

AC/DC: Power Up Tour with The Pretty Reckless

AC/DC return to the road in the United States for the first time in nine years on the 2025 Power Up North American Tour! Much…

Saturday, May 24th
8:00 p.m.11:00 p.m.
Soldier Field
1410 Special Olympics Dr, Chicago, IL 60605
Paul Simon – A Quiet Celebration Tour
May24
Music & Comedy

Paul Simon – A Quiet Celebration Tour

During “A Quiet Celebration Tour,” Paul Simon will present the live-debut performance of his critically acclaimed, Grammy-nominated album Seven Psalms, as well as perform a…

Saturday, May 24th
8:00 p.m.11:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Here 4 A Bit *Naughty Improv
May24
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 24th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
May24
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 24th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May24
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, May 24th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
May25
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Sunday, May 25th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Tuesday Good Show
May27
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 27th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Comic Court: The Best Comedy Show in the World
May27
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, May 27th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Dame Myra Hess Memorial Concerts | Johannes Gray, Cello and Anastasiya Magamedova, Piano
May28
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Dame Myra Hess Memorial Concerts | Johannes Gray, Cello and Anastasiya Magamedova, Piano

DAME MYRA HESS MEMORIAL CONCERTS | JOHANNES GRAY, CELLO ANASTASIYA MAGAMEDOVA, PIANO  Program Jean Sibelius – Malinconia, Op. 20 Felix Mendelssohn – Cello Sonata No.…

Wednesday, May 28th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Hooch & Holler Comedy Show
May28
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 28th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
bean-night

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