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Upcoming Chicago Events

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Matt Mathews – Boujee On A Budget Tour
May30
Music & Comedy

Matt Mathews – Boujee On A Budget Tour

Matt Mathews will perform live at The Chicago Theatre on May 30, 2025.

Friday, May 30th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
The Queens! 4 Legends. 1 Stage. Chaka. Patti. Gladys. Stephanie.
May30
Music & Comedy

The Queens! 4 Legends. 1 Stage. Chaka. Patti. Gladys. Stephanie.

Music history will be made as four of the most legendary voices in R&B, soul, and pop come together for an unforgettable tour! Chaka Khan,…

Friday, May 30th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Anthony ‘Scruncho’ McKinley
May30
Music & Comedy

Anthony ‘Scruncho’ McKinley

Anthony McKinley, (better known as Scruncho) is an American comedian and actor who was known for being in movies such as “How High”, “Budz House”, “Easy Money” and…

Friday, May 30th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Comedy Dance Chicago presents: 8-BITS
May30
Music & Comedy, Theatre & Performing Arts

Comedy Dance Chicago presents: 8-BITS

We’re back with all new bits! This joyful mixture of sketch comedy and dance is filled with a variety of characters that are sure to…

Friday, May 30th
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
May30
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 30th
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
May30
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 30th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The People’s Music School Presents: Performapaloozathon!
May31
Music & Comedy

The People’s Music School Presents: Performapaloozathon!

It’s The People’s Music School’s biggest performance of the year! Performapaloozathon is an all-day music event hosted by The People’s Music School, featuring 800+ TPMS…

Saturday, May 31st
10:00 a.m.4:00 p.m.
Gary Comer Youth Center
7200 S Ingleside Ave
Teatro Zinzanni
May31
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 31st
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
May31
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 31st
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May31
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 31st
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Miss Renee Live One Night Only
May31
Music & Comedy

Miss Renee Live One Night Only

HollywoodGenGen, widely recognized as “Miss Renee”, is an acclaimed actor, comedian, and social media influencer celebrated for their ability to connect with audiences through humor and…

Saturday, May 31st
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Nikki Glaser: Alive And Unwell Tour
May31
Music & Comedy

Nikki Glaser: Alive And Unwell Tour

Nikki Glaser will bring the ALIVE AND UNWELL TOUR to The Chicago Theatre on May 31 and June 1.

Saturday, May 31st
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
The Weeknd: After Hours Til Dawn Tour With Playboi Carti And Mike Dean
May31
Music & Comedy

The Weeknd: After Hours Til Dawn Tour With Playboi Carti And Mike Dean

Global superstar The Weeknd will embark on a brand-new stadium tour across North America this year featuring chart-topping, multi-platinum and genre-defying Atlanta rapper Playboi Carti…

Saturday, May 31st
7:00 p.m.10:00 p.m.
Soldier Field
1410 Special Olympics Dr, Chicago, IL 60605
Baby Wants Candy! The Original Completely Improvised Musical
May31
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 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May31
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 31st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Here 4 A Bit *Naughty Improv
May31
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 31st
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
May31
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 31st
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
May31
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 31st
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
Jun1
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, June 1st
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Nikki Glaser: Alive And Unwell Tour
Jun1
Music & Comedy

Nikki Glaser: Alive And Unwell Tour

Nikki Glaser will bring the ALIVE AND UNWELL TOUR to The Chicago Theatre on May 31 and June 1.

Sunday, June 1st
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Tuesday Good Show
Jun3
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, June 3rd
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Fridayy – Some Days I’m Good, Some Days I’m Not World Tour
Jun3
Music & Comedy

Fridayy – Some Days I’m Good, Some Days I’m Not World Tour

Fridayy will bring the Some Days I’m Good Some Days I’m Not World Tour to The Chicago Theatre on June 3.

Tuesday, June 3rd
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Dame Myra Hess Memorial Concerts | Trio Rai
Jun4
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Dame Myra Hess Memorial Concerts | Trio Rai

DAME MYRA HESS MEMORIAL CONCERTS | TRIO RAI Tiffany Chang, violin Leland Ko, cello Motti Fang-Bentov, piano   Program Melanie Bonis – Soir et Matin,…

Wednesday, June 4th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Widespread Panic Live In Concert
Jun4
Music & Comedy

Widespread Panic Live In Concert

Widespread Panic returns to The Chicago Theatre for three nights on June 4, 5, & 6.

Wednesday, June 4th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
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