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ComedySportz Chicago
Sep20
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, September 20th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Dinner Detective True Crime Murder Mystery Dinner Show
Sep20
Music & Comedy, Theatre & Performing Arts

The Dinner Detective True Crime Murder Mystery Dinner Show

The Dinner Detective is an interactive true crime mystery show set in the present day and based on real cold cases. Feast on a fantastic…

Saturday, September 20th
6:00 p.m.9:00 p.m.
Courtyard by Marriott Chicago Downtown
165 E. Ontario St
Symphony Ball: Joyce DiDonato & the Chicago Symphony Orchestra
Sep20
Music & Comedy, Theatre & Performing Arts

Symphony Ball: Joyce DiDonato & the Chicago Symphony Orchestra

Overview Kick off the new season in style! Superstar mezzo-soprano and 2025/26 CSO Artist-in-Residence Joyce DiDonato joins Nikolaj Szeps-Znaider and the CSO for a celebratory…

Saturday, September 20th
6:30 p.m.8:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
The Infinite Wrench
Sep20
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, September 20th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Darren Fleet at The Comedy Bar
Sep20
Music & Comedy

Darren Fleet at The Comedy Bar

DARREN FLEET has been shaking up pop culture and championing diversity, especially within the LGBTQ+ community, since 2014. Best known for his recurring role on…

Saturday, September 20th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Across The Waters: Song of Memory and Migration
Sep20
Music & Comedy

Across The Waters: Song of Memory and Migration

Àkójọpọ̀ and Hearing in Color welcome you to Across the Waters: Songs of Memory and Migration, a vocal chamber concert that explores the historical and cultural…

Saturday, September 20th
7:00 p.m.9:00 p.m.
2330 West Sunnyside Avenue Chicago, Illinois 60625
Teatro Zinzanni
Sep20
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, September 20th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Ethel Cain- The Willoughby Tucker Forever Tour
Sep20
Music & Comedy

Ethel Cain- The Willoughby Tucker Forever Tour

Florida-born singer, songwriter, producer, and model Ethel Cain will perform live at The Salt Shed Outdoors on Sep. 20, 2025.

Saturday, September 20th
7:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Atif Aslam – Borderless Tour
Sep20
Music & Comedy

Atif Aslam – Borderless Tour

Get ready for an unforgettable musical journey as the sensational Atif Aslam embarks on his highly anticipated North America Tour this September to October 2025!…

Saturday, September 20th
7:00 p.m.10:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
Baby Wants Candy! The Original Completely Improvised Musical
Sep20
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, September 20th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Sep20
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, September 20th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Shakespeare
Sep20
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare

Saturday, September 20th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Hot People Island
Sep20
Music & Comedy, Theatre & Performing Arts

Hot People Island

Hot People Island is a world premiere original comedy by Deana Velandra. In this play, a popular television network will take eight lucky certified Hot…

Saturday, September 20th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Wardruna: World Tour 2025 – Part ll
Sep20
Music & Comedy

Wardruna: World Tour 2025 – Part ll

Norwegian music collective Wardruna will perform live at Auditorium Theatre on Sep. 20, 2025 /w special guest Chelsea Wolfe.

Saturday, September 20th
7:30 p.m.10:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Goose: 2025 Fall Tour
Sep20
Music & Comedy

Goose: 2025 Fall Tour

Goose will perform live at Huntington Bank Pavilion at Northerly Island on Sep. 20, 2025.

Saturday, September 20th
7:30 p.m.10:30 p.m.
ComedySportz Chicago
Sep20
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, September 20th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Sep20
Music & Comedy, Theatre & Performing Arts

The Cosmic Underground Show

Magic. Mind Reading. Comedy. If you’re looking for that off-beat date night, cosmic-level celebration, or just need a laugh, The Cosmic Underground Show is boarding…

Saturday, September 20th
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Pásele
Sep20
Music & Comedy, Theatre & Performing Arts

Pásele

Celebrating Hispanic Heritage Month, ESCÁNDALO Comedy and iO Theater are bringing a new variety show, “Pásele,” featuring some of Chicago’s best Latine improvisers. The four…

Saturday, September 20th
8:30 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
Here 4 A Bit *Naughty Improv
Sep20
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, September 20th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Darren Fleet at The Comedy Bar
Sep20
Music & Comedy

Darren Fleet at The Comedy Bar

DARREN FLEET has been shaking up pop culture and championing diversity, especially within the LGBTQ+ community, since 2014. Best known for his recurring role on…

Saturday, September 20th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
Sep20
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, September 20th
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
Sep20
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, September 20th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stand Up for Pits Comedy Show
Sep21
Music & Comedy

Stand Up for Pits Comedy Show

3PM: DOORS/SILENT AUCTION 6PM: COMEDY SHOW The Stand Up For Pits Foundation (SUFP) is 501c3 nonprofit dedicated to educating, advocating, and saving the lives of…

Sunday, September 21st
6:00 p.m.8:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Wheel of Improv
Sep21
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!)…

Sunday, September 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
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