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Stir Friday Night Presents: The Best of Stir Friday Night! A 30th Anniversary Comedy Celebration
Oct18
Music & Comedy, Theatre & Performing Arts

Stir Friday Night Presents: The Best of Stir Friday Night! A 30th Anniversary Comedy Celebration

Cheers to 30 years! This October, Stir Friday Night, Chicago’s longest-running AAPI comedy team, is celebrating three decades of groundbreaking comedy. Featuring favorite sketches from…

Saturday, October 18th
7:30 p.m.9:30 p.m.
American Blues Theater
5627 N Lincoln Blvd
Chicago Symphony Orchestra: Mäkelä Conducts Symphonie fantastique
Oct18
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: Mäkelä Conducts Symphonie fantastique

Overview Love, witchcraft, murder — it’s all packed into Symphonie fantastique, Berlioz’s thriller about a lovesick artist obsessed with a young actress. Zell Music Director Designate…

Saturday, October 18th
7:30 p.m.9:40 p.m.
Chicago Symphony Center
220 S Michigan Ave
Ear Taxi Festival presents Invictus & An African American Requiem
Oct18
Festivals, Fairs & Special Events, Music & Comedy

Ear Taxi Festival presents Invictus & An African American Requiem

This culminating concert of the 2025 Ear Taxi Festival features the world premiere of Stacy Garrop’s Invictus and Midwestern premiere of Damien Geter’s powerful An…

Saturday, October 18th
7:30 p.m.10:00 p.m.
Harris Theater
205 E. Randolph Street
ComedySportz Chicago
Oct18
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, October 18th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Sarah Millican – Late Bloomer Tour
Oct18
Music & Comedy

Sarah Millican – Late Bloomer Tour

When Sarah Millican was a child, she wouldn’t say boo to a goose. Quiet at school, not many friends, no boobs ‘til she was 16. Now? NOW she…

Saturday, October 18th
8:00 p.m.10:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Brandy & Monica: The Boy Is Mine Tour
Oct18
Music & Comedy

Brandy & Monica: The Boy Is Mine Tour

The highly anticipated The Boy Is Mine Tour is coming to United Center on October 18! The iconic GRAMMY Award-winning artists, Brandy and Monica, will…

Saturday, October 18th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Here 4 A Bit *Naughty Improv
Oct18
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, October 18th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Matty Chymbor at The Comedy Bar
Oct18
Music & Comedy

Matty Chymbor at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Matty Chymbor is an LA based…

Saturday, October 18th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
Oct18
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, October 18th
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
Oct18
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, October 18th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
SCP Piano: Yunchan Lim
Oct19
Music & Comedy, Theatre & Performing Arts

SCP Piano: Yunchan Lim

Overview Yunchan Lim, who at 18 became the youngest-ever winner of the Van Cliburn Competition, climbs the summit of Baroque keyboard music in Bach’s Goldberg Variations. A…

Sunday, October 19th
3:00 p.m.4:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Kurbasy
Oct19
Music & Comedy

Kurbasy

Born from Lviv’s progressive Les Kurbas Theatre, Kurbasy channels ancient Ukrainian folklore through tight vocal harmonies, spectral instrumentation, and striking visual storytelling. Their performances are…

Sunday, October 19th
3:00 p.m.4:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Clued In: Where There’s a Will, There’s a Way
Oct19
Music & Comedy, Theatre & Performing Arts

Clued In: Where There’s a Will, There’s a Way

YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the…

Sunday, October 19th
4:00 p.m.5:30 p.m.
The Second City
1616 N. Wells St.
Brian Hooks at The Comedy Bar
Oct19
Music & Comedy

Brian Hooks at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Brian Hooks is a highly prolific…

Sunday, October 19th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Avatar: The Last Airbender in Concert
Oct19
Music & Comedy

Avatar: The Last Airbender in Concert

Avatar: The Last Airbender In Concert presents a live orchestral rendition of the series’ iconic soundtrack, paired with a two-hour special recap of the animated…

Sunday, October 19th
7:00 p.m.9:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Wheel of Improv
Oct19
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, October 19th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Magic Mondays
Oct20
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, October 20th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Late Nite Mic With Vik Pandya at The Comedy Bar
Oct20
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…

Monday, October 20th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Adam Sandler: You’re My Best Friend Tour
Oct20
Music & Comedy

Adam Sandler: You’re My Best Friend Tour

Adam Sandler returns to Chicago! He is bringing his You’re My Best Friend Tour to United Center on October 20, 2025! Adam Sandler needs no…

Monday, October 20th
7:30 p.m.10:00 p.m.
United Center
1901 W Madison St.
Tuesday Good Show
Oct21
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, October 21st
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tate McRae – Miss Possessive Tour
Oct21
Music & Comedy

Tate McRae – Miss Possessive Tour

Tate McRae is bringing her Miss Possessive Tour, with Zara Larsson, to United Center on October 21, 2025! Singer, songwriter, and dancer triple threat Tate…

Tuesday, October 21st
7:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Tomato Throw Show at The Comedy Bar
Oct21
Music & Comedy

Tomato Throw Show at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…

Tuesday, October 21st
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Dermot Kennedy: 2025 North American Fall Tour
Oct21
Music & Comedy

Dermot Kennedy: 2025 North American Fall Tour

Dermot Kennedy will perform live at House Of Blues on Oct. 21, 2025.

Tuesday, October 21st
8:00 p.m.11:00 p.m.
Crowd Work Wednesday at The Comedy Bar
Oct22
Music & Comedy

Crowd Work Wednesday at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…

Wednesday, October 22nd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
bean-night

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