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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 BlvdMusic & 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 AveFestivals, 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 StreetMusic & 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 StMusic & 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 DriveMusic & 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.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 FloorMusic & 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.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.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.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 AveMusic & 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 StMusic & 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…
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.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 DriveMusic & 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!)…
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…
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…
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.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 AveMusic & 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.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…
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.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.

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