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Trapped in a Musical – an improvised musical
Oct24
Music & Comedy, Theatre & Performing Arts

Trapped in a Musical – an improvised musical

Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…

Friday, October 24th
9:00 p.m.10:00 p.m.
Voila: The Improvised Musical
Oct24
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, October 24th
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
Oct24
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, October 24th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
ComedySportz Chicago
Oct25
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 25th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Dinner Detective True Crime Murder Mystery Dinner Show – Chicago, IL
Oct25
Music & Comedy

The Dinner Detective True Crime Murder Mystery Dinner Show – Chicago, IL

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, October 25th
6:00 p.m.9:00 p.m.
Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario St
The Infinite Wrench
Oct25
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, October 25th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
Oct25
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, October 25th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Chicago Composers Orchestra: refracted | mythos
Oct25
Music & Comedy

Chicago Composers Orchestra: refracted | mythos

Showcasing the depth and variety in contemporary American orchestral music through captivating works by American composers Soomin Kim, Paul Novak, Alexa Rinn and Evan Williams.…

Saturday, October 25th
7:30 p.m.8:15 p.m.
Baby Wants Candy! The Original Completely Improvised Musical
Oct25
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, October 25th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct25
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, October 25th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Shakespeare
Oct25
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

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

Saturday, October 25th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Chicago Symphony Orchestra: The Soldier’s Tale
Oct25
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: The Soldier’s Tale

Overview Step into the engrossing world of Stravinsky’s The Soldier’s Tale — a Faustian fable about a soldier-fiddler who makes a pact with the devil — in…

Saturday, October 25th
7:30 p.m.9:40 p.m.
Chicago Symphony Center
220 S Michigan Ave
The Nightmare Before Christmas In Concert
Oct25
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Nightmare Before Christmas In Concert

Venue: The Auditorium Date: October 25, 2025 Time: 7:30 PM Tickets: $69.50-$99.50 What’s this?! Back by popular demand, see one of Tim Burton’s most celebrated films like never before!…

Saturday, October 25th
7:30 p.m.10:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
ComedySportz Chicago
Oct25
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 25th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ben Schwartz & Friends
Oct25
Music & Comedy

Ben Schwartz & Friends

Ben Schwartz and Friends will come to The Chicago Theatre on Saturday, October 25.

Saturday, October 25th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
Oct25
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 25th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Oct25
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 25th
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
Oct25
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 25th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Clued In: Where There’s a Will, There’s a Way
Oct26
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 26th
4:00 p.m.5:30 p.m.
The Second City
1616 N. Wells St.
Herbie Hancock
Oct26
Music & Comedy, Theatre & Performing Arts

Herbie Hancock

Overview A living legend, always looking forward After Herbie Hancock’s 2024 performance at Symphony Center, the Chicago Tribune hailed him as “one of music’s most catalytic forces,”…

Sunday, October 26th
7:00 p.m.9:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Wheel of Improv
Oct26
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 26th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Late Nite Mic With Vik Pandya at The Comedy Bar
Oct27
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 27th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Tuesday Good Show
Oct28
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 28th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tomato Throw Show at The Comedy Bar
Oct28
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 28th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
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