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Comedy Shows in Chicago

All comedy events below have been confirmed by StageCaddy through venue websites or Instagram posts. Click or tap on the green confirmation badge to see when we last verified the information.

Special Event: Sarah Colonna

Special Event: Sarah Colonna

Comedy Vault
September 25th, 2026 12:30 AM
10/26/25

Sarah Colonna – Live at The Comedy Vault | September 24–26, 2026 Sarah Colonna is a stand-up comedian, actor, and New York Times bestselling author known for her sharp humor and fearless honesty. She most recently starred as Angie in Netflix’s hit show “Insatiable” and recurred as Lori in “Shameless” (Seasons 9 & 10). Sarah rose to fame as a popular roundtable regular, writer, and producer on E!’s “Chelsea Lately” and its scripted spin-off “After Lately.” Her film credits include “Back in the Day,” “Paradise,” “Battle Creek,” and “Killing Hasselhoff.” Beyond the screen, she’s the author of two New York Times bestselling books — Life As I Blow It and Has Anyone Seen My Pants? — showcasing her signature mix of humor, vulnerability, and wit.

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Special Event: Sarah Colonna

Special Event: Sarah Colonna

Comedy Vault
September 26th, 2026 12:00 AM
10/26/25

Sarah Colonna – Live at The Comedy Vault | September 24–26, 2026 Sarah Colonna is a stand-up comedian, actor, and New York Times bestselling author known for her sharp humor and fearless honesty. She most recently starred as Angie in Netflix’s hit show “Insatiable” and recurred as Lori in “Shameless” (Seasons 9 & 10). Sarah rose to fame as a popular roundtable regular, writer, and producer on E!’s “Chelsea Lately” and its scripted spin-off “After Lately.” Her film credits include “Back in the Day,” “Paradise,” “Battle Creek,” and “Killing Hasselhoff.” Beyond the screen, she’s the author of two New York Times bestselling books — Life As I Blow It and Has Anyone Seen My Pants? — showcasing her signature mix of humor, vulnerability, and wit.

standupGet Tickets →
Special Event: Sarah Colonna

Special Event: Sarah Colonna

Comedy Vault
September 26th, 2026 2:30 AM
10/26/25

Sarah Colonna – Live at The Comedy Vault | September 24–26, 2026 Sarah Colonna is a stand-up comedian, actor, and New York Times bestselling author known for her sharp humor and fearless honesty. She most recently starred as Angie in Netflix’s hit show “Insatiable” and recurred as Lori in “Shameless” (Seasons 9 & 10). Sarah rose to fame as a popular roundtable regular, writer, and producer on E!’s “Chelsea Lately” and its scripted spin-off “After Lately.” Her film credits include “Back in the Day,” “Paradise,” “Battle Creek,” and “Killing Hasselhoff.” Beyond the screen, she’s the author of two New York Times bestselling books — Life As I Blow It and Has Anyone Seen My Pants? — showcasing her signature mix of humor, vulnerability, and wit.

standupGet Tickets →
Special Event: Sarah Colonna

Special Event: Sarah Colonna

Comedy Vault
September 27th, 2026 12:00 AM
10/26/25

Sarah Colonna – Live at The Comedy Vault | September 24–26, 2026 Sarah Colonna is a stand-up comedian, actor, and New York Times bestselling author known for her sharp humor and fearless honesty. She most recently starred as Angie in Netflix’s hit show “Insatiable” and recurred as Lori in “Shameless” (Seasons 9 & 10). Sarah rose to fame as a popular roundtable regular, writer, and producer on E!’s “Chelsea Lately” and its scripted spin-off “After Lately.” Her film credits include “Back in the Day,” “Paradise,” “Battle Creek,” and “Killing Hasselhoff.” Beyond the screen, she’s the author of two New York Times bestselling books — Life As I Blow It and Has Anyone Seen My Pants? — showcasing her signature mix of humor, vulnerability, and wit.

standupGet Tickets →
Special Event: Sarah Colonna

Special Event: Sarah Colonna

Comedy Vault
September 27th, 2026 2:30 AM
10/26/25

Sarah Colonna – Live at The Comedy Vault | September 24–26, 2026 Sarah Colonna is a stand-up comedian, actor, and New York Times bestselling author known for her sharp humor and fearless honesty. She most recently starred as Angie in Netflix’s hit show “Insatiable” and recurred as Lori in “Shameless” (Seasons 9 & 10). Sarah rose to fame as a popular roundtable regular, writer, and producer on E!’s “Chelsea Lately” and its scripted spin-off “After Lately.” Her film credits include “Back in the Day,” “Paradise,” “Battle Creek,” and “Killing Hasselhoff.” Beyond the screen, she’s the author of two New York Times bestselling books — Life As I Blow It and Has Anyone Seen My Pants? — showcasing her signature mix of humor, vulnerability, and wit.

standupGet Tickets →
Special Event: Harland Williams

Special Event: Harland Williams

Comedy Vault
October 24th, 2026 12:00 AM
7/7/25

Comedian and Actor Harland Williams is known the world over for his hilarious movie roles and outlandish stand up and sketch comedy routines. From his unforgettable roles in films such as Dumb and Dumber, Something about Mary, Half Baked, Rocketman, Sorority Boys, Down Periscope and so many more.Harland has been described as a scene stealing actor whose unique portrayals of his characters keep them etched in the minds of filmgoers everywhere. Add to this his incredible stand up comedy routines, which have been seen on Letterman, The Tonight Show, Conan O’Brian, HBO, Comedy Central and everywhere else.Described as sharp, witty, unpredictable and original; Harland is the true master of joke telling and crowd interaction. His improvisational skills led to him winning the award for best improviser on NBC’s prime time series, ‘Thank God You Are Here’ (available on YouTube ). Harland Williams is the rare comic artist who has managed to master both Stand Up and Sketch comedy and combine them both masterfully into his shows. Fresh, funny and always full of the unexpected, Harland’s incredible shows are not to be missed.

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Special Event: Harland Williams

Special Event: Harland Williams

Comedy Vault
October 24th, 2026 2:30 AM
7/7/25

Comedian and Actor Harland Williams is known the world over for his hilarious movie roles and outlandish stand up and sketch comedy routines. From his unforgettable roles in films such as Dumb and Dumber, Something about Mary, Half Baked, Rocketman, Sorority Boys, Down Periscope and so many more.Harland has been described as a scene stealing actor whose unique portrayals of his characters keep them etched in the minds of filmgoers everywhere. Add to this his incredible stand up comedy routines, which have been seen on Letterman, The Tonight Show, Conan O’Brian, HBO, Comedy Central and everywhere else.Described as sharp, witty, unpredictable and original; Harland is the true master of joke telling and crowd interaction. His improvisational skills led to him winning the award for best improviser on NBC’s prime time series, ‘Thank God You Are Here’ (available on YouTube ). Harland Williams is the rare comic artist who has managed to master both Stand Up and Sketch comedy and combine them both masterfully into his shows. Fresh, funny and always full of the unexpected, Harland’s incredible shows are not to be missed.

standupGet Tickets →

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