Comedy in Chicago

Bill Burr Live

Thu, Oct 1 · 12:00 AM

The Chicago Theatre · Chicago, IL

Chicago Comedy Club

Thu, Oct 1 · 11:30 PM

Foundation Room at House of Blues Chicago · Chicago, IL

Insecure: The 10th Anniversary Tour

Fri, Oct 2 · 1:00 AM

The Chicago Theatre · Chicago, IL

Bill Burr Live

Sat, Oct 3 · 12:30 AM

The Chicago Theatre · Chicago, IL

Dale McPeek and Very Special Guests!

Sat, Oct 3 · 1:00 AM

Reggies Bananna's Shack · Chicago, IL

Bill Burr Live

Sun, Oct 4 · 12:00 AM

The Chicago Theatre · Chicago, IL

Grief Sucks: A One Man Show By KevOnStage

Sun, Oct 4 · 12:30 AM

Athenaeum Theatre · Chicago, IL

Bill Burr Live

Sun, Oct 4 · 3:00 AM

The Chicago Theatre · Chicago, IL

Starbomb featuring DJ Commander Meouch - Probably The Only Tour Ever

Thu, Oct 8 · 12:00 AM

Aragon Ballroom · Chicago, IL

ROBBY HOFFMAN - Ages 18+

Thu, Oct 8 · 1:00 AM

Vic Theatre · Chicago, IL

Tina Youkhana's Comedy Special!

Thu, Oct 8 · 10:00 PM

Reggies Bananna's Shack · Chicago, IL

Chicago Comedy Club

Thu, Oct 8 · 11:30 PM

Foundation Room at House of Blues Chicago · Chicago, IL

Jerry Seinfeld

Sat, Oct 10 · 12:00 AM

The Chicago Theatre · Chicago, IL

Robby Hoffman

Sat, Oct 10 · 12:00 AM

Vic Theatre · Chicago, IL

Robby Hoffman

Sat, Oct 10 · 2:30 AM

Vic Theatre · Chicago, IL

Jerry Seinfeld

Sat, Oct 10 · 10:00 PM

The Chicago Theatre · Chicago, IL

Jerry Seinfeld

Sun, Oct 11 · 1:00 AM

The Chicago Theatre · Chicago, IL

Brad Williams: The Tall Tales Tour

Sat, Oct 17 · 12:30 AM

The Chicago Theatre · Chicago, IL

Ben Schwartz & Friends

Sun, Oct 18 · 12:00 AM

The Chicago Theatre · Chicago, IL

Sweetest Day Comedy Jam

Sun, Oct 18 · 1:00 AM

Wintrust Arena · Chicago, IL

FOOS GONE WILD: The FOOS GONE WILD Tour 2026

Sun, Oct 18 · 11:30 PM

House of Blues Chicago · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Wed, Oct 21 · 8:00 PM

The Second City Mainstage Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Thu, Oct 22 · 8:00 PM

The Second City Mainstage Theatre · Chicago, IL

Adam Ray

Adam Ray

Fri, Oct 23 · 7:00 PM

Athenaeum Theatre - IL · Chicago, IL

Randy Feltface

Randy Feltface

Fri, Oct 23 · 7:00 PM

Vic Theatre - Chicago · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Fri, Oct 23 · 7:00 PM

The Second City Mainstage Theatre · Chicago, IL

Adam Ray

Adam Ray

Fri, Oct 23 · 9:30 PM

Athenaeum Theatre - IL · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Fri, Oct 23 · 10:00 PM

The Second City Mainstage Theatre · Chicago, IL

Vinny Guadagnino

Sat, Oct 24 · 2:30 AM

The Den Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Sat, Oct 24 · 7:00 PM

The Second City Mainstage Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Sat, Oct 24 · 10:00 PM

The Second City Mainstage Theatre · Chicago, IL

Vinny Guadagnino

Sun, Oct 25 · 12:15 AM

The Den Theatre · Chicago, IL

Vinny Guadagnino

Sun, Oct 25 · 2:30 AM

The Den Theatre · Chicago, IL

Brett Goldstein (15+)

Brett Goldstein

Sun, Oct 25 · 4:00 PM

The Chicago Theatre · Chicago, IL

Brett Goldstein (15+)

Brett Goldstein

Sun, Oct 25 · 7:00 PM

The Chicago Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Sun, Oct 25 · 7:00 PM

The Second City Mainstage Theatre · Chicago, IL

Brett Goldstein: Sex, Death & Small Talk

Mon, Oct 26 · 12:00 AM

The Chicago Theatre · Chicago, IL

Taylor Tomlinson

Taylor Tomlinson

Tue, Oct 27 · 6:30 PM

The Den Theatre · Chicago, IL

Joanne McNally (18+ Event)

Joanne McNally

Tue, Oct 27 · 7:30 PM

Vic Theatre - Chicago · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Tue, Oct 27 · 8:00 PM

The Second City Mainstage Theatre · Chicago, IL

Taylor Tomlinson

Taylor Tomlinson

Wed, Oct 28 · 6:30 PM

The Den Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Wed, Oct 28 · 8:00 PM

The Second City Mainstage Theatre · Chicago, IL

Chicago Comedy Club

Chicago Comedy Club

Thu, Oct 29 · 6:30 PM

Foundation Room at House of Blues Chicago · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Thu, Oct 29 · 8:00 PM

The Second City Mainstage Theatre · Chicago, IL

Taylor Tomlinson

Taylor Tomlinson

Fri, Oct 30 · 6:30 PM

The Den Theatre · Chicago, IL

The Second City - 113th Mainstage Revue

The Second City - 113th Mainstage Revue

Fri, Oct 30 · 7:00 PM

The Second City Mainstage Theatre · Chicago, IL

Don Lemon & DL Hughley

DL Hughley

Fri, Oct 30 · 7:30 PM

The Chicago Theatre · Chicago, IL

Taylor Tomlinson

Taylor Tomlinson

Fri, Oct 30 · 8:45 PM

The Den Theatre · Chicago, IL