Oct23Fri
ComedyRandy Feltface
7:00 PM · Vic Theatre
Oct 20 – 31
Comedy in Chicago, IL in October 2026
18 comedy shows in Chicago, IL in October 2026, including Brett Goldstein and Adam Ray.
October 2026
18 events · sorted by date
Oct23FriMultiple datesComedyThe Second City - 113th Mainstage Revue
7:00 PM · Second City-Chicago: Mainstage
Oct23FriComedyAdam Ray: WHO IS ME Tour
7:00 PM · Athenaeum Theatre
Oct23FriComedyVinny Guadagnino
9:30 PM · The Den Theatre
- Oct23FriComedy
Adam Ray: WHO IS ME Tour
9:30 PM · Athenaeum Theatre
- Oct24SatComedy
Vinny Guadagnino
7:15 PM · The Den Theatre
- Oct24SatComedy
Vinny Guadagnino
9:30 PM · The Den Theatre
Oct25SunComedyBrett Goldstein: Sex, Death & Small Talk
4:00 PM · The Chicago Theatre
- Oct25SunComedy
Brett Goldstein: Sex, Death & Small Talk
7:00 PM · The Chicago Theatre
Oct27TueComedyTaylor Tomlinson
6:30 PM · The Den Theatre
Oct27TueComedyJoanne McNally (18+ Event)
7:30 PM · Vic Theatre
- Oct28WedComedy
Taylor Tomlinson
6:30 PM · The Den Theatre
Oct29ThuMultiple datesComedyChicago Comedy Club
6:30 PM · House of Blues Chicago
- Oct29ThuMultiple datesComedy
Chicago Comedy Club
6:30 PM · Foundation Room at House of Blues Chicago
- Oct30FriComedy
Taylor Tomlinson
6:30 PM · The Den Theatre
Oct30FriComedyDon Lemon & DL Hughley: DL + DL 'Anything Goes'
7:30 PM · The Chicago Theatre
- Oct30FriComedy
Taylor Tomlinson
8:45 PM · The Den Theatre
- Oct31SatComedy
Best of The Second City
3:00 PM · The Comedy Bar - Chicago