Windsor Comedy Events

Comedy events Happening Next in Windsor, ON

Believe in Magic — A Halloween Evening with Medium Bella 🎃

 1295 Ottawa Street, Windsor, ON, Canada 31 Oct 2025
HALLOWEEN

Windsor Comedy Club Proshow

 468 Erie St E 7 Nov 2025
COMEDY CAD 23

Sebastian Maniscalco at The Colosseum at Caesars Windsor

 The Colosseum at Caesars Windsor 22 Nov 2025

Jason Rouse (Dark N' Dirty Tour) LIVE Comedy at Tipsy Toucan (November 1)

 The Tipsy Toucan 1 Nov 2025
COMEDY

Windsor Comedy Club Proshow

 468 Erie St E 8 Nov 2025
COMEDY CAD 23

Tim Reaburn's Heckle Show at Windsor Comedy Club vol.1

 89 university ave west, Windsor, ON, Canada, Ontario 30 Dec 2025
COMEDY

Jacob Balshin LIVE Comedy At Tipsy Toucan (November 8th)

 The Tipsy Toucan 8 Nov 2025
COMEDY CAD 12 TO 23

Bo Johnson Live in Windsor

 Meteor 14 Dec 2025
COMEDY CAD 22

\Windsor Comedy Club Proshow

 468 Erie St E 29 Nov 2025
COMEDY CAD 23

705 Comedy Tour at The Walkerville Brewery - Windsor

 Walkerville Brewery 15 Nov 2025
COMEDY CAD 28 TO 33

Flannel & Femme: Windsor

 Aloe Lounge 29 Nov 2025
POP-UPS CAD 17

Jeff Paul LIVE Comedy at Tipsy Toucan (November 21-22)

 The Tipsy Toucan 21 Nov 2025
COMEDY CAD 20 TO 25

The Vaudevillianaires' Krampus Ball with Posh Toboggan

 Meteor 20 Dec 2025
CONTESTS

Armin Arbabi LIVE Comedy at Tipsy Toucan (November 29th)

 The Tipsy Toucan 29 Nov 2025
COMEDY CAD 25

Round 8: Funniest comedian in Windsor Competition - a part of The Brewing For Comedy Festival III

 89 university ave west, Windsor, ON, Canada, Ontario 31 Dec 2025
COMEDY

Comedy Juggler Michael Connell "The Circuit" 52

 Royal Canadian Legion, Ambassador & Walkerville Branch 644 Windsor, Ontario 20 Nov 2025
COMEDY

Windsor Comedy Club Proshow

 468 Erie St E 15 Nov 2025
COMEDY CAD 23

Jo Koy at The Colosseum at Caesars Windsor

 The Colosseum at Caesars Windsor 8 Nov 2025
TRIPS-ADVENTURES

Armin Arbabi LIVE Comedy At Tipsy Toucan (December 19-20th)

 The Tipsy Toucan 19 Dec 2025
COMEDY CAD 21 TO 23

Mike Rita LIVE Comedy at Tipsy Toucan (November 7th)

 The Tipsy Toucan 7 Nov 2025
COMEDY CAD 35

Rob Mailloux LIVE Comedy At Tipsy Toucan (December 26-27th)

 The Tipsy Toucan 26 Dec 2025
COMEDY CAD 23

Kenny Vs Spenny Live In Windsor

 RockStar Music Hall 12 Dec 2025
COMEDY CAD 48 TO 99

The Cherry Rock Lounge Presents: Comedy and Dating Games for Singles

The Cherry Rock Lounge 30 Oct 2025
COMEDY

Culturally Inappropriate | STAND UP COMEDY TOUR | 2025

 Meteor 24 Jan 2026
COMEDY CAD 32

Sebastian Maniscalco

 The Colosseum At Caesars Windsor 21 Nov 2025
CALENDAR

Zabrina Douglas LIVE Comedy At Tipsy Toucan (December 5-6th)

 The Tipsy Toucan 5 Dec 2025
COMEDY CAD 21 TO 23

Jo Koy

 The Colosseum At Caesars Windsor 7 Nov 2025
TRIPS-ADVENTURES

The Dirty Show at Windsor Comedy Club

 89 university ave west, Windsor, ON, Canada, Ontario 30 Dec 2025
COMEDY

Sebastian Maniscalco: It Ain't Right Tour

 The Colosseum at Caesars Windsor 22 Nov 2025
THEATRE

Andrew Santino at The Colosseum at Caesars Windsor

 The Colosseum at Caesars Windsor 16 Jan 2026
TRIPS-ADVENTURES

Jo Koy and Friends

 The Colosseum at Caesars Windsor 8 Nov 2025
THEATRE

Courtney Gilmore LIVE Comedy At Tipsy Toucan (November 7-8th)

 1444 Ottawa Street,Windsor,N8X 2G1,CA 7 Nov 2025
COMEDY

Witch - Magic Worth Burning For

 Walkerville Magic Emporium & Theatre 31 Oct 2025
MAGIC-SHOW CAD 38

Late Show Presented by Windsor Comedy Club

 Craft Heads Brewing Company 4 Oct 2024
COMEDY FREE

Hannah Berner

 The Colosseum at Caesars Windsor 20 Feb 2026
TRIPS-ADVENTURES

Sebastian Maniscalco with Mike Yung

 The Colosseum at Caesars Windsor 23 Nov 2025
CONTESTS