Windsor Comedy Events

The Supervillians Of Comedy

256 Pelissier St 22 Aug 2026

Jim Jefferies

The Colosseum at Caesars Windsor 11 Sep 2026

Jim Jefferies | Official Caesars Ticket + Hotel Packages

The Colosseum at Caesars Windsor 11 Sep 2026

Leo Dufour LIVE Comedy At Tipsy Toucan (Oct 30th)

The Tipsy Toucan 30 Oct 2026

Bert Kreischer at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 1 Oct 2026

Armin Arbabi LIVE Comedy At Tipsy Toucan (Aug 22nd)

The Tipsy Toucan 22 Aug 2026

Jimmy Carr: Laughs Funny

8787 McHugh Street, Windsor, ON, Canada, Ontario N8S 0A1 13 Oct 2026

DJ Demers LIVE Comedy At Tipsy Toucan (Sep 5th)

The Tipsy Toucan 5 Sep 2026

M**der at Walkerville Brewery: A Stand-Up Comedy M**der Mystery

Walkerville Brewery 17 Oct 2026

Nick Burden LIVE Comedy At Tipsy Toucan (Aug 29th)

The Tipsy Toucan 29 Aug 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (Sep 12th)

The Tipsy Toucan 12 Sep 2026

Jimmy Carr

WFCU Centre 12 Oct 2026

Jordan Policicchio Live in Windsor

138 University Ave W 29 Aug 2026

Ben Albert: Live in Windsor

The Tipsy Toucan - Public House 17 Oct 2026

Bert Kreischer

The Colosseum At Caesars Windsor 30 Sep 2026

Alexa Stanton LIVE Comedy At Tipsy Toucan (Aug 15th)

The Tipsy Toucan 15 Aug 2026

The Rule Of Three

Meteor 22 Aug 2026

Next Stop Comedy at The Lion's Head Tavern! - Windsor, ON

Lion's Head Tavern 27 Feb 2026

Danny Martinello LIVE Comedy At Tipsy Toucan (Sep 19th)

The Tipsy Toucan 19 Sep 2026

Jimmy Carr at WFCU Centre

WFCU Centre 13 Oct 2026

Canadian Famous Comedy Tour LIVE at The Tipsy Toucan (Oct 3rd)

The Tipsy Toucan 3 Oct 2026

Going Metal Health Comedy Show

The Hook & Ladder Club Windsor 30 Aug 2026

Roast Court - Stand-Up Comedy Roast Battle Show

Water's Edge Event Centre 29 Aug 2026

Henry Sir: Live In Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 24 Sep 2026

Funnel Fest/Coach & Horses Reunion w/ Devilz By Definition, Georgie Von Porgie, DA, Piesucker

Dominion House Tavern (The DH) 25 Sep 2026

Hannah Osborne LIVE Comedy At Tipsy Toucan (Oct 10th)

The Tipsy Toucan 10 Oct 2026

Customer Appreciation Comedy at Sidelines!

Sidelines Sports Bar & Grill 21 Aug 2026

Freaky Friday: sxy circus bing-oooh!

Meteor 25 Sep 2026

Ron Josol LIVE Comedy At Tipsy Toucan (Nov 7th)

The Tipsy Toucan 7 Nov 2026

James Cummins LIVE Comedy At Tipsy Toucan (Sep 26th)

The Tipsy Toucan 26 Sep 2026

THURST with Kevin Bailey & Friends

261 Pelissier St., Windsor, ON, Canada, Ontario N9A 4K2 27 Aug 2026

Dan Duvall: Live at Windsor Laughs

Windsor Laughs Comedy Club at The Tipsy Toucan 12 Oct 2026

Longform Unleashed: Full-Show Improv

The Shadowbox Theatre 15 Aug 2026

Improv Drop In Event

2345 Edna St, Windsor, ON N8Y 4W8, Canada 9 Jun 2026

Ella Horwedel LIVE Comedy At Tipsy Toucan (Nov 28th)

The Tipsy Toucan 28 Nov 2026

Halloween Edition - M**der at Water's Edge: Stand-Up Comedy M**der Mystery

Water's Edge Event Centre 24 Oct 2026

Hassan Phills: Live in Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 20 Nov 2026

Josh Adams LIVE Comedy At Tipsy Toucan (Dec 12th)

The Tipsy Toucan 12 Dec 2026

Project Polly's Ep Release : A Villain's Masquerade

JJ's Roadhouse 31 Oct 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (Nov 14th)

The Tipsy Toucan 14 Nov 2026