Windsor Comedy Events

Jimmy Carr: Laughs Funny

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

Weird Al Yankovic at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 4 Jul 2026

Seth Meyers at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 11 Jul 2026

Jimmy Carr

WFCU Centre 12 Oct 2026

Bert Kreischer at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 1 Oct 2026

Dave Merheje-Summer Edition LIVE Comedy At Tipsy Toucan (July 31st)

The Tipsy Toucan 31 Jul 2026

Bert Kreischer

The Colosseum At Caesars Windsor 30 Sep 2026

Weird Al Yankovic with Puddles Piddy Party

The Colosseum at Caesars Windsor 4 Jul 2026

Jimmy Carr at WFCU Centre

WFCU Centre 13 Oct 2026

Seth Meyers

The Colosseum At Caesars Windsor 10 Jul 2026

Jim Jefferies | Official Caesars Ticket + Hotel Packages

The Colosseum at Caesars Windsor 11 Sep 2026

Seth Meyers

The Colosseum at Caesars Windsor 11 Jul 2026

Parking Jimmy Carr

WFCU Centre 13 Oct 2026

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

The Tipsy Toucan 7 Nov 2026

Jim Jefferies

The Colosseum at Caesars Windsor 11 Sep 2026

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

The Tipsy Toucan 19 Sep 2026

Kyle Lucey LIVE Comedy At Tipsy Toucan (July 4th)

The Tipsy Toucan 4 Jul 2026

Jeremy Dobski LIVE Comedy At Tipsy Toucan (July 25th)

The Tipsy Toucan 25 Jul 2026

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

The Tipsy Toucan 22 Aug 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (July 11th)

The Tipsy Toucan 11 Jul 2026

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

The Tipsy Toucan 30 Oct 2026

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

The Tipsy Toucan 12 Dec 2026

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

The Tipsy Toucan 10 Oct 2026

DIRTBALLS (Amish Patel/Gee Gethiga) LIVE Comedy At Tipsy Toucan (July 18th)

The Tipsy Toucan 18 Jul 2026

Hassan Phills: Live in Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 20 Nov 2026

Mid-Summer Comedy Show LIVE At Tipsy Toucan (Aug 1st)

The Tipsy Toucan 1 Aug 2026

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

Walkerville Brewery 17 Oct 2026

Alistair Ogden's Here For You | Live Stand Up Comedy in Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 8 Aug 2026

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

The Tipsy Toucan 28 Nov 2026

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

The Tipsy Toucan 15 Aug 2026

Jordan Policicchio Live in Windsor

138 University Ave W 29 Aug 2026

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

The Tipsy Toucan 29 Aug 2026

YESfest 2026 - Windsor's Improv Comedy Festival

Kordazone Theatre 17 Jul 2026

Funny to be HERE: An afternoon comedy showcase at WindsorEats

WindsorEats Food Hall 11 Jul 2026

Henry Sir: Live In Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 24 Sep 2026

Red Star - Outdoor Patio Street Fest

839 Erie Street East, Windsor, ON, Canada, Ontario N9A 3Y5 25 Jul 2026

Ben Albert: Live in Windsor

The Tipsy Toucan - Public House 17 Oct 2026

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

The Tipsy Toucan 14 Nov 2026

AFTER DARK

The Barbershop Bar 17 Jul 2026

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

Lion's Head Tavern 27 Feb 2026

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

The Tipsy Toucan 12 Sep 2026

The Rule Of Three

Meteor 22 Aug 2026

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

JJ's 31 Oct 2026

Going Metal Health Comedy Show

The Hook & Ladder Club Windsor 30 Aug 2026

Guinea Pigs Don't Wear Pants by Chris Paul Rainbows

Lanspeary Park 9 Aug 2026

KORDA AUDITIONS Little Shop of Horrors (2027 Season)

2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4 6 Jul 2026

Improv Drop In Event

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