Currently viewing the category: "Travel"
July 14th, 2025

Win a trip to the Osheaga Festival in MontrealWow, the winner of this one gets a real VIP package! The prize includes:
– 2 Platinum Passes to the Osheaga Music Festival
– Air fare & Accommodations
– Shaboozey Meet & Greet
– Backstage Access
– Side Stage Viewing
– Photoshoot
And much more, for a total value ranging from $25,000 to $30,000


Entry Frequency: single

Expires July 23, 2025

Trains and tennis! You can win a VIA trip to either Toronto or Montreal to attend the National Bank Open ($3,000 value). The prize includes rail service, accommodations and tickets.


Entry Frequency: single

Expires July 17, 2025

Blake Shelton fans, you can win a 3-night trip to Edmonton to see him play at the Big Valley Jamboree. The $3,500-value prize includes flights, hotel and tickets. To enter you need to send in a photo and describe why you are Blake’s biggest fan. Note: Can’t find official rules so the expiration date is just a guess.


Entry Frequency: single

Photo/Video required

Expires July 20, 2025

You can win a trip to the windy city to attend the ARC music festival, including flight allowance, accommodations and tickets ($3,000 value).


Entry Frequency: single
Not open to: QC

Expires July 18, 2025
July 12th, 2025

Ah, Dublin! So friendly, so fun. I guarantee you’d have a great time if you win this one – a 2-night trip to Dublin including flights, hotel and tix to see Billie Eilish ($4,000 value).


Entry Frequency: single

Expires July 17, 2025

BC and Ontario residents, it’s another chance to win a trip to Colombia including flights, hotel, cash and a special Corona event ($14,500 value). OR, you could win a Corona fridge and patio prize pack worth $920 or a Corona patio prize pack worth $470.


Entry Frequency: single
Open to: BC, ON

Expires August 25, 2025
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Ontarians, you can win a trip to Hong Kong worth $10,000. It includes flights, hotel and attraction passes.


Entry Frequency: daily
Open to: ON

Expires July 27, 2025
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This one’s for Ontarians only. You can win a trip to Colombia that includes flights, hotel, cash and a Corona event ($17,000 value).


Entry Frequency: daily
Open to: ON

Expires September 27, 2025
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Here’s another chance to win a trip to San Francisco. It includes travel funds, hotel, and tickets to the Stern Music Festival ($3,000 value).


Entry Frequency: single
Not open to: QC

Expires July 24, 2025

Here’s a contest from Coca Cola and you can win a trip to Orlando or San Francisco. Both trips include flights, and hotel. The Florida trip ($19,625 value) also includes a Disney package while the SF trip ($7,115 value) includes some cash. You may need a mobile device to enter.
I am so torn when I see prizes like this. I have lived in San Francisco and love that city dearly, but I’m pretty steadfast in avoiding US travel for the foreseeable future.


Entry Frequency: daily

Membership required

Expires August 24, 2025

Much like the Adventure of a Lifetime contest posted 2 days ago, to enter this one you must live within 60 kms of a Black Press publication location (BC, Alberta, Yukon, NWT & Nunavut. If you do, enter! It’s a great prize of a 3-night trip to Whitehorse including flight, accommodation and tours for a total value of $5,300.


Entry Frequency: unlimited
Open to: BC, AB, YT, NT, NU

Expires December 14, 2025

There are five great prizes of a $5,000 travel voucher here. You can enter in 2 ways: by purchasing a Westjet Vacations package for 1 entry or by the no-purchase postal mail option for 1 entry.


Entry Frequency: single

Expires July 31, 2025
July 11th, 2025

Ontarians, Deerhurst is a fantastic resort, and you can win a gift card for $3,000.


Entry Frequency: single
Open to: ON

Expires July 25, 2025
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July 10th, 2025

Win an Alaskan cruiseOk, there’s 2 grand prizes here of a 7-day Alaskan cruise with Holland America plus a bunch of Sony gear ($12,222 value). For secondary prizes, there are 4 pairs of Sony headphones worth $400. You can enter once via the web form and once through social media (see rules for details).


Entry Frequency: Up to 2 entries
Not open to: QC

Expires September 30, 2025

BC, ON, and QC residents, you can win a little getaway travel package and use of a Ford EV for your road trip ($5,000 value).


Entry Frequency: single
Open to: BC, ON, QC

Expires August 31, 2025

This sounds fun – a 5-night stay in the Muskokas and a boat rental ($5,800 value). You’ll need a boating license to accept the prize.


Entry Frequency: single
Not open to: QC
Boating license required

Expires August 5, 2025

You can win an overnight stay at the Royal York in Toronto, valued at $1,000. Check out the Library Bar while you’re there – great place to sip a whiskey.


Entry Frequency: single
Not open to: QC

Expires August 10, 2025