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Win a Trip Canada: The Best Travel Contests 2019

May 13, 2019, BY

If you’re like us, you love to travel but don’t love the high costs of family vacations. That’s why we always enter “win a trip Canada” contests for our chance to win amazing vacations.

Whether it be to Disney World, Las Vegas, Europe, or the Caribbean, there are always awesome travel contests available to Canadians.

In this post, we break down some of the best and most popular vacation contests Canada and how to enter them.

Pro tip: Be sure to keep checking our Travel Page to see the latest and greatest travel deals and contests.

Win A Trip Canada: General Guidelines

Before we dive into some of the most popular travel contests Canada, here are some general contest rules to look out for before entering any contests:

  • The most legitimate contests are run directly from the company (e.g. Sunwing giving out a free vacation)
  • Check to make sure you meet the minimum age requirements (many trips to the US or cruise contests require a minimum age of 21)
  • Be sure that the contest is valid in your province/territory of residence.
  • Be sure to check for the expiry date and if the contest is a daily entry

Win A Trip to Disney World or Orlando

win a trip canada

Travel contests for Orlando are always popular and there is almost always 1 free trip to Orlando up for grabs.

The current contest for a trip to Orlando is being run by Visit Orlando.

This contest includes:

  • Round-trip airfare to Orlando, Florida, for the winner and up to 3 guests
  • 4 nights Hotel accommodations
  • 8 single-day, theme park tickets to your choice of Walt Disney World,
  • Universal Orlando or SeaWorld Orlando
  • 5 Day Car Rental

You must be at least 21 years of age to enter this contest, and it is not open to residents of QC.

Disney itself often runs contests for the chance to win a Disney World or Disneyland vacation. There are currently none available, but we will post them as soon as one comes up.

Sunwing Travel Contest: Monthly Entry

win a trip canada

Could you use a Caribbean escape? Let’s be honest, who would really say no to a free all-inclusive vacation?

The sand in your toes, the sun on your skin, and free all you can eat and drink! All these great perks are why all-inclusive vacations are some of the most popular win a trip Canada contests.

Every month, Sunwing gives away 1 free all-inclusive vacation for 2 to Caribbean, Central America, or Mexico.

All you need to do to enter is fill in your information on the sign-up form.

You can enter this giveaway once every month, and a new winner is picked monthly.

Enter now for your chance to win a dream escape to a warm island.

Westjet Contest: Win A Trip Monthly

win a trip canada

Every month Westjet Magazine gives out a free trip.

This month’s trip is for a free trip for 2 to Charlottetown, PEI. The trial ends on May 31st so enter now while you can.

Win a $10,000 Adventure from Goodlife

win a trip canada

If you prefer a more active vacation, this is the contest for you!

This year, Goodlife is giving away a free $10,000 adventure vacation. The prize is awarded as a $10,000 gift certificate to travel company Exodus Travels.

There are also 80,000 Instant Win Prizes available to be won:

• Totes: 15,100 free bags
• 15,100 Towels 
• Phone poppers: 15,100
• 15,100 Buffs 
• 90 Water Bottles 
• 20 Back Packs
• 19,400 Exodus travel vouchers 
• 90 Exodus travel vouchers

This contest is valid from now until December 31st, and is not open to residents of QC.

Linen Chest Contest: Win A Trip to Paris

win a trip canada

Have you ever visited the City of Lights? This Linen Chest contest is your chance!

The Linen Chest is giving out 1 free trip for 2 to Paris worth $5,000! Hurry, because this contest closes on June 30th.

The trip includes:

  • roundtrip airfare to and from Paris
  • 4-nights hotel accommodations in Paris
  • $500 spending money

This is one prize we would love to win!

More Great Contests

We’ll keep adding more Win a Trip Canada contests to this list as they come available, but for now you can check out these other amazing contests and offers on our site:

We collect the best samples, freebies, coupons, deals, sweepstakes, contests and offers (collectively “offers”) from around the internet. The Offers are subject to change. The availability of the Offers we find and distribute are based on location and timing. By using this site, you agree to the web site terms and conditions. You acknowledge that the Offers are from third party entities which may allow you to order, receive or redeem various products and services by businesses that are not owned or operated by us. The delivery, maintenance, and all other matters concerning your transactions with these businesses are solely between you and such business. We are not liable for the accuracy, completeness, or usefulness of such information or the availability of any offers. We are not sponsored or endorsed by any of the third parties reflected on this website. The product names, logos, brands and trademarks shown are the property of the rightful owners.