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Win travel

Contests, Challenges & Travel Prizes

Skill-based challenges for Canada's smartest flyers. Prize pools are funded by sponsors and supporters — get notified when each round opens.

Opening soon

Deal Hunter of the Month

Find and submit the best flight deal from a Canadian airport.

How to win
Submit a real, bookable fare with dates and a screenshot. Judged on savings versus our price-watch threshold, usefulness and originality.
Prize
Travel gift card prize pool, announced when the round opens.
Frequency
Monthly
Notify me / enter
Opening soon

Cheap Trip Photo Challenge

Show us a stunning photo from a trip you flew to for less.

How to win
Upload a link to your original photo plus the story of the deal. Judged on photography and the value of the trip.
Prize
Travel gear and gift cards from sponsors.
Frequency
Seasonal
Notify me / enter
Opening soon

Refer-a-Flyer Race

Help friends stop overpaying for flights.

How to win
Share your personal link; confirmed subscribers who sign up count as referrals. Top referrers then answer a skill-based travel quiz.
Prize
Grand prize funded by sponsors and supporters.
Frequency
Quarterly
Notify me / enter

Want bigger prizes? Contest prize pools grow with sponsorships and reader support. Fund a prize or sponsor a contest.

Enter or get notified

You're in the loop

We'll confirm your entry or notify you as soon as the round opens.

Official rules (summary)

Each contest round is governed by specific rules published on this page when the round opens. The following standard terms apply to every CheapFly.ca contest unless the specific rules say otherwise.

  1. Sponsor: CheapFly.ca, together with any co-sponsor named in the round's rules.
  2. Eligibility: legal residents of Canada, excluding Quebec, who have reached the age of majority in their province or territory. Employees of the sponsor and their households are not eligible.
  3. No purchase necessary. Payment or contribution never increases your chances.
  4. Skill: entries are judged on published criteria. Selected entrants must correctly answer a mathematical skill-testing question, without assistance, within a time limit before being declared a winner.
  5. Entry period, prizes and approximate retail value are stated for each round. Prizes must be accepted as awarded and are not transferable unless stated.
  6. Original work: entries must be your own; you grant CheapFly.ca a non-exclusive licence to display them with credit.
  7. Privacy: personal information is used only to run the contest and as described in our privacy policy.
  8. Release: winners may be asked to sign a declaration and release before receiving a prize.

This summary does not replace the full rules for a specific round. Contests are void where prohibited by law.

Frequently asked questions

Who can enter?

Unless the rules for a specific contest say otherwise, contests are open to legal residents of Canada (excluding Quebec) who have reached the age of majority in their province or territory.

Do I have to buy anything?

No. No purchase or payment is ever required to enter or win a CheapFly contest.

Why is there a skill-testing question?

Canadian law requires prize contests to involve skill. Selected winners must correctly answer a time-limited mathematical skill-testing question before receiving a prize.

How are winners chosen?

Skill contests are judged against the published criteria by a panel. Any random-draw element is described in the specific contest rules, including the odds.

Can my business sponsor a prize?

Yes. Sponsors receive recognition across the contest page, newsletter and social posts. See the advertise and partner page or use the form below.