Boxing Day Flights
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Find cheap flights over Boxing Day from Canada
Boxing Day is one of Canada's biggest holidays — and one of the busiest travel days of the year. Whether you're escaping the winter cold or taking advantage of the long holiday weekend, booking your Boxing Day flights early is the best way to lock in great fares. Canadians love heading south to the Caribbean, Mexico, and the US, making December 26th a prime departure date. Use Kiwi.com to compare flight deals from Canadian airports and find the best prices for your Boxing Day getaway.
How to find cheap Boxing Day flights from Canada
Boxing Day (December 26) is a major public holiday across Canada and one of the country's biggest travel departure days. Flights from Toronto Pearson (YYZ), Vancouver (YVR), Montreal (YUL) and Calgary (YYC) to sun destinations sell out quickly, making early booking essential. The ideal booking window is August to September, well before families finalise their Christmas plans. Kiwi.com's flexible date calendar lets you compare the full Christmas-to-New-Year window and find whether December 26 or 27 is cheapest for your route. Midweek departures are typically 15–25% cheaper than Boxing Day Saturday flights. Toronto and Vancouver direct services to Mexico, Caribbean and Florida are in the highest demand, so book those routes first.
Top Boxing Day destinations for Canadian travellers
Mexico's Caribbean coast is Canada's top Boxing Day destination: Cancún (CUN) and Riviera Maya are served by direct flights from Toronto, Montreal, Calgary and Vancouver on Air Canada, WestJet and Sunwing. Cuba (Varadero VRA, Havana HAV) is a perennial favourite for Canadians seeking affordable all-inclusive resorts. The Dominican Republic (Punta Cana PUJ) and Jamaica (Montego Bay MBJ) round out the Caribbean options. Florida (Miami MIA, Orlando MCO, Fort Lauderdale FLL) is the most popular US destination for Canadian families. Las Vegas (LAS) and New York (JFK) are popular for couples. British Columbia skiers already at home favour direct hops to Whistler via helicopter, but international skiers consider flying to Reykjavik or Europe for a different experience.
Canadian airlines and Boxing Day travel deals
Air Canada and WestJet are Canada's dominant carriers and both run Boxing Day flight deals online from midnight on December 26, offering discounts on January through March travel. Sunwing specialises in all-inclusive packages to Mexico and Caribbean, with excellent deals during the Boxing Day sale. Flair Airlines and Lynx Air offer low base fares on domestic Canadian routes. For international routes, Air Transat is often the most competitive carrier from Montreal and Toronto to Caribbean and European destinations. Kiwi.com aggregates all these carriers and applies Virtual Interlining to find creative combinations, such as a cheap domestic leg to Toronto connecting with a Sunwing charter to Cancún.
When to book Boxing Day flights from Canada
August and September are the prime booking months for Boxing Day travel from Canada. Sun destination flights to Mexico, Cuba and the Dominican Republic fill up quickly once school families confirm their Christmas holidays. If you miss the early window, prices on popular routes typically spike again in November and December. A cost-saving strategy: fly out on December 27 or 28 rather than Boxing Day itself — often 20–30% cheaper — or return on January 3 or 4 rather than January 1. Sunwing and Air Transat package deals often include hotel, meals and transfers at better prices than booking separately. Use Kiwi.com's fare alert to track prices without checking manually every day.
What travelers say about Kiwi.com
Travelers booking flights with Kiwi.com often highlight the platform's easy booking process, cheap fares, and clear pricing.
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Real customer reviews from travelers who booked with us:
“I had a problem with my return flight as I had a stopover and my first flight was late and made me miss my second flight. kiwi quickly and easily rebooked me on the next flight. the process was transparent and guided by customer service over the phone instead of a machine or chat, which is greatly appreciated in such a delicate situation. I don't usually leave comments or ratings but on this occasion they have earned a positive comment.”
Guillermo D.
“I had heard not great things about kiwi so was really nervous about booking with them. however service was great and flights went smoothly (they even checked in for me!), so it was all in all a terrific experience. I especially liked how quickly they responded to my many queries and how patient they were with me. excellent customer service!”
Marvin Feung W.
“Ability to see prices by day! filters: departure by time, exclude country or airline, etc.!”
Anatolii O.
Updated: April 2026 · Selected reviews from verified customers who rated us 4–5 out of 5. Overall score: 4.5/5 based on 1905 post-booking reviews.
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Frequently asked questions about Boxing Day flights
Is Boxing Day a statutory holiday across all of Canada?
What are the cheapest warm-weather destinations for Canadians at Christmas?
Do Canadian airlines have Boxing Day flight sales?
Is it worth buying a Sunwing or Air Transat package vs booking separately?
What documents do Canadians need to visit Cuba?
How busy is Toronto Pearson airport on Boxing Day?
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