Escape Winter With These New Canadian Sun Routes

New direct flights are expanding winter escape options across the Caribbean, Mexico and Central America.

As winter settles in, Canadian travellers have more reasons than ever to look south. Over the past few months — and with a few more routes launching imminently — airlines have rolled out a wave of new sun destinations from Canadian airports, expanding nonstop access to beach favourites, cultural capitals and resort regions across Mexico, the Caribbean and Central America.

This winter’s flight network that goes well beyond the usual snowbird routes, with new options departing not just from Toronto and Montreal, but from cities like Ottawa and Halifax as well.

Porter Airlines Brings Sun Flying to Ottawa and Toronto

Porter Airlines has made one of the most notable moves this season, launching a slate of new winter sun routes that significantly expand leisure travel options from Eastern Canada.

From Ottawa, travellers now have direct access to several warm-weather destinations that previously required connections. New nonstop flights link the capital to Nassau and Grand Cayman in the Caribbean, as well as Cancún and Puerto Vallarta in Mexico and Liberia in Costa Rica — a gateway to the country’s Pacific beaches and national parks.

Porter has also added similar sun routes from Toronto Pearson, offering nonstop service to the same mix of Caribbean and Mexican destinations, along with Costa Rica. For travellers accustomed to long layovers or indirect routings, these flights represent a meaningful upgrade in convenience — particularly for winter getaways and family travel.

WestJet Expands Access to the Caribbean and Beyond

WestJet is also leaning into winter sun demand with new seasonal routes that broaden access to the Caribbean and Latin America. A new nonstop flight from Toronto to Havana opens the door to Cuba’s capital, pairing culture, history and nearby beach escapes in a single destination.

Out west, WestJet has expanded its Latin American footprint with new seasonal service from Calgary to destinations in Mexico and Central America, reinforcing the city’s role as a major western gateway for sun travel. These additions complement the airline’s already extensive winter schedule and reflect continued interest in destinations that offer more than just beach time.

Air Canada Grows Its Winter Sun Network

Air Canada has rounded out the season with a broad expansion of its winter schedule, adding new and seasonal routes across the Caribbean, Mexico and Latin America. Canadian travellers now have direct access to destinations such as Martinique, Jamaica and the Bahamas from a wider range of departure cities, along with new links to South American hubs and cultural centres.

This expanded network reflects a growing appetite for longer, experience-driven winter trips — whether that means pairing beaches with food and culture, or exploring destinations that feel less familiar than the classic all-inclusive circuit.

What This Means for Your Winter Travel

These new routes signal a shift in how Canadians travel south for the winter. More nonstop flights reduce travel time and friction, while a broader mix of destinations makes it easier to tailor trips around personal interests — from surf and wellness in Costa Rica to culture-forward city breaks in the Caribbean.

Maybe most notably, travellers departing from cities beyond Canada’s largest hubs now have better access to winter sun than ever before. For anyone looking to trade snow boots for sandals this season, the options have never looked brighter.

How to Find Flight Deals Using AI

By Reneé Morrison

Here's your sign to try Google's AI-powered Flight Deals feature.

I wasn’t even thinking about planning a mother-daughter getaway to Paris. I was just playing around with flight searches. I had opened Google Flights and decided to test out its AI Flight Deals feature to see the most heavily discounted nonstop flights from Montreal during the upcoming March spring break. I wasn’t searching for a specific destination, just the best value for direct routes to anywhere.

That’s when Paris appeared. A nonstop, round-trip flight for just over $600 Canadian, luggage included. A few clicks later, I had booked my first solo trip with my seven-year-old daughter. And mais oui, we’re squeezing in a day at Disneyland Paris between croissants and strolls in the Jardin de Luxembourg. 

Why AI works so well for finding travel deals

Previously, my deal-hunting mania revolved around refreshing pages, tracking one route, locking in exact dates. AI works differently. so instead of asking for one specific outcome, your best bet is to give it a bit of flexibility and let it scan patterns at scale.

AI is especially good at:

  • Comparing huge amounts of pricing data quickly

  • Flagging unusual price drops or underpriced routes

  • Responding well to flexible, human-style requests

The trick is learning how to ask better questions.

Here’s a travel prompt you can steal

If you’re using an AI chatbot or planning tool, try something like:

“Find the best-value nonstop flights from Montreal during (insert dates). I’m flexible on destination, prefer flights under X hours, and want luggage included. Focus on routes with recent price drops.”

This works because it mixes clear limits with openness. 

You can easily tweak it:

  • Add the length of your trip, with flexibility (sometimes, the prompt above will show you trips that are unreasonably short, so you can try specifying a range of how long you’d like to be away).

  • Add that you’re looking for warm weather, cultural cities or beach destinations

Where AI fits into trip planning

AI isn’t a booking engine, and it doesn’t need to be. Its real strength is helping you decide where to look before you decide what to book. Even if you prefer to use a travel agency for the actual booking of your trip, it can be useful for helping you spot which destinations will be accessible within your budget.

It’s especially helpful for:

  • Finding destinations you hadn’t considered

  • Comparing direct flights versus connections

  • Confirming what a good value is in terms of fare pricing

  • Narrowing options before heading to airline sites or your agent

Once a flight looks promising, it’s worth clicking through nearly to checkout to confirm the price is still valid. More than once, I’ve followed a deal only to discover the fare disappeared by the time I reached the booking page.

A few practical tips before you book

  • Flexibility matters (a lot). Even a one-day shift can change pricing.

  • Nonstop flights are not always the expensive option, especially on routes airlines want to fill.

  • Always check baggage rules before celebrating a low fare.

  • Think about value, not just price. Better timing or fewer connections can make a slightly higher fare worth it. You’ll end up spending that extra $100 on a mediocre airport lunch.

Happy deal-hunting!