Calgary Leads Winnipeg and More as WestJet Pushes Deeper into the Americas with New Winter Flights and Wider Connectivity

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Calgary Leads Winnipeg and More as WestJet Pushes Deeper into the Americas with New Winter Flights and Wider Connectivity. The airline is adding direct links to Brazil, Mexico, Belize, Costa Rica and the Dominican Republic. Meanwhile, more capacity is coming from Regina, Saskatoon and Edmonton. These changes matter because travellers gain easier access to warm-weather destinations, fewer connections and more seasonal choices. With new routes and added frequencies, WestJet is building a broader winter network across the Americas.

WestJet’s New Winter Routes at a Glance

The original five-route announcement focused on winter sun markets, while Calgary–São Paulo was announced separately as another major addition to WestJet’s international network.

Winnipeg Gets Two New Non-Stop Winter Destinations

Winnipeg is receiving two completely new routes.

The first is Winnipeg–Punta Cana, beginning on 28 November 2026 with one flight per week.

The second is Winnipeg–Belize City, launching on 14 December, also with one weekly service.

WestJet is also increasing frequencies from Winnipeg to existing destinations including Cancún, Puerto Vallarta, Los Cabos and Liberia.

The airline says its Latin America and Caribbean capacity from Winnipeg will be 26% higher year on year.

Regina Gains Its First WestJet Non-Stop to Los Cabos

WestJet will begin direct service between Regina and San José del Cabo, the airport serving Los Cabos, on 14 December 2026.

The route will operate once per week.

WestJet describes it as the first time the airline will connect Regina and Los Cabos non-stop.

The broader winter expansion will increase WestJet’s Latin America and Caribbean capacity from Regina by 64% year on year.

Calgary Opens a New Direct Route to Mérida

The new Calgary–Mérida service begins on 17 December 2026 with weekly flights.

WestJet says Mérida will be a new destination for the airline and that, at the time of the announcement, the service represented the only non-stop connection between Western Canada and Mérida.

The route forms part of a larger Calgary–Mexico expansion that also includes more service to Cancún and Los Cabos.

Overall Latin America and Caribbean capacity from Calgary is planned to increase 18% year on year.

Ottawa Gets Direct Access to Costa Rica’s Guanacaste Region

WestJet will launch Ottawa–Liberia service on 20 December 2026, with one weekly flight.

Liberia is a major gateway to Costa Rica’s Guanacaste region.

The official route announcement also notes that Canadian passenger traffic through Guanacaste Airport increased 28% during the first half of 2026 compared with the same period in 2025.

That gives the new Ottawa route a clear leisure-travel focus for the winter season.

Calgary–São Paulo Marks a Major South America Expansion

WestJet’s largest individual winter network development is the new Calgary–São Paulo route.

The outbound service is scheduled to begin on 8 November 2026, with the return starting on 9 November.

Flights will operate three times per week using a Boeing 787-9 Dreamliner.

WestJet says travellers will ultimately be able to connect onward to more than 60 destinations across South America through its partnership with LATAM.

WestJet Plans Its Biggest Latin America and Caribbean Winter Schedule

The new routes are part of a much larger winter programme.

WestJet says its winter 2026–27 Latin America and Caribbean operation will include:

WestJet describes this as its most extensive Latin America and Caribbean schedule yet.

Existing Routes Will Also Get More Capacity

WestJet is not relying only on new destinations.

Several established Canadian gateways will receive substantial increases in winter capacity.

Saskatoon will receive more flights to Puerto Vallarta and Cancún. Edmonton will gain twice as many weekly flights to Los Cabos and Montego Bay, while Winnipeg and Calgary will also see additional flying to established sun destinations.

New Year-Round Services Are Separate from the Winter Launches

WestJet also identifies several routes as new year-round services:

• Calgary–Mexico City
• Calgary–Mazatlán
• Winnipeg–Cancún
• Toronto–Puerto Plata

These should be treated separately from the six newly announced winter routes because some represent extended operating patterns rather than entirely new city pairs.

What the Expansion Means for Travellers

WestJet’s winter 2026–27 schedule gives travellers from Winnipeg, Regina, Calgary and Ottawa more direct access to warm-weather destinations.

The new network reaches the Dominican Republic, Belize, Mexico, Costa Rica and Brazil, while additional frequencies strengthen existing links across the Caribbean and Latin America.

With up to 1,252 weekly flights across 88 non-stop routes, WestJet is positioning the coming winter as its largest Latin America and Caribbean programme to date.

For passengers, the biggest changes are the new direct routes, wider destination choice and significantly higher winter capacity from several Canadian cities.

Calgary Leads Winnipeg and More as WestJet Pushes Deeper into the Americas with New Winter Flights and Wider Connectivity. The reason is clear. Calgary leads the expansion, while Winnipeg and more Canadian cities gain new winter flights and wider connectivity. WestJet pushes deeper into the Americas because demand for warm-weather travel supports more direct services. New routes to Brazil, Mexico, Belize, Costa Rica and the Dominican Republic widen choice. Extra frequencies also strengthen existing markets. For travellers, the result is simpler planning, more nonstop options and stronger access across the Americas during winter, making WestJet’s network broader and more useful.

Image: WestJet