Fareseeker

Sun flights from Canada

Mexico, the Caribbean and Central America: the cheapest round-trip flight we track to each destination, from Canadian cities.

Hide self-transfer flights Self-transfer: separate tickets, bags rechecked.

Round-trip flights only, in CAD with taxes. One card per destination: the lowest fare we track, its dates and the cheapest month to go. Prices checked less than an hour ago.

Mexico

Round trip
YWG Winnipeg
MZT Mazatlán
Oct 27 to Nov 1 5 nights · 2 stops
$883 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to Mazatlán fares

Caribbean

Cheapest in December
YWG Winnipeg
UVF Saint Lucia
Dec 2 to Dec 9 7 nights · 2 stops
$721 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to Saint Lucia fares
Cheapest in October
YWG Winnipeg
BGI Bridgetown
Oct 28 to Nov 6 9 nights · 2 stops
$856 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to Bridgetown fares
Cheapest in January
YWG Winnipeg
SDQ Santo Domingo
Jan 19 to Jan 30 11 nights · 2 stops
$1,568 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to Santo Domingo fares

Central America

Cheapest in December
YWG Winnipeg
SJO San José
Dec 7 to Dec 15 8 nights · 2 stops
$789 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to San José fares
Cheapest in January
YWG Winnipeg
SAL San Salvador
Jan 16 to Jan 23 7 nights · 2 stops
$1,066 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to San Salvador fares
Cheapest in October
YWG Winnipeg
PTY Panama
Oct 30 to Nov 8 9 nights · 2 stops
$1,338 CAD

This price is a self-transfer (separate tickets, bags rechecked).

All Winnipeg to Panama fares

Instead of Cuba this winter

Canadian airlines suspended their Cuba flights in 2026. These are the closest swaps for a beach week, at today’s lowest fares:

Questions

Are these all-inclusive packages?

No. These are round-trip flights only, in Canadian dollars with taxes included. Checked bags can cost extra with some airlines. Book the flight, then pick any hotel or resort; a flight-only fare is often cheaper than the same week in a package when you already know where you want to stay.

When is the cheapest time to fly south from Canada?

It depends on the destination, which is why each card shows the cheapest departure month we see right now. As a rule, early December and late January beat the holidays and March break, and in our own data booking four to eight weeks ahead has been about 2% under a route’s usual price.

Can I still fly to Cuba from Canada?

Canadian airlines suspended their Cuba flights in 2026, so we are not tracking Cuban fares while that lasts. Check with the airline before planning a trip. The Dominican Republic, Cancun and Jamaica are the closest swaps for a beach week, with current prices below.