Cheap flights from Winnipeg to Caribbean

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San Juan (SJU)
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Home Caribbean Cheap flights from Winnipeg to Caribbean

How to find the cheapest flight from
Winnipeg (YWG) to Caribbean

All the information you need to plan the best YWG to SJU flight in 2021: compare Winnipeg to Caribbean flight prices with the expected peak season, weather and rainfall in Caribbean.
How far in advance should I book a flight from Winnipeg to Caribbean?

To save on the cost of your flight from Winnipeg to Caribbean, book at least 30 days before your planned departure. Booking around this time can save you about 4% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 552 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 567.

Cheap flights from Winnipeg to Caribbean in June, July 2021

The best prices found for YWG to Caribbean flights for June, July
9 Jul - 16 Jul
C$ 1,173pp
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
PUJ
Punta Cana
PUJ
Punta Cana
Multiple Airlines
     
3 STOPS
YWG
Winnipeg
9 Jul - 16 Jul
C$ 1,215pp
YWG
Winnipeg
Multiple Airlines
 
1 STOP
NAS
Nassau Intl
NAS
Nassau Intl
Multiple Airlines
   
2 STOPS
YWG
Winnipeg
9 Jul - 16 Jul
C$ 1,227pp
YWG
Winnipeg
Multiple Airlines
 
1 STOP
NAS
Nassau Intl
NAS
Nassau Intl
Multiple Airlines
     
3 STOPS
YWG
Winnipeg

Winnipeg to Caribbean 2021 flight deals

Cheap flights to Caribbean from Winnipeg found for this year
4 Dec - 12 Dec
C$ 759pp
YWG
Winnipeg
United Airlines
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
United Airlines
   
2 STOPS
YWG
Winnipeg
28 Dec - 11 Jan
C$ 772pp
YWG
Winnipeg
United Airlines
   
2 STOPS
AUA
Oranjestad Reina Beatrix
AUA
Oranjestad Reina Beatrix
United Airlines
   
2 STOPS
YWG
Winnipeg
29 Dec - 7 Jan
C$ 777pp
YWG
Winnipeg
United Airlines
   
2 STOPS
AUA
Oranjestad Reina Beatrix
AUA
Oranjestad Reina Beatrix
United Airlines
   
2 STOPS
YWG
Winnipeg

Last minute flights from Winnipeg to Caribbean

Late deals on round-trip flights to Caribbean from Winnipeg, departing today and this week
29 Jun - 6 Jul
C$ 2,683pp
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
PUJ
Punta Cana
PUJ
Punta Cana
Multiple Airlines
   
2 STOPS
YWG
Winnipeg
29 Jun - 6 Jul
C$ 3,708pp
YWG
Winnipeg
Multiple Airlines
     
3 STOPS
PUJ
Punta Cana
PUJ
Punta Cana
Multiple Airlines
   
2 STOPS
YWG
Winnipeg

One-way flights to Caribbean from Winnipeg

The cheapest one-way flights from Winnipeg to Caribbean
4:50 a.m. - 7:34 a.m.
Multiple Airlines
2 stops
49h 44m
YWG - SXM
Multiple Airlines
C$ 394
Kiwi.com
10:00 a.m. - 8:25 a.m.
Air Canada
2 stops
21h 25m
YWG - SXM
Air Canada
C$ 418
10:00 a.m. - 8:25 a.m.
Air Canada
2 stops
21h 25m
YWG - SXM
Air Canada
C$ 448
Air Canada

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Winnipeg</span> to <span class="emphasized">Caribbean</span> flights.

Flight FAQs

From Winnipeg to Caribbean

What airport do you fly from for flights from Winnipeg to Caribbean?

Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Caribbean.

Which airlines flying from Winnipeg to Caribbean have flexible cancellations due to COVID-19?

Some of our airline partners flying from Winnipeg to Caribbean have new flexible policies in place due to COVID-19. WestJet, Air Canada, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like WestJet with this kind of flexibility.

Can I find flights from Winnipeg to Caribbean for under C$ 865 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Caribbean for under C$ 865. The cheapest flight booked recently is on United Airlines for just C$ 759, but on average you can expect to pay C$ 845.

Are there direct flights from Winnipeg to Caribbean for under C$ 742 on Cheapflights?

There are no direct flights from Winnipeg to Caribbean, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Winnipeg to Caribbean for under C$ 2,719?

There are currently 2+ open flights from Winnipeg to Caribbean within the next 7 days for less than C$ 2,719.

How popular is this flight route?

The Winnipeg to Caribbean flight path was viewed by 17 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What are the most popular airlines that fly from Winnipeg to Caribbean?

Before booking your flight from Winnipeg to Caribbean check out the most popular airlines for this route: Air Canada, Delta or United Airlines.

What are the most popular routes from Winnipeg to Caribbean?

The most popular flight routes from Winnipeg to Caribbean are Winnipeg - Simpson Bay Princess Juliana, Winnipeg - Montego Bay Sangster Intl and Winnipeg - Punta Cana.

What are the cheapest flights from Winnipeg to Caribbean?

While on average a flight from Winnipeg to Caribbean is generally C$ 404, our data shows the cheapest flight currently is C$ 284. When looking at the most popular route, (Winnipeg - Simpson Bay Princess Juliana), you can expect to pay C$ 929 for that flight.

How long is the flight from Winnipeg to Caribbean?

There are many flights that can get you from Winnipeg to Caribbean in 6h 30m. Fly via WestJet, Delta, or Air Canada to get the fastest option. This flight may include one or multiple stops.

What are the cheapest airlines to flying from Winnipeg to Caribbean round-trip?

Cheapflights users have booked flights from Winnipeg to Caribbean round-trip from C$ 759. Other airlines that can offer you cheap pricing are WestJet, from C$ 789, and Air Canada, from C$ 861.

What are the cheapest airlines to fly from Winnipeg to Caribbean one-way?

C$ 418 is the cheapest one-way deal found within the past few days, from Air Canada.

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Destination points for flights from Winnipeg to Caribbean

Select to see more specific information for flights from Winnipeg to all places in Caribbean.
Flights from Winnipeg to Havana from C$ 1,257 pp
Flights from Winnipeg to Kingston from C$ 1,031 pp
Flights from Winnipeg to Luis Munoz Marin Intl from C$ 665 pp
Flights from Winnipeg to Montego Bay from C$ 1,152 pp
Flights from Winnipeg to Nassau from C$ 892 pp
Flights from Winnipeg to Port-au-Prince from C$ 999 pp
Flights from Winnipeg to Puerto Plata from C$ 877 pp
Flights from Winnipeg to Punta Cana from C$ 919 pp
Flights from Winnipeg to Santo Domingo from C$ 1,553 pp
Flights from Winnipeg to Varadero from C$ 583 pp
Show more

Destination information for Caribbean

Things to know before you go - useful duration and weather info for your trip from Winnipeg to Caribbean.
Today's exchange rate
C$ 1 = $0.81

Airports servicing Winnipeg

Winnipeg (YWG)

Top 6 airlines flying from Winnipeg to Caribbean

The chart below displays the airlines Cheapflights users travelling from Winnipeg to Caribbean choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Aeromexico 		C$ 210 C$ 383 No cancel fee N/A
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Air Transat 		C$ 307 C$ 487 No cancel fee 50%
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Delta 		C$ 180 C$ 508 No cancel fee N/A
Search Delta flights
United Airlines 		C$ 294 C$ 570 No cancel fee 69%
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WestJet 		C$ 213 C$ 580 No cancel fee 60%
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Air Canada 		C$ 298 C$ 615 No cancel fee 67%
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Popular flight searches

Check out other popular destinations found by fellow travellers in 2021.
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