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Cheap flights from Winnipeg to Caribbean Islands from C$ 247

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 16/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
2 Jun — 9 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Caribbean Islands
Explore the most affordable flight options available from Winnipeg to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 May 2026.

Mon 22/67:00 a.m.
YWG
-
GCM
2 stops29h 45m
WestJet
Tue 11/81:45 p.m.
GCM
-
YWG
2 stops24h 30m
WestJet
Deal found 30/4C$ 511
Mon 1/65:10 p.m.
YWG
-
MBJ
1 stop18h 10m
Air Canada
Mon 8/612:30 p.m.
MBJ
-
YWG
1 stop22h 38m
Air Canada
Deal found 29/4C$ 520
Sun 21/66:00 a.m.
YWG
-
SXM
2 stops31h 20m
WestJet
Thu 25/63:20 p.m.
SXM
-
YWG
2 stops21h 55m
WestJet
Deal found 28/4C$ 537
Tue 9/610:10 a.m.
YWG
-
MBJ
2 stops25h 35m
WestJet
Wed 17/612:45 p.m.
MBJ
-
YWG
2 stops23h 30m
WestJet
Deal found 29/4C$ 550
Tue 9/67:20 p.m.
YWG
-
MBJ
1 stop16h 00m
Air Canada
Wed 17/612:30 p.m.
MBJ
-
YWG
1 stop10h 48m
Air Canada
Deal found 29/4C$ 553
Sat 6/61:25 p.m.
YWG
-
MBJ
2 stops45h 55m
Air Canada
Sat 13/612:30 p.m.
MBJ
-
YWG
1 stop8h 58m
Air Canada
Deal found 2/5C$ 559
Mon 17/86:05 p.m.
YWG
-
AUA
1 stop19h 10m
WestJet
Thu 20/83:05 p.m.
AUA
-
YWG
1 stop10h 50m
WestJet
Deal found 28/4C$ 559
Sun 14/65:10 a.m.
YWG
-
MBJ
1 stop30h 10m
Air Canada
Thu 18/612:30 p.m.
MBJ
-
YWG
1 stop22h 45m
Air Canada
Deal found 1/5C$ 560
Sat 6/61:25 p.m.
YWG
-
GCM
2 stops46h 00m
Multiple Airlines
Sat 13/61:45 p.m.
GCM
-
YWG
2 stops24h 20m
Multiple Airlines
Deal found 30/4C$ 563
Mon 27/76:25 p.m.
YWG
-
AUA
2 stops18h 50m
WestJet
Mon 10/83:05 p.m.
AUA
-
YWG
2 stops22h 10m
WestJet
Deal found 1/5C$ 568
Tue 11/82:55 p.m.
YWG
-
AUA
2 stops22h 20m
WestJet
Tue 18/83:05 p.m.
AUA
-
YWG
2 stops22h 10m
WestJet
Deal found 28/4C$ 569
Wed 12/89:05 p.m.
YWG
-
AUA
2 stops16h 10m
WestJet
Thu 20/83:05 p.m.
AUA
-
YWG
1 stop19h 40m
WestJet
Deal found 28/4C$ 572

Find flight deals from Winnipeg to Caribbean Islands

Keep the following information in mind while searching for Winnipeg to Caribbean Islands flight deals. Data was last updated 3 May 2026.

Round-trip from

C$ 511

One-way from

C$ 246

Popular in

December

Cheapest in

April

Average price

C$ 780
WestJet
  • WestJet
  • 22/6-11/8
  • 4 total stops
  • 44h 20m total
  • Winnipeg to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 12/6
  • 1 total stop
  • 11h 20m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 May 2026.
Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 22/6

9:05 p.m.-12:45 p.m.

2 stops15h 40m

George Town Owen Roberts Intl

Tue 11/8

1:45 p.m.-2:15 p.m.

2 stops24h 30m

C$ 511

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 21/6

6:05 p.m.-2:20 p.m.

1 stop19h 15m

Simpson Bay Princess Juliana

Thu 25/6

3:20 p.m.-12:00 p.m.

2 stops21h 40m

C$ 537

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

7:20 p.m.-11:20 a.m.

1 stop16h 00m

Montego Bay Sangster Intl

Thu 18/6

12:30 p.m.-11:20 p.m.

1 stop10h 50m

C$ 557

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 5/6

1:25 p.m.-4:30 p.m.

2 stops26h 05m

Punta Cana

Fri 12/6

5:25 p.m.-10:09 a.m.

1 stop17h 44m

C$ 575

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Sun 12/7

6:15 a.m.-2:15 p.m.

1 stop31h 00m

Oranjestad Reina Beatrix

Wed 15/7

3:05 p.m.-12:15 p.m.

2 stops22h 10m

C$ 582

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 8/7

1:30 p.m.-1:35 p.m.

2 stops23h 05m

Nassau Intl

Thu 9/7

6:30 p.m.-4:20 p.m.

1 stop22h 50m

C$ 598

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 23/6

4:15 p.m.-11:45 a.m.

2 stops19h 30m

Montego Bay Sangster Intl

Thu 25/6

12:45 p.m.-9:20 a.m.

2 stops20h 35m

C$ 598

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

9:05 p.m.-11:45 a.m.

2 stops14h 40m

Montego Bay Sangster Intl

Thu 18/6

12:45 p.m.-9:40 p.m.

2 stops32h 55m

C$ 599

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/6

3:15 p.m.-11:20 a.m.

1 stop20h 05m

Montego Bay Sangster Intl

Sat 13/6

12:30 p.m.-9:28 p.m.

1 stop8h 58m

C$ 602

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Mon 27/7

10:45 a.m.-2:15 p.m.

1 stop26h 30m

Oranjestad Reina Beatrix

Mon 10/8

3:05 p.m.-12:55 a.m.

1 stop10h 50m

C$ 607

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 58 resultsSorted by cheapest first
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Best time to book a flight from Winnipeg to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Caribbean Islands

How far ahead should I book a flight from Winnipeg to Caribbean Islands?

To ensure you get the cheapest price possible for a flight from Winnipeg to Caribbean Islands, you should look to book at least 74 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Winnipeg to Caribbean Islands?

Currently, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 188). Flying from Winnipeg to Caribbean Islands in January is currently the most expensive (average of C$ 451). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated 3 May 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andWestJet from Winnipeg to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
436 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.8
Good
547 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,331 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,993 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    If you book a flight to Caribbean Islands from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • How long is the flight from Winnipeg to Caribbean Islands?

    A quick flight from Winnipeg to Caribbean Islands can take about 14h 20m. WestJet provides one of the quickest options available for as low as C$ 822. Winnipeg and Caribbean Islands are separated by a distance of 4461 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Winnipeg to Caribbean Islands?

    The most popular flight routes from Winnipeg to Caribbean Islands are Winnipeg - Punta Cana, Winnipeg - Montego Bay Sangster Intl and Winnipeg - Kingston Norman Manley.

  • Can I find deals for flights from Winnipeg to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Caribbean Islands.

  • Can I find deals for business class flights from Winnipeg to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Winnipeg to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Caribbean Islands?

    Currently, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 188). Flying from Winnipeg to Caribbean Islands in January is currently the most expensive (average of C$ 451). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 4 airlines flying from Winnipeg to Caribbean Islands

Discover the top 4 airlines that operate flights from Winnipeg to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 382AverageC$ 766FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 470AverageC$ 798FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 490AverageC$ 730FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air TransatCheapestC$ 782AverageC$ 905FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Caribbean Islands?

When you search for this flight from Winnipeg to Caribbean Islands, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Caribbean Islands?

Cheapflights helps you find that perfect flight to Caribbean Islands from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Winnipeg to Caribbean Islands with no change fees?

Need flexible booking options for your flight to Caribbean Islands from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Winnipeg to Caribbean Islands become cheaper?

Yes! Start tracking prices for Winnipeg to Caribbean Islands flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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