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Cheap flights from Winnipeg to Caribbean from C$ 284

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
9 Jul — 16 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Caribbean

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Caribbean
Explore the most affordable flight options available from Winnipeg to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 June 2026.

Sat 22/84:15 p.m.
YWG
-
SXM
2 stops21h 05m
WestJet
Sun 30/83:20 p.m.
SXM
-
YWG
1 stop10h 35m
WestJet
Deal found 6/6C$ 561
Fri 16/1010:30 p.m.
YWG
-
MBJ
2 stops20h 00m
WestJet
Mon 26/101:55 p.m.
MBJ
-
YWG
2 stops22h 10m
WestJet
Deal found 8/6C$ 626
Sat 1/88:00 a.m.
YWG
-
NAS
2 stops26h 10m
WestJet
Sun 9/812:00 p.m.
NAS
-
YWG
1 stop27h 25m
WestJet
Deal found 6/6C$ 627
Tue 9/66:15 a.m.
YWG
-
PUJ
1 stop30h 50m
WestJet
Wed 17/63:00 p.m.
PUJ
-
YWG
1 stop10h 55m
WestJet
Deal found 6/6C$ 640
Sun 8/115:00 a.m.
YWG
-
NAS
1 stop9h 40m
WestJet
Sun 8/118:30 p.m.
NAS
-
YWG
2 stops49h 35m
WestJet
Deal found 6/6C$ 650
Sun 8/114:55 p.m.
YWG
-
NAS
2 stops21h 45m
WestJet
Wed 18/114:50 p.m.
NAS
-
YWG
2 stops43h 15m
WestJet
Deal found 6/6C$ 662
Tue 8/121:45 p.m.
YWG
-
MBJ
1 stop22h 05m
Air Canada
Fri 18/121:50 p.m.
MBJ
-
YWG
2 stops31h 38m
Air Canada
Deal found 8/6C$ 674
Sat 12/121:45 p.m.
YWG
-
MBJ
2 stops24h 00m
Air Canada
Sat 19/126:20 p.m.
MBJ
-
YWG
1 stop16h 24m
Air Canada
Deal found 8/6C$ 678
Mon 21/97:00 a.m.
YWG
-
SJU
1 stop30h 44m
Air Canada
Fri 25/93:56 p.m.
SJU
-
YWG
1 stop31h 37m
Air Canada
Deal found 8/6C$ 686
Thu 3/95:15 p.m.
YWG
-
MBJ
1 stop18h 05m
Air Canada
Sat 5/912:30 p.m.
MBJ
-
YWG
2 stops31h 31m
Air Canada
Deal found 8/6C$ 690
Sun 5/75:00 a.m.
YWG
-
NAS
1 stop11h 30m
Air Canada
Sun 12/76:30 p.m.
NAS
-
YWG
1 stop17h 45m
Air Canada
Deal found 6/6C$ 692
Sat 5/125:00 a.m.
YWG
-
PLS
1 stop7h 35m
WestJet
Sat 19/122:30 p.m.
PLS
-
YWG
1 stop11h 15m
WestJet
Deal found 7/6C$ 692

Find flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 9 June 2026.

Round-trip from

C$ 561

One-way from

C$ 284

Popular in

December

Cheapest in

April

Average price

C$ 901
WestJet
  • WestJet
  • 22/8-30/8
  • 3 total stops
  • 31h 40m total
  • Winnipeg to Caribbean
Search Deals
WestJet
  • WestJet
  • 11/8
  • 2 total stops
  • 26h 10m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Caribbean 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 9 June 2026.
Use the filters below to find and compare flights from Winnipeg to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 22/8

4:15 p.m.-2:20 p.m.

2 stops21h 05m

Simpson Bay Princess Juliana

Sun 30/8

3:20 p.m.-12:55 a.m.

1 stop10h 35m

C$ 561

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 16/10

6:05 p.m.-6:30 p.m.

1 stop24h 25m

Montego Bay Sangster Intl

Mon 26/10

1:55 p.m.-12:45 a.m.

1 stop10h 50m

C$ 626

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sat 1/8

4:15 p.m.-11:10 a.m.

2 stops17h 55m

Nassau Intl

Sun 9/8

12:00 p.m.-6:10 p.m.

2 stops31h 10m

C$ 633

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 8/11

5:00 a.m.-3:40 p.m.

1 stop9h 40m

Nassau Intl

Wed 18/11

4:50 p.m.-11:05 a.m.

2 stops43h 15m

C$ 668

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 21/9

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Fri 25/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 686
Quickest round-trip

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 5/7

5:00 a.m.-5:30 p.m.

1 stop11h 30m

Nassau Intl

Sun 12/7

6:30 p.m.-10:05 a.m.

2 stops16h 35m

C$ 696

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Sat 5/12

5:00 a.m.-1:35 p.m.

1 stop7h 35m

Providenciales

Sat 19/12

2:30 p.m.-10:50 p.m.

2 stops33h 20m

C$ 708

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 22/9

1:25 p.m.-11:20 a.m.

2 stops21h 55m

Montego Bay Sangster Intl

Sat 26/9

12:30 p.m.-9:57 a.m.

1 stop21h 27m

C$ 731

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 1/7

1:10 p.m.-11:10 a.m.

2 stops45h 00m

Nassau Intl

Sun 5/7

12:00 p.m.-12:00 p.m.

2 stops25h 00m

C$ 750

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 22/9

8:45 a.m.-11:43 a.m.

2 stops26h 58m

Montego Bay Sangster Intl

Sat 26/9

2:40 p.m.-10:33 p.m.

2 stops31h 53m

C$ 767

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 55 resultsSorted by cheapest first
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6

Best time to book a flight from Winnipeg to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 192). Flying from Winnipeg to Caribbean in June is currently the most expensive (average of C$ 487). 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.

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

The price you pay for your flight from Winnipeg to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 72 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated 9 June 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andWestJet from Winnipeg to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
555 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
WestJet
7.2
Good
3,356 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,154 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Caribbean. 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?

    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.

  • How long is the flight from Winnipeg to Caribbean?

    Airlines like WestJet and Air Canada fly from Winnipeg to Caribbean in about 21h 05m. The time it takes to get you to your destination can typically vary by up to 9h 39m. Winnipeg and Caribbean are separated by a distance of 4661 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?

    The most popular route from Winnipeg to Caribbean is Winnipeg - Punta Cana. You may also consider Winnipeg - Montego Bay Sangster Intl or Winnipeg - Nassau Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Caribbean 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?

    Currently, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 192). Flying from Winnipeg to Caribbean in June is currently the most expensive (average of C$ 487). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Winnipeg to Caribbean

Discover the top 4 airlines that operate flights from Winnipeg to Caribbean. 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 9 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 392AverageC$ 868FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 493AverageC$ 871FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 502AverageC$ 749FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air TransatCheapestC$ 802AverageC$ 929FlexibilityNo 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?

When you search for this flight from Winnipeg to Caribbean, 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?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Caribbean for you. Better yet — we are completely free to use.

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

Yes! Cheapflights helps users easily find flights from Winnipeg to Caribbean with no change fees.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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