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Cheap flights from Winnipeg to Caribbean Islands from C$ 226

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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
21 Apr — 28 Apr1
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 22 March 2026.

Sat 13/68:00 a.m.
YWG
-
MBJ
2 stops27h 45m
WestJet
Sun 21/67:30 p.m.
MBJ
-
YWG
1 stop14h 15m
WestJet
Deal found 21/3C$ 494
Sat 13/69:05 p.m.
YWG
-
MBJ
2 stops14h 40m
WestJet
Sat 27/67:30 p.m.
MBJ
-
YWG
1 stop14h 15m
WestJet
Deal found 19/3C$ 503
Sat 13/610:45 a.m.
YWG
-
MBJ
1 stop7h 45m
WestJet
Wed 24/612:45 p.m.
MBJ
-
YWG
2 stops23h 30m
WestJet
Deal found 19/3C$ 508
Sat 4/48:00 a.m.
YWG
-
MBJ
Nonstop5h 25m
WestJet
Sat 11/42:25 p.m.
MBJ
-
YWG
Nonstop5h 53m
WestJet
Deal found 18/3C$ 514
Fri 10/77:10 p.m.
YWG
-
MBJ
2 stops23h 20m
WestJet
Tue 14/712:45 p.m.
MBJ
-
YWG
1 stop25h 40m
WestJet
Deal found 17/3C$ 517
Sun 26/76:00 a.m.
YWG
-
MBJ
2 stops12h 30m
WestJet
Thu 6/812:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 21/3C$ 520
Sat 30/510:10 a.m.
YWG
-
PUJ
2 stops31h 35m
WestJet
Sat 6/67:40 p.m.
PUJ
-
YWG
2 stops22h 45m
WestJet
Deal found 20/3C$ 534
Sun 26/46:00 a.m.
YWG
-
NAS
2 stops29h 25m
Air Canada
Thu 30/41:15 p.m.
NAS
-
YWG
1 stop26h 59m
Air Canada
Deal found 19/3C$ 539
Sun 31/56:15 a.m.
YWG
-
PUJ
1 stop11h 30m
WestJet
Sat 6/67:40 p.m.
PUJ
-
YWG
2 stops19h 25m
WestJet
Deal found 20/3C$ 557
Tue 7/48:05 p.m.
YWG
-
POP
1 stop18h 22m
WestJet
Tue 14/44:30 p.m.
POP
-
YWG
2 stops32h 17m
WestJet
Deal found 19/3C$ 573
Tue 16/64:25 p.m.
YWG
-
PUJ
1 stop20h 40m
WestJet
Sat 20/67:40 p.m.
PUJ
-
YWG
1 stop15h 05m
WestJet
Deal found 19/3C$ 578
Fri 17/46:00 a.m.
YWG
-
NAS
2 stops35h 40m
Porter Airlines
Fri 24/43:15 p.m.
NAS
-
YWG
1 stop9h 20m
Porter Airlines
Deal found 21/3C$ 584

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 22 March 2026.

Round-trip from

C$ 494

One-way from

C$ 226

Popular in

December

Cheapest in

April

Average price

C$ 837
WestJet
  • WestJet
  • 13/6-21/6
  • 3 total stops
  • 42h 00m total
  • Winnipeg to Caribbean Islands
Search Deals
WestJet
  • WestJet
  • 5/5
  • 2 total stops
  • 17h 15m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 22 March 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

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 26/4

6:00 a.m.-12:25 p.m.

2 stops29h 25m

Nassau Intl

Thu 30/4

1:15 p.m.-3:14 p.m.

1 stop26h 59m

C$ 539

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/6

12:50 p.m.-11:45 a.m.

2 stops22h 55m

Montego Bay Sangster Intl

Sat 27/6

7:30 p.m.-12:55 a.m.

1 stop29h 25m

C$ 543

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Tue 7/4

8:05 p.m.-3:27 p.m.

1 stop18h 22m

Puerto Plata La Union

Tue 14/4

4:30 p.m.-11:47 p.m.

2 stops32h 17m

C$ 573

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 17/4

6:00 a.m.-6:40 p.m.

2 stops35h 40m

Nassau Intl

Fri 24/4

3:15 p.m.-11:35 p.m.

1 stop9h 20m

C$ 584

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 12/4

6:00 a.m.-12:25 p.m.

2 stops29h 25m

Nassau Intl

Thu 16/4

9:10 p.m.-8:17 p.m.

2 stops24h 07m

C$ 584
Quickest round-trip

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 12/4

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

1 stop9h 40m

Nassau Intl

Thu 16/4

8:30 p.m.-11:32 a.m.

1 stop16h 02m

C$ 591

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 17/4

12:00 p.m.-3:40 p.m.

1 stop26h 40m

Nassau Intl

Fri 24/4

4:50 p.m.-10:52 a.m.

1 stop19h 02m

C$ 628

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 24/4

2:00 p.m.-2:57 p.m.

1 stop23h 57m

Nassau Intl

Sat 2/5

1:15 p.m.-11:52 a.m.

2 stops47h 37m

C$ 634

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Sun 5/4

1:45 p.m.-5:25 p.m.

1 stop26h 40m

Providenciales

Thu 9/4

6:40 p.m.-10:09 a.m.

1 stop16h 29m

C$ 637

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 21/5

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

2 stops14h 40m

Montego Bay Sangster Intl

Thu 11/6

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

1 stop12h 10m

C$ 642

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/3

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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

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$ 295). Flying from Winnipeg to Caribbean Islands in February is currently the most expensive (average of C$ 613). 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.

What is the cheapest time of day to fly from YWG to EPX?

Find hourly flight availability from Winnipeg to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 22 March 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Caribbean Islands as you normally would.

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 22 March 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andUnited Airlines 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
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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
426 reviews
Porter Airlines
8.0
Very good
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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
7.7
Good
521 reviews
Porter Airlines
8.0
Very good
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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.
United Airlines
7.4
Good
9,456 reviews
Porter Airlines
8.0
Very good
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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
3,300 reviews
Porter Airlines
8.0
Very good
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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
10,830 reviews
Porter Airlines
8.0
Very good
426 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

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 22h 55m. Air Canada provides one of the quickest options available for as low as C$ 543. Winnipeg and Caribbean Islands are separated by a distance of 3890 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 - Montego Bay Sangster Intl, Winnipeg - Punta Cana and Winnipeg - Puerto Plata La Union.

  • 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$ 295). Flying from Winnipeg to Caribbean Islands in February is currently the most expensive (average of C$ 613). 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 22 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 386AverageC$ 779FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 474AverageC$ 820FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 494AverageC$ 737FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air TransatCheapestC$ 789AverageC$ 914FlexibilityNo 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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