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Cheap flights from Winnipeg to Caribbean Islands from C$ 279

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 13/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
8 Apr — 15 Apr1
1 adult

Cheap 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 April 2025.

Round-trip from

C$ 628

One-way from

C$ 279

Popular in

December

Cheapest in

October

Average price

C$ 674
WestJet
  • WestJet
  • 12/4-19/4
  • 2 total stops
  • 46h 18m total
  • Winnipeg to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 13/4
  • 2 total stops
  • 29h 30m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Winnipeg to Caribbean Islands

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 April 2025.

Sat 12/48:25 p.m.YWG - MBJ
2 stops40h 23mWestJet
Sat 19/42:30 p.m.MBJ - YWG
Nonstop5h 55mWestJet
Deal found 2/4C$ 628
Fri 11/44:25 p.m.YWG - PUJ
2 stops22h 00mUnited Airlines
Thu 17/42:20 p.m.PUJ - YWG
2 stops47h 49mUnited Airlines
Deal found 2/4C$ 631
Sun 6/46:45 a.m.YWG - PUJ
2 stops29h 00mAir Canada
Sun 13/410:05 p.m.PUJ - YWG
2 stops36h 50mAir Canada
Deal found 2/4C$ 669
Wed 7/59:40 a.m.YWG - PUJ
1 stop13h 02mMultiple Airlines
Tue 13/512:42 p.m.PUJ - YWG
2 stops28h 46mMultiple Airlines
Deal found 2/4C$ 687
Tue 1/710:00 a.m.YWG - PUJ
2 stops27h 23mWestJet
Mon 7/711:45 a.m.PUJ - YWG
2 stops24h 56mWestJet
Deal found 2/4C$ 722
Sat 5/42:20 p.m.YWG - MBJ
2 stops22h 50mUnited Airlines
Sat 12/412:52 p.m.MBJ - YWG
1 stop24h 17mUnited Airlines
Deal found 1/4C$ 765
Sat 3/56:30 a.m.YWG - MBJ
1 stop11h 56mMultiple Airlines
Thu 8/512:07 p.m.MBJ - YWG
2 stops28h 21mMultiple Airlines
Deal found 3/4C$ 768
Mon 28/76:35 p.m.YWG - MBJ
1 stop16h 40mAir Canada
Tue 12/812:10 p.m.MBJ - YWG
2 stops21h 54mAir Canada
Deal found 1/4C$ 801
Mon 22/96:55 p.m.YWG - PUJ
1 stop17h 30mAir Transat
Mon 6/102:45 p.m.PUJ - YWG
1 stop21h 05mAir Transat
Deal found 2/4C$ 831
Thu 24/76:10 a.m.YWG - MBJ
1 stop9h 40mAir Transat
Sun 10/85:00 p.m.MBJ - YWG
1 stop17h 50mAir Transat
Deal found 1/4C$ 883
Fri 16/54:25 p.m.YWG - PLS
2 stops45h 00mUnited Airlines
Wed 21/55:15 p.m.PLS - YWG
2 stops20h 54mUnited Airlines
Deal found 2/4C$ 913
Fri 25/41:40 p.m.YWG - CUR
1 stop22h 50mMultiple Airlines
Fri 2/56:20 p.m.CUR - YWG
2 stops24h 15mMultiple Airlines
Deal found 2/4C$ 944

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 April 2025.
Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.

Fly from

Winnipeg

Fly to

Caribbean Islands

Route

Depart

Return

Price

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Wed 7/5

9:40 a.m.-11:42 p.m.

1 stop13h 02m

Punta Cana

Tue 13/5

12:42 p.m.-4:28 p.m.

2 stops28h 46m

C$ 687

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 21/4

8:00 p.m.-1:00 p.m.

1 stop16h 00m

Punta Cana

Mon 28/4

4:15 p.m.-5:41 p.m.

2 stops26h 26m

C$ 709

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Wed 7/5

2:20 p.m.-12:40 p.m.

2 stops45h 20m

Punta Cana

Tue 13/5

4:35 p.m.-1:09 p.m.

2 stops21h 34m

C$ 761

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 16/5

9:05 p.m.-11:42 a.m.

2 stops14h 37m

Montego Bay Sangster Intl

Fri 6/6

12:45 p.m.-12:13 a.m.

1 stop11h 28m

C$ 764

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 3/5

6:30 a.m.-6:26 p.m.

1 stop11h 56m

Montego Bay Sangster Intl

Thu 8/5

12:07 p.m.-4:28 p.m.

2 stops28h 21m

C$ 768

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 28/7

6:35 p.m.-11:15 a.m.

1 stop16h 40m

Montego Bay Sangster Intl

Tue 12/8

12:10 p.m.-10:04 a.m.

2 stops21h 54m

C$ 801

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 3/5

2:20 p.m.-1:30 p.m.

2 stops23h 10m

Montego Bay Sangster Intl

Thu 8/5

4:12 p.m.-1:09 p.m.

2 stops44h 57m

C$ 820

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 22/9

6:55 p.m.-1:25 p.m.

1 stop17h 30m

Punta Cana

Mon 6/10

2:45 p.m.-10:50 a.m.

1 stop21h 05m

C$ 831

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 24/7

6:10 a.m.-3:50 p.m.

1 stop9h 40m

Montego Bay Sangster Intl

Sun 10/8

5:00 p.m.-10:50 a.m.

1 stop17h 50m

C$ 883

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Fri 16/5

4:25 p.m.-2:25 p.m.

2 stops45h 00m

Providenciales

Wed 21/5

5:15 p.m.-1:09 p.m.

2 stops20h 54m

C$ 913

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 20 results
1
2

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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 254). Flying from Winnipeg to Caribbean Islands in July is currently the most expensive (average of C$ 580). 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 3 April 2025.

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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 40.0 - 180.0 mm per month. October is typically the wettest month, when rainfall can reach 180.0 mm. February is typically the driest time to visit Caribbean Islands when rainfall is around 40.0 mm.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

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 April 2025.
To help decide which airline to fly from Winnipeg to Caribbean Islands, see what other customers have to say about Delta, Air Transat and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good
Air Transat
7.8
Good
382 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good
United Airlines
7.4
Good
8,619 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good
WestJet
7.2
Good
2,795 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good
Air Canada
7.0
Good
9,029 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Colin,Sep 2024

LHR - BOS

Delta One is very poor quality seating for first class. On multiple trips pieces have come off the seat. Staff and food have been good

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.

  • 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 - Oranjestad Reina Beatrix.

  • 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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 254). Flying from Winnipeg to Caribbean Islands in July is currently the most expensive (average of C$ 580). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Winnipeg to Caribbean Islands

Discover the top 5 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 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 479AverageC$ 839FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 486AverageC$ 797FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 521AverageC$ 826FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 733AverageC$ 1,228FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 832AverageC$ 997FlexibilityNo 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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