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Cheap flights from Winnipeg to Caribbean Islands from C$ 286

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 16/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
27 Jan — 3 Feb1
1 adult

Cheap flight deals from Winnipeg to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 22 January 2025.

Round-trip from

C$ 551

One-way from

C$ 286
Air Canada
  • Air Canada
  • 28/3-9/4
  • 2 total stops
  • 36h 47m total
  • Winnipeg to Caribbean Islands
16/3
  • 16/3
  • 1 total stop
  • 11h 50m total
  • Winnipeg to Caribbean Islands

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 22 January 2025.

Fri 28/36:45 a.m.YWG - MBJ
2 stops28h 25mAir Canada
Wed 9/41:15 p.m.MBJ - YWG
2 stops30h 30mAir Canada
Deal found 22/1C$ 551
Fri 14/35:00 a.m.YWG - MBJ
1 stop7h 48mWestJet
Wed 19/31:55 p.m.MBJ - YWG
1 stop10h 39mWestJet
Deal found 22/1C$ 554
Mon 24/28:00 a.m.YWG - SJU
1 stop13h 25mMultiple Airlines
Fri 28/28:45 a.m.SJU - YWG
2 stops16h 47mMultiple Airlines
Deal found 22/1C$ 557
Mon 31/36:35 p.m.YWG - ANU
2 stops42h 46mWestJet
Wed 9/43:30 p.m.ANU - YWG
2 stops32h 48mWestJet
Deal found 22/1C$ 584
Tue 25/25:00 a.m.YWG - PUJ
1 stop9h 45mMultiple Airlines
Mon 10/311:38 a.m.PUJ - YWG
2 stops28h 30mMultiple Airlines
Deal found 21/1C$ 593
Wed 22/15:15 p.m.YWG - PUJ
2 stops20h 39mWestJet
Wed 29/15:00 p.m.PUJ - YWG
2 stops20h 35mWestJet
Deal found 21/1C$ 601
Sun 23/37:05 p.m.YWG - SJU
2 stops24h 38mAir Canada
Sun 30/32:25 p.m.SJU - YWG
2 stops18h 57mAir Canada
Deal found 22/1C$ 610
Thu 23/11:00 p.m.YWG - POP
2 stops48h 45mWestJet
Wed 5/24:40 p.m.POP - YWG
2 stops18h 28mWestJet
Deal found 22/1C$ 644
Wed 22/16:45 a.m.YWG - PUJ
1 stop13h 30mAir Canada
Wed 29/110:50 a.m.PUJ - YWG
1 stop25h 17mAir Canada
Deal found 22/1C$ 653
Tue 4/25:00 a.m.YWG - MBJ
1 stop7h 48mMultiple Airlines
Tue 11/21:45 p.m.MBJ - YWG
2 stops21h 22mMultiple Airlines
Deal found 22/1C$ 657
Mon 27/17:05 p.m.YWG - POP
1 stop15h 20mAir Canada
Tue 4/24:00 p.m.POP - YWG
1 stop26h 28mAir Canada
Deal found 22/1C$ 695
Mon 24/22:15 p.m.YWG - PUJ
1 stop24h 56mUnited Airlines
Tue 11/312:00 p.m.PUJ - YWG
2 stops26h 27mUnited Airlines
Deal found 21/1C$ 697

Find flights from Winnipeg to Caribbean Islands within your budget

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 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 16/3

8:00 a.m.-1:27 p.m.

Nonstop5h 27m

Montego Bay Sangster Intl

Sun 23/3

7:25 p.m.-3:35 p.m.

2 stops44h 10m

C$ 550

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/3

7:05 p.m.-11:10 a.m.

1 stop16h 05m

Montego Bay Sangster Intl

Wed 9/4

1:15 p.m.-9:57 a.m.

1 stop20h 42m

C$ 551

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 24/2

8:00 a.m.-11:25 p.m.

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Fri 28/2

8:45 a.m.-11:32 p.m.

2 stops16h 47m

C$ 557

WinnipegSt. John's

YWG - ANU

YWGANU

Winnipeg

Mon 31/3

6:35 p.m.-2:21 p.m.

2 stops42h 46m

St. John's V.C. Bird Intl

Wed 9/4

3:30 p.m.-11:18 p.m.

2 stops32h 48m

C$ 584

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 25/2

5:00 a.m.-4:45 p.m.

1 stop9h 45m

Punta Cana

Mon 10/3

11:38 a.m.-3:08 p.m.

2 stops28h 30m

C$ 593

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 23/3

7:05 p.m.-8:43 p.m.

2 stops24h 38m

San Juan Luis Munoz Marin Intl

Sun 30/3

2:25 p.m.-8:22 a.m.

2 stops18h 57m

C$ 610

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 4/2

5:00 a.m.-1:48 p.m.

1 stop7h 48m

Montego Bay Sangster Intl

Tue 11/2

1:45 p.m.-10:07 a.m.

2 stops21h 22m

C$ 657

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 19/3

4:35 p.m.-2:41 p.m.

2 stops21h 06m

Puerto Plata La Union

Mon 24/3

3:50 p.m.-12:08 p.m.

2 stops21h 18m

C$ 660

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 24/2

1:45 p.m.-1:45 p.m.

1 stop22h 00m

Punta Cana

Wed 12/3

9:50 p.m.-4:28 p.m.

2 stops19h 38m

C$ 690

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 24/2

2:15 p.m.-5:11 p.m.

1 stop24h 56m

Punta Cana

Tue 11/3

12:00 p.m.-1:27 p.m.

2 stops26h 27m

C$ 697

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/1

Showing 1-10 of 42 results
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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.

Travel insights for flights from Winnipeg to Caribbean Islands

Get recent, data-driven insights about flights from Winnipeg to Caribbean Islands including ideal travel times, pricing trends, and more.

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 May 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 22 January 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 22 January 2025.
To help decide which airline to fly from Winnipeg to Caribbean Islands, see what other customers have to say about Air Canada, United Airlines and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

8.0
Very good
8,514 reviews
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

7.8
Good
381 reviews
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

7.4
Good
8,975 reviews
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

7.2
Good
2,829 reviews
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

7.0
Good
8,635 reviews
8.0
Very good
8,514 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 cheapest airlines to fly from Winnipeg to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as C$ 291 on Air Canada. Other airlines that offer cheap prices include WestJet from C$ 330 and United Airlines from C$ 354 one-way.

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

  • 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 May 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.

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 22 January 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 469AverageC$ 826FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 488AverageC$ 800FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 531AverageC$ 817FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 735AverageC$ 1,232FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 842AverageC$ 1,107FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

Fly with Cheapflights

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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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