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Cheap flights from Winnipeg to Caribbean from C$ 300

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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
31 Mar — 7 Apr1
1 adult

Cheap flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 26 March 2025.

Round-trip from

C$ 536

One-way from

C$ 300

Popular in

December

Cheapest in

October

Average price

C$ 665

Good round-trip deal

C$ 552 or less
WestJet
  • WestJet
  • 12/4-19/4
  • 2 total stops
  • 51h 53m total
  • Winnipeg to Caribbean
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WestJet
  • WestJet
  • 8/5
  • 2 total stops
  • 40h 53m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Winnipeg to Caribbean.
Search Deals

Find flight deals from Winnipeg to Caribbean

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 26 March 2025.

Sat 12/48:25 p.m.YWG - MBJ
2 stops45h 58mWestJet
Sat 19/42:30 p.m.MBJ - YWG
Nonstop5h 55mWestJet
Deal found 26/3C$ 536
Mon 28/42:35 p.m.YWG - MBJ
1 stop21h 07mMultiple Airlines
Wed 7/512:07 p.m.MBJ - YWG
2 stops28h 21mMultiple Airlines
Deal found 25/3C$ 612
Mon 31/34:25 p.m.YWG - PUJ
2 stops23h 04mUnited Airlines
Sun 6/44:35 p.m.PUJ - YWG
2 stops45h 34mUnited Airlines
Deal found 25/3C$ 632
Fri 11/412:25 p.m.YWG - NAS
2 stops27h 51mWestJet
Tue 15/43:50 p.m.NAS - YWG
1 stop20h 32mWestJet
Deal found 25/3C$ 654
Wed 28/59:05 p.m.YWG - PUJ
2 stops39h 38mWestJet
Sun 1/64:15 p.m.PUJ - YWG
1 stop18h 28mWestJet
Deal found 25/3C$ 655
Tue 1/42:55 p.m.YWG - PUJ
1 stop8h 00mAir Canada
Tue 8/49:50 a.m.PUJ - YWG
1 stop25h 05mAir Canada
Deal found 25/3C$ 674
Fri 27/66:30 p.m.YWG - KIN
2 stops21h 15mWestJet
Wed 2/73:30 p.m.KIN - YWG
2 stops29h 56mWestJet
Deal found 26/3C$ 715
Sat 21/62:35 p.m.YWG - PUJ
1 stop23h 43mMultiple Airlines
Thu 26/64:13 p.m.PUJ - YWG
1 stop25h 15mMultiple Airlines
Deal found 24/3C$ 779
Tue 8/42:20 p.m.YWG - AUA
2 stops24h 00mUnited Airlines
Sat 26/43:10 p.m.AUA - YWG
2 stops22h 59mUnited Airlines
Deal found 25/3C$ 788
Mon 28/44:25 p.m.YWG - MBJ
2 stops22h 45mUnited Airlines
Wed 7/52:40 p.m.MBJ - YWG
2 stops24h 51mUnited Airlines
Deal found 25/3C$ 794
Mon 22/96:55 p.m.YWG - PUJ
1 stop17h 30mAir Transat
Mon 6/102:45 p.m.PUJ - YWG
1 stop28h 15mAir Transat
Deal found 25/3C$ 834
Fri 27/66:30 a.m.YWG - KIN
1 stop8h 00mMultiple Airlines
Wed 2/76:25 p.m.KIN - YWG
1 stop19h 18mMultiple Airlines
Deal found 25/3C$ 861

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

Fly from

Winnipeg

Fly to

Caribbean

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 12/4

8:25 p.m.-6:23 p.m.

2 stops45h 58m

Montego Bay Sangster Intl

Sat 19/4

2:30 p.m.-8:25 p.m.

Nonstop5h 55m

C$ 536

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 28/4

2:35 p.m.-11:42 a.m.

1 stop21h 07m

Montego Bay Sangster Intl

Wed 7/5

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

2 stops28h 21m

C$ 612

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 5/6

5:30 p.m.-1:43 p.m.

2 stops19h 13m

Punta Cana

Tue 10/6

12:25 p.m.-11:41 a.m.

2 stops24h 16m

C$ 629

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Wed 2/4

6:45 p.m.-10:35 p.m.

2 stops26h 50m

Punta Cana

Wed 9/4

9:50 a.m.-9:55 a.m.

1 stop25h 05m

C$ 631

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 11/4

12:25 p.m.-5:16 p.m.

2 stops27h 51m

Nassau Intl

Tue 15/4

3:50 p.m.-11:22 a.m.

1 stop20h 32m

C$ 654

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 12/5

6:30 a.m.-3:18 p.m.

1 stop7h 48m

Punta Cana

Tue 20/5

3:22 p.m.-4:28 p.m.

2 stops26h 06m

C$ 675

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Fri 27/6

6:30 p.m.-3:45 p.m.

2 stops21h 15m

Kingston Norman Manley

Wed 2/7

3:30 p.m.-9:26 p.m.

2 stops29h 56m

C$ 715

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 12/5

2:20 p.m.-3:25 p.m.

2 stops24h 05m

Punta Cana

Tue 20/5

2:20 p.m.-1:09 p.m.

2 stops23h 49m

C$ 758

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Tue 8/4

2:20 p.m.-3:20 p.m.

2 stops24h 00m

Oranjestad Reina Beatrix

Sat 26/4

3:10 p.m.-1:09 p.m.

2 stops22h 59m

C$ 788

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 28/4

4:25 p.m.-3:10 p.m.

2 stops22h 45m

Montego Bay Sangster Intl

Wed 7/5

2:40 p.m.-3:31 p.m.

2 stops24h 51m

C$ 794

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

Showing 1-10 of 25 results
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2
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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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 254). Flying from Winnipeg to Caribbean 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 CB?

Find hourly flight availability from Winnipeg to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 26 March 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 as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 40.0 mm.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 26 March 2025.
United Airlines
7.4
Good
8,608 reviews
Check prices

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.0

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
United Airlines
7.4
Good
8,608 reviews
United Airlines
7.4
Good
8,608 reviews
Check prices

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.0

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
WestJet
7.2
Good
2,785 reviews
United Airlines
7.4
Good
8,608 reviews
Check prices

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.0

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
Air Canada
7.0
Good
8,967 reviews
United Airlines
7.4
Good
8,608 reviews
Check prices

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.0

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
Flair Airlines
6.0
Okay
239 reviews
United Airlines
7.4
Good
8,608 reviews
Check prices

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.0

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

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.

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

    The most popular route from Winnipeg to Caribbean is Winnipeg - Montego Bay Sangster Intl. You may also consider Winnipeg - Punta Cana 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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 254). Flying from Winnipeg to Caribbean 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

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 5 airlines flying from Winnipeg to Caribbean

Discover the top 5 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 26 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 479AverageC$ 843FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 486AverageC$ 797FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 521AverageC$ 864FlexibilityNo 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?

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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