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Cheap flights from Winnipeg to Caribbean from C$ 249

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
26 Feb — 5 Mar1
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 21 February 2025.

Round-trip from

C$ 396

One-way from

C$ 249

Popular in

December

Cheapest in

April

Average price

C$ 763

Good round-trip deal

C$ 554 or less

Good one-way deal

C$ 312 or less
26/3-3/4
  • 26/3-3/4
  • 4 total stops
  • 44h 58m total
  • Winnipeg to Caribbean
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WestJet
  • WestJet
  • 5/4
  • 2 total stops
  • 31h 34m 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$ 21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Winnipeg to Caribbean.
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Price to beat on a one-way 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 21 February 2025.

Wed 26/37:30 a.m.YWG - SJU
2 stops25h 14mMultiple Airlines
Thu 3/46:00 a.m.SJU - YWG
2 stops19h 44mMultiple Airlines
Deal found 20/2C$ 396
Sat 22/38:00 a.m.YWG - MBJ
Nonstop5h 27mWestJet
Sat 29/32:30 p.m.MBJ - YWG
Nonstop5h 55mWestJet
Deal found 20/2C$ 521
Wed 26/34:30 p.m.YWG - SJU
2 stops18h 17mUnited Airlines
Wed 2/41:05 a.m.SJU - YWG
2 stops15h 26mUnited Airlines
Deal found 20/2C$ 554
Wed 21/510:45 a.m.YWG - SXM
1 stop25h 30mWestJet
Sun 1/62:10 p.m.SXM - YWG
2 stops19h 51mWestJet
Deal found 20/2C$ 598
Tue 22/45:00 a.m.YWG - PUJ
1 stop8h 50mMultiple Airlines
Tue 29/43:48 p.m.PUJ - YWG
2 stops25h 40mMultiple Airlines
Deal found 18/2C$ 621
Mon 21/46:45 a.m.YWG - PUJ
2 stops14h 50mAir Canada
Mon 28/46:30 a.m.PUJ - YWG
2 stops14h 15mAir Canada
Deal found 18/2C$ 622
Sun 2/38:00 a.m.YWG - MBJ
Nonstop5h 27mMultiple Airlines
Tue 11/312:07 p.m.MBJ - YWG
2 stops27h 01mMultiple Airlines
Deal found 20/2C$ 629
Mon 24/22:15 p.m.YWG - PUJ
1 stop24h 56mUnited Airlines
Mon 3/35:25 p.m.PUJ - YWG
2 stops22h 02mUnited Airlines
Deal found 20/2C$ 631
Thu 22/53:50 p.m.YWG - MBJ
2 stops27h 35mAir Canada
Wed 11/68:20 p.m.MBJ - YWG
1 stop19h 52mAir Canada
Deal found 20/2C$ 696
Sat 22/312:20 p.m.YWG - PUJ
1 stop25h 30mWestJet
Fri 28/38:05 p.m.PUJ - YWG
1 stop16h 17mWestJet
Deal found 19/2C$ 700
Sat 15/35:00 a.m.YWG - NAS
1 stop8h 56mMultiple Airlines
Wed 19/33:50 p.m.NAS - YWG
1 stop9h 44mMultiple Airlines
Deal found 20/2C$ 724
Wed 16/44:25 p.m.YWG - KIN
2 stops46h 15mWestJet
Wed 30/43:30 p.m.KIN - YWG
2 stops32h 11mWestJet
Deal found 20/2C$ 739

Find flights from Winnipeg to Caribbean within your budget

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 21 February 2025.

Fly from

Winnipeg

Fly to

Caribbean

Route

Depart

Return

Price

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 26/3

7:30 a.m.-9:44 a.m.

2 stops25h 14m

San Juan Luis Munoz Marin Intl

Thu 3/4

6:00 a.m.-12:44 a.m.

2 stops19h 44m

C$ 396

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 22/3

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

Nonstop5h 27m

Montego Bay Sangster Intl

Sat 29/3

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

Nonstop5h 55m

C$ 521

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 26/5

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

1 stop21h 07m

Montego Bay Sangster Intl

Tue 3/6

3:33 p.m.-4:28 p.m.

1 stop24h 55m

C$ 550

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 26/3

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

2 stops18h 17m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:05 a.m.-3:31 p.m.

2 stops15h 26m

C$ 554

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Wed 21/5

8:00 a.m.-1:15 p.m.

2 stops28h 15m

Simpson Bay Princess Juliana

Sun 1/6

2:10 p.m.-9:01 a.m.

2 stops19h 51m

C$ 598

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 22/4

5:00 a.m.-2:50 p.m.

1 stop8h 50m

Punta Cana

Tue 29/4

3:48 p.m.-4:28 p.m.

2 stops25h 40m

C$ 621

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 21/4

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

2 stops14h 50m

Punta Cana

Mon 28/4

6:30 a.m.-7:45 p.m.

2 stops14h 15m

C$ 622

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 24/2

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

1 stop24h 56m

Punta Cana

Mon 3/3

5:25 p.m.-1:27 p.m.

2 stops22h 02m

C$ 631

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 18/5

6:30 p.m.-7:25 p.m.

1 stop24h 55m

Montego Bay Sangster Intl

Mon 26/5

8:20 p.m.-9:40 a.m.

1 stop13h 20m

C$ 658

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Sun 2/3

5:00 a.m.-3:41 p.m.

1 stop8h 41m

Puerto Plata La Union

Wed 2/4

3:40 p.m.-12:44 a.m.

2 stops34h 04m

C$ 666

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/2

Showing 1-10 of 37 results
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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.

Travel insights for flights from Winnipeg to Caribbean

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

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 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 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 21 February 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 21 February 2025.
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

Air Transat
7.8
Good
380 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

Air Canada
7.0
Good
8,748 reviews
Delta
8.0
Very good
8,220 reviews
Check prices

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

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

    The cheapest airlines for a one-way flight from Winnipeg to Caribbean are WestJet (C$ 249), United Airlines (C$ 321), and Air Canada (C$ 332).

  • 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 - San Juan Luis Munoz Marin 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 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

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 21 February 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 478AverageC$ 832FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 483AverageC$ 816FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 517AverageC$ 798FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 728AverageC$ 1,176FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 826AverageC$ 991FlexibilityNo 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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