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Cheap flights from Winnipeg to Caribbean from C$ 306

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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
29 Apr — 6 May1
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 24 April 2025.

Round-trip from

C$ 589

One-way from

C$ 306

Popular in

July

Cheapest in

October

Average price

C$ 662

Good round-trip deal

C$ 735 or less
12/5-18/5
  • 12/5-18/5
  • 3 total stops
  • 70h 02m total
  • Winnipeg to Caribbean
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7/5
  • 7/5
  • 2 total stops
  • 33h 06m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 119 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).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Winnipeg to Caribbean.
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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 24 April 2025.

Thu 22/56:15 p.m.YWG - MBJ
2 stops17h 27mWestJet
Wed 11/610:30 a.m.MBJ - YWG
2 stops22h 31mWestJet
Deal found 23/4C$ 590
Mon 12/59:00 a.m.YWG - SJU
1 stop25h 31mMultiple Airlines
Sun 18/58:57 p.m.SJU - YWG
2 stops44h 31mMultiple Airlines
Deal found 23/4C$ 601
Tue 20/56:30 a.m.YWG - PUJ
1 stop8h 57mMultiple Airlines
Tue 27/512:02 p.m.PUJ - YWG
2 stops29h 26mMultiple Airlines
Deal found 22/4C$ 665
Sun 4/56:30 a.m.YWG - NAS
1 stop26h 53mWestJet
Thu 8/511:15 a.m.NAS - YWG
1 stop13h 58mWestJet
Deal found 23/4C$ 672
Sun 4/55:00 a.m.YWG - NAS
1 stop11h 30mAir Canada
Thu 8/56:30 p.m.NAS - YWG
1 stop22h 07mAir Canada
Deal found 23/4C$ 706
Thu 1/54:35 p.m.YWG - KIN
1 stop20h 00mAir Canada
Thu 8/51:45 p.m.KIN - YWG
2 stops25h 15mAir Canada
Deal found 24/4C$ 708
Sat 7/65:10 p.m.YWG - MBJ
1 stop18h 32mMultiple Airlines
Sat 14/612:07 p.m.MBJ - YWG
3 stops36h 24mMultiple Airlines
Deal found 23/4C$ 720
Thu 24/44:25 p.m.YWG - NAS
2 stops44h 25mUnited Airlines
Thu 1/52:53 p.m.NAS - YWG
2 stops23h 16mUnited Airlines
Deal found 23/4C$ 752
Tue 3/63:45 p.m.YWG - MBJ
2 stops19h 30mAir Canada
Sun 8/612:10 p.m.MBJ - YWG
2 stops22h 00mAir Canada
Deal found 23/4C$ 758
Fri 16/54:25 p.m.YWG - MBJ
1 stop23h 20mUnited Airlines
Fri 6/64:12 p.m.MBJ - YWG
2 stops25h 52mUnited Airlines
Deal found 23/4C$ 812
Sat 2/810:45 a.m.YWG - PUJ
1 stop25h 58mWestJet
Sat 9/89:30 p.m.PUJ - YWG
2 stops18h 00mWestJet
Deal found 22/4C$ 824
Thu 1/54:30 p.m.YWG - KIN
2 stops22h 00mMultiple Airlines
Thu 8/51:34 p.m.KIN - YWG
3 stops26h 21mMultiple Airlines
Deal found 24/4C$ 842

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 24 April 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

Thu 22/5

6:15 p.m.-11:42 a.m.

2 stops17h 27m

Montego Bay Sangster Intl

Wed 11/6

10:30 a.m.-9:01 a.m.

2 stops22h 31m

C$ 590

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 12/5

9:00 a.m.-11:31 a.m.

1 stop25h 31m

San Juan Luis Munoz Marin Intl

Sun 18/5

8:57 p.m.-4:28 p.m.

2 stops44h 31m

C$ 601

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 20/5

6:30 a.m.-4:27 p.m.

1 stop8h 57m

Punta Cana

Tue 27/5

12:02 p.m.-4:28 p.m.

2 stops29h 26m

C$ 665

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 4/5

6:30 a.m.-10:23 a.m.

1 stop26h 53m

Nassau Intl

Thu 8/5

11:15 a.m.-12:13 a.m.

1 stop13h 58m

C$ 672

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 4/5

5:00 a.m.-5:30 p.m.

1 stop11h 30m

Nassau Intl

Thu 8/5

6:30 p.m.-3:37 p.m.

1 stop22h 07m

C$ 706

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 7/6

5:10 p.m.-11:42 a.m.

1 stop18h 32m

Montego Bay Sangster Intl

Sat 14/6

12:07 p.m.-12:31 a.m.

3 stops36h 24m

C$ 720

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/6

2:50 p.m.-11:15 a.m.

1 stop20h 25m

Montego Bay Sangster Intl

Sun 8/6

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

2 stops22h 00m

C$ 758

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 16/5

4:25 p.m.-3:45 p.m.

1 stop23h 20m

Montego Bay Sangster Intl

Fri 6/6

4:12 p.m.-6:04 p.m.

2 stops25h 52m

C$ 812

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 2/8

10:45 a.m.-1:43 p.m.

1 stop25h 58m

Punta Cana

Sat 9/8

9:30 p.m.-2:30 p.m.

2 stops18h 00m

C$ 824

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 12/5

6:30 a.m.-11:42 p.m.

2 stops16h 12m

San Juan Luis Munoz Marin Intl

Sun 18/5

12:50 p.m.-1:43 p.m.

2 stops25h 53m

C$ 868

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/4

Showing 1-10 of 25 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.

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 24 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 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 24 April 2025.
Air Transat
7.8
Good
385 reviews
Check prices

Boarding

7.9

Overall

7.8

Crew

8.5

Entertainment

7.1

Comfort

7.4

Food

6.7

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Transat
7.8
Good
385 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Boarding

7.9

Overall

7.8

Crew

8.5

Entertainment

7.1

Comfort

7.4

Food

6.7

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
United Airlines
7.4
Good
8,685 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Boarding

7.9

Overall

7.8

Crew

8.5

Entertainment

7.1

Comfort

7.4

Food

6.7

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
WestJet
7.2
Good
2,816 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Boarding

7.9

Overall

7.8

Crew

8.5

Entertainment

7.1

Comfort

7.4

Food

6.7

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Canada
7.0
Good
9,192 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Boarding

7.9

Overall

7.8

Crew

8.5

Entertainment

7.1

Comfort

7.4

Food

6.7

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.

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$ 367), Air Canada (C$ 368), and United Airlines (C$ 447).

  • 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 - Puerto Plata La Union.

  • 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

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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 24 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 464AverageC$ 806FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 471AverageC$ 731FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 504AverageC$ 931FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 710AverageC$ 1,189FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 805AverageC$ 966FlexibilityNo 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?

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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