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Cheap flights from Winnipeg to Caribbean Islands from C$ 265

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
6 May — 13 May1
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 1 May 2025.

Round-trip from

C$ 589

One-way from

C$ 265

Popular in

July

Cheapest in

October

Average price

C$ 770
WestJet
  • WestJet
  • 29/5-2/6
  • 3 total stops
  • 57h 13m total
  • Winnipeg to Caribbean Islands
Search Deals
WestJet
  • WestJet
  • 3/6
  • 2 total stops
  • 36h 18m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 117 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 May 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 1 May 2025.

Thu 29/510:45 a.m.YWG - MBJ
1 stop24h 57mWestJet
Mon 2/62:55 p.m.MBJ - YWG
2 stops32h 16mWestJet
Deal found 29/4C$ 589
Sat 14/65:30 p.m.YWG - PUJ
2 stops19h 13mWestJet
Sat 21/62:45 p.m.PUJ - YWG
2 stops31h 46mWestJet
Deal found 29/4C$ 615
Tue 13/59:00 a.m.YWG - SJU
1 stop25h 31mMultiple Airlines
Tue 20/59:30 p.m.SJU - YWG
2 stops15h 55mMultiple Airlines
Deal found 29/4C$ 677
Tue 10/65:30 p.m.YWG - PUJ
2 stops19h 13mMultiple Airlines
Tue 17/66:10 a.m.PUJ - YWG
3 stops17h 36mMultiple Airlines
Deal found 30/4C$ 687
Mon 5/54:25 p.m.YWG - NAS
2 stops22h 33mUnited Airlines
Mon 12/55:00 p.m.NAS - YWG
2 stops21h 09mUnited Airlines
Deal found 30/4C$ 692
Sun 8/68:00 a.m.YWG - NAS
2 stops32h 30mAir Canada
Thu 12/66:30 p.m.NAS - YWG
2 stops24h 20mAir Canada
Deal found 30/4C$ 694
Mon 5/56:15 p.m.YWG - NAS
2 stops39h 08mWestJet
Mon 12/511:15 a.m.NAS - YWG
1 stop23h 28mWestJet
Deal found 30/4C$ 745
Sat 5/74:25 p.m.YWG - PUJ
2 stops19h 15mUnited Airlines
Fri 18/74:35 p.m.PUJ - YWG
2 stops21h 34mUnited Airlines
Deal found 29/4C$ 752
Thu 29/56:55 p.m.YWG - MBJ
1 stop16h 47mMultiple Airlines
Tue 3/612:07 p.m.MBJ - YWG
2 stops28h 21mMultiple Airlines
Deal found 30/4C$ 753
Tue 8/76:35 p.m.YWG - PUJ
2 stops17h 50mAir Canada
Mon 21/72:50 p.m.PUJ - YWG
1 stop27h 48mAir Canada
Deal found 29/4C$ 766
Mon 23/67:00 p.m.YWG - MBJ
1 stop16h 10mAir Canada
Mon 30/612:05 p.m.MBJ - YWG
2 stops22h 09mAir Canada
Deal found 29/4C$ 775
Tue 13/59:00 a.m.YWG - SJU
1 stop12h 47mWestJet
Tue 20/57:30 a.m.SJU - YWG
1 stop9h 58mWestJet
Deal found 29/4C$ 808

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 1 May 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

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 29/5

10:45 a.m.-11:42 a.m.

1 stop24h 57m

Montego Bay Sangster Intl

Mon 2/6

2:55 p.m.-11:11 p.m.

2 stops32h 16m

C$ 589

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 14/6

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

2 stops19h 13m

Punta Cana

Sat 21/6

2:45 p.m.-9:31 p.m.

2 stops31h 46m

C$ 615

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 13/5

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

1 stop25h 31m

San Juan Luis Munoz Marin Intl

Tue 20/5

9:30 p.m.-12:25 p.m.

2 stops15h 55m

C$ 677

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 10/6

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

2 stops19h 13m

Punta Cana

Tue 17/6

6:10 a.m.-10:46 p.m.

3 stops17h 36m

C$ 687

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 8/6

8:00 a.m.-5:30 p.m.

2 stops32h 30m

Nassau Intl

Thu 12/6

6:30 p.m.-5:50 p.m.

2 stops24h 20m

C$ 694

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 5/7

4:25 p.m.-12:40 p.m.

2 stops19h 15m

Punta Cana

Fri 18/7

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

2 stops21h 34m

C$ 752

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 29/5

6:55 p.m.-11:42 a.m.

1 stop16h 47m

Montego Bay Sangster Intl

Tue 3/6

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

2 stops28h 21m

C$ 753

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 8/7

5:10 p.m.-1:25 p.m.

2 stops19h 15m

Punta Cana

Mon 21/7

2:50 p.m.-10:14 a.m.

2 stops20h 24m

C$ 766

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/6

7:00 p.m.-11:10 a.m.

1 stop16h 10m

Montego Bay Sangster Intl

Mon 30/6

12:05 p.m.-10:14 a.m.

2 stops22h 09m

C$ 775

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 13/5

9:00 a.m.-10:47 p.m.

1 stop12h 47m

San Juan Luis Munoz Marin Intl

Tue 20/5

7:30 a.m.-4:28 p.m.

1 stop9h 58m

C$ 808

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/4

Showing 1-10 of 30 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.

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 1 May 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 1 May 2025.
To help decide which airline to fly from Winnipeg to Caribbean Islands, see what other customers have to say about Air Transat, United Airlines and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
385 reviews
Check prices

Food

6.7

Comfort

7.4

Crew

8.5

Entertainment

7.1

Overall

7.8

Boarding

7.9

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

Food

6.7

Comfort

7.4

Crew

8.5

Entertainment

7.1

Overall

7.8

Boarding

7.9

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
8,696 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Food

6.7

Comfort

7.4

Crew

8.5

Entertainment

7.1

Overall

7.8

Boarding

7.9

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
2,826 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Food

6.7

Comfort

7.4

Crew

8.5

Entertainment

7.1

Overall

7.8

Boarding

7.9

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
9,245 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Food

6.7

Comfort

7.4

Crew

8.5

Entertainment

7.1

Overall

7.8

Boarding

7.9

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 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$ 265 on WestJet. Other airlines that offer cheap prices include Air Canada from C$ 304 and United Airlines from C$ 322 one-way.

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

    The most popular flight routes from Winnipeg to Caribbean Islands are Winnipeg - Punta Cana, Winnipeg - Montego Bay Sangster Intl and Winnipeg - Willemstad Hato Int..

  • 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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Alternative routes for Winnipeg to Caribbean Islands

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 1 May 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 463AverageC$ 805FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 470AverageC$ 730FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 503AverageC$ 922FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 708AverageC$ 1,186FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 804AverageC$ 964FlexibilityNo 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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