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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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

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 4 November 2025.

Round-trip from

C$ 483

One-way from

C$ 286

Popular in

November

Cheapest in

April

Average price

C$ 1,157
WestJet
  • WestJet
  • 7/1-28/1
  • 4 total stops
  • 46h 14m total
  • Winnipeg to Caribbean Islands
Search Deals
WestJet
  • WestJet
  • 7/1
  • 2 total stops
  • 25h 38m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 172 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Find flight deals from Winnipeg to Caribbean Islands

Enter your travel dates to find the best prices.

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 4 November 2025.

Wed 19/117:30 a.m.YWG - SJU
2 stops31h 51mMultiple Airlines
Fri 28/116:01 a.m.SJU - YWG
1 stop11h 06mMultiple Airlines
Deal found 2/11C$ 494
Thu 4/129:00 p.m.YWG - SJU
2 stops16h 21mMultiple Airlines
Thu 11/124:31 p.m.SJU - YWG
1 stop24h 36mMultiple Airlines
Deal found 4/11C$ 538
Fri 28/118:40 a.m.YWG - MBJ
1 stop31h 10mUnited Airlines
Fri 5/122:48 p.m.MBJ - YWG
1 stop22h 09mUnited Airlines
Deal found 4/11C$ 539
Wed 24/128:05 p.m.YWG - NAS
1 stop18h 45mWestJet
Wed 31/126:15 p.m.NAS - YWG
1 stop18h 20mWestJet
Deal found 1/11C$ 562
Wed 19/117:30 a.m.YWG - SJU
1 stop15h 36mMultiple Airlines
Thu 27/119:30 p.m.SJU - YWG
2 stops19h 37mMultiple Airlines
Deal found 2/11C$ 570
Tue 4/118:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Fri 14/112:55 p.m.MBJ - YWG
2 stops28h 11mWestJet
Deal found 2/11C$ 577
Tue 23/124:25 p.m.YWG - NAS
1 stop19h 25mMultiple Airlines
Wed 31/126:15 p.m.NAS - YWG
1 stop18h 20mMultiple Airlines
Deal found 2/11C$ 578
Wed 10/125:30 a.m.YWG - PUJ
1 stop14h 05mAir Canada
Wed 17/125:00 p.m.PUJ - YWG
1 stop19h 16mAir Canada
Deal found 3/11C$ 585
Tue 23/129:00 p.m.YWG - NAS
2 stops36h 37mWestJet
Wed 31/126:15 p.m.NAS - YWG
1 stop18h 20mWestJet
Deal found 2/11C$ 595
Tue 4/118:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Mon 10/117:25 p.m.MBJ - YWG
2 stops39h 43mWestJet
Deal found 2/11C$ 606
Fri 28/118:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Fri 5/122:55 p.m.MBJ - YWG
1 stop10h 47mWestJet
Deal found 4/11C$ 609
Thu 4/122:20 p.m.YWG - PUJ
1 stop23h 42mUnited Airlines
Tue 9/1212:56 p.m.PUJ - YWG
2 stops25h 01mUnited Airlines
Deal found 2/11C$ 611

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 4 November 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

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 7/1

4:10 p.m.-4:33 p.m.

2 stops22h 23m

Puerto Plata La Union

Wed 28/1

5:30 p.m.-3:21 p.m.

2 stops23h 51m

C$ 483

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 18/3

12:40 p.m.-3:27 p.m.

2 stops25h 47m

Puerto Plata La Union

Wed 25/3

4:30 p.m.-10:07 a.m.

2 stops18h 37m

C$ 531

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 4/12

9:00 p.m.-3:21 p.m.

2 stops16h 21m

San Juan Luis Munoz Marin Intl

Thu 11/12

4:31 p.m.-6:06 p.m.

2 stops27h 35m

C$ 543

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 24/12

8:05 p.m.-3:50 p.m.

1 stop18h 45m

Nassau Intl

Wed 31/12

6:15 p.m.-11:35 a.m.

1 stop18h 20m

C$ 562

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 6/4

5:00 a.m.-2:30 p.m.

1 stop8h 30m

Punta Cana

Wed 8/4

3:30 p.m.-7:09 p.m.

1 stop28h 39m

C$ 563

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 19/11

7:30 a.m.-1:06 a.m.

1 stop15h 36m

San Juan Luis Munoz Marin Intl

Thu 27/11

9:30 p.m.-3:07 p.m.

2 stops19h 37m

C$ 570

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Mon 6/4

5:00 a.m.-3:27 p.m.

1 stop9h 27m

Puerto Plata La Union

Thu 9/4

4:30 p.m.-11:32 a.m.

1 stop20h 02m

C$ 571

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Tue 3/2

6:45 a.m.-4:27 p.m.

2 stops55h 42m

Puerto Plata La Union

Wed 11/2

5:30 p.m.-11:32 a.m.

1 stop20h 02m

C$ 571

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 23/12

4:25 p.m.-12:50 p.m.

1 stop19h 25m

Nassau Intl

Wed 31/12

6:15 p.m.-11:35 a.m.

1 stop18h 20m

C$ 578

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 24/1

2:20 p.m.-12:59 p.m.

2 stops44h 39m

Punta Cana

Sat 31/1

3:28 p.m.-11:57 a.m.

2 stops22h 29m

C$ 581

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 60 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, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 394). Flying from Winnipeg to Caribbean Islands in August is currently the most expensive (average of C$ 613). 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 4 November 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Winnipeg to Caribbean Islands by exploring options for tickets at noon.

What is the cheapest day to fly from Winnipeg to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Caribbean Islands. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Caribbean Islands flight should consider departing on Thursday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 4 November 2025.
Get a feel of what it's like to fly with Air Transat,United Airlines, andWestJet from Winnipeg to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Transat
7.8
Good
470 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
United Airlines
7.4
Good
8,998 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
WestJet
7.2
Good
3,153 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Canada
7.1
Good
10,400 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Sunwing Airlines
6.7
Okay
36 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Food

6.8

Overall

7.8

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.

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.

  • How long is the flight from Winnipeg to Caribbean Islands?

    A quick flight from Winnipeg to Caribbean Islands can take about 8h 50m. WestJet provides one of the quickest options available for as low as C$ 590. Winnipeg and Caribbean Islands are separated by a distance of 3890 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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 - San Juan Luis Munoz Marin Intl.

  • 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, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 394). Flying from Winnipeg to Caribbean Islands in August is currently the most expensive (average of C$ 613). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Winnipeg to Caribbean Islands

Discover the top 6 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 4 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 494AverageC$ 847FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 510AverageC$ 788FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 519AverageC$ 850FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 711AverageC$ 1,105FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Sunwing AirlinesCheapestC$ 719AverageC$ 1,162FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 816AverageC$ 935FlexibilityNo 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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