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Cheap flights from Winnipeg to Caribbean Islands from C$ 222

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 28/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 18 December 2025.

Wed 24/125:30 a.m.YWG - NAS
1 stop13h 40mAir Canada
Mon 29/121:15 p.m.NAS - YWG
1 stop22h 01mAir Canada
Deal found 17/12C$ 620
Wed 17/122:20 p.m.YWG - AUA
2 stops21h 20mUnited Airlines
Wed 24/122:50 p.m.AUA - YWG
1 stop23h 07mUnited Airlines
Deal found 16/12C$ 670
Wed 31/127:05 p.m.YWG - PLS
1 stop16h 10mAir Canada
Sat 28/26:40 p.m.PLS - YWG
2 stops26h 48mAir Canada
Deal found 17/12C$ 744
Thu 18/128:40 a.m.YWG - PUJ
1 stop31h 38mUnited Airlines
Thu 25/125:20 p.m.PUJ - YWG
2 stops20h 37mUnited Airlines
Deal found 17/12C$ 750
Sat 27/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 17/12C$ 900
Fri 19/125:30 a.m.YWG - NAS
2 stops30h 05mMultiple Airlines
Fri 26/123:15 p.m.NAS - YWG
1 stop9h 20mMultiple Airlines
Deal found 17/12C$ 902
Wed 31/128:20 p.m.YWG - PUJ
1 stop17h 15mMultiple Airlines
Thu 8/111:55 p.m.PUJ - YWG
2 stops13h 40mMultiple Airlines
Deal found 16/12C$ 915
Tue 30/128:20 p.m.YWG - PUJ
1 stop16h 00mMultiple Airlines
Thu 8/111:55 p.m.PUJ - YWG
2 stops21h 17mMultiple Airlines
Deal found 16/12C$ 980
Wed 31/127:05 p.m.YWG - PUJ
2 stops24h 40mAir Canada
Wed 7/14:00 p.m.PUJ - YWG
2 stops22h 39mAir Canada
Deal found 16/12C$ 992
Tue 16/128:05 p.m.YWG - SJU
2 stops19h 23mWestJet
Tue 23/127:30 a.m.SJU - YWG
2 stops43h 05mWestJet
Deal found 15/12C$ 999
Wed 31/127:05 p.m.YWG - PUJ
2 stops24h 40mAir Canada
Thu 8/15:45 p.m.PUJ - YWG
2 stops18h 31mAir Canada
Deal found 16/12C$ 1,025
Sat 20/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 17/12C$ 1,031

Find 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 18 December 2025.

Round-trip from

C$ 417

One-way from

C$ 222

Popular in

December

Cheapest in

April

Average price

C$ 1,051
31/1-7/2
  • 31/1-7/2
  • 4 total stops
  • 38h 21m total
  • Winnipeg to Caribbean Islands
Search Deals
28/2
  • 28/2
  • 1 total stop
  • 16h 55m total
  • Winnipeg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 170 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 18 December 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

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 31/1

9:00 p.m.-3:12 p.m.

2 stops16h 12m

San Juan Luis Munoz Marin Intl

Sat 7/2

7:00 p.m.-3:09 p.m.

2 stops22h 09m

C$ 417

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 29/3

6:55 p.m.-3:40 p.m.

2 stops43h 45m

Nassau Intl

Fri 3/4

4:50 p.m.-10:07 a.m.

2 stops42h 17m

C$ 488

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

9:00 p.m.-1:44 p.m.

2 stops15h 44m

George Town Owen Roberts Intl

Thu 22/1

2:50 p.m.-11:35 a.m.

1 stop21h 45m

C$ 490

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 10/2

8:05 p.m.-3:40 p.m.

1 stop18h 35m

Nassau Intl

Thu 12/2

8:30 p.m.-11:32 a.m.

1 stop16h 02m

C$ 502

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 11/1

7:30 a.m.-12:31 a.m.

1 stop15h 01m

San Juan Luis Munoz Marin Intl

Sat 17/1

4:35 p.m.-3:07 p.m.

1 stop24h 32m

C$ 506

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 16/1

4:00 p.m.-9:47 a.m.

1 stop15h 47m

San Juan Luis Munoz Marin Intl

Sat 24/1

5:50 p.m.-3:07 p.m.

2 stops23h 17m

C$ 508

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

6:00 a.m.-12:25 p.m.

2 stops53h 25m

George Town Owen Roberts Intl

Thu 22/1

1:30 p.m.-8:28 p.m.

2 stops31h 58m

C$ 510

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Mon 26/1

9:00 p.m.-4:33 p.m.

2 stops17h 33m

Puerto Plata La Union

Sun 8/2

5:30 p.m.-12:39 a.m.

1 stop9h 09m

C$ 510

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 11/1

12:40 p.m.-1:44 p.m.

2 stops24h 04m

George Town Owen Roberts Intl

Thu 15/1

2:50 p.m.-10:41 p.m.

2 stops32h 51m

C$ 510

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 2/3

6:55 p.m.-3:40 p.m.

2 stops19h 45m

Nassau Intl

Wed 4/3

6:15 p.m.-10:40 p.m.

2 stops29h 25m

C$ 513

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

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$ 366). Flying from Winnipeg to Caribbean Islands in August is currently the most expensive (average of C$ 602). 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 18 December 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 18% 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 18 December 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
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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
483 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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
9,093 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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
3,204 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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
10,534 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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
483 reviews
Check prices

Overall

7.8

Comfort

7.3

Crew

8.4

Entertainment

7.1

Food

6.8

Boarding

7.9

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 22h 40m. WestJet provides one of the quickest options available for as low as C$ 661. 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 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$ 253 on WestJet. Other airlines that offer cheap prices include Air Canada from C$ 276 and Air Transat from C$ 361 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 - Montego Bay Sangster Intl, Winnipeg - Punta Cana 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$ 366). Flying from Winnipeg to Caribbean Islands in August is currently the most expensive (average of C$ 602). 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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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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 485AverageC$ 765FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 503AverageC$ 863FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 544AverageC$ 724FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 698AverageC$ 1,085FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Sunwing AirlinesCheapestC$ 733AverageC$ 1,278FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 801AverageC$ 918FlexibilityNo 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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