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Cheap flights from Winnipeg to Caribbean from C$ 225

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
22 Aug — 29 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Caribbean

Enter your travel dates to find the best prices.

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 23 July 2026.

Tue 29/94:10 p.m.
YWG
-
NAS
1 stop20h 25m
Air Canada
Sat 3/106:30 p.m.
NAS
-
YWG
1 stop17h 42m
Air Canada
Deal found 19/7C$ 510
Sat 5/122:05 p.m.
YWG
-
NAS
1 stop22h 10m
Air Canada
Sat 12/129:25 p.m.
NAS
-
YWG
1 stop13h 44m
Air Canada
Deal found 18/7C$ 534
Thu 8/108:00 a.m.
YWG
-
NAS
2 stops26h 10m
WestJet
Tue 13/1012:00 p.m.
NAS
-
YWG
2 stops22h 35m
WestJet
Deal found 19/7C$ 536
Wed 19/85:25 p.m.
YWG
-
NAS
1 stop23h 05m
Air Canada
Wed 26/82:35 p.m.
NAS
-
YWG
1 stop20h 30m
Air Canada
Deal found 20/7C$ 543
Tue 29/910:45 a.m.
YWG
-
NAS
1 stop23h 25m
WestJet
Sat 3/1012:00 p.m.
NAS
-
YWG
2 stops34h 40m
WestJet
Deal found 21/7C$ 551
Sat 5/94:10 p.m.
YWG
-
PUJ
1 stop22h 55m
Air Canada
Fri 11/95:05 p.m.
PUJ
-
YWG
1 stop23h 04m
Air Canada
Deal found 19/7C$ 590
Sun 6/94:10 p.m.
YWG
-
PUJ
1 stop22h 55m
Air Canada
Sun 13/95:05 p.m.
PUJ
-
YWG
1 stop23h 04m
Air Canada
Deal found 18/7C$ 592
Tue 15/94:10 p.m.
YWG
-
PUJ
1 stop22h 55m
Air Canada
Tue 29/94:20 p.m.
PUJ
-
YWG
1 stop19h 52m
Air Canada
Deal found 18/7C$ 599
Tue 8/126:15 a.m.
YWG
-
MBJ
1 stop10h 09m
WestJet
Fri 18/128:25 p.m.
MBJ
-
YWG
1 stop16h 10m
WestJet
Deal found 20/7C$ 600
Thu 26/112:05 p.m.
YWG
-
PUJ
1 stop26h 40m
Air Canada
Thu 3/125:30 p.m.
PUJ
-
YWG
Nonstop6h 30m
Air Canada
Deal found 20/7C$ 637
Wed 11/118:05 a.m.
YWG
-
PUJ
1 stop8h 40m
Air Canada
Sun 15/1112:35 p.m.
PUJ
-
YWG
1 stop23h 25m
Air Canada
Deal found 20/7C$ 641
Thu 12/118:05 a.m.
YWG
-
PUJ
1 stop13h 30m
Air Canada
Sat 21/111:05 p.m.
PUJ
-
YWG
1 stop23h 19m
Air Canada
Deal found 20/7C$ 648

Find flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 23 July 2026.

Round-trip from

C$ 510

One-way from

C$ 225

Popular in

December

Cheapest in

April

Average price

C$ 922

Good round-trip deal

C$ 679 or less
Air Canada
  • Air Canada
  • 29/9-3/10
  • 2 total stops
  • 38h 07m total
  • Winnipeg to Caribbean
Search Deals
WestJet
  • WestJet
  • 3/9
  • 2 total stops
  • 26h 10m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Caribbean.
Search Deals

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 23 July 2026.
Use the filters below to find and compare flights from Winnipeg to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 29/9

1:30 p.m.-1:35 p.m.

2 stops23h 05m

Nassau Intl

Sat 3/10

6:30 p.m.-11:12 a.m.

1 stop17h 42m

C$ 510

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sat 5/12

2:05 p.m.-1:15 p.m.

1 stop22h 10m

Nassau Intl

Sat 12/12

9:25 p.m.-10:09 a.m.

1 stop13h 44m

C$ 534

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 29/9

4:15 p.m.-11:10 a.m.

2 stops17h 55m

Nassau Intl

Sat 3/10

12:00 p.m.-12:00 p.m.

2 stops25h 00m

C$ 536

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Thu 8/10

8:00 a.m.-11:10 a.m.

2 stops26h 10m

Nassau Intl

Tue 13/10

12:00 p.m.-12:55 a.m.

1 stop13h 55m

C$ 545

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 11/1

6:00 a.m.-12:10 p.m.

2 stops29h 10m

George Town Owen Roberts Intl

Thu 14/1

1:10 p.m.-9:24 p.m.

1 stop9h 14m

C$ 588
Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:35 a.m.

1 stop16h 10m

C$ 616

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 26/11

2:05 p.m.-6:45 p.m.

1 stop26h 40m

Punta Cana

Thu 3/12

5:30 p.m.-10:00 p.m.

Nonstop6h 30m

C$ 637

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Sun 29/11

2:05 p.m.-3:45 p.m.

2 stops23h 40m

Willemstad Hato Int.

Thu 10/12

4:45 p.m.-6:25 p.m.

2 stops27h 40m

C$ 658

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

2:05 p.m.-1:25 p.m.

1 stop22h 20m

Montego Bay Sangster Intl

Fri 22/1

2:20 p.m.-10:00 a.m.

1 stop20h 40m

C$ 660

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

12:55 p.m.-1:54 p.m.

2 stops23h 59m

Montego Bay Sangster Intl

Fri 22/1

2:55 p.m.-11:05 a.m.

2 stops21h 10m

C$ 665

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/7

Showing 1-10 of 60 resultsSorted by cheapest first
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2
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6

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$ 761). Flying from Winnipeg to Caribbean in December is currently the most expensive (average of C$ 1,005). 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.

How far ahead should I book a flight from Winnipeg to Caribbean?

The price you pay for your flight from Winnipeg to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 23 July 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andWestJet from Winnipeg to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Entertainment

6.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
448 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Entertainment

6.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Transat
7.8
Good
566 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Entertainment

6.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
WestJet
7.2
Good
3,411 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Entertainment

6.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,371 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Entertainment

6.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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.

  • How long is the flight from Winnipeg to Caribbean?

    Airlines like Air Canada and WestJet fly from Winnipeg to Caribbean in about 17h 55m. The time it takes to get you to your destination can typically vary by up to 5h 10m. Winnipeg and Caribbean are separated by a distance of 3244 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?

    The most popular route from Winnipeg to Caribbean is Winnipeg - Punta Cana. You may also consider Winnipeg - Montego Bay Sangster Intl or Winnipeg - Kingston Norman Manley.

  • 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$ 761). Flying from Winnipeg to Caribbean in December is currently the most expensive (average of C$ 1,005). 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 4 airlines flying from Winnipeg to Caribbean

Discover the top 4 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 23 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 382AverageC$ 862FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 508AverageC$ 698FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 599AverageC$ 928FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 603AverageC$ 939FlexibilityNo 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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