Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Caribbean Islands from C$ 259

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
20 Jul — 27 Jul1
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 20 June 2026.

Mon 19/101:25 p.m.
YWG
-
NAS
2 stops27h 05m
Air Canada
Fri 23/106:30 p.m.
NAS
-
YWG
2 stops26h 30m
Air Canada
Deal found 19/6C$ 563
Sun 12/78:00 a.m.
YWG
-
MBJ
2 stops27h 45m
WestJet
Sun 19/77:30 p.m.
MBJ
-
YWG
2 stops26h 10m
WestJet
Deal found 16/6C$ 644
Sat 3/107:00 a.m.
YWG
-
MBJ
2 stops28h 45m
WestJet
Sat 10/107:30 p.m.
MBJ
-
YWG
2 stops37h 50m
WestJet
Deal found 20/6C$ 648
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 19/6C$ 650
Sat 4/76:15 a.m.
YWG
-
MBJ
1 stop29h 30m
WestJet
Sat 18/77:30 p.m.
MBJ
-
YWG
2 stops40h 30m
WestJet
Deal found 16/6C$ 669
Thu 1/108:00 a.m.
YWG
-
KIN
2 stops30h 30m
WestJet
Fri 9/103:30 p.m.
KIN
-
YWG
2 stops18h 05m
WestJet
Deal found 16/6C$ 683
Sun 25/106:00 a.m.
YWG
-
CUR
2 stops31h 20m
Air Canada
Wed 4/114:45 p.m.
CUR
-
YWG
1 stop25h 14m
Air Canada
Deal found 20/6C$ 686
Mon 21/91:30 p.m.
YWG
-
KIN
2 stops24h 25m
Air Canada
Fri 25/93:05 p.m.
KIN
-
YWG
2 stops28h 55m
Air Canada
Deal found 19/6C$ 712
Fri 7/812:50 p.m.
YWG
-
PUJ
2 stops24h 15m
WestJet
Tue 18/82:35 p.m.
PUJ
-
YWG
2 stops26h 10m
WestJet
Deal found 18/6C$ 712
Tue 27/108:15 a.m.
YWG
-
PLS
1 stop27h 45m
Air Canada
Sat 31/101:30 p.m.
PLS
-
YWG
1 stop22h 14m
Air Canada
Deal found 17/6C$ 716
Wed 14/101:25 p.m.
YWG
-
KIN
2 stops24h 30m
Air Canada
Fri 16/103:05 p.m.
KIN
-
YWG
1 stop18h 52m
Air Canada
Deal found 17/6C$ 717
Sat 21/1112:55 p.m.
YWG
-
CUR
2 stops24h 22m
WestJet
Fri 27/114:10 p.m.
CUR
-
YWG
2 stops30h 55m
WestJet
Deal found 15/6C$ 732

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 20 June 2026.

Round-trip from

C$ 563

One-way from

C$ 259

Popular in

December

Cheapest in

April

Average price

C$ 914
Air Canada
  • Air Canada
  • 19/10-23/10
  • 4 total stops
  • 53h 35m total
  • Winnipeg to Caribbean Islands
Search Deals
WestJet
  • WestJet
  • 11/8
  • 2 total stops
  • 21h 20m total
  • Winnipeg to Caribbean Islands
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 June 2026
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 20 June 2026.
Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 19/10

1:25 p.m.-5:30 p.m.

2 stops27h 05m

Nassau Intl

Fri 23/10

6:30 p.m.-8:00 p.m.

2 stops26h 30m

C$ 563

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 3/10

7:00 a.m.-11:45 a.m.

2 stops28h 45m

Montego Bay Sangster Intl

Sat 10/10

7:30 p.m.-9:20 a.m.

2 stops37h 50m

C$ 648

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.-9:05 p.m.

2 stops49h 40m

C$ 652

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 4/7

6:15 a.m.-11:45 a.m.

1 stop29h 30m

Montego Bay Sangster Intl

Sat 18/7

7:30 p.m.-12:00 p.m.

2 stops40h 30m

C$ 669

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Sun 25/10

6:00 a.m.-2:20 p.m.

2 stops31h 20m

Willemstad Hato Int.

Wed 4/11

4:45 p.m.-3:59 p.m.

1 stop25h 14m

C$ 686

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 5/8

1:30 p.m.-11:20 a.m.

2 stops21h 50m

Montego Bay Sangster Intl

Thu 13/8

12:30 p.m.-10:00 a.m.

1 stop21h 30m

C$ 692

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 21/9

7:10 p.m.-11:20 a.m.

1 stop16h 10m

Montego Bay Sangster Intl

Fri 25/9

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

1 stop29h 42m

C$ 698

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 21/9

1:30 p.m.-1:55 p.m.

2 stops24h 25m

Kingston Norman Manley

Fri 25/9

3:05 p.m.-8:00 p.m.

2 stops28h 55m

C$ 712

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Tue 27/10

6:00 a.m.-1:00 p.m.

2 stops30h 00m

Providenciales

Sat 31/10

1:30 p.m.-10:44 a.m.

1 stop22h 14m

C$ 716

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 7/8

12:50 p.m.-2:05 p.m.

2 stops24h 15m

Punta Cana

Tue 18/8

2:35 p.m.-11:45 a.m.

1 stop22h 10m

C$ 717

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/6

Showing 1-10 of 52 resultsSorted by cheapest first
1
2
3
...
6

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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 195). Flying from Winnipeg to Caribbean Islands in June is currently the most expensive (average of C$ 494). 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 Islands?

To ensure you get the cheapest price possible for a flight from Winnipeg to Caribbean Islands, you should look to book at least 70 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 20 June 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, 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.
Porter Airlines
8.0
Very good
438 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
556 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
WestJet
7.2
Good
3,375 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,229 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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 27h 05m. Air Canada provides one of the quickest options available for as low as C$ 563. Winnipeg and Caribbean Islands 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 Islands?

    The most popular flight routes from Winnipeg to Caribbean Islands are Winnipeg - Punta Cana, Winnipeg - Willemstad Hato Int. and Winnipeg - Santo Domingo Las Americas.

  • 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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 195). Flying from Winnipeg to Caribbean Islands in June is currently the most expensive (average of C$ 494). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Pearson Intl flights
Winnipeg to Vancouver Intl flights
Winnipeg to Hamilton flights
Winnipeg to Toronto Island flights
Winnipeg to Calgary flights
Winnipeg to Abbotsford flights
Winnipeg to Pierre Elliott Trudeau Intl flights
Winnipeg to Ottawa flights
Winnipeg to Region of Waterloo Intl flights
Winnipeg to Halifax flights
Winnipeg to Cancún flights
Winnipeg to Edmonton flights
Winnipeg to Kelowna flights
Winnipeg to Las Vegas flights
Winnipeg to Saskatoon flights
Winnipeg to Newark flights
Winnipeg to O'Hare Intl flights
Winnipeg to LaGuardia flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Mexico City flights
Winnipeg to San Francisco flights
Winnipeg to Puerto Vallarta flights
Winnipeg to Minneapolis flights
Winnipeg to Seattle flights
Winnipeg to Orlando flights
Winnipeg to Dulles Intl flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Los Angeles flights
Winnipeg to Denver flights
Winnipeg to Reagan-National flights
Winnipeg to Atlanta flights
Winnipeg to Victoria flights
Winnipeg to Baltimore flights
Winnipeg to San Diego flights
Winnipeg to Hobby flights
Winnipeg to George Bush Intcntl flights
Winnipeg to London flights
Winnipeg to St. John's flights
Winnipeg to Indianapolis flights
Winnipeg to Honolulu flights
Winnipeg to Québec City flights
Winnipeg to Ontario flights
Winnipeg to Churchill flights
Winnipeg to Philadelphia flights
Winnipeg to Thunder Bay flights
Winnipeg to Nashville flights
Winnipeg to Portland flights
Winnipeg to Boston flights

Top 4 airlines flying from Winnipeg to Caribbean Islands

Discover the top 4 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 20 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 398AverageC$ 883FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 500AverageC$ 884FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 510AverageC$ 760FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air TransatCheapestC$ 814AverageC$ 943FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.