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Cheap flights from Winnipeg to Caribbean from C$ 263

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 23/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
4 Jul — 11 Jul1
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 4 June 2026.

Sat 5/91:30 p.m.
YWG
-
PUJ
2 stops25h 35m
Air Canada
Fri 11/95:05 p.m.
PUJ
-
YWG
1 stop17h 54m
Air Canada
Deal found 30/5C$ 609
Tue 15/91:25 p.m.
YWG
-
PUJ
2 stops25h 40m
Air Canada
Tue 29/94:20 p.m.
PUJ
-
YWG
1 stop19h 52m
Air Canada
Deal found 2/6C$ 617
Fri 12/61:25 p.m.
YWG
-
PUJ
2 stops26h 05m
Air Canada
Wed 17/65:25 p.m.
PUJ
-
YWG
1 stop17h 40m
Air Canada
Deal found 30/5C$ 631
Mon 8/65:10 a.m.
YWG
-
NAS
1 stop11h 20m
Air Canada
Thu 11/61:40 p.m.
NAS
-
YWG
2 stops31h 22m
Air Canada
Deal found 1/6C$ 632
Sun 14/61:25 p.m.
YWG
-
PUJ
2 stops21h 30m
Air Canada
Fri 19/65:05 p.m.
PUJ
-
YWG
2 stops19h 10m
Air Canada
Deal found 1/6C$ 646
Thu 17/95:10 p.m.
YWG
-
PUJ
1 stop21h 15m
Air Canada
Thu 1/104:20 p.m.
PUJ
-
YWG
1 stop24h 57m
Air Canada
Deal found 2/6C$ 648
Mon 9/118:15 a.m.
YWG
-
PUJ
1 stop13h 20m
Air Canada
Sun 15/113:20 p.m.
PUJ
-
YWG
1 stop20h 56m
Air Canada
Deal found 31/5C$ 650
Wed 29/71:30 p.m.
YWG
-
GCM
2 stops21h 55m
Air Canada
Mon 31/812:25 p.m.
GCM
-
YWG
2 stops21h 40m
Air Canada
Deal found 2/6C$ 666
Tue 8/121:45 p.m.
YWG
-
MBJ
1 stop22h 05m
Air Canada
Fri 18/121:50 p.m.
MBJ
-
YWG
2 stops31h 38m
Air Canada
Deal found 3/6C$ 670
Wed 24/61:30 p.m.
YWG
-
KIN
2 stops20h 55m
Air Canada
Mon 29/63:05 p.m.
KIN
-
YWG
2 stops28h 56m
Air Canada
Deal found 1/6C$ 678
Tue 18/87:40 p.m.
YWG
-
GCM
2 stops25h 20m
Multiple Airlines
Sat 22/810:40 a.m.
GCM
-
YWG
2 stops23h 25m
Multiple Airlines
Deal found 30/5C$ 696
Mon 19/101:25 p.m.
YWG
-
MBJ
2 stops21h 55m
Air Canada
Fri 23/1012:30 p.m.
MBJ
-
YWG
2 stops31h 30m
Air Canada
Deal found 1/6C$ 698

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 4 June 2026.

Round-trip from

C$ 609

One-way from

C$ 263

Popular in

December

Cheapest in

April

Average price

C$ 781

Good round-trip deal

C$ 768 or less
Air Canada
  • Air Canada
  • 5/9-11/9
  • 3 total stops
  • 43h 29m total
  • Winnipeg to Caribbean
Search Deals
WestJet
  • WestJet
  • 23/6
  • 2 total stops
  • 17h 55m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 137 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 4 June 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

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Wed 29/7

1:30 p.m.-11:25 a.m.

2 stops21h 55m

George Town Owen Roberts Intl

Mon 31/8

12:25 p.m.-10:05 a.m.

2 stops21h 40m

C$ 695

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Tue 18/8

7:40 p.m.-9:00 p.m.

2 stops25h 20m

George Town Owen Roberts Intl

Sat 22/8

10:40 a.m.-10:05 a.m.

2 stops23h 25m

C$ 696

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 19/10

1:25 p.m.-11:20 a.m.

2 stops21h 55m

Montego Bay Sangster Intl

Fri 23/10

12:30 p.m.-8:00 p.m.

2 stops31h 30m

C$ 698

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 26/10

5:15 a.m.-3:30 p.m.

2 stops34h 15m

George Town Owen Roberts Intl

Wed 28/10

12:10 p.m.-6:29 p.m.

1 stop30h 19m

C$ 699

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Mon 2/11

8:15 a.m.-1:00 p.m.

1 stop27h 45m

Providenciales

Thu 5/11

1:30 p.m.-3:59 p.m.

1 stop27h 29m

C$ 706

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 15/6

1:25 p.m.-4:30 p.m.

2 stops26h 05m

Punta Cana

Thu 18/6

5:05 p.m.-10:05 a.m.

1 stop18h 00m

C$ 707

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 13/10

4:05 p.m.-5:00 p.m.

2 stops47h 55m

Simpson Bay Princess Juliana

Wed 4/11

3:35 p.m.-1:44 p.m.

1 stop24h 09m

C$ 716

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 1/10

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

1 stop10h 50m

Simpson Bay Princess Juliana

Thu 8/10

6:00 p.m.-9:57 a.m.

1 stop16h 57m

C$ 721

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 15/9

7:10 p.m.-3:25 p.m.

1 stop19h 15m

Punta Cana

Tue 29/9

4:20 p.m.-11:12 a.m.

1 stop19h 52m

C$ 738

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 21/6

7:10 p.m.-4:05 p.m.

2 stops19h 55m

Punta Cana

Wed 1/7

4:25 p.m.-3:14 p.m.

2 stops23h 49m

C$ 738

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 59 resultsSorted by cheapest first
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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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 191). Flying from Winnipeg to Caribbean in June is currently the most expensive (average of C$ 484). 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 73 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 4 June 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
440 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
440 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
554 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
3,350 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
11,123 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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. 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, WestJet, and United Airlines fly from Winnipeg to Caribbean in about 8h 35m. The time it takes to get you to your destination can typically vary by up to 14h 02m. Winnipeg and Caribbean are separated by a distance of 4094 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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 191). Flying from Winnipeg to Caribbean in June is currently the most expensive (average of C$ 484). 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 4 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 390AverageC$ 844FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 490AverageC$ 860FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 500AverageC$ 745FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air TransatCheapestC$ 798AverageC$ 924FlexibilityNo 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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