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Cheap flights from Winnipeg to Caribbean from C$ 191

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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
9 Apr — 16 Apr1
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 10 March 2026.

Fri 11/99:05 p.m.
YWG
-
MBJ
2 stops21h 25m
WestJet
Fri 18/912:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 5/3C$ 463
Thu 10/99:05 p.m.
YWG
-
MBJ
2 stops14h 40m
WestJet
Sat 19/97:30 p.m.
MBJ
-
YWG
2 stops16h 30m
WestJet
Deal found 5/3C$ 471
Thu 10/96:05 p.m.
YWG
-
MBJ
1 stop17h 40m
WestJet
Fri 18/912:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 5/3C$ 480
Sat 25/77:10 p.m.
YWG
-
MBJ
2 stops16h 35m
WestJet
Tue 4/812:45 p.m.
MBJ
-
YWG
2 stops31h 30m
WestJet
Deal found 8/3C$ 482
Thu 28/59:05 p.m.
YWG
-
NAS
2 stops13h 05m
WestJet
Wed 3/612:00 p.m.
NAS
-
YWG
2 stops24h 10m
WestJet
Deal found 9/3C$ 483
Fri 12/62:55 p.m.
YWG
-
MBJ
2 stops27h 35m
WestJet
Sun 21/612:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 5/3C$ 483
Fri 11/94:25 p.m.
YWG
-
MBJ
1 stop26h 05m
WestJet
Sat 19/97:30 p.m.
MBJ
-
YWG
1 stop18h 55m
WestJet
Deal found 5/3C$ 486
Fri 5/64:55 p.m.
YWG
-
NAS
2 stops17h 15m
WestJet
Wed 17/612:00 p.m.
NAS
-
YWG
2 stops24h 10m
WestJet
Deal found 6/3C$ 487
Sat 13/67:10 p.m.
YWG
-
MBJ
2 stops16h 35m
WestJet
Sun 21/67:30 p.m.
MBJ
-
YWG
1 stop18h 55m
WestJet
Deal found 5/3C$ 488
Sun 14/610:45 a.m.
YWG
-
MBJ
1 stop7h 45m
WestJet
Sat 20/67:30 p.m.
MBJ
-
YWG
1 stop14h 15m
WestJet
Deal found 5/3C$ 490
Sat 4/48:00 a.m.
YWG
-
MBJ
Nonstop5h 25m
WestJet
Sat 11/42:25 p.m.
MBJ
-
YWG
Nonstop5h 53m
WestJet
Deal found 7/3C$ 491
Mon 8/610:30 p.m.
YWG
-
AUA
2 stops38h 45m
WestJet
Tue 16/63:05 p.m.
AUA
-
YWG
2 stops48h 10m
WestJet
Deal found 5/3C$ 503

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 10 March 2026.

Round-trip from

C$ 482

One-way from

C$ 191

Popular in

December

Cheapest in

April

Average price

C$ 828

Good round-trip deal

C$ 626 or less
WestJet
  • WestJet
  • 25/7-4/8
  • 4 total stops
  • 48h 05m total
  • Winnipeg to Caribbean
Search Deals
WestJet
  • WestJet
  • 11/4
  • Nonstop
  • 5h 25m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 10 March 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

Fri 5/6

4:55 p.m.-11:10 a.m.

2 stops17h 15m

Nassau Intl

Wed 17/6

12:00 p.m.-11:10 a.m.

2 stops24h 10m

C$ 487

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Thu 28/5

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

2 stops15h 00m

Nassau Intl

Wed 3/6

12:00 p.m.-2:15 p.m.

2 stops27h 15m

C$ 490

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 21/5

6:05 p.m.-11:45 a.m.

1 stop17h 40m

Montego Bay Sangster Intl

Thu 11/6

12:45 p.m.-12:55 a.m.

1 stop12h 10m

C$ 498

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Mon 8/6

10:30 p.m.-2:15 p.m.

2 stops38h 45m

Oranjestad Reina Beatrix

Tue 16/6

3:05 p.m.-2:15 p.m.

2 stops48h 10m

C$ 503

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 10/4

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

2 stops19h 45m

Nassau Intl

Mon 13/4

4:50 p.m.-8:05 p.m.

2 stops28h 15m

C$ 513

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 25/5

4:05 p.m.-5:30 p.m.

2 stops24h 25m

Nassau Intl

Mon 1/6

6:30 p.m.-10:09 a.m.

2 stops40h 39m

C$ 522

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 21/4

6:15 a.m.-3:40 p.m.

2 stops32h 25m

Nassau Intl

Tue 28/4

12:00 p.m.-5:15 p.m.

1 stop30h 15m

C$ 522

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 11/6

7:10 p.m.-11:45 a.m.

2 stops16h 35m

Montego Bay Sangster Intl

Sat 20/6

7:30 p.m.-3:25 p.m.

2 stops19h 55m

C$ 522

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 7/4

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

1 stop18h 35m

Nassau Intl

Tue 14/4

4:50 p.m.-12:40 a.m.

2 stops32h 50m

C$ 524

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 30/5

9:05 p.m.-11:45 a.m.

2 stops14h 40m

Montego Bay Sangster Intl

Tue 2/6

12:45 p.m.-2:05 p.m.

2 stops25h 20m

C$ 526

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 60 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$ 292). Flying from Winnipeg to Caribbean in February is currently the most expensive (average of C$ 607). 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 CB?

Find hourly flight availability from Winnipeg to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 10 March 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Caribbean as you normally would.

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 10 March 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andUnited Airlines 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
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
423 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.7
Good
520 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,409 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,288 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,800 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 WestJet, Air Canada, and United Airlines fly from Winnipeg to Caribbean in about 17h 15m. The time it takes to get you to your destination can typically vary by up to 7h 50m. 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 - Puerto Plata La Union.

  • 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$ 292). Flying from Winnipeg to Caribbean in February is currently the most expensive (average of C$ 607). 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 5 airlines flying from Winnipeg to Caribbean

Discover the top 5 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 10 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 382AverageC$ 776FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 469AverageC$ 847FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 489AverageC$ 729FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 544AverageC$ 676FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air TransatCheapestC$ 818AverageC$ 904FlexibilityNo 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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