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Cheap flights from Winnipeg to Caribbean from C$ 229

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 25/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 11 September 2025.

Round-trip from

C$ 520

One-way from

C$ 229

Popular in

November

Cheapest in

September

Average price

C$ 650

Good round-trip deal

C$ 1,006 or less
WestJet
  • WestJet
  • 27/10-3/11
  • 4 total stops
  • 36h 50m total
  • Winnipeg to Caribbean
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WestJet
  • WestJet
  • 25/10
  • 2 total stops
  • 43h 14m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Winnipeg to Caribbean.
Search Deals

Find flight deals from Winnipeg to Caribbean

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 11 September 2025.

Mon 27/105:00 a.m.YWG - NAS
1 stop9h 50mWestJet
Mon 3/114:50 p.m.NAS - YWG
1 stop8h 45mWestJet
Deal found 11/9C$ 520
Mon 27/109:00 p.m.YWG - MBJ
2 stops15h 54mWestJet
Mon 3/117:25 p.m.MBJ - YWG
2 stops20h 56mWestJet
Deal found 11/9C$ 520
Mon 27/106:00 a.m.YWG - NAS
2 stops29h 55mAir Canada
Mon 3/111:35 p.m.NAS - YWG
2 stops31h 53mAir Canada
Deal found 11/9C$ 561
Mon 22/98:10 p.m.YWG - PUJ
1 stop18h 10mAir Canada
Mon 6/104:25 p.m.PUJ - YWG
2 stops18h 45mAir Canada
Deal found 11/9C$ 575
Wed 29/108:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Sun 2/111:25 p.m.MBJ - YWG
1 stop23h 10mWestJet
Deal found 10/9C$ 579
Fri 14/117:30 a.m.YWG - MBJ
1 stop30h 45mMultiple Airlines
Sat 29/112:50 p.m.MBJ - YWG
1 stop10h 51mMultiple Airlines
Deal found 10/9C$ 583
Thu 13/118:20 p.m.YWG - PUJ
1 stop24h 10mMultiple Airlines
Thu 20/119:30 a.m.PUJ - YWG
1 stop12h 05mMultiple Airlines
Deal found 10/9C$ 583
Tue 2/1212:20 p.m.YWG - PUJ
1 stop23h 15mWestJet
Sat 6/127:20 a.m.PUJ - YWG
1 stop30h 15mWestJet
Deal found 10/9C$ 621
Sat 4/106:30 a.m.YWG - MBJ
2 stops30h 11mMultiple Airlines
Sat 11/1012:45 p.m.MBJ - YWG
1 stop11h 28mMultiple Airlines
Deal found 9/9C$ 635
Sat 25/105:10 p.m.YWG - PUJ
2 stops24h 45mMultiple Airlines
Sat 1/117:02 a.m.PUJ - YWG
1 stop13h 33mMultiple Airlines
Deal found 10/9C$ 636
Thu 2/109:05 p.m.YWG - MBJ
2 stops38h 36mWestJet
Fri 10/1012:45 p.m.MBJ - YWG
2 stops32h 40mWestJet
Deal found 10/9C$ 650
Wed 17/95:00 a.m.YWG - PUJ
1 stop9h 20mAir Canada
Thu 18/94:25 p.m.PUJ - YWG
2 stops19h 15mAir Canada
Deal found 10/9C$ 654

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 11 September 2025.
Use the filters below to find and compare flights from Winnipeg to Caribbean that are best for you.

Fly from

Winnipeg

Fly to

Caribbean

Route

Depart

Return

Price

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 27/10

5:00 a.m.-3:50 p.m.

1 stop9h 50m

Nassau Intl

Mon 3/11

4:50 p.m.-12:35 a.m.

1 stop8h 45m

C$ 520

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 27/10

9:00 p.m.-12:54 p.m.

2 stops15h 54m

Montego Bay Sangster Intl

Mon 3/11

7:25 p.m.-3:21 p.m.

2 stops20h 56m

C$ 520

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 27/10

6:00 a.m.-12:55 p.m.

2 stops29h 55m

Nassau Intl

Mon 3/11

1:35 p.m.-10:16 a.m.

1 stop21h 41m

C$ 561

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 9/11

7:30 a.m.-3:15 p.m.

1 stop30h 45m

Montego Bay Sangster Intl

Sun 16/11

4:30 p.m.-12:39 a.m.

2 stops33h 09m

C$ 579

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 14/11

7:30 a.m.-3:15 p.m.

1 stop30h 45m

Montego Bay Sangster Intl

Sat 29/11

2:50 p.m.-12:41 a.m.

1 stop10h 51m

C$ 583

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 22/11

12:20 p.m.-12:29 p.m.

1 stop23h 09m

Montego Bay Sangster Intl

Sat 29/11

2:50 p.m.-11:53 a.m.

1 stop22h 03m

C$ 600

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

5:00 a.m.-12:54 p.m.

1 stop7h 54m

Montego Bay Sangster Intl

Sun 2/11

8:25 p.m.-3:21 p.m.

2 stops19h 56m

C$ 600

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 25/10

5:10 p.m.-6:55 p.m.

2 stops24h 45m

Punta Cana

Sat 1/11

7:02 a.m.-7:35 p.m.

1 stop13h 33m

C$ 636

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 2/10

9:05 p.m.-11:41 a.m.

2 stops38h 36m

Montego Bay Sangster Intl

Fri 10/10

12:45 p.m.-9:25 p.m.

2 stops32h 40m

C$ 650

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Sat 22/11

12:20 p.m.-3:17 p.m.

1 stop24h 57m

Willemstad Hato Int.

Sun 7/12

4:10 p.m.-11:35 a.m.

1 stop21h 25m

C$ 668

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 56 results
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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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 254). Flying from Winnipeg to Caribbean in July is currently the most expensive (average of C$ 580). 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 11 September 2025.

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 11 September 2025.
Get a feel of what it's like to fly with Air Transat,United Airlines, 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.
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
Air Transat
7.7
Good
438 reviews
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
United Airlines
7.4
Good
8,937 reviews
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
WestJet
7.2
Good
3,091 reviews
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
Air Canada
7.1
Good
10,000 reviews
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
Sunwing Airlines
6.7
Okay
36 reviews
Air Transat
7.7
Good
438 reviews
Check prices

Entertainment

7.0

Food

6.7

Boarding

7.9

Comfort

7.3

Overall

7.7

Crew

8.4

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.

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 9h 50m. The time it takes to get you to your destination can typically vary by up to 20h 05m. 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 cheapest airlines to fly from Winnipeg to Caribbean one-way?

    The cheapest airlines for a one-way flight from Winnipeg to Caribbean are WestJet (C$ 229), Air Canada (C$ 247), and Flair Airlines (C$ 320).

  • What are the most popular routes from Winnipeg to Caribbean?

    The most popular route from Winnipeg to Caribbean is Winnipeg - Montego Bay Sangster Intl. You may also consider Winnipeg - Punta Cana or Winnipeg - Oranjestad Reina Beatrix.

  • 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$ 254). Flying from Winnipeg to Caribbean in July is currently the most expensive (average of C$ 580). 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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Top 6 airlines flying from Winnipeg to Caribbean

Discover the top 6 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 488AverageC$ 972FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 499AverageC$ 870FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 504AverageC$ 790FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 702AverageC$ 1,091FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Sunwing AirlinesCheapestC$ 710AverageC$ 1,147FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 806AverageC$ 966FlexibilityNo 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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