Cheap flights from Winnipeg to Caribbean from C$ 298

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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
3 Aug — 10 Aug1
1 adult

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 29 July 2025.

Round-trip from

C$ 551

One-way from

C$ 298

Popular in

November

Cheapest in

September

Average price

C$ 893

Good round-trip deal

C$ 809 or less
WestJet
  • WestJet
  • 17/11-24/11
  • 4 total stops
  • 36h 16m total
  • Winnipeg to Caribbean
11/9
  • 11/9
  • 1 total stop
  • 17h 07m total
  • Winnipeg to Caribbean
Highest demand for flights based on searches. 7% potential increase in price (C$ 89 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease (C$ 21 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Winnipeg to Caribbean.

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 29 July 2025.

Wed 3/124:10 p.m.YWG - PUJ
2 stops21h 25mWestJet
Wed 10/122:30 p.m.PUJ - YWG
2 stops23h 23mWestJet
Deal found 29/7C$ 534
Mon 22/95:00 a.m.YWG - PUJ
1 stop9h 20mAir Canada
Mon 6/104:25 p.m.PUJ - YWG
2 stops18h 45mAir Canada
Deal found 27/7C$ 582
Mon 3/115:00 a.m.YWG - POP
1 stop9h 33mWestJet
Mon 15/125:30 p.m.POP - YWG
1 stop9h 05mWestJet
Deal found 28/7C$ 599
Sat 18/104:25 p.m.YWG - PUJ
2 stops19h 15mUnited Airlines
Fri 24/104:35 p.m.PUJ - YWG
2 stops23h 56mUnited Airlines
Deal found 28/7C$ 609
Sun 16/118:15 a.m.YWG - AUA
2 stops30h 10mAir Canada
Thu 20/112:50 p.m.AUA - YWG
2 stops45h 26mAir Canada
Deal found 27/7C$ 613
Tue 4/116:30 a.m.YWG - POP
2 stops29h 44mAir Canada
Fri 12/122:50 p.m.POP - YWG
1 stop23h 49mAir Canada
Deal found 27/7C$ 628
Thu 25/98:10 p.m.YWG - GCM
2 stops40h 20mAir Canada
Thu 9/1012:50 p.m.GCM - YWG
2 stops21h 20mAir Canada
Deal found 27/7C$ 628
Tue 9/93:45 p.m.YWG - MBJ
2 stops43h 25mAir Canada
Tue 23/912:10 p.m.MBJ - YWG
2 stops22h 30mAir Canada
Deal found 29/7C$ 630
Wed 10/97:00 a.m.YWG - NAS
2 stops29h 31mUnited Airlines
Tue 16/92:33 p.m.NAS - YWG
2 stops23h 36mUnited Airlines
Deal found 28/7C$ 631
Fri 29/86:30 a.m.YWG - MBJ
1 stop11h 56mWestJet
Fri 5/912:45 p.m.MBJ - YWG
1 stop11h 28mWestJet
Deal found 28/7C$ 652
Fri 1/84:25 p.m.YWG - MBJ
2 stops23h 01mUnited Airlines
Sat 16/84:33 p.m.MBJ - YWG
2 stops30h 00mUnited Airlines
Deal found 27/7C$ 668
Mon 10/115:00 a.m.YWG - AUA
1 stop8h 40mMultiple Airlines
Thu 20/112:50 p.m.AUA - YWG
2 stops27h 45mMultiple Airlines
Deal found 29/7C$ 678

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 29 July 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

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 17/11

6:55 p.m.-1:35 p.m.

2 stops16h 40m

Punta Cana

Mon 24/11

7:20 a.m.-12:56 a.m.

2 stops19h 36m

C$ 551

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 22/9

5:00 a.m.-3:20 p.m.

1 stop9h 20m

Punta Cana

Mon 6/10

4:25 p.m.-10:10 a.m.

2 stops18h 45m

C$ 582

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 18/10

4:25 p.m.-12:40 p.m.

2 stops19h 15m

Punta Cana

Fri 24/10

4:35 p.m.-3:31 p.m.

2 stops23h 56m

C$ 609

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Thu 25/9

8:10 p.m.-12:30 p.m.

2 stops40h 20m

George Town Owen Roberts Intl

Thu 9/10

12:50 p.m.-10:10 a.m.

2 stops21h 20m

C$ 628

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/9

3:45 p.m.-11:10 a.m.

2 stops43h 25m

Montego Bay Sangster Intl

Tue 23/9

12:10 p.m.-10:40 a.m.

2 stops22h 30m

C$ 630

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 10/9

7:00 a.m.-1:31 p.m.

2 stops29h 31m

Nassau Intl

Tue 16/9

2:33 p.m.-1:09 p.m.

2 stops23h 36m

C$ 631

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 29/8

6:30 a.m.-6:26 p.m.

1 stop11h 56m

Montego Bay Sangster Intl

Fri 5/9

12:45 p.m.-12:13 a.m.

1 stop11h 28m

C$ 652

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

7:30 a.m.-7:53 a.m.

1 stop24h 23m

Montego Bay Sangster Intl

Sun 2/11

1:25 p.m.-12:42 a.m.

1 stop12h 17m

C$ 716

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 22/9

5:00 a.m.-3:20 p.m.

1 stop9h 20m

Punta Cana

Mon 6/10

2:45 p.m.-12:13 a.m.

1 stop10h 28m

C$ 719

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 15/9

4:25 p.m.-11:43 a.m.

2 stops19h 18m

Montego Bay Sangster Intl

Fri 17/10

12:52 p.m.-3:31 p.m.

2 stops26h 39m

C$ 735

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

Showing 1-10 of 29 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 29 July 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 29 July 2025.
Get a feel of what it's like to fly with Delta,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.

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
8.0
Very good

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

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.

  • 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$ 311), United Airlines (C$ 316), and Air Transat (C$ 471).

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

  • 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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Alternative routes for Winnipeg to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 467AverageC$ 782FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 472AverageC$ 847FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 483AverageC$ 858FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 703AverageC$ 1,136FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 805AverageC$ 957FlexibilityNo 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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