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Cheap flights from Winnipeg to Caribbean from C$ 242

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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 28 October 2025.

Tue 28/105:30 a.m.YWG - PUJ
2 stops30h 30mAir Canada
Tue 4/1110:25 p.m.PUJ - YWG
2 stops37h 51mAir Canada
Deal found 27/10C$ 557
Thu 11/129:00 p.m.YWG - CUR
2 stops16h 32mWestJet
Thu 18/124:40 p.m.CUR - YWG
1 stop10h 02mWestJet
Deal found 27/10C$ 564
Sun 16/117:05 p.m.YWG - PUJ
1 stop15h 00mAir Canada
Fri 21/1110:25 p.m.PUJ - YWG
1 stop13h 24mAir Canada
Deal found 27/10C$ 621
Tue 2/128:40 a.m.YWG - PUJ
1 stop31h 38mUnited Airlines
Sat 6/124:25 p.m.PUJ - YWG
1 stop21h 32mUnited Airlines
Deal found 28/10C$ 629
Sat 1/117:05 p.m.YWG - MBJ
2 stops23h 00mMultiple Airlines
Mon 3/117:25 p.m.MBJ - YWG
2 stops20h 56mMultiple Airlines
Deal found 27/10C$ 632
Sat 1/115:00 a.m.YWG - POP
1 stop9h 33mWestJet
Tue 16/125:30 p.m.POP - YWG
1 stop9h 12mWestJet
Deal found 27/10C$ 638
Thu 11/125:00 a.m.YWG - PUJ
1 stop8h 35mWestJet
Sun 14/122:30 p.m.PUJ - YWG
1 stop30h 42mWestJet
Deal found 27/10C$ 656
Tue 25/118:05 p.m.YWG - KIN
1 stop18h 28mWestJet
Tue 2/124:30 p.m.KIN - YWG
1 stop20h 05mWestJet
Deal found 28/10C$ 664
Sun 2/115:00 a.m.YWG - PUJ
1 stop8h 35mWestJet
Sun 9/114:30 p.m.PUJ - YWG
1 stop10h 05mWestJet
Deal found 26/10C$ 664
Sun 2/117:30 a.m.YWG - PUJ
2 stops29h 50mMultiple Airlines
Sun 9/114:30 p.m.PUJ - YWG
1 stop10h 12mMultiple Airlines
Deal found 26/10C$ 676
Fri 31/109:00 p.m.YWG - POP
2 stops42h 33mWestJet
Tue 16/125:30 p.m.POP - YWG
1 stop27h 42mWestJet
Deal found 27/10C$ 677
Tue 2/124:10 p.m.YWG - PUJ
2 stops21h 25mWestJet
Sat 6/127:20 a.m.PUJ - YWG
1 stop19h 15mWestJet
Deal found 28/10C$ 680

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 28 October 2025.

Round-trip from

C$ 487

One-way from

C$ 242

Popular in

November

Cheapest in

April

Average price

C$ 810

Good round-trip deal

C$ 799 or less

Good one-way deal

C$ 543 or less
WestJet
  • WestJet
  • 25/3-14/4
  • 2 total stops
  • 38h 27m total
  • Winnipeg to Caribbean
Search Deals
10/12
  • 10/12
  • 1 total stop
  • 13h 17m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 170 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 October 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Caribbean.
Search Deals
Price to beat on a one-way 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 28 October 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 6/4

8:05 p.m.-2:30 p.m.

1 stop17h 25m

Punta Cana

Wed 8/4

3:30 p.m.-12:39 a.m.

1 stop10h 09m

C$ 518

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Wed 21/1

5:00 a.m.-6:45 p.m.

1 stop11h 45m

Oranjestad Reina Beatrix

Wed 28/1

7:35 p.m.-3:21 p.m.

2 stops21h 46m

C$ 533

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 31/1

2:20 p.m.-12:59 p.m.

2 stops20h 39m

Punta Cana

Wed 4/3

5:20 p.m.-11:39 a.m.

2 stops20h 19m

C$ 534

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 5/2

2:20 p.m.-5:25 p.m.

2 stops25h 05m

Punta Cana

Wed 4/3

5:20 p.m.-11:39 a.m.

2 stops20h 19m

C$ 534

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Wed 25/2

8:05 p.m.-1:30 p.m.

1 stop15h 25m

Punta Cana

Wed 4/3

4:30 p.m.-8:05 p.m.

2 stops29h 35m

C$ 541

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 24/1

6:55 p.m.-3:06 p.m.

3 stops18h 11m

San Juan Luis Munoz Marin Intl

Sat 31/1

4:11 p.m.-3:09 p.m.

1 stop24h 58m

C$ 554

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 31/1

9:00 p.m.-3:06 p.m.

2 stops16h 06m

San Juan Luis Munoz Marin Intl

Sat 7/2

4:11 p.m.-3:09 p.m.

1 stop24h 58m

C$ 557

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Thu 9/4

5:00 a.m.-3:27 p.m.

1 stop9h 27m

Puerto Plata La Union

Mon 13/4

4:30 p.m.-7:09 p.m.

1 stop27h 39m

C$ 558

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Tue 13/1

9:00 p.m.-3:40 p.m.

2 stops16h 40m

Oranjestad Reina Beatrix

Fri 23/1

4:30 p.m.-11:35 a.m.

1 stop21h 05m

C$ 561

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Mon 6/4

5:00 a.m.-3:27 p.m.

1 stop9h 27m

Puerto Plata La Union

Thu 9/4

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

1 stop9h 09m

C$ 572

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 60 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, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 393). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 611). 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 28 October 2025.

When flying from Winnipeg to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 16% versus a flight in the afternoon.

What is the cheapest day to fly from Winnipeg to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Caribbean. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Caribbean flight should consider departing on Thursday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 28 October 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
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Transat
7.8
Good
469 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
United Airlines
7.4
Good
8,996 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
WestJet
7.2
Good
3,148 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Canada
7.1
Good
10,370 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Sunwing Airlines
6.7
Okay
36 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Crew

8.5

Food

6.8

Comfort

7.4

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.

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, United Airlines, and Air Canada fly from Winnipeg to Caribbean in about 17h 25m. The time it takes to get you to your destination can typically vary by up to 17h. Winnipeg and Caribbean are separated by a distance of 4323 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$ 283), Flair Airlines (C$ 297), and Air Canada (C$ 322).

  • 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 - San Juan Luis Munoz Marin Intl.

  • 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, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 393). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 611). 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

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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 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 28 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 492AverageC$ 838FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 509AverageC$ 785FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 516AverageC$ 847FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 709AverageC$ 1,101FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Sunwing AirlinesCheapestC$ 717AverageC$ 1,132FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 813AverageC$ 932FlexibilityNo 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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