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Cheap flights from Winnipeg to Caribbean from C$ 204

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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
26 Feb — 5 Mar1
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 27 January 2026.

Fri 27/36:55 p.m.
YWG
-
NAS
2 stops23h 00m
Multiple Airlines
Sat 4/47:40 p.m.
NAS
-
YWG
2 stops16h 52m
Multiple Airlines
Deal found 26/1C$ 526
Thu 19/26:15 a.m.
YWG
-
NAS
2 stops12h 10m
WestJet
Thu 26/211:20 a.m.
NAS
-
YWG
1 stop14h 15m
WestJet
Deal found 25/1C$ 530
Sun 22/35:00 a.m.
YWG
-
NAS
1 stop9h 40m
WestJet
Sun 29/34:50 p.m.
NAS
-
YWG
1 stop8h 49m
WestJet
Deal found 26/1C$ 534
Thu 5/31:45 p.m.
YWG
-
PUJ
1 stop27h 10m
Air Canada
Wed 11/39:35 p.m.
PUJ
-
YWG
2 stops20h 00m
Air Canada
Deal found 25/1C$ 539
Sat 21/312:20 p.m.
YWG
-
NAS
1 stop26h 20m
WestJet
Sat 28/36:15 p.m.
NAS
-
YWG
1 stop18h 17m
WestJet
Deal found 26/1C$ 542
Thu 5/28:05 p.m.
YWG
-
NAS
1 stop18h 35m
WestJet
Sun 8/28:30 p.m.
NAS
-
YWG
1 stop16h 02m
WestJet
Deal found 26/1C$ 548
Sat 31/19:00 p.m.
YWG
-
NAS
2 stops17h 40m
WestJet
Sat 7/26:15 p.m.
NAS
-
YWG
2 stops40h 52m
WestJet
Deal found 26/1C$ 556
Thu 5/312:40 p.m.
YWG
-
CUR
2 stops24h 48m
WestJet
Fri 13/33:25 p.m.
CUR
-
YWG
2 stops29h 40m
WestJet
Deal found 26/1C$ 559
Fri 20/36:00 a.m.
YWG
-
NAS
1 stop7h 15m
Porter Airlines
Fri 27/33:15 p.m.
NAS
-
YWG
1 stop9h 20m
Porter Airlines
Deal found 26/1C$ 564
Thu 26/28:05 p.m.
YWG
-
PUJ
1 stop17h 30m
Multiple Airlines
Tue 10/37:05 p.m.
PUJ
-
YWG
1 stop25h 30m
Multiple Airlines
Deal found 27/1C$ 567
Sun 1/32:20 p.m.
YWG
-
PUJ
2 stops44h 39m
United Airlines
Wed 11/31:55 p.m.
PUJ
-
YWG
1 stop23h 02m
United Airlines
Deal found 24/1C$ 571
Thu 26/22:20 p.m.
YWG
-
PUJ
2 stops25h 05m
United Airlines
Tue 10/31:55 p.m.
PUJ
-
YWG
1 stop23h 02m
United Airlines
Deal found 27/1C$ 572

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 27 January 2026.

Round-trip from

C$ 508

One-way from

C$ 204

Popular in

December

Cheapest in

April

Average price

C$ 809

Good round-trip deal

C$ 946 or less
WestJet
  • WestJet
  • 24/3-29/3
  • 3 total stops
  • 26h 29m total
  • Winnipeg to Caribbean
Search Deals
WestJet
  • WestJet
  • 5/3
  • 2 total stops
  • 17h 40m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 213 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 27 January 2026.
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

Fri 27/3

6:55 p.m.-6:55 p.m.

2 stops23h 00m

Nassau Intl

Sat 4/4

7:40 p.m.-11:32 a.m.

2 stops16h 52m

C$ 526

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Thu 19/2

6:15 a.m.-7:25 p.m.

2 stops12h 10m

Nassau Intl

Thu 26/2

11:20 a.m.-12:35 a.m.

1 stop14h 15m

C$ 530

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Mon 20/4

5:00 a.m.-2:35 p.m.

1 stop8h 35m

Oranjestad Reina Beatrix

Mon 27/4

3:05 p.m.-12:55 a.m.

1 stop10h 50m

C$ 531

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 20/3

5:00 a.m.-3:40 p.m.

1 stop9h 40m

Nassau Intl

Sun 29/3

4:50 p.m.-12:39 a.m.

1 stop8h 49m

C$ 534

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 22/3

5:00 a.m.-3:40 p.m.

1 stop9h 40m

Nassau Intl

Sat 28/3

6:15 p.m.-11:32 a.m.

1 stop18h 17m

C$ 534

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 5/3

1:45 p.m.-6:55 p.m.

1 stop27h 10m

Punta Cana

Wed 11/3

9:35 p.m.-4:35 p.m.

2 stops20h 00m

C$ 539

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Thu 5/3

12:40 p.m.-3:28 p.m.

2 stops24h 48m

Willemstad Hato Int.

Fri 13/3

3:25 p.m.-8:05 p.m.

2 stops29h 40m

C$ 559

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 1/3

2:20 p.m.-4:02 p.m.

1 stop23h 42m

Punta Cana

Wed 11/3

3:25 p.m.-11:57 a.m.

1 stop21h 32m

C$ 571

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 1/3

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

2 stops25h 05m

Punta Cana

Mon 9/3

3:25 p.m.-11:57 a.m.

1 stop21h 32m

C$ 572

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 1/3

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

2 stops25h 05m

Punta Cana

Tue 10/3

1:55 p.m.-11:57 a.m.

1 stop23h 02m

C$ 572

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 58 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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 322). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 598). 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 27 January 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 27 January 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
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.7
Good
501 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,205 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,251 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,660 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Food

7.5

Entertainment

6.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 12h 10m. The time it takes to get you to your destination can typically vary by up to 15h. 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$ 247), Air Canada (C$ 274), and Air Transat (C$ 359).

  • 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 - Nassau 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, March is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 322). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 598). 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 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 27 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 473AverageC$ 869FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 482AverageC$ 760FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 493AverageC$ 781FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 549AverageC$ 665FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 694AverageC$ 1,078FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air TransatCheapestC$ 826AverageC$ 980FlexibilityNo 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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