How long is the flight from Winnipeg to Caribbean?

Airlines like Air Canada, WestJet, and Flair Airlines fly from Winnipeg to Caribbean in about 10h 15m. The time it takes to get you to your destination can typically vary by up to 21h 40m. 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.

In terms of precipitation, rainfall in Caribbean ranges from 53.0 - 152.0 mm per month. October is typically the wettest month, when rainfall can reach 152.0 mm. February is typically the driest time to visit Caribbean when rainfall is around 53.0 mm.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

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.

What is the cheapest time of day to fly from YWG to CB?

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.

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.

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.

C$ 245+ Cheap Flights from Winnipeg to Caribbean

Cheap flight deals from Winnipeg to Caribbean

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

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 25 October 2026.

Sun 6/1210:35 a.m. -

1 stop28h 00m

Thu 10/123:35 p.m. -

1 stop10h 09m

Deal found 23/10C$ 483

Thu 10/128:20 p.m. -

2 stops17h 05m

Thu 17/121:05 p.m. -

1 stop9h 19m

Deal found 22/10C$ 534

Sun 13/129:20 a.m. -

Nonstop5h 20m

Sun 20/123:40 p.m. -

Nonstop5h 40m

Deal found 21/10C$ 562

Sat 28/119:05 a.m. -

1 stop13h 30m

Thu 3/125:30 p.m. -

Nonstop6h 30m

Deal found 20/10C$ 564

Wed 2/128:15 a.m. -

1 stop12h 25m

Tue 8/127:45 p.m. -

1 stop16h 15m

Deal found 20/10C$ 569

Sun 6/129:20 a.m. -

Nonstop5h 20m

Sun 13/123:40 p.m. -

Nonstop5h 40m

Deal found 23/10C$ 573

Thu 10/123:05 p.m. -

1 stop22h 10m

Thu 17/1212:30 p.m. -

1 stop9h 54m

Deal found 22/10C$ 574

Mon 30/117:55 p.m. -

1 stop16h 15m

Fri 4/121:05 p.m. -

1 stop26h 04m

Deal found 21/10C$ 578

Sun 6/129:05 a.m. -

1 stop8h 40m

Sun 13/127:45 p.m. -

1 stop16h 30m

Deal found 22/10C$ 578

Sun 29/117:00 a.m. -

2 stops28h 30m

Thu 3/122:05 p.m. -

1 stop20h 55m

Deal found 19/10C$ 581

Sun 13/126:10 a.m. -

Nonstop5h 35m

Sun 20/122:50 p.m. -

1 stop10h 54m

Deal found 23/10C$ 581

Tue 17/1112:20 p.m. -

1 stop8h 20m

Tue 24/1112:35 p.m. -

1 stop23h 25m

Deal found 21/10C$ 592

Best flights from Winnipeg to Caribbean
Discover carefully curated flight deals from Winnipeg to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 25 October 2026.

Thu 10/128:20 p.m. -

2 stops17h 05m

Thu 17/121:05 p.m. -

1 stop9h 19m

Deal found 22/10C$ 534

Sun 29/116:00 a.m. -

1 stop10h 15m

Mon 30/115:05 p.m. -

1 stop19h 00m

Deal found 23/10C$ 601

Sat 23/17:00 a.m. -

1 stop12h 00m

Sat 6/29:00 p.m. -

1 stop14h 15m

Deal found 24/10C$ 786

Sat 16/17:55 p.m. -

2 stops41h 53m

Fri 22/11:25 p.m. -

2 stops21h 44m

Deal found 20/10C$ 816

Mon 30/117:55 p.m. -

1 stop16h 15m

Fri 4/121:05 p.m. -

1 stop26h 04m

Deal found 21/10C$ 578

Wed 18/116:00 a.m. -

1 stop10h 15m

Wed 25/115:05 p.m. -

1 stop19h 00m

Deal found 21/10C$ 609

Sun 6/129:05 a.m. -

1 stop8h 40m

Sun 13/127:45 p.m. -

1 stop16h 30m

Deal found 22/10C$ 578

Sun 6/129:05 p.m. -

1 stop17h 30m

Thu 10/123:35 p.m. -

2 stops33h 24m

Deal found 23/10C$ 633

Sun 29/117:55 p.m. -

1 stop24h 30m

Thu 3/122:05 p.m. -

1 stop20h 55m

Deal found 19/10C$ 581

Sun 22/116:00 a.m. -

1 stop10h 15m

Wed 2/125:05 p.m. -

1 stop8h 39m

Deal found 20/10C$ 636

Wed 2/127:00 a.m. -

2 stops39h 35m

Tue 8/127:45 p.m. -

2 stops24h 40m

Deal found 20/10C$ 591

Sun 13/129:40 a.m. -

2 stops26h 33m

Sat 23/13:20 p.m. -

2 stops28h 08m

Deal found 21/10C$ 854

Sun 29/117:55 p.m. -

1 stop21h 25m

Thu 3/121:50 p.m. -

1 stop8h 34m

Deal found 24/10C$ 599

Mon 22/29:35 p.m. -

2 stops15h 27m

Tue 23/31:15 p.m. -

1 stop20h 00m

Deal found 23/10C$ 927

Sun 29/117:00 a.m. -

2 stops30h 15m

Mon 30/119:25 p.m. -

1 stop15h 24m

Deal found 23/10C$ 602

Tue 20/48:40 a.m. -

2 stops28h 30m

Tue 27/44:12 p.m. -

2 stops19h 27m

Deal found 23/10C$ 902

Sat 16/19:15 a.m. -

Nonstop5h 35m

Fri 22/18:35 p.m. -

1 stop14h 30m

Deal found 24/10C$ 786

Wed 16/126:00 a.m. -

1 stop9h 30m

Wed 13/13:40 p.m. -

1 stop20h 20m

Deal found 21/10C$ 963

Thu 10/128:15 a.m. -

1 stop12h 10m

Thu 17/129:25 p.m. -

2 stops20h 13m

Deal found 22/10C$ 613

Tue 13/48:40 a.m. -

2 stops37h 43m

Mon 17/512:30 a.m. -

2 stops36h 09m

Deal found 21/10C$ 942

Sun 29/116:00 a.m. -

1 stop9h 30m

Thu 3/125:30 p.m. -

1 stop9h 14m

Deal found 19/10C$ 823

Tue 17/117:00 a.m. -

2 stops15h 35m

Tue 24/111:05 p.m. -

2 stops22h 55m

Deal found 21/10C$ 622

Sun 29/118:15 a.m. -

2 stops38h 20m

Sun 6/1210:40 p.m. -

1 stop27h 04m

Deal found 22/10C$ 627

Mon 23/117:55 p.m. -

2 stops21h 25m

Fri 27/1112:45 p.m. -

2 stops28h 53m

Deal found 25/10C$ 1,141

Sat 20/26:00 a.m. -

1 stop23h 15m

Sat 27/27:45 p.m. -

Nonstop6h 40m

Deal found 25/10C$ 867

Sun 6/129:05 a.m. -

2 stops27h 05m

Thu 10/121:10 p.m. -

2 stops22h 05m

Deal found 20/10C$ 641

Tue 6/48:40 a.m. -

2 stops37h 43m

Mon 24/512:30 a.m. -

2 stops16h 08m

Deal found 22/10C$ 1,138

Thu 3/1210:35 a.m. -

1 stop27h 25m

Fri 11/123:50 p.m. -

1 stop21h 15m

Deal found 20/10C$ 870

Sat 13/39:35 p.m. -

2 stops40h 00m

Sat 20/312:10 p.m. -

1 stop9h 07m

Deal found 24/10C$ 1,221

Tue 6/46:55 p.m. -

1 stop19h 35m

Thu 15/44:30 p.m. -

1 stop18h 28m

Deal found 23/10C$ 647

Find flight deals from Winnipeg to Caribbean

Round-trip from	C$ 482
One-way from	C$ 245
Popular in	August
Cheapest in	March
Average price	C$ 801
Good round-trip deal	C$ 672 or less
Good one-way deal	C$ 291 or less

WestJet
6/12-10/12
2 total stops
38h 09m total
Winnipeg to Caribbean

Search Deals

9/12-31/12
1 total stop
27h 35m total
Winnipeg to Caribbean

Search Deals

Highest demand for flights based on searches. 4% potential increase in price (C$ 45 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Wed 9/12

11:00 a.m.-2:35 p.m.

1 stop27h 35m

George Town Owen Roberts Intl

Wed 31/12

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

Nonstop0h 00m

C$ 245

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Tue 24/11

12:20 p.m.-12:10 p.m.

1 stop23h 50m

George Town Owen Roberts Intl

Wed 31/12

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

Nonstop0h 00m

C$ 256

WinnipegNassau

YWG Winnipeg - NAS Nassau Intl

YWGNAS

Winnipeg

Mon 7/12

9:05 a.m.-1:15 p.m.

1 stop28h 10m

Nassau Intl

Wed 31/12

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

Nonstop0h 00m

C$ 259

WinnipegGeorge Town

YWG Winnipeg - GCM George Town Owen Roberts Intl

YWGGCM

Winnipeg

Wed 9/12

7:00 a.m.-12:10 p.m.

2 stops29h 10m

George Town Owen Roberts Intl

Wed 31/12

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

Nonstop0h 00m

C$ 265

Quickest round-trip

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 6/12

9:20 a.m.-2:40 p.m.

Nonstop5h 20m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 300

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Sun 6/12

9:05 a.m.-6:45 p.m.

1 stop8h 40m

Punta Cana

Wed 31/12

12:00 a.m.-10:30 p.m.

Nonstop0h 00m

C$ 321

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Thu 4/2

11:00 a.m.-2:35 p.m.

1 stop26h 35m

Punta Cana

Wed 31/12

12:00 a.m.-10:30 p.m.

Nonstop0h 00m

C$ 323

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Tue 8/12

9:05 a.m.-11:35 p.m.

1 stop13h 30m

Punta Cana

Wed 31/12

12:00 a.m.-10:30 p.m.

Nonstop0h 00m

C$ 323

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Thu 10/12

6:15 a.m.-9:40 p.m.

1 stop14h 25m

Punta Cana

Wed 31/12

12:00 a.m.-10:30 p.m.

Nonstop0h 00m

C$ 328

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Wed 16/12

3:05 p.m.-1:45 p.m.

1 stop21h 40m

Punta Cana

Wed 31/12

12:00 a.m.-10:30 p.m.

Nonstop0h 00m

C$ 329

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/10

Showing 1-10 of 60 resultsSorted by cheapest first

...

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.

YWG-GCM

YWG-PUJ

YWG-MBJ

YWG-NAS

YWG-POP

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

YWG-0CB

YWG-GCM

YWG-PUJ

YWG-MBJ

YWG-NAS

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$ 732). Flying from Winnipeg to Caribbean in February is currently the most expensive (average of C$ 962). 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.

How far ahead should I book a flight from Winnipeg to Caribbean?

The price you pay for your flight from Winnipeg to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Caribbean

Get a feel of what it's like to fly with WestJet and Air Canada 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.

WestJet

7.2

Good

3,445 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

WestJet

7.2

Good

3,445 reviews

WestJet

7.2

Good

3,445 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

Air Canada

7.1

Good

11,810 reviews

WestJet

7.2

Good

3,445 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

Related info for your journey

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 Air Canada, WestJet, and Flair Airlines fly from Winnipeg to Caribbean in about 10h 15m. The time it takes to get you to your destination can typically vary by up to 21h 40m. 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, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 732). Flying from Winnipeg to Caribbean in February is currently the most expensive (average of C$ 962). 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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Top 2 airlines flying from Winnipeg to Caribbean

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 299	AverageC$ 832	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
WestJet	CheapestC$ 380	AverageC$ 738	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

Fly with Cheapflights

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.

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Cheap flights from Winnipeg to Caribbean from C$ 245

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Winnipeg to Caribbean

Cheapest flights from Winnipeg to CaribbeanExplore 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 25 October 2026.

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 25 October 2026.

Best flights from Winnipeg to CaribbeanDiscover carefully curated flight deals from Winnipeg to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 25 October 2026.

Discover carefully curated flight deals from Winnipeg to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 25 October 2026.

Direct flights from Winnipeg to CaribbeanExplore direct flight options from Winnipeg to Caribbean based on user searches, and compare prices and availability for your desired travel dates. Data last updated 25 October 2026.

Explore direct flight options from Winnipeg to Caribbean based on user searches, and compare prices and availability for your desired travel dates. Data last updated 25 October 2026.

Last-minute flights from Winnipeg to CaribbeanDiscover last-minute flight deals from Winnipeg to Caribbean. Data last updated 25 October 2026 and is based on user searches.

Discover last-minute flight deals from Winnipeg to Caribbean. Data last updated 25 October 2026 and is based on user searches.

One-way flights from Winnipeg to CaribbeanSearch for one-way flight options from Winnipeg to Caribbean. Find affordable one-way fares based on user searches. Data last updated 25 October 2026.

Search for one-way flight options from Winnipeg to Caribbean. Find affordable one-way fares based on user searches. Data last updated 25 October 2026.

Find flight deals from Winnipeg to Caribbean

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Cheapflights Fare Finder

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

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.

Cheapflights Insights

What is the cheapest month to book a flight from Winnipeg to Caribbean?

How far ahead should I book a flight from Winnipeg to Caribbean?

The price you pay for your flight from Winnipeg to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Caribbean

Get a feel of what it's like to fly with WestJet and Air Canada 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.

Related info for your journey

What airport do you fly from for flights from Winnipeg to Caribbean?

How long is the flight from Winnipeg to Caribbean?

What are the most popular routes from Winnipeg to Caribbean?

Can I find deals for flights from Winnipeg to Caribbean that include hotel bookings?

How can I find direct flights from Winnipeg to Caribbean?

Can I find deals for business class flights from Winnipeg to Caribbean?

What is the cheapest month to book a flight from Winnipeg to Caribbean?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Caribbean

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

Complete your trip

Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to

Book a non-stop flight to one of these other cities located in .

Search flights from Winnipeg to Caribbean by cabin class

Find flights from Winnipeg to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Winnipeg and Caribbean flights

Browse other Winnipeg and Caribbean flight options. Last updated on 25 October 2026.

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Top 2 airlines flying from Winnipeg to Caribbean

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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 25 October 2026.

Best flights from Winnipeg to Caribbean
Discover carefully curated flight deals from Winnipeg to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 25 October 2026.

Direct flights from Winnipeg to Caribbean
Explore direct flight options from Winnipeg to Caribbean based on user searches, and compare prices and availability for your desired travel dates. Data last updated 25 October 2026.

Last-minute flights from Winnipeg to Caribbean
Discover last-minute flight deals from Winnipeg to Caribbean. Data last updated 25 October 2026 and is based on user searches.

One-way flights from Winnipeg to Caribbean
Search for one-way flight options from Winnipeg to Caribbean. Find affordable one-way fares based on user searches. Data last updated 25 October 2026.