How popular is this Winnipeg to Jamaica flight route?

Flights from Winnipeg to Jamaica have been viewed 32 times in the past calendar month.

How long is the flight from Winnipeg to Jamaica?

Airlines like WestJet, Air Canada, and United Airlines fly from Winnipeg to Jamaica in about 9h 05m. The time it takes to get you to your destination can typically vary by up to 19h 54m. There are 3890 km between Winnipeg and Jamaica. Both multi-stop and direct flights can be found to your destination and back.

In terms of precipitation, rainfall in Jamaica ranges from 40.0 - 180.0 mm per month. October is typically the wettest month, when rainfall can reach 180.0 mm. February is typically the driest time to visit Jamaica when rainfall is around 40.0 mm.

If weather is an important factor for your trip to Jamaica, 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 cheapest flights from Winnipeg to Jamaica?

The cheapest flight price from Winnipeg to Jamaica is C$ 391. On average you can expect to pay C$ 683. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 573.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Jamaica as you normally would.

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

Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Jamaica.

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

Yes. In addition to deals on Winnipeg to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Winnipeg to Jamaica?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Jamaica.

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

Yes. Cheapflights offers flight deals from Winnipeg to Jamaica 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$ 237+ Cheap Flights from Winnipeg to Jamaica

Cheap flight deals from Winnipeg to Jamaica

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

Cheapest flights from Winnipeg to Jamaica
Explore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 September 2026.

Sun 6/128:20 a.m. -

Nonstop5h 20m

Sun 13/123:40 p.m. -

Nonstop5h 40m

Deal found 17/9C$ 461

Fri 27/116:00 a.m. -

2 stops12h 35m

Sun 13/121:45 p.m. -

Nonstop6h 00m

Deal found 17/9C$ 478

Sun 13/128:20 a.m. -

Nonstop5h 20m

Sun 20/123:40 p.m. -

Nonstop5h 40m

Deal found 17/9C$ 562

Sun 6/126:55 p.m. -

1 stop21h 25m

Sun 13/122:40 p.m. -

2 stops22h 05m

Deal found 17/9C$ 577

Sat 5/128:00 a.m. -

Nonstop5h 35m

Sat 30/18:35 p.m. -

1 stop15h 30m

Deal found 18/9C$ 580

Fri 23/1012:50 p.m. -

2 stops25h 40m

Mon 26/103:30 p.m. -

1 stop9h 14m

Deal found 22/9C$ 607

Fri 25/98:00 a.m. -

2 stops30h 30m

Fri 2/103:30 p.m. -

1 stop18h 15m

Deal found 19/9C$ 618

Thu 22/104:05 p.m. -

2 stops46h 25m

Tue 27/103:30 p.m. -

1 stop9h 14m

Deal found 21/9C$ 619

Tue 8/123:05 p.m. -

1 stop25h 15m

Fri 18/121:50 p.m. -

2 stops29h 35m

Deal found 20/9C$ 622

Sat 24/106:15 a.m. -

1 stop8h 15m

Tue 27/103:30 p.m. -

1 stop9h 14m

Deal found 21/9C$ 626

Tue 20/104:25 p.m. -

1 stop22h 05m

Tue 27/103:30 p.m. -

1 stop19h 35m

Deal found 20/9C$ 636

Sun 25/107:00 a.m. -

2 stops31h 30m

Mon 2/114:30 p.m. -

2 stops32h 29m

Deal found 22/9C$ 638

Best flights from Winnipeg to Jamaica
Discover carefully curated flight deals from Winnipeg to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 22 September 2026.

Fri 23/106:05 p.m. -

1 stop20h 25m

Mon 26/103:30 p.m. -

1 stop9h 14m

Deal found 21/9C$ 612

Mon 30/117:15 a.m. -

1 stop9h 05m

Sun 27/123:40 p.m. -

Nonstop5h 40m

Deal found 18/9C$ 683

Sat 12/128:40 a.m. -

2 stops28h 59m

Fri 29/11:25 p.m. -

2 stops34h 08m

Deal found 18/9C$ 711

Mon 30/117:00 a.m. -

1 stop8h 45m

Wed 30/122:25 p.m. -

1 stop8h 32m

Deal found 18/9C$ 753

Mon 26/109:35 p.m. -

2 stops16h 55m

Thu 29/103:00 p.m. -

2 stops27h 25m

Deal found 20/9C$ 765

Mon 23/118:05 p.m. -

1 stop18h 25m

Fri 27/114:30 p.m. -

1 stop9h 14m

Deal found 20/9C$ 634

Mon 7/128:40 a.m. -

2 stops28h 34m

Wed 27/11:25 p.m. -

2 stops34h 08m

Deal found 18/9C$ 711

Tue 8/126:55 p.m. -

1 stop16h 55m

Fri 18/122:20 p.m. -

1 stop20h 40m

Deal found 17/9C$ 729

Mon 19/104:05 p.m. -

2 stops46h 25m

Fri 23/103:30 p.m. -

2 stops24h 30m

Deal found 17/9C$ 713

Sun 29/112:40 p.m. -

1 stop25h 40m

Thu 31/121:50 p.m. -

1 stop8h 34m

Deal found 20/9C$ 764

Thu 22/102:55 p.m. -

3 stops23h 35m

Thu 29/106:55 p.m. -

2 stops22h 30m

Deal found 22/9C$ 865

Mon 30/115:15 a.m. -

1 stop29h 20m

Wed 30/1212:45 p.m. -

2 stops54h 40m

Deal found 18/9C$ 778

Wed 16/125:00 a.m. -

1 stop13h 35m

Sat 26/128:35 p.m. -

1 stop29h 09m

Deal found 22/9C$ 783

Fri 16/107:10 p.m. -

1 stop16h 10m

Fri 23/1012:30 p.m. -

2 stops21h 29m

Deal found 18/9C$ 781

Fri 27/115:00 a.m. -

1 stop9h 30m

Sun 13/128:35 p.m. -

2 stops48h 15m

Deal found 19/9C$ 1,060

Sun 20/128:20 a.m. -

Nonstop5h 20m

Sun 27/122:20 p.m. -

2 stops29h 05m

Deal found 17/9C$ 807

Mon 30/118:05 p.m. -

1 stop18h 25m

Sun 3/18:35 p.m. -

2 stops39h 30m

Deal found 19/9C$ 1,739

Sat 5/126:10 a.m. -

2 stops56h 20m

Sun 3/18:35 p.m. -

2 stops29h 09m

Deal found 19/9C$ 1,744

Find flight deals from Winnipeg to Jamaica

Round-trip from	C$ 461
One-way from	C$ 237
Popular in	December
Cheapest in	October
Average price	C$ 879
Good round-trip deal	C$ 391 or less

Air Canada
6/12-13/12
Nonstop
11h 00m total
Winnipeg to Jamaica

Search Deals

Air Canada
6/12-31/12
Nonstop
5h 20m total
Winnipeg to Jamaica

Search Deals

Highest demand for flights based on searches. 8% potential increase in price (C$ 109 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2026

Search Deals

Price to beat on a round-trip flight from Winnipeg to Jamaica.

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 6/12

8:20 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$ 237

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Fri 23/10

8:10 p.m.-2:30 p.m.

1 stop18h 20m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 350

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Thu 5/11

5:15 a.m.-11:35 a.m.

1 stop29h 20m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 352

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Thu 5/11

12:10 p.m.-3:30 p.m.

2 stops26h 20m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 363

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Fri 6/11

6:00 a.m.-1:30 p.m.

2 stops30h 30m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 369

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Fri 23/10

7:00 a.m.-2:30 p.m.

2 stops31h 30m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 374

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Fri 6/11

6:55 p.m.-1:30 p.m.

1 stop17h 35m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 376

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Mon 2/11

8:40 a.m.-12:13 p.m.

2 stops26h 33m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 441

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Mon 2/11

7:15 a.m.-5:20 p.m.

1 stop9h 05m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 461

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 19/12

2:05 p.m.-1:25 p.m.

1 stop22h 20m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 481

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/9

Showing 1-10 of 34 resultsSorted by cheapest first

Best time to book a flight from Winnipeg to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Winnipeg with our price prediction graph.

YWG-KIN

YWG-MBJ

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 Jamaica

YWG-JM0

YWG-KIN

YWG-MBJ

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

Currently, April is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 704). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 1,097). 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 Jamaica?

To ensure you get the cheapest price possible for a flight from Winnipeg to Jamaica, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Reviews of airlines servicing Jamaica

Read reviews from past customers who have flown WestJet and Air Canada from Winnipeg to Jamaica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

WestJet

7.2

Good

3,446 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

3,446 reviews

WestJet

7.2

Good

3,446 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

11,665 reviews

WestJet

7.2

Good

3,446 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 Jamaica?
Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Jamaica.
How popular is this Winnipeg to Jamaica flight route?
Flights from Winnipeg to Jamaica have been viewed 32 times in the past calendar month.
How long is the flight from Winnipeg to Jamaica?
Airlines like WestJet, Air Canada, and United Airlines fly from Winnipeg to Jamaica in about 9h 05m. The time it takes to get you to your destination can typically vary by up to 19h 54m. There are 3890 km between Winnipeg and Jamaica. Both multi-stop and direct flights can be found to your destination and back.
What are the cheapest flights from Winnipeg to Jamaica?
The cheapest flight price from Winnipeg to Jamaica is C$ 391. On average you can expect to pay C$ 683. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 573.
Can I find deals for flights from Winnipeg to Jamaica that include hotel bookings?
Yes. In addition to deals on Winnipeg to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Winnipeg to Jamaica?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Jamaica.
Can I find deals for business class flights from Winnipeg to Jamaica?
Yes. Cheapflights offers flight deals from Winnipeg to Jamaica 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 Jamaica?
Currently, April is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 704). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 1,097). 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 Jamaica

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 463	AverageC$ 856	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
WestJet	CheapestC$ 529	AverageC$ 817	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

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How does Cheapflights help users find flights from Winnipeg to Jamaica?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Jamaica. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Jamaica?

Cheapflights helps you find that perfect flight to Jamaica from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Winnipeg to Jamaica with no change fees?

Yes, we can. To see specific flights from Winnipeg to Jamaica with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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Cheap flights from Winnipeg to Jamaica from C$ 237

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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Winnipeg to Jamaica

Cheapest flights from Winnipeg to JamaicaExplore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 September 2026.

Explore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 September 2026.

Best flights from Winnipeg to JamaicaDiscover carefully curated flight deals from Winnipeg to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 22 September 2026.

Discover carefully curated flight deals from Winnipeg to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 22 September 2026.

Direct flights from Winnipeg to JamaicaExplore direct flight options from Winnipeg to Jamaica based on user searches, and compare prices and availability for your desired travel dates. Data last updated 22 September 2026.

Explore direct flight options from Winnipeg to Jamaica based on user searches, and compare prices and availability for your desired travel dates. Data last updated 22 September 2026.

Last-minute flights from Winnipeg to JamaicaDiscover last-minute flight deals from Winnipeg to Jamaica. Data last updated 22 September 2026 and is based on user searches.

Discover last-minute flight deals from Winnipeg to Jamaica. Data last updated 22 September 2026 and is based on user searches.

One-way flights from Winnipeg to JamaicaSearch for one-way flight options from Winnipeg to Jamaica. Find affordable one-way fares based on user searches. Data last updated 22 September 2026.

Search for one-way flight options from Winnipeg to Jamaica. Find affordable one-way fares based on user searches. Data last updated 22 September 2026.

Find flight deals from Winnipeg to Jamaica

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Cheapflights Fare Finder

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

Best time to book a flight from Winnipeg to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Winnipeg with our price prediction graph.

Cheapflights Insights

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

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

To ensure you get the cheapest price possible for a flight from Winnipeg to Jamaica, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Reviews of airlines servicing Jamaica

Read reviews from past customers who have flown WestJet and Air Canada from Winnipeg to Jamaica. Users can see the overall rating for each airline as well as how each is rated 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 Jamaica?

How popular is this Winnipeg to Jamaica flight route?

How long is the flight from Winnipeg to Jamaica?

What are the cheapest flights from Winnipeg to Jamaica?

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

How can I find direct flights from Winnipeg to Jamaica?

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

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

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 Jamaica

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

Complete your trip

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

Direct flights to

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Search flights from Winnipeg to Jamaica by cabin class

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

Winnipeg and Jamaica flights

Browse other Winnipeg and Jamaica flight options. Last updated on 22 September 2026.

Popular flight searches

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Top 2 airlines flying from Winnipeg to Jamaica

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How does Cheapflights help users find flights from Winnipeg to Jamaica?

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Jamaica?

Can Cheapflights find flights from Winnipeg to Jamaica with no change fees?

Can Cheapflights notify me if prices for flights from Winnipeg to Jamaica become cheaper?

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Cheapest flights from Winnipeg to Jamaica
Explore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 September 2026.

Best flights from Winnipeg to Jamaica
Discover carefully curated flight deals from Winnipeg to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 22 September 2026.

Direct flights from Winnipeg to Jamaica
Explore direct flight options from Winnipeg to Jamaica based on user searches, and compare prices and availability for your desired travel dates. Data last updated 22 September 2026.

Last-minute flights from Winnipeg to Jamaica
Discover last-minute flight deals from Winnipeg to Jamaica. Data last updated 22 September 2026 and is based on user searches.

One-way flights from Winnipeg to Jamaica
Search for one-way flight options from Winnipeg to Jamaica. Find affordable one-way fares based on user searches. Data last updated 22 September 2026.