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Cheap flights from Winnipeg to Jamaica from C$ 326

YWG — MBJ
5 Dec — 12 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Jamaica

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Jamaica

Sun 6/129:20 a.m. -
Nonstop5h 20m
Sun 13/123:40 p.m. -
Nonstop5h 40m
Deal found 5/11C$ 622
Sun 29/117:55 p.m. -
1 stop21h 25m
Thu 3/121:50 p.m. -
2 stops29h 35m
Deal found 31/10C$ 650
Sun 27/126:10 a.m. -
Nonstop5h 35m
Sun 27/128:35 p.m. -
1 stop29h 09m
Deal found 3/11C$ 658
Sat 5/127:00 a.m. -
1 stop10h 20m
Sat 12/128:35 p.m. -
1 stop29h 09m
Deal found 4/11C$ 689
Fri 27/117:55 p.m. -
1 stop17h 35m
Sun 13/124:15 p.m. -
1 stop18h 00m
Deal found 1/11C$ 697
Fri 27/117:55 p.m. -
1 stop17h 35m
Fri 4/128:35 p.m. -
1 stop13h 40m
Deal found 1/11C$ 699
Sun 29/119:05 p.m. -
1 stop16h 30m
Sun 6/122:50 p.m. -
1 stop10h 54m
Deal found 2/11C$ 703
Sun 13/129:20 a.m. -
Nonstop5h 20m
Sun 10/11:50 p.m. -
2 stops29h 35m
Deal found 3/11C$ 713
Sat 28/116:00 a.m. -
1 stop13h 35m
Sat 5/128:35 p.m. -
1 stop15h 30m
Deal found 4/11C$ 720
Wed 2/129:05 p.m. -
1 stop21h 50m
Tue 8/127:55 p.m. -
1 stop14h 20m
Deal found 3/11C$ 785
Thu 3/127:00 a.m. -
1 stop11h 55m
Tue 8/127:55 p.m. -
1 stop14h 20m
Deal found 3/11C$ 791
Sat 5/1211:00 a.m. -
1 stop31h 55m
Tue 8/127:55 p.m. -
1 stop14h 20m
Deal found 3/11C$ 796

Find flight deals from Winnipeg to Jamaica

Round-trip from

C$ 566

One-way from

C$ 326

Popular in

July

Cheapest in

October

Average price

C$ 854

Good round-trip deal

C$ 660 or less

Good one-way deal

C$ 290 or less
Flair Airlines
  • Flair Airlines
  • 17/1-24/1
  • 2 total stops
  • 46h 15m total
  • Winnipeg to Jamaica
Search Deals
Air Canada
  • 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$ 110 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Price to beat on a round-trip flight from Winnipeg to Jamaica.
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Price to beat on a one-way flight from Winnipeg to Jamaica.
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Cheapflights Fare Finder

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

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

9:20 a.m.-3:40 p.m.

Nonstop5h 20m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 326

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 10/1

6:00 a.m.-2:30 p.m.

1 stop31h 30m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 330

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 6/12

7:55 p.m.-5:42 p.m.

1 stop20h 47m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 426

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 6/12

3:15 p.m.-3:14 p.m.

2 stops22h 59m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 449

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Sat 14/11

9:35 p.m.-7:55 p.m.

2 stops21h 20m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 483

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Tue 15/12

9:05 p.m.-8:35 p.m.

1 stop22h 30m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 521

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Mon 9/11

7:55 p.m.-2:48 p.m.

2 stops41h 53m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 530

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Tue 1/12

10:30 p.m.-7:55 p.m.

3 stops44h 25m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 637

WinnipegKingston

YWG Winnipeg - KIN Kingston Norman Manley

YWGKIN

Winnipeg

Sat 14/11

3:15 p.m.-2:52 p.m.

3 stops22h 37m

Kingston Norman Manley

Wed 31/12

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

Nonstop0h 00m

C$ 668

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sun 20/12

6:10 a.m.-12:45 p.m.

Nonstop5h 35m

Montego Bay Sangster Intl

Wed 31/12

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

Nonstop0h 00m

C$ 686

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 29 resultsSorted by cheapest first
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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.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Jamaica

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

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 639). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 982). 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 73 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
3,441 reviews
Check prices

Entertainment

6.1

Comfort

7.1

Crew

7.9

Overall

7.2

Food

6.2

Boarding

7.4

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
3,441 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Entertainment

6.1

Comfort

7.1

Crew

7.9

Overall

7.2

Food

6.2

Boarding

7.4

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
11,861 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Entertainment

6.1

Comfort

7.1

Crew

7.9

Overall

7.2

Food

6.2

Boarding

7.4

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 25 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like WestJet, United Airlines, and Air Canada fly from Winnipeg to Jamaica in about 19h 30m. The time it takes to get you to your destination can typically vary by up to 33h 04m. There are 3993 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$ 281. On average you can expect to pay C$ 587. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 482.

  • 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, October is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 639). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 982). 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

Top 2 airlines flying from Winnipeg to Jamaica

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 462AverageC$ 791FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 495AverageC$ 783FlexibilityNo cancel feeOn-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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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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