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Cheap flights from Winnipeg to Jamaica from C$ 336

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
3 Sep — 10 Sep1
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
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 4 August 2026.

Sat 31/106:45 a.m. -
2 stops31h 09m
Wed 4/112:55 p.m. -
2 stops31h 10m
Deal found 3/8C$ 582
Tue 8/124:55 p.m. -
2 stops25h 34m
Fri 18/128:25 p.m. -
1 stop29h 20m
Deal found 1/8C$ 583
Tue 8/126:00 a.m. -
2 stops29h 50m
Fri 11/122:20 p.m. -
2 stops29h 05m
Deal found 31/7C$ 585
Tue 8/1212:20 p.m. -
1 stop24h 34m
Fri 11/122:55 p.m. -
1 stop21h 40m
Deal found 1/8C$ 610
Mon 23/1112:55 p.m. -
2 stops49h 35m
Fri 27/114:30 p.m. -
2 stops55h 20m
Deal found 2/8C$ 634
Tue 13/1012:25 p.m. -
2 stops47h 20m
Sat 31/101:55 p.m. -
2 stops22h 10m
Deal found 3/8C$ 635
Mon 26/106:45 a.m. -
2 stops31h 45m
Thu 29/1011:45 a.m. -
1 stop9h 29m
Deal found 1/8C$ 707
Mon 28/93:20 p.m. -
1 stop22h 35m
Thu 1/103:05 p.m. -
2 stops28h 55m
Deal found 30/7C$ 777
Mon 26/107:15 p.m. -
2 stops39h 20m
Thu 29/1011:45 a.m. -
2 stops30h 40m
Deal found 31/7C$ 822
Fri 7/87:45 a.m. -
1 stop9h 25m
Mon 31/86:25 p.m. -
1 stop14h 15m
Deal found 3/8C$ 1,501

Find flight deals from Winnipeg to Jamaica

Keep the following information in mind while searching for Winnipeg to Jamaica flight deals. Data was last updated 4 August 2026.

Round-trip from

C$ 582

One-way from

C$ 336

Popular in

December

Cheapest in

April

Average price

C$ 883

Good round-trip deal

C$ 692 or less
WestJet
  • WestJet
  • 31/10-4/11
  • 4 total stops
  • 62h 19m total
  • Winnipeg to Jamaica
Search Deals
5/9
  • 5/9
  • 2 total stops
  • 13h 06m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Jamaica.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Jamaica 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 4 August 2026.
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

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 31/10

12:20 p.m.-7:29 p.m.

1 stop31h 09m

Montego Bay Sangster Intl

Wed 4/11

2:55 p.m.-12:45 a.m.

1 stop10h 50m

C$ 582

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:00 a.m.-12:50 p.m.

2 stops29h 50m

Montego Bay Sangster Intl

Fri 11/12

2:20 p.m.-6:25 p.m.

2 stops29h 05m

C$ 595

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

12:20 p.m.-1:54 p.m.

1 stop24h 34m

Montego Bay Sangster Intl

Fri 11/12

2:55 p.m.-11:05 a.m.

2 stops45h 10m

C$ 610

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 26/10

6:45 a.m.-2:30 p.m.

2 stops31h 45m

Kingston Norman Manley

Thu 29/10

11:45 a.m.-9:14 p.m.

1 stop9h 29m

C$ 707

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

6:45 a.m.-4:29 p.m.

1 stop32h 44m

Montego Bay Sangster Intl

Fri 22/1

2:55 p.m.-11:35 a.m.

1 stop21h 40m

C$ 724

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

12:55 p.m.-4:29 p.m.

1 stop26h 34m

Montego Bay Sangster Intl

Sat 30/1

11:55 a.m.-11:35 a.m.

1 stop24h 40m

C$ 731
Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 10/1

12:55 p.m.-1:54 p.m.

2 stops23h 59m

Montego Bay Sangster Intl

Sun 31/1

3:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 734

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 28/9

3:20 p.m.-1:55 p.m.

1 stop22h 35m

Kingston Norman Manley

Thu 1/10

3:05 p.m.-8:00 p.m.

2 stops28h 55m

C$ 777
Cheapest one-way

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 5/9

6:15 a.m.-7:21 p.m.

2 stops13h 06m

C$ 336
Quickest one-way

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 5/9

6:15 a.m.-2:30 p.m.

1 stop8h 15m

C$ 368

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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
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

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$ 706). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 1,143). 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 59 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

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated 4 August 2026.
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
3,426 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Overall

7.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,426 reviews
WestJet
7.2
Good
3,426 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Overall

7.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
Air Canada
7.1
Good
11,426 reviews
WestJet
7.2
Good
3,426 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Overall

7.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Jamaica. 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 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 37 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like WestJet and Air Canada fly from Winnipeg to Jamaica in about 29h 50m. The time it takes to get you to your destination can typically vary by up to 1h 19m. 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$ 634. On average you can expect to pay C$ 772. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 663.

  • 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$ 706). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 1,143). 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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Top 2 airlines flying from Winnipeg to Jamaica

Discover the top 2 airlines that operate flights from Winnipeg to Jamaica. 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 4 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 464AverageC$ 908FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 592AverageC$ 841FlexibilityNo cancel feeOn-time60%
Search WestJet 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 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.

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