C$ 335 Find Cheap Flights from Winnipeg to Jamaica – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Jamaica departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Best Jamaica Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stopC$ 558
Kingston
Kingston2 stopsC$ 632
Montego Bay
Montego Bay1 stopC$ 558
Kingston
Kingston2 stopsC$ 632

Cheap Flights from Winnipeg to Jamaica

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Jamaica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Jamaica

Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:55 p.m. - 12:50 p.m.
YWG
-
MBJ
16h 55m
1 stop
Air Canada Logo
2:20 p.m. - 10:05 a.m.
MBJ
-
YWG
20h 45m
1 stop
C$ 558Air Canada
Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:00 a.m. - 12:50 p.m.
YWG
-
MBJ
29h 50m
2 stops
Air Canada Logo
2:20 p.m. - 6:25 p.m.
MBJ
-
YWG
29h 05m
2 stops
C$ 558Air Canada
Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:55 p.m. - 5:20 p.m.
YWG
-
MBJ
21h 25m
1 stop
Air Canada Logo
2:20 p.m. - 6:25 p.m.
MBJ
-
YWG
29h 05m
2 stops
C$ 558Air Canada
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
4:55 p.m. - 7:29 p.m.
YWG
-
MBJ
25h 34m
2 stops
WestJet Logo
8:25 p.m. - 12:45 a.m.
MBJ
-
YWG
29h 20m
1 stop
C$ 580WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
4:55 p.m. - 7:29 p.m.
YWG
-
MBJ
25h 34m
2 stops
WestJet Logo
8:25 p.m. - 12:45 a.m.
MBJ
-
YWG
29h 20m
1 stop
C$ 581WestJet
Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:55 p.m. - 12:50 p.m.
YWG
-
MBJ
16h 55m
1 stop
Air Canada Logo
2:20 p.m. - 10:05 a.m.
MBJ
-
YWG
20h 45m
1 stop
C$ 583Air Canada
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
4:55 p.m. - 7:29 p.m.
YWG
-
MBJ
25h 34m
2 stops
WestJet Logo
8:25 p.m. - 12:45 a.m.
MBJ
-
YWG
29h 20m
1 stop
C$ 584WestJet
Mon, 26 Oct - Thu, 29 Oct
Multiple Airlines Logo
12:55 p.m. - 2:30 p.m.
YWG
-
KIN
25h 35m
2 stops
Multiple Airlines Logo
11:45 a.m. - 6:25 p.m.
KIN
-
YWG
30h 40m
2 stops
C$ 705Multiple Airlines
Mon, 26 Oct - Thu, 29 Oct
Multiple Airlines Logo
6:45 a.m. - 2:30 p.m.
YWG
-
KIN
31h 45m
2 stops
Multiple Airlines Logo
11:45 a.m. - 9:14 p.m.
KIN
-
YWG
9h 29m
1 stop
C$ 705Multiple Airlines
Mon, 26 Oct - Thu, 29 Oct
Multiple Airlines Logo
8:05 p.m. - 2:30 p.m.
YWG
-
KIN
18h 25m
1 stop
Multiple Airlines Logo
11:45 a.m. - 9:14 p.m.
KIN
-
YWG
9h 29m
1 stop
C$ 710Multiple Airlines
Booking Insights

KAYAK's insights & trends for Winnipeg to Jamaica flights

Get data-powered insights and trends into flights from Winnipeg to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Winnipeg to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Winnipeg found in the last 5 days was to Montego Bay, at C$ 632 round-trip. The most popular route is from Winnipeg (YWG) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 632.

What is the cheapest time of day to fly to Jamaica?

The average price for all round-trip flights from Winnipeg to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost C$ 851 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 851.

Can I save money by flying with a layover from Winnipeg to Jamaica?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 856, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Winnipeg to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Jamaica is April, when tickets cost C$ 703 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is C$ 1,121 and C$ 934 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Jamaica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Winnipeg to Jamaica, you should book around 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

June

Cheapest flight

C$ 335
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Winnipeg to Kingston

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Winnipeg to Jamaica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Jamaica is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Jamaica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Jamaica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Jamaica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Winnipeg to Jamaica

 
Need help choosing which airline to fly with from Winnipeg to Jamaica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
WestJetOverall score based on 3426 reviews
7.9Crew
7.4Boarding
7.0Comfort
6.1Entertainment
6.2Food
Airline reviews

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

10.0 ExcellentAnonymous, Nov 2025
YWG - YYC
Read more WestJet reviews

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Flight got cancelled. I had to spend many hours on phone to have it rescheduled at my convenience

I like the fact air Canada is on time The food you guys serve is not good

Upgraded to sit at the exit door so good leg room.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

It was swiss air flight and they were very helpful and kind

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

Information on your arrival and departure airports