C$ 338 Find Cheap Flights from Winnipeg to Jamaica

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 3/10. 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 Bay2 stopsC$ 624
Kingston
Kingston2 stopsC$ 712
Montego Bay
Montego Bay2 stopsC$ 624
Kingston
Kingston2 stopsC$ 712

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

Sat, 17 Oct - Sat, 31 Oct
WestJet Logo
4:15 p.m. - 11:45 a.m.
YWG
-
MBJ
19h 30m
2 stops
WestJet Logo
1:50 p.m. - 11:50 p.m.
MBJ
-
YWG
34h 00m
2 stops
C$ 624WestJet
Sat, 17 Oct - Sat, 31 Oct
WestJet Logo
4:15 p.m. - 11:45 a.m.
YWG
-
MBJ
43h 30m
2 stops
WestJet Logo
1:50 p.m. - 12:55 a.m.
MBJ
-
YWG
11h 05m
1 stop
C$ 631WestJet
Sat, 17 Oct - Sat, 31 Oct
WestJet Logo
4:25 p.m. - 11:45 a.m.
YWG
-
MBJ
19h 20m
1 stop
WestJet Logo
1:50 p.m. - 3:20 p.m.
MBJ
-
YWG
25h 30m
1 stop
C$ 637WestJet
Sat, 3 Oct - Sat, 10 Oct
WestJet Logo
7:00 a.m. - 11:45 a.m.
YWG
-
MBJ
28h 45m
2 stops
WestJet Logo
7:30 p.m. - 9:20 a.m.
MBJ
-
YWG
37h 50m
2 stops
C$ 648WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
6:15 a.m. - 5:24 p.m.
YWG
-
MBJ
10h 09m
1 stop
WestJet Logo
8:25 p.m. - 11:35 a.m.
MBJ
-
YWG
16h 10m
1 stop
C$ 650WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
6:15 a.m. - 5:24 p.m.
YWG
-
MBJ
10h 09m
1 stop
WestJet Logo
8:25 p.m. - 9:05 p.m.
MBJ
-
YWG
49h 40m
2 stops
C$ 652WestJet
Mon, 21 Sep - Fri, 25 Sep
Air Canada Logo
1:30 p.m. - 1:55 p.m.
YWG
-
KIN
24h 25m
2 stops
Air Canada Logo
3:05 p.m. - 8:00 p.m.
KIN
-
YWG
28h 55m
2 stops
C$ 712Air Canada
Mon, 21 Sep - Fri, 25 Sep
Air Canada Logo
1:30 p.m. - 1:55 p.m.
YWG
-
KIN
24h 25m
2 stops
Air Canada Logo
3:05 p.m. - 11:17 p.m.
KIN
-
YWG
8h 12m
1 stop
C$ 713Air Canada
Wed, 14 Oct - Fri, 16 Oct
Air Canada Logo
1:25 p.m. - 1:55 p.m.
YWG
-
KIN
24h 30m
2 stops
Air Canada Logo
3:05 p.m. - 9:57 a.m.
KIN
-
YWG
18h 52m
1 stop
C$ 718Air Canada
Mon, 3 Aug - Mon, 10 Aug
Multiple Airlines Logo
7:00 a.m. - 2:30 p.m.
YWG
-
KIN
55h 30m
2 stops
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
C$ 853Multiple 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$ 678 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$ 678.

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$ 881 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$ 881.

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$ 671, 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 March, when tickets cost C$ 195 (return) on average. On the other hand, the most expensive months are February and May, when the average cost of round-trip tickets is C$ 752 and C$ 532 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 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJune
Cheapest flightC$ 338
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Winnipeg to Montego Bay

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 3377 reviews
7.9Crew
6.2Food
6.1Entertainment
7.4Boarding
7.0Comfort
Airline reviews

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

10.0 ExcellentAnonymous, Jun 2026
YYJ - YYC
Read more WestJet reviews

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

I like the idea of a non-overnight flight to Europe.

The food was very good. I was nit expecting a meal on a red eye trip. I was pleasantly surprised! Plus we arrived a few minutes earlier than expected!

The crew was excellent. The turbulence was very bad and they were unable to serve our dinner. The captain informed the passengers that we were going to get water and snack instead. They provided us ample snacks instead. Otherwise the trip was good.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

I loved the fact it was on time and it was a smooth flight to my destination.

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

The meal options were ok but the actual food was terrible. On my return journey, they simply said that there was no vegetarian option and somehow struggled to give me dinner and did not give me any breakfast at all which in my opinion was terrible. Not having ANY vegetarian meal was surprising and never had such an experience in the recent years.

Every flight was canceled and they didn’t care much about their passengers

Smooth ride but I wish they have better food selections.

Flight got delayed But satisfied with the pricing of tickets

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

I was through check-in right away and on the plane before I knew it perfect in every way

Multiple delays and gate changes resulting in arrival with a 5 hour delay.

Mutiple delays and changes of gate resulting in arrival 5 hours after intended.

Excellent flight crew. Very comfortable plane. Entertainment options on air Canada were great!

One crew member, Brandy was very helpful with recovering phone lost in customs. The plane was ancient and poorly maintained. Checked baggage did not arrive with flight. Almost missed flight because if insanely short layover time. Air Canada is worst flight I have ever booked with Kayak. Wanted to charge for headsets for on flight media.

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

Information on your arrival and departure airports