C$ 262 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 8/11. 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

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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$ 579
Kingston
Kingston2 stopsC$ 852
Montego Bay
Montego Bay1 stopC$ 579
Kingston
Kingston2 stopsC$ 852

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

Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
8:05 p.m. - 12:54 p.m.YWG-MBJ
16h 49m1 stop
WestJet Logo
1:25 p.m. - 11:35 a.m.MBJ-YWG
23h 10m1 stop
C$ 579WestJet
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Fri, 14 Nov - Sat, 29 Nov
 Logo
7:30 a.m. - 3:15 p.m.YWG-MBJ
30h 45m1 stop
 Logo
2:50 p.m. - 12:41 a.m.MBJ-YWG
10h 51m1 stop
C$ 583
Find Deal
Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
6:55 p.m. - 12:54 p.m.YWG-MBJ
17h 59m2 stops
WestJet Logo
8:25 p.m. - 3:21 p.m.MBJ-YWG
19h 56m2 stops
C$ 600WestJet
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Thu, 30 Oct - Tue, 4 Nov
 Logo
9:00 p.m. - 2:15 p.m.YWG-MBJ
17h 15m2 stops
 Logo
2:50 p.m. - 11:53 a.m.MBJ-YWG
22h 03m1 stop
C$ 616
Find Deal
Thu, 30 Oct - Tue, 4 Nov
United Airlines Logo
2:20 p.m. - 3:12 p.m.YWG-MBJ
48h 52m2 stops
United Airlines Logo
1:25 p.m. - 11:57 a.m.MBJ-YWG
23h 32m2 stops
C$ 621United Airlines
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Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
8:05 p.m. - 6:23 p.m.YWG-MBJ
22h 18m1 stop
WestJet Logo
8:25 p.m. - 11:35 a.m.MBJ-YWG
16h 10m1 stop
C$ 629WestJet
Find Deal
Thu, 30 Oct - Tue, 4 Nov
WestJet Logo
12:20 p.m. - 12:54 p.m.YWG-MBJ
24h 34m1 stop
WestJet Logo
7:25 p.m. - 12:42 a.m.MBJ-YWG
30h 17m1 stop
C$ 633WestJet
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Air Canada Logo
8:15 a.m. - 6:05 p.m.YWG-MBJ
8h 50m1 stop
Air Canada Logo
7:05 p.m. - 4:35 p.m.MBJ-YWG
22h 30m1 stop
C$ 680Air Canada
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Fri, 28 Nov - Fri, 5 Dec
Air Canada Logo
6:00 a.m. - 6:05 p.m.YWG-MBJ
11h 05m2 stops
Air Canada Logo
7:05 p.m. - 4:35 p.m.MBJ-YWG
22h 30m1 stop
C$ 682Air Canada
Find Deal
Mon, 15 Sep - Fri, 17 Oct
United Airlines Logo
4:25 p.m. - 11:43 a.m.YWG-MBJ
19h 18m2 stops
United Airlines Logo
12:52 p.m. - 3:31 p.m.MBJ-YWG
26h 39m2 stops
C$ 891United Airlines
Find Deal
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 72 hours was to Montego Bay, at C$ 860 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 72 hours was C$ 860.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 886 on average.

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 September, when tickets cost C$ 650 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is C$ 935 and C$ 902 respectively.

What’s the cheapest day of the week to fly from Winnipeg to Jamaica?

The average price of all round-trip flights from Winnipeg to Jamaica clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Winnipeg to Jamaica, look for departures on Mondays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Jamaica, Saturday is the cheapest day to fly and Wednesday is the most expensive.

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 4 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonNovember
Cheapest flightC$ 262
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 8% 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.

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

    The cheapest time of day to fly to Jamaica is generally in the afternoon, when round-trip flights cost C$ 460 on average. Morning departures are around 18% more expensive than evening flights, 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$ 609.

Reviews of the top 3 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.
7.4
United AirlinesOverall score based on 8937 reviews
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

10.0 ExcellentPaulos, Aug 2025YUL - IAD
Read more United Airlines reviews

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

The experience was good just the upcharge of over a hundred dollars was not cool.

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.

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Good, a bit cramped in the seat as my neighbour was a bit large

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

While I appreciated the food (it was unexpected), it was interruptive for sleeping. We paid extra for reserved seats, but when we checked in they gave us different seats. I had to call WestJet arounf 11:30pm the night before our flight to get this fixed. We were give seats in the emengency row to resolve the issue.

Not enough food option. And not enough advices or information about what we are gonna eat.

Please make more option. And be more precise on the type of food you giving. Diner and breakfast can be different

I like how spacious the plane was but I did not like the fact that there was no entertainment

Had to cancel flight due to strike. Hope things will be better next August when we will rebook. Very disappointing as it was our 50th wedding anniversary celebration l!

I’ve wasted 7 hours of my time because of the delayed. ;(

The crew were fabulous. The flight was bumpy and I always like the captain to tell me what that is about or my imagination gets carries away.

Overall great. The crews were lovely. The seats are awful. I always emerge with a back ache.

I liked the behaviour of the crew members.The flight was good.

Would like whole can of pop for 2. Treats were not great . The garlic pretzels were terrible for someone who can't eat garlic. Passenger was 84.

I had boarding pass on my phone. Husband and I were seated together. Agent printed out boarding passes and we were separated for the flight

1 hour late No hot drinks No restroom in the back of the plane

You was on strike and I had to get another r flight and you did not give me my money back

Food can be better. Taste and option, the pasta wasn't the greatest.

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