C$ 312 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 11/9. 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

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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 Bay2 stopsC$ 631
Kingston
Kingston3 stopsC$ 938
Montego Bay
Montego Bay2 stopsC$ 631
Kingston
Kingston3 stopsC$ 938

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, 9 Sep - Tue, 23 Sep
Air Canada Logo
11:40 a.m. - 11:10 a.m.YWG-MBJ
47h 30m2 stops
Air Canada Logo
12:10 p.m. - 10:38 a.m.MBJ-YWG
22h 28m1 stop
C$ 631Air Canada
Find Deal
Fri, 29 Aug - Fri, 5 Sep
WestJet Logo
6:30 a.m. - 6:26 p.m.YWG-MBJ
11h 56m1 stop
WestJet Logo
12:45 p.m. - 12:13 a.m.MBJ-YWG
11h 28m1 stop
C$ 653WestJet
Find Deal
Fri, 29 Aug - Fri, 5 Sep
WestJet Logo
6:30 a.m. - 6:26 p.m.YWG-MBJ
11h 56m1 stop
WestJet Logo
12:45 p.m. - 5:40 p.m.MBJ-YWG
28h 55m2 stops
C$ 667WestJet
Find Deal
Wed, 29 Oct - Sun, 2 Nov
 Logo
7:30 a.m. - 7:53 a.m.YWG-MBJ
24h 23m1 stop
 Logo
8:25 p.m. - 11:35 a.m.MBJ-YWG
16h 10m1 stop
C$ 715
Find Deal
Wed, 29 Oct - Sun, 2 Nov
 Logo
7:30 a.m. - 7:53 a.m.YWG-MBJ
24h 23m1 stop
 Logo
1:25 p.m. - 12:42 a.m.MBJ-YWG
12h 17m1 stop
C$ 718
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. - 1:09 p.m.MBJ-YWG
24h 17m2 stops
C$ 735United Airlines
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$ 737United Airlines
Find Deal
Mon, 15 Sep - Fri, 17 Oct
Air Canada Logo
8:10 p.m. - 11:10 a.m.YWG-MBJ
15h 00m1 stop
Air Canada Logo
12:10 p.m. - 9:10 p.m.MBJ-YWG
9h 00m1 stop
C$ 781Air Canada
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Sat, 27 Dec - Sun, 4 Jan
Delta Logo
6:55 p.m. - 2:13 p.m.YWG-MBJ
18h 18m2 stops
Delta Logo
8:00 a.m. - 3:07 p.m.MBJ-YWG
8h 07m1 stop
C$ 1,149Delta
Find Deal
Sat, 27 Dec - Sun, 4 Jan
Delta Logo
6:55 p.m. - 2:13 p.m.YWG-MBJ
18h 18m2 stops
Delta Logo
8:00 a.m. - 3:07 p.m.MBJ-YWG
8h 07m1 stop
C$ 1,151Delta
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Winnipeg to Jamaica.

The cheapest ticket to Jamaica from Winnipeg found in the last 72 hours was to Montego Bay, at C$ 364 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$ 364.

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$ 753 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$ 645 (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$ 929 and C$ 896 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 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.


Good to know

Low seasonSeptember
Cheapest flightC$ 312
Best time to beat the crowds (17% less expensive on average)
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 16% 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$ 598.

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 8896 reviews
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

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

10.0 ExcellentAnonymous, Jul 2025YYZ - SFO
Read more United Airlines reviews

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.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

7 hour layover was a drag. Free internet on the long leg was great.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

From vancouver go calgary nd vice vetsa fligjt was delayed

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

It was good! Short flight and it was on time!

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

My flight was delayed three times then eventually cancelled the next flight was the following day scheduled for 1030 it was delayed I had to cancel reservations I had to put people up in hotels on the other end as they came out of town to pick me up all at my expense because WestJet couldn’t get it together I’m very disappointed in WestJet’s performance and how they handled the situation Get your customers to where they need to be in a timely fashion, even if that means putting them on your competitors jets Customer service should be number one I will think twice now with booking with WestJet

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Everything could have been better from the planes not being delayed to the rudeness of staff to it was just horrible will not use kayak again or Air Canada I can't see what would ever change my mind now

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

Bad experience flying with air Canada . Seats not comfortable . Checked bag was delayed and was bought home next day by airport employee. Had to buy toiletries since bag was delayed . No compensation was even suggested . Will not fly air canada again

I n the Toronto airport I had trouble finding my zone. It was 47. I went from Zone 1 to the end of the line.didn't find it. Then saw my zone somewhat by accident over by where you first come in. Signs could be more helpful or more personnel directing people like me.

When I came in the front door in Montreal airport I didn't know where to go, first time traveling. Signs were not directing me.

The AC could have been better . Other than that , all was good

No room when you sit. Fell very cramped. Food was only ok. Service was acceptable. Entertainment system was very buggy.

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

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