C$ 330 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 7/7. 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$ 725
Kingston
Kingston1 stopC$ 682
Montego Bay
Montego Bay2 stopsC$ 725
Kingston
Kingston1 stopC$ 682

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, 24 Jun - Fri, 27 Jun
Air Canada Logo
7:00 p.m. - 12:35 p.m.YWG-KIN
17h 35m1 stop
Air Canada Logo
1:45 p.m. - 10:19 a.m.KIN-YWG
44h 34m2 stops
C$ 682Air Canada
Find Deal
Tue, 24 Jun - Fri, 27 Jun
Air Canada Logo
7:00 p.m. - 12:35 p.m.YWG-KIN
17h 35m1 stop
Air Canada Logo
1:45 p.m. - 10:19 a.m.KIN-YWG
44h 34m2 stops
C$ 684Air Canada
Find Deal
Thu, 7 Aug - Thu, 14 Aug
WestJet Logo
9:05 p.m. - 6:26 p.m.YWG-MBJ
21h 21m2 stops
WestJet Logo
12:45 p.m. - 5:41 p.m.MBJ-YWG
28h 56m2 stops
C$ 725WestJet
Find Deal
Thu, 7 Aug - Thu, 14 Aug
WestJet Logo
5:45 p.m. - 6:26 p.m.YWG-MBJ
24h 41m1 stop
WestJet Logo
12:45 p.m. - 5:41 p.m.MBJ-YWG
28h 56m2 stops
C$ 731WestJet
Find Deal
Thu, 7 Aug - Thu, 14 Aug
WestJet Logo
5:45 p.m. - 6:26 p.m.YWG-MBJ
24h 41m1 stop
WestJet Logo
12:45 p.m. - 12:13 a.m.MBJ-YWG
11h 28m1 stop
C$ 744WestJet
Find Deal
Thu, 7 Aug - Thu, 14 Aug
Air Canada Logo
5:00 a.m. - 12:35 p.m.YWG-KIN
7h 35m1 stop
Air Canada Logo
1:45 p.m. - 9:40 a.m.KIN-YWG
19h 55m1 stop
C$ 763Air Canada
Find Deal
Fri, 25 Jul - Fri, 1 Aug
 Logo
9:05 p.m. - 7:55 a.m.YWG-MBJ
34h 50m2 stops
 Logo
12:45 p.m. - 12:13 a.m.MBJ-YWG
11h 28m1 stop
C$ 798
Find Deal
Tue, 24 Jun - Fri, 27 Jun
Air Canada Logo
5:10 p.m. - 12:35 p.m.YWG-KIN
19h 25m1 stop
Air Canada Logo
1:45 p.m. - 4:18 p.m.KIN-YWG
26h 33m1 stop
C$ 808Air Canada
Find Deal
Tue, 24 Jun - Fri, 27 Jun
Air Canada Logo
8:00 a.m. - 12:35 p.m.YWG-KIN
28h 35m2 stops
Air Canada Logo
1:45 p.m. - 10:19 a.m.KIN-YWG
44h 34m2 stops
C$ 813Air Canada
Find Deal
Tue, 24 Jun - Fri, 27 Jun
WestJet Logo
10:00 a.m. - 2:30 p.m.YWG-KIN
28h 30m2 stops
WestJet Logo
3:30 p.m. - 11:42 p.m.KIN-YWG
32h 12m2 stops
C$ 822WestJet
Find Deal
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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$ 1,069 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$ 1,069.

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$ 718 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$ 641 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is C$ 859 and C$ 849 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 the flight from Winnipeg to Jamaica, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.


Good to know

Low seasonAugust
High seasonJanuary
Cheapest flightC$ 330
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 8% 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.

  • 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$ 599.

Top 3 airlines serving 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 8790 reviews
7.0Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

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

10.0 ExcellentAnonymous, May 2025YVR - SFO
Read more United Airlines reviews

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.

headphone jack didnt work for the first flight and not much variety

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

Lots of overhead storage, good crew, good service, smooth landing.

Lots of overhead storage and a good crew and service.

The small prop plane was crowded and the overhead luggage storage is a smaller than on the jets. Other than that, the crew was good, the flight was on time and the landing was smooth.

There was a medical emergency that the crew handled very well. There was no “entertainment” of any sort-no movie/music/whatever. Food was typical of airlines: mediocre.

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

Terrible decision to take a night flight. Not enough time to sleep and premium seat has no foot rest ao couldn’t get comfortable!

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

Was on a Swoop plane. No wifi and no Westjet connect

Food hope it make it international not mainly like pilipino food

Just a little improvement on food but everything is excellent

Like- beer/wine for free Dis-like- all other aspects- customer service was horrible the entire trip. No help from Air Canada after they changed flight 6+ hours later. Also they put us on standby for no reason. Then almost 2 hours to get our bags after we arrived back at airport

This was actually a bus ride to the KW airport. It was smooth and comfortable and on time.

The plane in use lacked an entertainment system (perhaps because it was still being updated?). It was an overnight flight so it wasn't terrible but still. The actual seat was adequate but not great. As an economy flyer, food review is largely irrelevant. I am unhappy with this race to the bottom for services provided especially as it applies to baggage restrictions.

Service Director cut all cabin lights and window screens defaulted to dark, but it was an afternoon flight going west. I spent hours trying to see what was reading as reading lights weren't working either. What the hell.

Good flight, friendly crew and overall - good service on United Airlines.

Enjoyed the flights with Air Canada. Friendly, courteous staff and flight crew - kept us informed and efficiently got us boarded and to destination on time. Seats were reasonably comfortable and good room in the overhead spaces.

The food could have been better. The flight attendant was the friendliest and most helpful I have ever had.

In flight WiFi not working. entertainment system not functioning Food was mediocre poor for business class Service was ok but not excellent Crew were pleasant. Announcements were made at a ridiculous volume.

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

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