C$ 304 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 24/1. 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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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$ 646
Kingston
Kingston1 stopC$ 662
Montego Bay
Montego Bay1 stopC$ 646
Kingston
Kingston1 stopC$ 662

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, 1 Nov - Mon, 3 Nov
Multiple Airlines Logo
7:05 p.m. - 6:05 p.m.YWG-MBJ
23h 00m2 stops
Multiple Airlines Logo
7:25 p.m. - 3:21 p.m.MBJ-YWG
20h 56m2 stops
C$ 630Multiple Airlines
Find Deal
Sat, 1 Nov - Mon, 3 Nov
Multiple Airlines Logo
5:30 p.m. - 6:05 p.m.YWG-MBJ
24h 35m2 stops
Multiple Airlines Logo
7:25 p.m. - 3:21 p.m.MBJ-YWG
20h 56m2 stops
C$ 634Multiple Airlines
Find Deal
Wed, 7 Jan - Wed, 21 Jan
Air Canada Logo
6:00 a.m. - 6:05 p.m.YWG-MBJ
11h 05m2 stops
Air Canada Logo
7:05 p.m. - 8:28 p.m.MBJ-YWG
26h 23m2 stops
C$ 646Air Canada
Find Deal
Tue, 25 Nov - Tue, 2 Dec
WestJet Logo
8:05 p.m. - 3:33 p.m.YWG-KIN
18h 28m1 stop
WestJet Logo
4:30 p.m. - 11:35 a.m.KIN-YWG
20h 05m1 stop
C$ 662WestJet
Find Deal
Sat, 1 Nov - Mon, 3 Nov
United Airlines Logo
5:30 p.m. - 2:29 p.m.YWG-MBJ
20h 59m2 stops
United Airlines Logo
2:48 p.m. - 11:57 a.m.MBJ-YWG
22h 09m1 stop
C$ 680United Airlines
Find Deal
Wed, 26 Nov - Wed, 3 Dec
WestJet Logo
5:00 a.m. - 3:33 p.m.YWG-KIN
9h 33m1 stop
WestJet Logo
4:30 p.m. - 12:09 p.m.KIN-YWG
20h 39m2 stops
C$ 691WestJet
Find Deal
Tue, 25 Nov - Tue, 2 Dec
WestJet Logo
8:05 p.m. - 3:33 p.m.YWG-KIN
18h 28m1 stop
WestJet Logo
4:30 p.m. - 3:21 p.m.KIN-YWG
23h 51m2 stops
C$ 692WestJet
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$ 697Air Canada
Find Deal
Fri, 28 Nov - Fri, 5 Dec
United Airlines Logo
8:40 a.m. - 4:50 p.m.YWG-MBJ
31h 10m1 stop
United Airlines Logo
1:25 p.m. - 11:57 a.m.MBJ-YWG
23h 32m2 stops
C$ 701United Airlines
Find Deal
Sat, 24 Jan - Sat, 7 Feb
Flair Airlines Logo
8:20 p.m. - 11:30 a.m.YWG-MBJ
14h 10m1 stop
Flair Airlines Logo
12:30 p.m. - 7:35 p.m.MBJ-YWG
32h 05m1 stop
C$ 780Flair 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$ 756 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$ 756.

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$ 911, 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$ 671 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is C$ 1,148 and C$ 929 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 Saturday, 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 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 304
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly (26% more expensive 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$ 641 on average. Morning departures are around 20% 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$ 862.

Top tips for finding cheap flights to Jamaica

  • Looking for a cheap flight? 25% of our users found tickets from Winnipeg to the following destinations at these prices or less: Montego Bay C$ 541 one-way - C$ 796 round-trip

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 8999 reviews
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

4.0 OkayAnonymous, Oct 2025YVR - SFO
Read more United Airlines reviews

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

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

The only thing I can't give good or really good is the fact that we didn't have food ,just a packet of pretzels or cookies which is normal,and ofcourse there isn't any entertainment. I've always flowen WestJet ..I really like the airlines..this plane was smaller one ,pretty tight seating.

Again, flight was late. It’s expected of this airline now i guess.

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

Counter representative refused to check my luggage despite paying for it in advance

We landed 26 min early. It was awesome! Smooth ride too.

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

There is no snack and nit much that would be considered gluten free in yiur food selections. One of your snacks should be a gluten free cookie or small bar etc. maybe it was me but I didn’t see any free movies just internet connection and YouTube .

What do you expect from a Dash 8 plane? No seats really comfortable.

Delayed 8 hours, This is the 2nd time in a month that my flight was not on time.

I like the free air Canada wifi and being able to watch things on there. The basic snacks are good, just wish I could have both. If I’m being really picky, the flight attendant who filled my drink, filled it half with fizz and didn’t take the second to let it go down and add more, so I got maybe half a cup of pop.

Seats too small and too cramped, I have stomach cancer and I threw up after the flight . No advance boarding for disabled people. No aisle seats available for disabled people who have to use the washroom frequently. No space for cabin baggage for disabled people who have to carry bulky medications or equipment to use on the flight. Baggage rules and fees are ridiculous. I have been an aeroplan member for 30 years and I fly frequently, but from now on I will choose offshore carriers. .

Snacks were just placed and many people were hungry and unaware they were available. Ran out of water bottles. Attendants not available. Missed entire meal.

Very Bad experience with Swiss, they robbed me for additional baggage and misguided. The flight was delayed for 2hr 55 minutes, screens were not functional and food was also bad.

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

Too many delays. Seats too small. A budget airline. Will never fly Air Canada again.

On board wifi or other entertainment. Landlines option was good but ran late to Pearson

It was crazy, boarded over a hour late from scheduled departure. Then when arrived in BNA issued with getting off the plane…over 1/2 hour. Not looking forward to flying Air Canada, ever again.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

Flight was late leaving. Charge for luggage which still has not arrived and will be delivered in a week.

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

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