C$ 340 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 29/6. 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 Bay1 stopC$ 632
Kingston
Kingston2 stopsC$ 718
Montego Bay
Montego Bay1 stopC$ 632
Kingston
Kingston2 stopsC$ 718

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

Sun, 19 Apr - Sun, 10 May
United Airlines Logo
2:00 p.m. - 12:50 p.m.
YWG
-
MBJ
22h 50m
1 stop
United Airlines Logo
2:40 p.m. - 11:52 a.m.
MBJ
-
YWG
21h 12m
2 stops
C$ 632United Airlines
Fri, 10 Apr - Fri, 24 Apr
United Airlines Logo
2:00 p.m. - 12:50 p.m.
YWG
-
MBJ
22h 50m
1 stop
United Airlines Logo
1:52 p.m. - 11:52 a.m.
MBJ
-
YWG
22h 00m
1 stop
C$ 665United Airlines
Thu, 21 May - Thu, 11 Jun
WestJet Logo
4:25 p.m. - 11:45 a.m.
YWG
-
MBJ
19h 20m
1 stop
WestJet Logo
12:45 p.m. - 12:55 a.m.
MBJ
-
YWG
12h 10m
1 stop
C$ 668WestJet
Thu, 21 May - Thu, 11 Jun
WestJet Logo
2:55 p.m. - 11:45 a.m.
YWG
-
MBJ
20h 50m
2 stops
WestJet Logo
12:45 p.m. - 2:15 p.m.
MBJ
-
YWG
25h 30m
2 stops
C$ 673WestJet
Thu, 21 May - Thu, 11 Jun
WestJet Logo
6:05 p.m. - 11:45 a.m.
YWG
-
MBJ
17h 40m
1 stop
WestJet Logo
12:45 p.m. - 2:15 p.m.
MBJ
-
YWG
25h 30m
2 stops
C$ 677WestJet
Thu, 21 May - Thu, 11 Jun
WestJet Logo
8:00 a.m. - 11:45 a.m.
YWG
-
MBJ
27h 45m
2 stops
WestJet Logo
12:45 p.m. - 2:15 p.m.
MBJ
-
YWG
25h 30m
2 stops
C$ 679WestJet
Thu, 21 May - Thu, 11 Jun
WestJet Logo
6:15 a.m. - 11:45 a.m.
YWG
-
MBJ
29h 30m
1 stop
WestJet Logo
12:45 p.m. - 2:15 p.m.
MBJ
-
YWG
49h 30m
2 stops
C$ 683WestJet
Thu, 21 May - Thu, 11 Jun
WestJet Logo
6:15 a.m. - 11:45 a.m.
YWG
-
MBJ
29h 30m
1 stop
WestJet Logo
12:45 p.m. - 5:15 p.m.
MBJ
-
YWG
28h 30m
1 stop
C$ 687WestJet
Fri, 10 Apr - Fri, 24 Apr
United Airlines Logo
2:00 p.m. - 1:30 p.m.
YWG
-
MBJ
23h 30m
2 stops
United Airlines Logo
4:12 p.m. - 11:52 a.m.
MBJ
-
YWG
19h 40m
2 stops
C$ 690United Airlines
Mon, 2 Mar - Mon, 9 Mar
Multiple Airlines Logo
6:55 p.m. - 4:24 p.m.
YWG
-
KIN
20h 29m
2 stops
Multiple Airlines Logo
12:17 p.m. - 6:05 p.m.
KIN
-
YWG
29h 48m
3 stops
C$ 871Multiple 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 72 hours was to Montego Bay, at C$ 753 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$ 753.

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$ 749 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 April, when tickets cost C$ 658 (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$ 1,227 and C$ 968 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 Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Jamaica, Saturday is the cheapest day to fly and Sunday 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 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 340
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 6% 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 morning, when round-trip flights cost C$ 870 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$ 870.

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 3255 reviews
6.2Food
7.4Boarding
7.9Crew
7.0Comfort
6.1Entertainment
Airline reviews

As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.

10.0 ExcellentAnonymous, Feb 2026
YYZ - MID
Read more WestJet reviews

As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Experience was good, the wifi hook up is somewhat tough

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

The delays were never ending and we were never properly informed as to why. 1st and 2nd delay were handled well, but by the time we received our 7th delay, and then subsequently asked to willingly get bumped, it turned into one of the worst flying situations of my life. I didn’t get home until 2am which is roughly 5 hours later than originally planned.

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

No food, water, snacks.”beverages”. This was on Christmas Day. Upgrading cost $100, for what exactly?

Again, we were rerouted all the way to Zurich and had a longer journey than expected.

I wish Air Canada would provide a meal on the 5 hrs or more time flight to the passengers.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Terrible… Luggage’s missing for 5-days. Not expedited despite notifying them that insulin and ozempic were in bags and required refrigeration. I’m extremely disappointed. Meds were useless upon delivery as ice pack had dissolved and meds were warm and not useable because their efficacy and potency are now questionable . I’m so disappointed and expecting a full refund for the checked in bags.

Terrible, luggage’s with b/p and diabetes meds including insulin and ozempic. I’ve in them had dissolved and rendered useless

Very bed experience never want to travel air canada anymore

Overall very good 👍 the only disappointment was that I pre ordered a vegan meal and the longest flight YVR-SIN wasn’t on board even though check in said it was and my email booking shows that confirmed ✅ luckily some passengers were not on board and there was a vegetarian meal available, but still, I think you should know because every all the other flights were vegan meals except for the longest so that was a bit of a concern at the beginning of the flight.

Overall a good experience as this leg I was in Business Class. The Lounge was amazing with a view of the planes. The flight attendant spoke way to quickly when giving the information for take off and landing and it would be of no use to a first time traveler. Overall a great airline to travel on.

It was a very small plane and was ok. No food or entertainment so there should be an option for NA.

I travelled in Business class for the first time and wish I could do that again.

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

Information on your arrival and departure airports