C$ 368 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 19/5. 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.
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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$ 589
Kingston
Kingston2 stopsC$ 608

Cheap Flight Deals from Winnipeg to Jamaica (YWG-JM0)

 
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.

Recent round-trip flight deals from Winnipeg to Jamaica

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Winnipeg to Jamaica.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
WestJet Logo
6:15 p.m. - 11:42 a.m.YWG-MBJ
17h 27m2 stops
WestJet Logo
10:30 a.m. - 12:31 a.m.MBJ-YWG
14h 01m2 stops
C$ 589WestJet
Find Deal
Thu, 22 May - Wed, 11 Jun
WestJet Logo
9:05 p.m. - 11:42 a.m.YWG-MBJ
14h 37m2 stops
WestJet Logo
10:30 a.m. - 9:31 p.m.MBJ-YWG
35h 01m2 stops
C$ 599WestJet
Find Deal
Thu, 22 May - Wed, 11 Jun
 Logo
9:40 a.m. - 8:53 a.m.YWG-KIN
23h 13m2 stops
 Logo
6:25 p.m. - 4:25 p.m.KIN-YWG
22h 00m1 stop
C$ 608
Find Deal
Wed, 21 May - Wed, 28 May
 Logo
9:40 a.m. - 8:53 a.m.YWG-KIN
23h 13m2 stops
 Logo
6:25 p.m. - 4:25 p.m.KIN-YWG
22h 00m1 stop
C$ 614
Find Deal
Wed, 21 May - Wed, 28 May
 Logo
6:30 a.m. - 2:30 p.m.YWG-KIN
8h 00m1 stop
 Logo
6:25 p.m. - 4:25 p.m.KIN-YWG
22h 00m1 stop
C$ 617
Find Deal
Wed, 21 May - Wed, 28 May
 Logo
6:30 a.m. - 2:30 p.m.YWG-KIN
8h 00m1 stop
 Logo
6:25 p.m. - 4:25 p.m.KIN-YWG
22h 00m1 stop
C$ 621
Find Deal
Wed, 21 May - Wed, 28 May
 Logo
11:25 a.m. - 12:29 p.m.YWG-KIN
25h 04m3 stops
 Logo
6:25 p.m. - 4:25 p.m.KIN-YWG
22h 00m1 stop
C$ 657
Find Deal
Wed, 21 May - Wed, 28 May
Air Canada Logo
3:45 p.m. - 11:15 a.m.YWG-MBJ
19h 30m2 stops
Air Canada Logo
12:10 p.m. - 10:10 a.m.MBJ-YWG
22h 00m2 stops
C$ 758Air Canada
Find Deal
Tue, 3 Jun - Sun, 8 Jun
Air Canada Logo
5:10 p.m. - 11:15 a.m.YWG-MBJ
18h 05m1 stop
Air Canada Logo
12:10 p.m. - 9:07 p.m.MBJ-YWG
8h 57m1 stop
C$ 778Air Canada
Find Deal
Fri, 6 Jun - Fri, 13 Jun
United Airlines Logo
4:35 p.m. - 3:10 p.m.YWG-MBJ
46h 35m2 stops
United Airlines Logo
4:12 p.m. - 9:40 a.m.MBJ-YWG
41h 28m2 stops
C$ 1,628United Airlines
Find Deal
Thu, 22 May - Wed, 11 Jun

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$ 462 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$ 462.

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

The average price for all round-trip flights from Winnipeg to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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 19% 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$ 613.

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 October, when tickets cost C$ 636 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is C$ 874 and C$ 868 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 18 weeks before departure.

Good to know

Low season

August

High season

December

Cheapest flight

C$ 368
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly (30% 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.

See more FAQs

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 2815 reviews
7.4Boarding
7.9Crew
6.1Entertainment
7.0Comfort
6.2Food
Airline reviews

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

10.0 ExcellentMary, Apr 2025YVR - MSP
Read more WestJet reviews

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

crew was great, wifi was very poor could not even load a youtube video

WestJet was able to re-book us to the next available flight at no charge when air traffic controller staffing shortage delayed our inbound flight

Our flight was delayed for almost 2 hours resulting in a rush to connect to our next flight

I am a tall woman and could not move my legs enough to reach down under the seat in front of me to retrieve anything I put down there. I sat in both aisle and window seats and felt extremely cramped. In the aisle seat, if the stewardess was heavy, it was impossible to pass, and she would knock my arm shoulder and thigh every time she went by. If I can avoid it, I will not be flying this airline again.

We never had an experience they canceled the flight and they did not offer us an alternative flight. I had to book one on my own expense. They offered us food voucher and we could not use them at the airport it kept saying not attached to an existing flight. The people at the counter were rude and cold and they did not care about our situation

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Get our, as a group, skis on time to their destination. Have more attendants checking people in. There was only one. The line was a block long :( . Also flight change with 5-hour delay

Found the seats very crowded—too close together ! And waited a long time for our luggage All staff at both ends were excellent!!!

First flight out in the morning is often the best chance of running on time. Not in this case, which unfortunately is now what passengers can expect as what is common. - If you are late for a flight, too bad for you. - If West Jet is late, too bad for you. - Bags don't make it? Too bad for you. - Flight change by 1+ days, too bad for you Prices continue to increase, while customer service nosedives. This is backwards and in any other develop country would be considered unacceptable - except for Canada. Too bad for us.

They lost my checked in luggage, why do I pay for my cargo not arriving at the same destination as me?

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

Not enough electronic outlets for charging in the Air Canada waiting to board area but the Most important thing….the plane was booked to only 40% capacity and my row of 2 other seats were empty. My row happened to be one of the few rows that did NOT have raising arm rests. The flight attendant made effort to seat me in a different row. I needed wheelchair assistance due to a cyst on my knee and struggled to move from seat to seat to get to the row. Those 2 empty seats tormented me the entire 15+ hour flight as I had to be upright the entire flight and was not able to elevate my knee. Lots of other passengers were laying down due to the arm rest being able to retract. It is a shame that he couldn’t be gracious and find a row that I could move to.

Crew was pleasant and efficient. The speaker system for instructions was hard to understand

There is not enough space between two chairs and raws.

Just kinda of a bus ride … we could do better. Delay in the flight :(

My experience was poor with customer Services. Please consider flexibility with cancellation due to emergency health condition. Thank you.

During the pre-departure safety briefing, the flight attendants rushed through the mandatory safety announcements in both official languages, making it difficult for passengers to clearly understand the instructions. Given the importance of these messages for passenger safety, this lack of clarity was concerning. Perhaps use a recoded message to alleviate this concern. Additionally, the flight attendants appeared to lack the professional attentiveness typically expected during a flight. Rather than focusing on timely and courteous service, they seemed more engaged in personal conversations than in addressing the needs of passengers. I hope this feedback is taken constructively and helps in maintaining the high standards of professionalism and care that travelers expect from a national carrier: AC.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

Seats were comfortable, flights boarded easily, arrived early in Toronto and on time in Nassau

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