C$ 302 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 25/1. 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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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$ 595
Kingston
Kingston2 stopsC$ 1,318
Montego Bay
Montego Bay1 stopC$ 595
Kingston
Kingston2 stopsC$ 1,318

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

Fri, 27 Feb - Sat, 7 Mar
Multiple Airlines Logo
7:30 a.m. - 8:50 a.m.
YWG
-
MBJ
24h 20m1 stop
Multiple Airlines Logo
4:32 p.m. - 2:09 p.m.
MBJ
-
YWG
22h 37m1 stop
C$ 595Multiple Airlines
Sat, 24 Jan - Sat, 31 Jan
Multiple Airlines Logo
8:20 p.m. - 12:29 p.m.
YWG
-
MBJ
15h 09m1 stop
Multiple Airlines Logo
2:35 p.m. - 3:09 p.m.
MBJ
-
YWG
25h 34m1 stop
C$ 622Multiple Airlines
Fri, 27 Feb - Tue, 3 Mar
Multiple Airlines Logo
7:30 a.m. - 8:50 a.m.
YWG
-
MBJ
24h 20m1 stop
Multiple Airlines Logo
1:00 p.m. - 3:09 p.m.
MBJ
-
YWG
27h 09m2 stops
C$ 625Multiple Airlines
Wed, 25 Feb - Sat, 7 Mar
Multiple Airlines Logo
7:30 a.m. - 12:02 p.m.
YWG
-
MBJ
27h 32m2 stops
Multiple Airlines Logo
4:32 p.m. - 2:09 p.m.
MBJ
-
YWG
22h 37m1 stop
C$ 633Multiple Airlines
Fri, 27 Feb - Wed, 4 Mar
Multiple Airlines Logo
7:30 a.m. - 8:50 a.m.
YWG
-
MBJ
24h 20m1 stop
Multiple Airlines Logo
1:00 p.m. - 7:35 p.m.
MBJ
-
YWG
31h 35m2 stops
C$ 658Multiple Airlines
Tue, 24 Feb - Sat, 7 Mar
Multiple Airlines Logo
12:10 p.m. - 12:02 p.m.
YWG
-
MBJ
22h 52m2 stops
Multiple Airlines Logo
4:32 p.m. - 2:09 p.m.
MBJ
-
YWG
22h 37m1 stop
C$ 660Multiple Airlines
Sun, 18 Jan - Thu, 22 Jan
United Airlines Logo
2:20 p.m. - 1:53 p.m.
YWG
-
KIN
46h 33m2 stops
United Airlines Logo
3:00 p.m. - 11:57 a.m.
KIN
-
YWG
45h 57m2 stops
C$ 1,318United Airlines
Sun, 18 Jan - Thu, 22 Jan
United Airlines Logo
2:20 p.m. - 1:53 p.m.
YWG
-
KIN
46h 33m2 stops
United Airlines Logo
3:00 p.m. - 11:57 a.m.
KIN
-
YWG
45h 57m2 stops
C$ 1,319United Airlines
Sun, 18 Jan - Thu, 22 Jan
Delta Logo
7:30 a.m. - 8:00 p.m.
YWG
-
KIN
11h 30m1 stop
Delta Logo
9:00 a.m. - 11:03 a.m.
KIN
-
YWG
27h 03m2 stops
C$ 1,765Delta
Sun, 18 Jan - Thu, 22 Jan
Delta Logo
7:30 a.m. - 8:00 p.m.
YWG
-
KIN
11h 30m1 stop
Delta Logo
9:00 a.m. - 10:08 a.m.
KIN
-
YWG
26h 08m2 stops
C$ 1,767Delta
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$ 460 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$ 460.

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$ 724, 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 December and November, when the average cost of round-trip tickets is C$ 1,051 and C$ 1,033 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 22% 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$ 357
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 6% 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$ 633 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$ 841.

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 3202 reviews
7.9Crew
6.1Entertainment
7.1Comfort
7.4Boarding
6.2Food
Airline reviews

Great seats, super comfortable, but no in flight entertainment which was a let down

10.0 ExcellentCharles, Dec 2025
YYZ - CUN
Read more WestJet reviews

Great seats, super comfortable, but no in flight entertainment which was a let down

Not sure what happened, but for some reason we had to sit on the plane for an extra 10 minutes once we arrived in Abbotsford. Obviously, it was an engine issue.

8 hrs. Of waiting instead of couple of hours..the only good thing I'm still able to go to my destination...

Flight delayed missed connecting flight crew not very helpful very frustrating customer service

Our biggest complaint was a major schedule change that was not communicated to us in any way. Luckily the time change went later not earlier so we did not miss the flight. Our email addresses and phone numbers were on file but we received no email no text message no nothing. Short flight so not much to say.

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I when to Jamaica for my dad funeral and I did not get my luggage from westjet . I add to buy clothes putting me financial debt i did no want to be in Westjet did not call me to apologize are to inquire about my luggage I am still angry about it

Ground staff was not helpful, but staff at the business counter were excellent.

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

The plug in to charge our phones are all loose my block would not stay in!!

My seat was covered in vomit and I will be reaching out to Air Canada

We were happy with the service and cost of checking a bag

I would like to review the next flight from Toronto to Fort Myers as it was a disaster!!

This flight with a lot empty place , and I have more room, feeling comfortable.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Flight was cancelled. Not enough agents to deal with the people in the line. We left and found our own way to Vancouver.

Flight was good, breakfast could be much better. We had come from a domestic flight on the same aircraft and the domestic flight was much better regarding service compared to this international flight.

Flight was great. Meal was really good. Boarding was terrible. Too many people in a small boarding lounge, zones not clearly marked.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

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

Information on your arrival and departure airports