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Cheap flights from Winnipeg to Jamaica from C$ 336

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Jamaica departing on 5/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
6:55 p.m. - 12:50 p.m.
YWG
-
MBJ
16h 55m
1 stop
Air Canada Logo
2:20 p.m. - 10:05 a.m.
MBJ
-
YWG
20h 45m
1 stop
C$ 559Air Canada
Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:00 a.m. - 12:50 p.m.
YWG
-
MBJ
29h 50m
2 stops
Air Canada Logo
2:20 p.m. - 6:25 p.m.
MBJ
-
YWG
29h 05m
2 stops
C$ 559Air Canada
Tue, 8 Dec - Fri, 11 Dec
Air Canada Logo
6:55 p.m. - 5:20 p.m.
YWG
-
MBJ
21h 25m
1 stop
Air Canada Logo
2:20 p.m. - 6:25 p.m.
MBJ
-
YWG
29h 05m
2 stops
C$ 559Air Canada
Tue, 8 Dec - Fri, 11 Dec
WestJet Logo
4:55 p.m. - 7:29 p.m.
YWG
-
MBJ
25h 34m
2 stops
WestJet Logo
8:25 p.m. - 12:45 a.m.
MBJ
-
YWG
29h 20m
1 stop
C$ 571WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
12:20 p.m. - 7:29 p.m.
YWG
-
MBJ
30h 09m
1 stop
WestJet Logo
2:55 p.m. - 11:35 a.m.
MBJ
-
YWG
21h 40m
1 stop
C$ 581WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
4:55 p.m. - 7:29 p.m.
YWG
-
MBJ
25h 34m
2 stops
WestJet Logo
8:25 p.m. - 12:45 a.m.
MBJ
-
YWG
29h 20m
1 stop
C$ 581WestJet
Tue, 8 Dec - Fri, 18 Dec
Air Canada Logo
6:55 p.m. - 12:50 p.m.
YWG
-
MBJ
16h 55m
1 stop
Air Canada Logo
2:20 p.m. - 10:05 a.m.
MBJ
-
YWG
20h 45m
1 stop
C$ 584Air Canada
Tue, 8 Dec - Fri, 11 Dec
Multiple Airlines Logo
12:55 p.m. - 2:30 p.m.
YWG
-
KIN
25h 35m
2 stops
Multiple Airlines Logo
11:45 a.m. - 6:25 p.m.
KIN
-
YWG
30h 40m
2 stops
C$ 706Multiple Airlines
Mon, 26 Oct - Thu, 29 Oct
Multiple Airlines Logo
6:45 a.m. - 2:30 p.m.
YWG
-
KIN
31h 45m
2 stops
Multiple Airlines Logo
11:45 a.m. - 9:14 p.m.
KIN
-
YWG
9h 29m
1 stop
C$ 706Multiple Airlines
Mon, 26 Oct - Thu, 29 Oct
Multiple Airlines Logo
8:05 p.m. - 2:30 p.m.
YWG
-
KIN
18h 25m
1 stop
Multiple Airlines Logo
11:45 a.m. - 9:14 p.m.
KIN
-
YWG
9h 29m
1 stop
C$ 712Multiple Airlines
Mon, 26 Oct - Thu, 29 Oct

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Air Canada flights from Winnipeg to Jamaica

Our best Air Canada deals on Winnipeg to Jamaica flight tickets
Air Canada
8 Dec
YWG6:55 p.m.Winnipeg
21h 25m
1 stop
MBJ5:20 p.m.Montego Bay Sangster Intl
11 Dec
MBJ2:20 p.m.Montego Bay Sangster Intl
29h 05m
2 stops
YWG6:25 p.m.Winnipeg
C$ 559
Air Canada
8 Dec
YWG6:55 p.m.Winnipeg
21h 25m
1 stop
MBJ5:20 p.m.Montego Bay Sangster Intl
11 Dec
MBJ2:20 p.m.Montego Bay Sangster Intl
29h 05m
2 stops
YWG6:25 p.m.Winnipeg
C$ 584
Air Canada
8 Dec
YWG6:00 a.m.Winnipeg
29h 50m
2 stops
MBJ12:50 p.m.Montego Bay Sangster Intl
11 Dec
MBJ2:20 p.m.Montego Bay Sangster Intl
29h 05m
2 stops
YWG6:25 p.m.Winnipeg
C$ 594

WestJet flights from Winnipeg to Jamaica

Our best WestJet deals on Winnipeg to Jamaica flight tickets
WestJet
8 Dec
YWG4:55 p.m.Winnipeg
25h 34m
2 stops
MBJ7:29 p.m.Montego Bay Sangster Intl
18 Dec
MBJ8:25 p.m.Montego Bay Sangster Intl
29h 20m
1 stop
YWG12:45 a.m.Winnipeg
C$ 571
WestJet
8 Dec
YWG4:55 p.m.Winnipeg
25h 34m
2 stops
MBJ7:29 p.m.Montego Bay Sangster Intl
18 Dec
MBJ8:25 p.m.Montego Bay Sangster Intl
29h 20m
1 stop
YWG12:45 a.m.Winnipeg
C$ 581
WestJet
8 Dec
YWG4:55 p.m.Winnipeg
25h 34m
2 stops
MBJ7:29 p.m.Montego Bay Sangster Intl
18 Dec
MBJ8:25 p.m.Montego Bay Sangster Intl
29h 20m
1 stop
YWG12:45 a.m.Winnipeg
C$ 583

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 3 August 2026.
Use the filters below to find and compare flights from Winnipeg to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:55 p.m.-12:50 p.m.

1 stop16h 55m

Montego Bay Sangster Intl

Fri 11/12

2:20 p.m.-10:05 a.m.

1 stop20h 45m

C$ 559

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:00 a.m.-12:50 p.m.

2 stops29h 50m

Montego Bay Sangster Intl

Fri 11/12

2:20 p.m.-6:25 p.m.

2 stops29h 05m

C$ 559

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:55 p.m.-5:20 p.m.

1 stop21h 25m

Montego Bay Sangster Intl

Fri 11/12

2:20 p.m.-6:25 p.m.

2 stops29h 05m

C$ 559

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

4:55 p.m.-7:29 p.m.

2 stops25h 34m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-12:45 a.m.

1 stop29h 20m

C$ 571

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

12:20 p.m.-7:29 p.m.

1 stop30h 09m

Montego Bay Sangster Intl

Fri 18/12

2:55 p.m.-11:35 a.m.

1 stop21h 40m

C$ 581

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

4:55 p.m.-7:29 p.m.

2 stops25h 34m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-12:45 a.m.

1 stop29h 20m

C$ 581

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:55 p.m.-12:50 p.m.

1 stop16h 55m

Montego Bay Sangster Intl

Fri 11/12

2:20 p.m.-10:05 a.m.

1 stop20h 45m

C$ 584

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 26/10

12:55 p.m.-2:30 p.m.

2 stops25h 35m

Kingston Norman Manley

Thu 29/10

11:45 a.m.-6:25 p.m.

2 stops30h 40m

C$ 706

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 26/10

6:45 a.m.-2:30 p.m.

2 stops31h 45m

Kingston Norman Manley

Thu 29/10

11:45 a.m.-9:14 p.m.

1 stop9h 29m

C$ 706
Quickest round-trip

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 26/10

8:05 p.m.-2:30 p.m.

1 stop18h 25m

Kingston Norman Manley

Thu 29/10

11:45 a.m.-9:14 p.m.

1 stop9h 29m

C$ 712

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Jamaica from

How to get the cheapest flight ticket from Winnipeg to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jamaica?

In general, April is the cheapest month to fly from Winnipeg to Jamaica. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 705. If you aren’t able to travel during the month of April, then book flights to Jamaica from Winnipeg during September instead. Flights to Jamaica in September, while not as cheap as those in April, still average around C$ 781.

What is the cheapest day to depart on your flight to Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Saturday when prices can be found for as low as C$ 814. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Jamaica is Sunday, with ticket prices averaging around C$ 1,021.

What is the cheapest Winnipeg to Jamaica flight route?

Fly from Winnipeg to Montego Bay Sangster Intl for the best Winnipeg - Jamaica flight prices

How far in advance should I book a flight from Winnipeg to Jamaica?

You are more likely to see cheaper flights to Jamaica from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around C$ 881 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Winnipeg for as low as C$ 660 on momondo.

What cabin class options are available on Winnipeg to Jamaica flights?

There is only 1 cabin class available to choose from on Winnipeg to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Winnipeg to Jamaica flights?

You could potentially save up to 21% on your flight if you consider stops on a Winnipeg to Jamaica flight.

Cheap Winnipeg to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Jamaica

Best price found

C$ 691

Fastest flight time

5h 30m

Direct flights

Mon and Sun

Airports in Jamaica

11 airports
The best flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 691
The fastest flight from Winnipeg to Jamaica takes 5h 30m
Direct flights go from Winnipeg to Jamaica on Monday and Sunday. There are no airlines offering direct flights.
There are 11 airports in Jamaica. From Winnipeg there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Winnipeg to Jamaica

  • When did momondo last update prices for flights from Winnipeg Airport to Jamaica?

    Prices for flights from Winnipeg Airport to Jamaica refresh daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Jamaica?

  • How old do you have to be to fly from Winnipeg Airport to Jamaica?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The travel and health documents required for your trip to Jamaica can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Jamaica. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Winnipeg to Jamaica?

Best airlines flying from Winnipeg to Jamaica

Compare and see reviews for airlines that fly from Winnipeg to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 464Free CancellationRating
7.1
11,422 reviews
Search Air Canada flights
WestJetPriceFrom C$ 591Free CancellationRating
7.2
3,425 reviews
Search WestJet flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Jamaica?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Jamaica from Winnipeg.

Can I find flights from Winnipeg to Jamaica with flexible booking policies on momondo?

Yes. All flights to Jamaica from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to Jamaica?

momondo helps you find the best flight between Winnipeg and Jamaica by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Winnipeg to Jamaica right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Jamaica, momondo offers a useful price alert feature which will track prices for flights to Jamaica from Winnipeg and alert you when they change.

An easier way to manage your Jamaica trip

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Find better results for your trip to Jamaica

Popular Cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo
Flights to Montego Bayfrom C$ 366
Flights to Kingstonfrom C$ 491