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Cheap flights from Winnipeg to Jamaica from C$ 321

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 20/12. 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

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Find the cheapest flights from Winnipeg to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
8:05 p.m. - 1:54 p.m.YWG-MBJ
16h 49m1 stop
WestJet Logo
2:55 p.m. - 8:06 p.m.MBJ-YWG
30h 11m2 stops
C$ 619WestJet
Find Deal
Fri, 28 Nov - Fri, 5 Dec
United Airlines Logo
2:20 p.m. - 1:46 p.m.YWG-MBJ
22h 26m1 stop
United Airlines Logo
3:36 p.m. - 11:57 a.m.MBJ-YWG
21h 21m2 stops
C$ 622United Airlines
Find Deal
Fri, 28 Nov - Fri, 5 Dec
WestJet Logo
4:10 p.m. - 1:54 p.m.YWG-MBJ
20h 44m2 stops
WestJet Logo
8:25 p.m. - 7:12 p.m.MBJ-YWG
23h 47m1 stop
C$ 625WestJet
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. - 4:35 p.m.MBJ-YWG
22h 30m1 stop
C$ 626Air Canada
Find Deal
Wed, 7 Jan - Wed, 21 Jan
WestJet Logo
5:00 a.m. - 1:54 p.m.YWG-MBJ
7h 54m1 stop
WestJet Logo
2:55 p.m. - 12:42 a.m.MBJ-YWG
10h 47m1 stop
C$ 627WestJet
Find Deal
Fri, 28 Nov - Fri, 5 Dec
WestJet Logo
12:20 p.m. - 1:54 p.m.YWG-MBJ
24h 34m1 stop
WestJet Logo
2:55 p.m. - 12:42 a.m.MBJ-YWG
10h 47m1 stop
C$ 629WestJet
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. - 10:16 a.m.MBJ-YWG
16h 11m1 stop
C$ 663Air Canada
Find Deal
Wed, 7 Jan - Wed, 21 Jan
United Airlines Logo
2:20 p.m. - 2:37 p.m.YWG-MBJ
23h 17m2 stops
United Airlines Logo
2:20 p.m. - 11:39 a.m.MBJ-YWG
21h 19m2 stops
C$ 689United Airlines
Find Deal
Mon, 23 Feb - Mon, 9 Mar
Flair Airlines Logo
8:20 p.m. - 2:30 p.m.YWG-KIN
17h 10m1 stop
Flair Airlines Logo
3:30 p.m. - 7:35 p.m.KIN-YWG
29h 05m1 stop
C$ 900Flair Airlines
Find Deal
Wed, 19 Nov - Sun, 30 Nov
Delta Logo
4:10 p.m. - 7:56 p.m.YWG-KIN
26h 46m2 stops
Delta Logo
9:00 a.m. - 11:38 p.m.KIN-YWG
15h 38m2 stops
C$ 1,597Delta
Find Deal
Thu, 25 Dec - Wed, 7 Jan

WestJet flights from Winnipeg to Jamaica

Our best WestJet deals on Winnipeg to Jamaica flight tickets
WestJet
28 Nov
YWG8:05 p.m.Winnipeg
16h 49m
1 stop
MBJ1:54 p.m.Montego Bay Sangster Intl
5 Dec
MBJ2:55 p.m.Montego Bay Sangster Intl
30h 11m
2 stops
YWG8:06 p.m.Winnipeg
C$ 619
Find similar
WestJet
7 Jan
YWG4:10 p.m.Winnipeg
20h 44m
2 stops
MBJ1:54 p.m.Montego Bay Sangster Intl
21 Jan
MBJ8:25 p.m.Montego Bay Sangster Intl
23h 47m
1 stop
YWG7:12 p.m.Winnipeg
C$ 625
Find similar
WestJet
28 Nov
YWG5:00 a.m.Winnipeg
7h 54m
1 stop
MBJ1:54 p.m.Montego Bay Sangster Intl
5 Dec
MBJ2:55 p.m.Montego Bay Sangster Intl
10h 47m
1 stop
YWG12:42 a.m.Winnipeg
C$ 627
Find similar

United Airlines flights from Winnipeg to Jamaica

Our best United Airlines deals on Winnipeg to Jamaica flight tickets
United Airlines
28 Nov
YWG2:20 p.m.Winnipeg
22h 26m
1 stop
MBJ1:46 p.m.Montego Bay Sangster Intl
5 Dec
MBJ3:36 p.m.Montego Bay Sangster Intl
21h 21m
2 stops
YWG11:57 a.m.Winnipeg
C$ 622
Find similar
United Airlines
23 Feb
YWG2:20 p.m.Winnipeg
23h 17m
2 stops
MBJ2:37 p.m.Montego Bay Sangster Intl
9 Mar
MBJ2:20 p.m.Montego Bay Sangster Intl
21h 19m
2 stops
YWG11:39 a.m.Winnipeg
C$ 689
Find similar
United Airlines
1 Mar
YWG2:20 p.m.Winnipeg
22h 26m
1 stop
MBJ1:46 p.m.Montego Bay Sangster Intl
8 Mar
MBJ1:48 p.m.Montego Bay Sangster Intl
21h 51m
1 stop
YWG11:39 a.m.Winnipeg
C$ 715
Find similar

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 4 November 2025.
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

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

8:05 p.m.-1:54 p.m.

1 stop16h 49m

Montego Bay Sangster Intl

Fri 5/12

2:55 p.m.-8:06 p.m.

2 stops30h 11m

C$ 619

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

2:20 p.m.-1:46 p.m.

1 stop22h 26m

Montego Bay Sangster Intl

Fri 5/12

3:36 p.m.-11:57 a.m.

2 stops21h 21m

C$ 622

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 7/1

4:10 p.m.-1:54 p.m.

2 stops20h 44m

Montego Bay Sangster Intl

Wed 21/1

8:25 p.m.-7:12 p.m.

1 stop23h 47m

C$ 625

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 7/1

6:00 a.m.-6:05 p.m.

2 stops11h 05m

Montego Bay Sangster Intl

Wed 21/1

7:05 p.m.-4:35 p.m.

1 stop22h 30m

C$ 626

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

5:00 a.m.-1:54 p.m.

1 stop7h 54m

Montego Bay Sangster Intl

Fri 5/12

2:55 p.m.-12:42 a.m.

1 stop10h 47m

C$ 627

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

12:20 p.m.-1:54 p.m.

1 stop24h 34m

Montego Bay Sangster Intl

Fri 5/12

2:55 p.m.-12:42 a.m.

1 stop10h 47m

C$ 629

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 7/1

8:15 a.m.-6:05 p.m.

1 stop8h 50m

Montego Bay Sangster Intl

Wed 21/1

7:05 p.m.-10:16 a.m.

1 stop16h 11m

C$ 663

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

2:20 p.m.-2:37 p.m.

2 stops23h 17m

Montego Bay Sangster Intl

Mon 9/3

2:20 p.m.-11:39 a.m.

2 stops21h 19m

C$ 689

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Wed 19/11

8:20 p.m.-2:30 p.m.

1 stop17h 10m

Kingston Norman Manley

Sun 30/11

3:30 p.m.-7:35 p.m.

1 stop29h 05m

C$ 900

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 25/12

4:10 p.m.-7:56 p.m.

2 stops26h 46m

Kingston Norman Manley

Wed 7/1

9:00 a.m.-11:38 p.m.

2 stops15h 38m

C$ 1,597

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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$ 677. If you aren’t able to travel during the month of April, then book flights to Jamaica from Winnipeg during March instead. Flights to Jamaica in March, while not as cheap as those in April, still average around C$ 724.

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 Monday when prices can be found for as low as C$ 630. 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 Saturday, with ticket prices averaging around C$ 927.

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

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Winnipeg to Jamaica during this time can be as low as C$ 646. Try not to purchase tickets in the morning because they tend to be around C$ 876. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 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$ 846 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$ 706 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 27% 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$ 545

Fastest flight time

5h 30m

Direct flights

Mon and Sun

Airports in Jamaica

1 airport
The best one-way flight to Jamaica from Winnipeg in the past 72 hours is C$ 545. The best round-trip flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 802.
The fastest flight from Winnipeg to Jamaica takes 5h 30m
Direct flights go from Winnipeg to Jamaica on Monday and Sunday. The only airline offering direct flights is WestJet.
There is 1 airport near Jamaica: Montego Bay Sangster Intl (MBJ)
Search flight deals

  • 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$ 494Free CancellationRating
7.1
10,403 reviews
Search Air Canada flights
WestJetPriceFrom C$ 519Free CancellationRating
7.2
3,153 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 848Free CancellationRating
7.4
9,002 reviews
Search United Airlines 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Jamaica

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Popular flights according to clicks in the last 7 days on momondo
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