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Cheap flights from Winnipeg to Jamaica from C$ 291

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 30/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Jamaica

Cheap round-trip flights

WestJet Logo
8:05 p.m. - 12:54 p.m.YWG-MBJ
16h 49m1 stop
WestJet Logo
8:25 p.m. - 12:42 a.m.MBJ-YWG
29h 17m1 stop
C$ 556WestJet
Find Deal
Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
12:40 p.m. - 12:54 p.m.YWG-MBJ
24h 14m2 stops
WestJet Logo
8:25 p.m. - 12:42 a.m.MBJ-YWG
29h 17m1 stop
C$ 561WestJet
Find Deal
Wed, 29 Oct - Sun, 2 Nov
Logo
7:30 a.m. - 2:22 p.m.YWG-MBJ
29h 52m1 stop
Logo
4:51 p.m. - 6:05 p.m.MBJ-YWG
26h 14m2 stops
C$ 567
Find Deal
Sun, 8 Feb - Thu, 19 Feb
Logo
7:30 a.m. - 2:22 p.m.YWG-MBJ
29h 52m1 stop
Logo
4:51 p.m. - 3:09 p.m.MBJ-YWG
23h 18m1 stop
C$ 574
Find Deal
Fri, 6 Feb - Thu, 19 Feb
WestJet Logo
9:00 p.m. - 12:54 p.m.YWG-MBJ
15h 54m2 stops
WestJet Logo
8:25 p.m. - 3:21 p.m.MBJ-YWG
19h 56m2 stops
C$ 577WestJet
Find Deal
Wed, 29 Oct - Sun, 2 Nov
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$ 638Air Canada
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. - 12:39 p.m.MBJ-YWG
18h 34m2 stops
C$ 646Air Canada
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Air Transat Logo
12:10 p.m. - 11:15 a.m.YWG-MBJ
22h 05m1 stop
Air Transat Logo
1:25 p.m. - 11:35 p.m.MBJ-YWG
10h 10m1 stop
C$ 723Air Transat
Find Deal
Mon, 23 Feb - Wed, 11 Mar
Air Transat Logo
6:00 a.m. - 11:15 a.m.YWG-MBJ
28h 15m1 stop
Air Transat Logo
1:25 p.m. - 3:30 p.m.MBJ-YWG
26h 05m1 stop
C$ 735Air Transat
Find Deal
Mon, 23 Feb - Tue, 10 Mar
United Airlines Logo
2:20 p.m. - 1:46 p.m.YWG-MBJ
22h 26m1 stop
United Airlines Logo
2:20 p.m. - 11:39 a.m.MBJ-YWG
21h 19m2 stops
C$ 778United Airlines
Find Deal
Mon, 23 Feb - Mon, 9 Mar

WestJet flights from Winnipeg to Jamaica

Our best WestJet deals on Winnipeg to Jamaica flight tickets
WestJet
29 Oct
YWG8:05 p.m.Winnipeg
16h 49m
1 stop
MBJ12:54 p.m.Montego Bay Sangster Intl
2 Nov
MBJ8:25 p.m.Montego Bay Sangster Intl
29h 17m
1 stop
YWG12:42 a.m.Winnipeg
C$ 556
Find similar
WestJet
29 Oct
YWG12:40 p.m.Winnipeg
24h 14m
2 stops
MBJ12:54 p.m.Montego Bay Sangster Intl
2 Nov
MBJ8:25 p.m.Montego Bay Sangster Intl
29h 17m
1 stop
YWG12:42 a.m.Winnipeg
C$ 561
Find similar
WestJet
29 Oct
YWG9:00 p.m.Winnipeg
15h 54m
2 stops
MBJ12:54 p.m.Montego Bay Sangster Intl
2 Nov
MBJ8:25 p.m.Montego Bay Sangster Intl
19h 56m
2 stops
YWG3:21 p.m.Winnipeg
C$ 577
Find similar

Air Transat flights from Winnipeg to Jamaica

Our best Air Transat deals on Winnipeg to Jamaica flight tickets
Air Transat
23 Feb
YWG12:10 p.m.Winnipeg
22h 05m
1 stop
MBJ11:15 a.m.Montego Bay Sangster Intl
11 Mar
MBJ1:25 p.m.Montego Bay Sangster Intl
10h 10m
1 stop
YWG11:35 p.m.Winnipeg
C$ 723
Find similar
Air Transat
23 Feb
YWG6:00 a.m.Winnipeg
28h 15m
1 stop
MBJ11:15 a.m.Montego Bay Sangster Intl
10 Mar
MBJ1:25 p.m.Montego Bay Sangster Intl
26h 05m
1 stop
YWG3:30 p.m.Winnipeg
C$ 735
Find similar
Air Transat
2 Feb
YWG12:10 p.m.Winnipeg
22h 05m
1 stop
MBJ11:15 a.m.Montego Bay Sangster Intl
1 Mar
MBJ8:15 p.m.Montego Bay Sangster Intl
20h 15m
1 stop
YWG3:30 p.m.Winnipeg
C$ 741
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 15 September 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

Wed 29/10

8:05 p.m.-12:54 p.m.

1 stop16h 49m

Montego Bay Sangster Intl

Sun 2/11

8:25 p.m.-12:42 a.m.

1 stop29h 17m

C$ 556

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

12:40 p.m.-12:54 p.m.

2 stops24h 14m

Montego Bay Sangster Intl

Sun 2/11

8:25 p.m.-12:42 a.m.

1 stop29h 17m

C$ 561

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 8/2

7:30 a.m.-2:22 p.m.

1 stop29h 52m

Montego Bay Sangster Intl

Thu 19/2

4:51 p.m.-6:05 p.m.

2 stops26h 14m

C$ 567

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 6/2

7:30 a.m.-2:22 p.m.

1 stop29h 52m

Montego Bay Sangster Intl

Thu 19/2

4:51 p.m.-3:09 p.m.

1 stop23h 18m

C$ 574

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

9:00 p.m.-12:54 p.m.

2 stops15h 54m

Montego Bay Sangster Intl

Sun 2/11

8:25 p.m.-3:21 p.m.

2 stops19h 56m

C$ 577

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

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

1 stop8h 50m

Montego Bay Sangster Intl

Fri 5/12

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

1 stop16h 11m

C$ 638

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

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

1 stop8h 50m

Montego Bay Sangster Intl

Fri 5/12

7:05 p.m.-12:39 p.m.

2 stops18h 34m

C$ 646

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

12:10 p.m.-11:15 a.m.

1 stop22h 05m

Montego Bay Sangster Intl

Wed 11/3

1:25 p.m.-11:35 p.m.

1 stop10h 10m

C$ 723

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

6:00 a.m.-11:15 a.m.

1 stop28h 15m

Montego Bay Sangster Intl

Tue 10/3

1:25 p.m.-3:30 p.m.

1 stop26h 05m

C$ 735

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

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

1 stop22h 26m

Montego Bay Sangster Intl

Mon 9/3

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

2 stops21h 19m

C$ 778

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$ 667. 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$ 688.

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$ 621. 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 Thursday, with ticket prices averaging around C$ 897.

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$ 637. Try not to purchase tickets in the morning because they tend to be around C$ 838. 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$ 812 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$ 649 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 40% 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$ 735

Fastest flight time

5h 25m

Direct flights

Mon and Sun

Airports in Jamaica

1 airport
The best flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 735
The fastest flight from Winnipeg to Jamaica takes 5h 25m
Direct flights go from Winnipeg to Jamaica on Monday and Sunday. There are no airlines offering direct flights.
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$ 487Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
WestJetPriceFrom C$ 512Free CancellationRating
7.2
3,091 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 836Free CancellationRating
7.4
8,929 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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