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Cheap flights from Winnipeg to Jamaica from C$ 363

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 29/6. 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.
WestJet Logo
8:00 a.m. - 11:45 a.m.
YWG
-
MBJ
27h 45m
2 stops
WestJet Logo
7:30 p.m. - 9:40 p.m.
MBJ
-
YWG
26h 10m
2 stops
C$ 638WestJet
Sun, 12 Jul - Sun, 19 Jul
WestJet Logo
6:15 a.m. - 5:24 p.m.
YWG
-
MBJ
10h 09m
1 stop
WestJet Logo
2:55 p.m. - 11:35 a.m.
MBJ
-
YWG
21h 40m
1 stop
C$ 648WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
6:15 a.m. - 5:24 p.m.
YWG
-
MBJ
10h 09m
1 stop
WestJet Logo
8:25 p.m. - 11:05 a.m.
MBJ
-
YWG
39h 40m
2 stops
C$ 651WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
6:15 a.m. - 6:30 p.m.
YWG
-
MBJ
12h 15m
1 stop
WestJet Logo
7:30 p.m. - 5:15 p.m.
MBJ
-
YWG
21h 45m
1 stop
C$ 658WestJet
Sun, 12 Jul - Sun, 19 Jul
WestJet Logo
6:15 a.m. - 11:45 a.m.
YWG
-
MBJ
29h 30m
1 stop
WestJet Logo
7:30 p.m. - 12:00 p.m.
MBJ
-
YWG
40h 30m
2 stops
C$ 664WestJet
Sat, 4 Jul - Sat, 18 Jul
WestJet Logo
6:15 a.m. - 9:30 a.m.
YWG
-
MBJ
27h 15m
1 stop
WestJet Logo
7:30 p.m. - 9:45 a.m.
MBJ
-
YWG
14h 15m
1 stop
C$ 669WestJet
Sat, 4 Jul - Sat, 18 Jul
Air Canada Logo
2:05 p.m. - 11:20 a.m.
YWG
-
MBJ
21h 15m
1 stop
Air Canada Logo
12:30 p.m. - 9:57 a.m.
MBJ
-
YWG
21h 27m
1 stop
C$ 671Air Canada
Mon, 7 Sep - Thu, 10 Sep
WestJet Logo
7:05 a.m. - 7:29 p.m.
YWG
-
MBJ
35h 24m
2 stops
WestJet Logo
8:25 p.m. - 11:05 a.m.
MBJ
-
YWG
39h 40m
2 stops
C$ 673WestJet
Tue, 8 Dec - Fri, 18 Dec
WestJet Logo
12:00 p.m. - 7:29 p.m.
YWG
-
MBJ
30h 29m
2 stops
WestJet Logo
8:25 p.m. - 11:05 a.m.
MBJ
-
YWG
39h 40m
2 stops
C$ 675WestJet
Tue, 8 Dec - Fri, 18 Dec
Air Canada Logo
7:40 p.m. - 11:20 a.m.
YWG
-
MBJ
15h 40m
1 stop
Air Canada Logo
12:30 p.m. - 8:00 p.m.
MBJ
-
YWG
31h 30m
2 stops
C$ 676Air Canada
Mon, 7 Sep - Thu, 10 Sep

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WestJet flights from Winnipeg to Jamaica

Our best WestJet deals on Winnipeg to Jamaica flight tickets
WestJet
12 Jul
YWG8:00 a.m.Winnipeg
27h 45m
2 stops
MBJ11:45 a.m.Montego Bay Sangster Intl
19 Jul
MBJ7:30 p.m.Montego Bay Sangster Intl
26h 10m
2 stops
YWG9:40 p.m.Winnipeg
C$ 638
WestJet
8 Dec
YWG6:15 a.m.Winnipeg
10h 09m
1 stop
MBJ5:24 p.m.Montego Bay Sangster Intl
18 Dec
MBJ2:55 p.m.Montego Bay Sangster Intl
21h 40m
1 stop
YWG11:35 a.m.Winnipeg
C$ 648
WestJet
8 Dec
YWG6:15 a.m.Winnipeg
10h 09m
1 stop
MBJ5:24 p.m.Montego Bay Sangster Intl
18 Dec
MBJ8:25 p.m.Montego Bay Sangster Intl
39h 40m
2 stops
YWG11:05 a.m.Winnipeg
C$ 651

Air Canada flights from Winnipeg to Jamaica

Our best Air Canada deals on Winnipeg to Jamaica flight tickets
Air Canada
7 Sep
YWG2:05 p.m.Winnipeg
21h 15m
1 stop
MBJ11:20 a.m.Montego Bay Sangster Intl
10 Sep
MBJ12:30 p.m.Montego Bay Sangster Intl
21h 27m
1 stop
YWG9:57 a.m.Winnipeg
C$ 671
Air Canada
7 Sep
YWG7:40 p.m.Winnipeg
15h 40m
1 stop
MBJ11:20 a.m.Montego Bay Sangster Intl
10 Sep
MBJ12:30 p.m.Montego Bay Sangster Intl
31h 30m
2 stops
YWG8:00 p.m.Winnipeg
C$ 676
Air Canada
7 Sep
YWG4:05 p.m.Winnipeg
19h 15m
2 stops
MBJ11:20 a.m.Montego Bay Sangster Intl
10 Sep
MBJ12:30 p.m.Montego Bay Sangster Intl
26h 39m
2 stops
YWG3:09 p.m.Winnipeg
C$ 692

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 18 June 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

Sun 12/7

8:00 a.m.-11:45 a.m.

2 stops27h 45m

Montego Bay Sangster Intl

Sun 19/7

7:30 p.m.-9:40 p.m.

2 stops26h 10m

C$ 638
Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 18/12

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

1 stop21h 40m

C$ 648

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:05 a.m.

2 stops39h 40m

C$ 651

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 12/7

6:15 a.m.-6:30 p.m.

1 stop12h 15m

Montego Bay Sangster Intl

Sun 19/7

7:30 p.m.-5:15 p.m.

1 stop21h 45m

C$ 658

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 4/7

6:15 a.m.-11:45 a.m.

1 stop29h 30m

Montego Bay Sangster Intl

Sat 18/7

7:30 p.m.-12:00 p.m.

2 stops40h 30m

C$ 664

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 4/7

6:15 a.m.-9:30 a.m.

1 stop27h 15m

Montego Bay Sangster Intl

Sat 18/7

7:30 p.m.-9:45 a.m.

1 stop14h 15m

C$ 669

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 7/9

2:05 p.m.-11:20 a.m.

1 stop21h 15m

Montego Bay Sangster Intl

Thu 10/9

12:30 p.m.-9:57 a.m.

1 stop21h 27m

C$ 671

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

7:05 a.m.-7:29 p.m.

2 stops35h 24m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:05 a.m.

2 stops39h 40m

C$ 673

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

12:00 p.m.-7:29 p.m.

2 stops30h 29m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:05 a.m.

2 stops39h 40m

C$ 675

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 7/9

7:40 p.m.-11:20 a.m.

1 stop15h 40m

Montego Bay Sangster Intl

Thu 10/9

12:30 p.m.-8:00 p.m.

2 stops31h 30m

C$ 676

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, March 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$ 194. If you aren’t able to travel during the month of March, then book flights to Jamaica from Winnipeg during August instead. Flights to Jamaica in August, while not as cheap as those in March, still average around C$ 310.

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$ 840. 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$ 1,009.

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$ 890 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$ 634 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 58% 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$ 776

Fastest flight time

5h 20m

Direct flights

None
The best flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 776
The fastest flight from Winnipeg to Jamaica takes 5h 20m
There are no direct flights from Winnipeg to Jamaica. Popular non-direct route for this connection is Winnipeg Airport - Montego Bay Sangster Intl Airport.
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$ 394Free CancellationRating
7.1
11,210 reviews
Search Air Canada flights
WestJetPriceFrom C$ 513Free CancellationRating
7.2
3,375 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

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