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Cheap flights from Winnipeg to Jamaica from C$ 265

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 30/1. 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
7:50 a.m. - 3:33 p.m.
YWG
-
KIN
30h 43m2 stops
WestJet Logo
4:30 p.m. - 12:09 p.m.
KIN
-
YWG
20h 39m2 stops
C$ 606WestJet
Thu, 8 Jan - Fri, 16 Jan
WestJet Logo
7:50 a.m. - 3:33 p.m.
YWG
-
KIN
30h 43m2 stops
WestJet Logo
4:30 p.m. - 11:35 a.m.
KIN
-
YWG
20h 05m1 stop
C$ 614WestJet
Thu, 8 Jan - Fri, 16 Jan
WestJet Logo
8:05 p.m. - 3:33 p.m.
YWG
-
KIN
18h 28m1 stop
WestJet Logo
4:30 p.m. - 12:35 a.m.
KIN
-
YWG
9h 05m1 stop
C$ 626WestJet
Thu, 8 Jan - Fri, 16 Jan
Multiple Airlines Logo
5:00 a.m. - 12:12 p.m.
YWG
-
KIN
30h 12m2 stops
Multiple Airlines Logo
3:30 p.m. - 7:35 p.m.
KIN
-
YWG
29h 05m1 stop
C$ 672Multiple Airlines
Sat, 17 Jan - Thu, 29 Jan
United Airlines Logo
8:45 a.m. - 11:43 a.m.
YWG
-
MBJ
26h 58m2 stops
United Airlines Logo
2:40 p.m. - 8:52 p.m.
MBJ
-
YWG
30h 12m2 stops
C$ 705United Airlines
Mon, 30 Mar - Sat, 4 Apr
WestJet Logo
6:55 p.m. - 12:24 p.m.
YWG
-
MBJ
16h 29m2 stops
WestJet Logo
7:25 p.m. - 11:40 p.m.
MBJ
-
YWG
29h 15m2 stops
C$ 723WestJet
Sat, 28 Feb - Sat, 7 Mar
WestJet Logo
8:00 a.m. - 2:25 p.m.
YWG
-
MBJ
5h 25mdirect
WestJet Logo
3:25 p.m. - 8:18 p.m.
MBJ
-
YWG
5h 53mdirect
C$ 729WestJet
Sat, 28 Feb - Sat, 7 Mar
WestJet Logo
8:05 p.m. - 6:17 p.m.
YWG
-
MBJ
22h 12m1 stop
WestJet Logo
2:25 p.m. - 8:18 p.m.
MBJ
-
YWG
5h 53mdirect
C$ 733WestJet
Mon, 30 Mar - Sat, 4 Apr
WestJet Logo
12:20 p.m. - 12:24 p.m.
YWG
-
MBJ
23h 04m1 stop
WestJet Logo
3:25 p.m. - 8:18 p.m.
MBJ
-
YWG
5h 53mdirect
C$ 737WestJet
Sat, 28 Feb - Sat, 7 Mar
WestJet Logo
5:00 a.m. - 12:24 p.m.
YWG
-
MBJ
30h 24m1 stop
WestJet Logo
7:25 p.m. - 11:39 p.m.
MBJ
-
YWG
29h 14m1 stop
C$ 743WestJet
Sat, 28 Feb - Sat, 7 Mar

United Airlines flights from Winnipeg to Jamaica

Our best United Airlines deals on Winnipeg to Jamaica flight tickets
United Airlines
30 Mar
YWG8:45 a.m.Winnipeg
26h 58m
2 stops
MBJ11:43 a.m.Montego Bay Sangster Intl
4 Apr
MBJ2:40 p.m.Montego Bay Sangster Intl
30h 12m
2 stops
YWG8:52 p.m.Winnipeg
C$ 705
Find similar
United Airlines
1 Mar
YWG2:20 p.m.Winnipeg
22h 40m
2 stops
MBJ2:00 p.m.Montego Bay Sangster Intl
8 Mar
MBJ1:48 p.m.Montego Bay Sangster Intl
22h 09m
1 stop
YWG11:57 a.m.Winnipeg
C$ 802
Find similar
United Airlines
1 Mar
YWG2:20 p.m.Winnipeg
22h 40m
2 stops
MBJ2:00 p.m.Montego Bay Sangster Intl
8 Mar
MBJ1:48 p.m.Montego Bay Sangster Intl
22h 09m
1 stop
YWG11:57 a.m.Winnipeg
C$ 813
Find similar

Air Canada flights from Winnipeg to Jamaica

Our best Air Canada deals on Winnipeg to Jamaica flight tickets
Air Canada
7 Jan
YWG1:30 p.m.Winnipeg
22h 00m
1 stop
MBJ12:30 p.m.Montego Bay Sangster Intl
21 Jan
MBJ1:30 p.m.Montego Bay Sangster Intl
21h 19m
1 stop
YWG9:49 a.m.Winnipeg
C$ 883
Find similar
Air Canada
7 Jan
YWG6:00 a.m.Winnipeg
29h 30m
2 stops
MBJ12:30 p.m.Montego Bay Sangster Intl
21 Jan
MBJ1:30 p.m.Montego Bay Sangster Intl
21h 46m
2 stops
YWG10:16 a.m.Winnipeg
C$ 887
Find similar
Air Canada
3 Jan
YWG7:05 p.m.Winnipeg
17h 05m
1 stop
MBJ1:10 p.m.Montego Bay Sangster Intl
14 Jan
MBJ1:30 p.m.Montego Bay Sangster Intl
21h 19m
1 stop
YWG9:49 a.m.Winnipeg
C$ 996
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 18 December 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

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 8/1

7:50 a.m.-3:33 p.m.

2 stops30h 43m

Kingston Norman Manley

Fri 16/1

4:30 p.m.-12:09 p.m.

2 stops20h 39m

C$ 606

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 8/1

7:50 a.m.-3:33 p.m.

2 stops30h 43m

Kingston Norman Manley

Fri 16/1

4:30 p.m.-11:35 a.m.

1 stop20h 05m

C$ 614

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 8/1

8:05 p.m.-3:33 p.m.

1 stop18h 28m

Kingston Norman Manley

Fri 16/1

4:30 p.m.-12:35 a.m.

1 stop9h 05m

C$ 626

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 17/1

5:00 a.m.-12:12 p.m.

2 stops30h 12m

Kingston Norman Manley

Thu 29/1

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

1 stop29h 05m

C$ 672

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 30/3

8:45 a.m.-11:43 a.m.

2 stops26h 58m

Montego Bay Sangster Intl

Sat 4/4

2:40 p.m.-8:52 p.m.

2 stops30h 12m

C$ 705

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/2

6:55 p.m.-12:24 p.m.

2 stops16h 29m

Montego Bay Sangster Intl

Sat 7/3

7:25 p.m.-11:40 p.m.

2 stops29h 15m

C$ 723

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/2

8:00 a.m.-2:25 p.m.

Nonstop5h 25m

Montego Bay Sangster Intl

Sat 7/3

3:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 729

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 30/3

8:05 p.m.-6:17 p.m.

1 stop22h 12m

Montego Bay Sangster Intl

Sat 4/4

2:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 733

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/2

12:20 p.m.-12:24 p.m.

1 stop23h 04m

Montego Bay Sangster Intl

Sat 7/3

3:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 737

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/2

5:00 a.m.-12:24 p.m.

1 stop30h 24m

Montego Bay Sangster Intl

Sat 7/3

7:25 p.m.-11:39 p.m.

1 stop29h 14m

C$ 743

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$ 671. 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$ 712.

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$ 618. 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$ 828.

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$ 634. Try not to purchase tickets in the morning because they tend to be around C$ 826. 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$ 836 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$ 670 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 12% 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$ 335

Fastest flight time

5h 25m

Direct flights

Sun

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Winnipeg in the past 72 hours is C$ 335. The best round-trip flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 682.
The fastest flight from Winnipeg to Jamaica takes 5h 25m
Direct flights go from Winnipeg to Jamaica on Sunday. The only airline offering direct flights is WestJet.
There are 11 airports in Jamaica. From Winnipeg there are direct flights to 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$ 485Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
WestJetPriceFrom C$ 505Free CancellationRating
7.2
3,204 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

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

Popular Cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo
Flights to Montego Bayfrom C$ 406
Flights to Kingstonfrom C$ 463