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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 17/5. 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.
Air Canada Logo
7:20 p.m. - 11:20 a.m.
YWG
-
MBJ
16h 00m
1 stop
Air Canada Logo
12:30 p.m. - 11:08 a.m.
MBJ
-
YWG
22h 38m
1 stop
C$ 524Air Canada
Mon, 1 Jun - Mon, 8 Jun
Air Canada Logo
1:25 p.m. - 11:20 a.m.
YWG
-
MBJ
21h 55m
2 stops
Air Canada Logo
12:30 p.m. - 11:08 a.m.
MBJ
-
YWG
22h 38m
1 stop
C$ 531Air Canada
Mon, 1 Jun - Mon, 8 Jun
Air Canada Logo
1:25 p.m. - 11:20 a.m.
YWG
-
MBJ
45h 55m
2 stops
Air Canada Logo
12:30 p.m. - 9:28 p.m.
MBJ
-
YWG
8h 58m
1 stop
C$ 560Air Canada
Sat, 6 Jun - Sat, 13 Jun
Air Canada Logo
5:10 a.m. - 11:20 a.m.
YWG
-
MBJ
30h 10m
1 stop
Air Canada Logo
12:30 p.m. - 11:20 p.m.
MBJ
-
YWG
10h 50m
1 stop
C$ 561Air Canada
Sun, 14 Jun - Thu, 18 Jun
Air Canada Logo
7:20 p.m. - 11:20 a.m.
YWG
-
MBJ
16h 00m
1 stop
Air Canada Logo
12:30 p.m. - 10:05 a.m.
MBJ
-
YWG
21h 35m
2 stops
C$ 564Air Canada
Tue, 9 Jun - Wed, 17 Jun
Air Canada Logo
7:20 p.m. - 11:20 a.m.
YWG
-
MBJ
16h 00m
1 stop
Air Canada Logo
12:30 p.m. - 10:05 a.m.
MBJ
-
YWG
21h 35m
2 stops
C$ 565Air Canada
Sun, 14 Jun - Thu, 18 Jun
Air Canada Logo
7:20 p.m. - 11:20 a.m.
YWG
-
MBJ
16h 00m
1 stop
Air Canada Logo
12:30 p.m. - 10:05 a.m.
MBJ
-
YWG
21h 35m
2 stops
C$ 566Air Canada
Sun, 14 Jun - Thu, 18 Jun
WestJet Logo
6:00 a.m. - 11:45 a.m.
YWG
-
MBJ
29h 45m
2 stops
WestJet Logo
12:45 p.m. - 2:05 p.m.
MBJ
-
YWG
25h 20m
2 stops
C$ 602WestJet
Sun, 14 Jun - Thu, 18 Jun
Air Canada Logo
5:10 p.m. - 11:20 a.m.
YWG
-
MBJ
18h 10m
1 stop
Air Canada Logo
12:30 p.m. - 9:28 p.m.
MBJ
-
YWG
8h 58m
1 stop
C$ 609Air Canada
Sat, 6 Jun - Sat, 13 Jun
WestJet Logo
8:00 a.m. - 2:30 p.m.
YWG
-
KIN
30h 30m
2 stops
WestJet Logo
3:30 p.m. - 2:15 p.m.
KIN
-
YWG
46h 45m
2 stops
C$ 662WestJet
Fri, 29 May - Fri, 5 Jun

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Air Canada flights from Winnipeg to Jamaica

Our best Air Canada deals on Winnipeg to Jamaica flight tickets
Air Canada
1 Jun
YWG7:20 p.m.Winnipeg
16h 00m
1 stop
MBJ11:20 a.m.Montego Bay Sangster Intl
8 Jun
MBJ12:30 p.m.Montego Bay Sangster Intl
22h 38m
1 stop
YWG11:08 a.m.Winnipeg
C$ 524
Air Canada
1 Jun
YWG1:25 p.m.Winnipeg
21h 55m
2 stops
MBJ11:20 a.m.Montego Bay Sangster Intl
8 Jun
MBJ12:30 p.m.Montego Bay Sangster Intl
22h 38m
1 stop
YWG11:08 a.m.Winnipeg
C$ 531
Air Canada
6 Jun
YWG1:25 p.m.Winnipeg
45h 55m
2 stops
MBJ11:20 a.m.Montego Bay Sangster Intl
13 Jun
MBJ12:30 p.m.Montego Bay Sangster Intl
8h 58m
1 stop
YWG9:28 p.m.Winnipeg
C$ 560

WestJet flights from Winnipeg to Jamaica

Our best WestJet deals on Winnipeg to Jamaica flight tickets
WestJet
14 Jun
YWG6:00 a.m.Winnipeg
29h 45m
2 stops
MBJ11:45 a.m.Montego Bay Sangster Intl
18 Jun
MBJ12:45 p.m.Montego Bay Sangster Intl
25h 20m
2 stops
YWG2:05 p.m.Winnipeg
C$ 602
WestJet
21 May
YWG6:00 a.m.Winnipeg
29h 45m
2 stops
MBJ11:45 a.m.Montego Bay Sangster Intl
11 Jun
MBJ12:45 p.m.Montego Bay Sangster Intl
12h 10m
1 stop
YWG12:55 a.m.Winnipeg
C$ 629
WestJet
9 Jun
YWG12:50 p.m.Winnipeg
22h 55m
2 stops
MBJ11:45 a.m.Montego Bay Sangster Intl
17 Jun
MBJ12:45 p.m.Montego Bay Sangster Intl
36h 10m
2 stops
YWG12:55 a.m.Winnipeg
C$ 636

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 6 May 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

Mon 1/6

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

1 stop16h 00m

Montego Bay Sangster Intl

Mon 8/6

12:30 p.m.-11:08 a.m.

1 stop22h 38m

C$ 524

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 1/6

1:25 p.m.-11:20 a.m.

2 stops21h 55m

Montego Bay Sangster Intl

Mon 8/6

12:30 p.m.-11:08 a.m.

1 stop22h 38m

C$ 531

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/6

1:25 p.m.-11:20 a.m.

2 stops45h 55m

Montego Bay Sangster Intl

Sat 13/6

12:30 p.m.-9:28 p.m.

1 stop8h 58m

C$ 560

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

5:10 a.m.-11:20 a.m.

1 stop30h 10m

Montego Bay Sangster Intl

Thu 18/6

12:30 p.m.-11:20 p.m.

1 stop10h 50m

C$ 561

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/6

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

1 stop16h 00m

Montego Bay Sangster Intl

Wed 17/6

12:30 p.m.-10:05 a.m.

2 stops21h 35m

C$ 564

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

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

1 stop16h 00m

Montego Bay Sangster Intl

Thu 18/6

12:30 p.m.-10:05 a.m.

2 stops21h 35m

C$ 565

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

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

1 stop16h 00m

Montego Bay Sangster Intl

Thu 18/6

12:30 p.m.-10:05 a.m.

2 stops21h 35m

C$ 566

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

6:00 a.m.-11:45 a.m.

2 stops29h 45m

Montego Bay Sangster Intl

Thu 18/6

12:45 p.m.-2:05 p.m.

2 stops25h 20m

C$ 602
Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/6

5:10 p.m.-11:20 a.m.

1 stop18h 10m

Montego Bay Sangster Intl

Sat 13/6

12:30 p.m.-9:28 p.m.

1 stop8h 58m

C$ 609

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Fri 29/5

8:00 a.m.-2:30 p.m.

2 stops30h 30m

Kingston Norman Manley

Fri 5/6

3:30 p.m.-2:15 p.m.

2 stops46h 45m

C$ 662

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$ 188. If you aren’t able to travel during the month of March, then book flights to Jamaica from Winnipeg during April instead. Flights to Jamaica in April, while not as cheap as those in March, still average around C$ 282.

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$ 821. 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$ 991.

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$ 867 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$ 640 on momondo.

Can stopping save me money on Winnipeg to Jamaica flights?

You could potentially save up to 64% 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$ 1,252

Fastest flight time

12h 50m

Direct flights

None
The best flight deal from Winnipeg to Jamaica found on momondo in the last 72 hours is C$ 1,252
The fastest flight from Winnipeg to Jamaica takes 12h 50m
There are no direct flights from Winnipeg to Jamaica. There are no popular flight routes from Winnipeg to Jamaica.
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$ 383Free CancellationRating
7.1
11,000 reviews
Search Air Canada flights
WestJetPriceFrom C$ 498Free CancellationRating
7.2
3,331 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

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