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Cheap flights from Winnipeg to Jamaica from C$ 342

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 14/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
28 feb. — 7 mar.1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Jamaica

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Jamaica
Explore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 enero 2026.

sáb. 18/49:25 a.m.
YWG
-
MBJ
1 stop25h 59m
Multiple Airlines
sáb. 25/41:22 p.m.
MBJ
-
YWG
2 stops26h 03m
Multiple Airlines
Deal found 28/1C$ 618
lun. 2/38:00 a.m.
YWG
-
MBJ
1 stop27h 02m
Multiple Airlines
mié. 4/31:00 p.m.
MBJ
-
YWG
2 stops31h 09m
Multiple Airlines
Deal found 27/1C$ 641
lun. 2/38:00 a.m.
YWG
-
MBJ
1 stop27h 02m
Multiple Airlines
mar. 10/311:57 a.m.
MBJ
-
YWG
2 stops27h 12m
Multiple Airlines
Deal found 27/1C$ 656
vie. 24/45:00 a.m.
YWG
-
KIN
1 stop9h 30m
WestJet
vie. 1/53:30 p.m.
KIN
-
YWG
2 stops30h 40m
WestJet
Deal found 27/1C$ 658
mié. 4/35:00 a.m.
YWG
-
KIN
1 stop9h 30m
WestJet
mar. 24/34:30 p.m.
KIN
-
YWG
1 stop19h 02m
WestJet
Deal found 27/1C$ 671
mar. 10/35:00 a.m.
YWG
-
MBJ
2 stops30h 02m
Multiple Airlines
sáb. 14/311:30 a.m.
MBJ
-
YWG
1 stop32h 05m
Multiple Airlines
Deal found 28/1C$ 673
vie. 27/27:30 a.m.
YWG
-
MBJ
1 stop26h 54m
Multiple Airlines
mié. 4/31:00 p.m.
MBJ
-
YWG
2 stops31h 09m
Multiple Airlines
Deal found 27/1C$ 680
mar. 3/32:20 p.m.
YWG
-
MBJ
2 stops46h 45m
United Airlines
vie. 6/32:48 p.m.
MBJ
-
YWG
1 stop22h 09m
United Airlines
Deal found 27/1C$ 683
dom. 19/42:00 p.m.
YWG
-
MBJ
1 stop22h 50m
United Airlines
dom. 10/54:12 p.m.
MBJ
-
YWG
2 stops28h 45m
United Airlines
Deal found 27/1C$ 688
mar. 10/32:20 p.m.
YWG
-
MBJ
2 stops22h 45m
United Airlines
lun. 16/31:48 p.m.
MBJ
-
YWG
1 stop22h 09m
United Airlines
Deal found 27/1C$ 694
mar. 3/35:00 a.m.
YWG
-
MBJ
1 stop13h 17m
Multiple Airlines
mié. 4/31:00 p.m.
MBJ
-
YWG
2 stops31h 09m
Multiple Airlines
Deal found 27/1C$ 706
vie. 27/25:00 a.m.
YWG
-
KIN
1 stop9h 30m
WestJet
vie. 6/34:30 p.m.
KIN
-
YWG
1 stop9h 05m
WestJet
Deal found 28/1C$ 710

Find flight deals from Winnipeg to Jamaica

Keep the following information in mind while searching for Winnipeg to Jamaica flight deals. Data was last updated 29 enero 2026.

Round-trip from

C$ 618

One-way from

C$ 342

Popular in

December

Cheapest in

April

Average price

C$ 802
18/4-25/4
  • 18/4-25/4
  • 3 total stops
  • 52h 02m total
  • Winnipeg to Jamaica
Search Deals
WestJet
  • WestJet
  • 14/3
  • 2 total stops
  • 43h 35m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 210 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 29 enero 2026.
Use the filters below to find and compare flights from Winnipeg to Jamaica that are best for you.

Fly from

Winnipeg

Fly to

Jamaica

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

sáb. 18/4

9:25 a.m.-11:24 a.m.

1 stop25h 59m

Montego Bay Sangster Intl

sáb. 25/4

1:22 p.m.-3:25 p.m.

2 stops26h 03m

C$ 618

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

mié. 4/3

5:00 a.m.-3:30 p.m.

1 stop9h 30m

Kingston Norman Manley

mar. 24/3

4:30 p.m.-11:32 a.m.

1 stop19h 02m

C$ 671

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mar. 10/3

5:00 a.m.-11:02 a.m.

2 stops30h 02m

Montego Bay Sangster Intl

sáb. 14/3

11:30 a.m.-7:35 p.m.

1 stop32h 05m

C$ 673

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mié. 4/3

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

2 stops22h 45m

Montego Bay Sangster Intl

vie. 6/3

3:55 p.m.-11:57 a.m.

2 stops21h 02m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mar. 3/3

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

2 stops46h 45m

Montego Bay Sangster Intl

lun. 9/3

2:20 p.m.-11:57 a.m.

2 stops21h 37m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mié. 4/3

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

2 stops22h 45m

Montego Bay Sangster Intl

lun. 9/3

1:48 p.m.-11:57 a.m.

1 stop22h 09m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mar. 3/3

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

2 stops46h 45m

Montego Bay Sangster Intl

mar. 10/3

1:48 p.m.-11:57 a.m.

1 stop22h 09m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

vie. 27/2

2:20 p.m.-2:00 p.m.

2 stops22h 40m

Montego Bay Sangster Intl

lun. 9/3

1:48 p.m.-11:57 a.m.

1 stop22h 09m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

mar. 3/3

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

2 stops46h 45m

Montego Bay Sangster Intl

vie. 6/3

2:48 p.m.-11:57 a.m.

1 stop22h 09m

C$ 683

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

vie. 27/2

5:00 a.m.-3:30 p.m.

1 stop9h 30m

Kingston Norman Manley

vie. 6/3

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

1 stop9h 05m

C$ 710

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

Showing 1-10 of 27 results
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Best time to book a flight from Winnipeg to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Jamaica

What is the cheapest month to book a flight from Winnipeg to Jamaica?

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 415). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 672). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to JM?

Find hourly flight availability from Winnipeg to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 enero 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Jamaica as you normally would.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated 29 enero 2026.
Read reviews from past customers who have flown WestJet and Air Canada from Winnipeg to Jamaica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,253 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Boarding

7.4

Crew

7.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,253 reviews
WestJet
7.2
Good
3,253 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Boarding

7.4

Crew

7.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
Air Canada
7.1
Good
10,667 reviews
WestJet
7.2
Good
3,253 reviews
Check prices

Comfort

7.0

Entertainment

6.1

Food

6.2

Boarding

7.4

Crew

7.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Jamaica?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Jamaica.

  • How popular is this Winnipeg to Jamaica flight route?

    Flights from Winnipeg to Jamaica have been viewed 62 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like WestJet and United Airlines fly from Winnipeg to Jamaica in about 9h 30m. The time it takes to get you to your destination can typically vary by up to 13h 15m. There are 3993 km between Winnipeg and Jamaica. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Winnipeg to Jamaica that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Jamaica.

  • Can I find deals for business class flights from Winnipeg to Jamaica?

    Yes. Cheapflights offers flight deals from Winnipeg to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Jamaica?

    Currently, October is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 415). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 672). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 2 airlines flying from Winnipeg to Jamaica

Discover the top 2 airlines that operate flights from Winnipeg to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 29 enero 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 478AverageC$ 774FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 496AverageC$ 763FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Jamaica?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Jamaica. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Jamaica?

Cheapflights helps you find that perfect flight to Jamaica from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Winnipeg to Jamaica with no change fees?

Yes, we can. To see specific flights from Winnipeg to Jamaica with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Winnipeg to Jamaica become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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