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Cheap flights from Winnipeg to Jamaica from C$ 291

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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
3 Jun — 10 Jun1
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 4 May 2026.

Mon 1/67:20 p.m.
YWG
-
MBJ
1 stop16h 00m
Air Canada
Mon 8/612:30 p.m.
MBJ
-
YWG
1 stop22h 38m
Air Canada
Deal found 2/5C$ 523
Tue 9/67:20 p.m.
YWG
-
MBJ
1 stop16h 00m
Air Canada
Wed 17/612:30 p.m.
MBJ
-
YWG
1 stop10h 48m
Air Canada
Deal found 1/5C$ 553
Tue 9/67:00 a.m.
YWG
-
MBJ
2 stops28h 45m
WestJet
Wed 17/612:45 p.m.
MBJ
-
YWG
1 stop25h 40m
WestJet
Deal found 1/5C$ 557
Sat 6/61:25 p.m.
YWG
-
MBJ
2 stops45h 55m
Air Canada
Sat 13/612:30 p.m.
MBJ
-
YWG
1 stop8h 58m
Air Canada
Deal found 2/5C$ 559
Sun 14/65:10 a.m.
YWG
-
MBJ
1 stop30h 10m
Air Canada
Thu 18/612:30 p.m.
MBJ
-
YWG
1 stop10h 50m
Air Canada
Deal found 3/5C$ 560
Sun 14/69:05 p.m.
YWG
-
MBJ
2 stops14h 40m
WestJet
Thu 18/612:45 p.m.
MBJ
-
YWG
2 stops32h 55m
WestJet
Deal found 30/4C$ 599
Fri 8/57:10 p.m.
YWG
-
KIN
2 stops19h 20m
WestJet
Fri 15/53:30 p.m.
KIN
-
YWG
2 stops19h 40m
WestJet
Deal found 1/5C$ 658
Mon 18/59:05 p.m.
YWG
-
KIN
2 stops41h 25m
WestJet
Fri 5/63:30 p.m.
KIN
-
YWG
2 stops41h 50m
WestJet
Deal found 30/4C$ 659
Fri 29/58:00 a.m.
YWG
-
KIN
2 stops30h 30m
WestJet
Fri 5/63:30 p.m.
KIN
-
YWG
2 stops46h 45m
WestJet
Deal found 1/5C$ 660
Tue 19/56:05 p.m.
YWG
-
KIN
1 stop20h 25m
WestJet
Fri 5/63:30 p.m.
KIN
-
YWG
1 stop9h 25m
WestJet
Deal found 30/4C$ 669
Thu 18/69:05 p.m.
YWG
-
KIN
2 stops17h 25m
WestJet
Wed 1/73:30 p.m.
KIN
-
YWG
2 stops20h 30m
WestJet
Deal found 30/4C$ 671
Tue 9/64:15 p.m.
YWG
-
KIN
2 stops22h 15m
WestJet
Wed 1/73:30 p.m.
KIN
-
YWG
2 stops20h 30m
WestJet
Deal found 30/4C$ 673

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 4 May 2026.

Round-trip from

C$ 520

One-way from

C$ 291

Popular in

December

Cheapest in

April

Average price

C$ 780

Good round-trip deal

C$ 1,250 or less
Air Canada
  • Air Canada
  • 1/6-8/6
  • 2 total stops
  • 40h 48m total
  • Winnipeg to Jamaica
Search Deals
Air Canada
  • Air Canada
  • 15/6
  • 1 total stop
  • 18h 10m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Jamaica.
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 4 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

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$ 530
Quickest round-trip

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.-11:20 p.m.

1 stop10h 50m

C$ 557

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$ 559

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/6

7:00 a.m.-11:45 a.m.

2 stops28h 45m

Montego Bay Sangster Intl

Wed 17/6

12:45 p.m.-9:40 p.m.

2 stops32h 55m

C$ 565

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 14/6

9:05 p.m.-11:45 a.m.

2 stops14h 40m

Montego Bay Sangster Intl

Thu 18/6

12:45 p.m.-9:40 p.m.

2 stops32h 55m

C$ 599

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$ 660

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 27/6

7:10 p.m.-2:30 p.m.

2 stops43h 20m

Kingston Norman Manley

Fri 10/7

3:30 p.m.-9:20 a.m.

2 stops17h 50m

C$ 696

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 21/9

9:05 p.m.-2:30 p.m.

2 stops41h 25m

Kingston Norman Manley

Fri 25/9

3:30 p.m.-12:15 p.m.

2 stops20h 45m

C$ 726

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 21/9

3:20 p.m.-1:55 p.m.

1 stop22h 35m

Kingston Norman Manley

Fri 25/9

3:05 p.m.-6:12 p.m.

1 stop27h 07m

C$ 773

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 11/6

10:30 p.m.-2:30 p.m.

2 stops40h 00m

Kingston Norman Manley

Thu 18/6

10:01 a.m.-10:43 a.m.

3 stops24h 42m

C$ 968

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/4

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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

How far ahead should I book a flight from Winnipeg to Jamaica?

To ensure you get the cheapest price possible for a flight from Winnipeg to Jamaica, you should look to book at least 80 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, March is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 188). Flying from Winnipeg to Jamaica in February is currently the most expensive (average of C$ 722). 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.

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 4 May 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
3,331 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Food

6.2

Crew

7.9

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,331 reviews
WestJet
7.2
Good
3,331 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Food

6.2

Crew

7.9

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
Air Canada
7.1
Good
10,995 reviews
WestJet
7.2
Good
3,331 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Food

6.2

Crew

7.9

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 47 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like Air Canada and WestJet fly from Winnipeg to Jamaica in about 21h 55m. The time it takes to get you to your destination can typically vary by up to 8h 35m. There are 3890 km between Winnipeg and Jamaica. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest flights from Winnipeg to Jamaica?

    The cheapest flight price from Winnipeg to Jamaica is C$ 1,169. On average you can expect to pay C$ 1,339. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 560.

  • 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, March is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 188). Flying from Winnipeg to Jamaica in February is currently the most expensive (average of C$ 722). 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 4 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 382AverageC$ 830FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 497AverageC$ 792FlexibilityNo 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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