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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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
28 May — 4 Jun1
1 adult

Cheap flight deals from Winnipeg to Jamaica

Keep the following information in mind while searching for Winnipeg to Jamaica flight deals. Data was last updated 23 May 2025.

Round-trip from

C$ 714

One-way from

C$ 291

Popular in

December

Cheapest in

October

Average price

C$ 749

Good round-trip deal

C$ 736 or less
WestJet
  • WestJet
  • 21/6-28/6
  • 2 total stops
  • 24h 58m total
  • Winnipeg to Jamaica
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WestJet
  • WestJet
  • 4/6
  • 2 total stops
  • 41h 25m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 59 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 17 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Winnipeg to Jamaica.
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Find flight deals from Winnipeg to Jamaica

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 23 May 2025.

Wed 4/66:15 p.m.YWG - KIN
2 stops44h 15mWestJet
Wed 11/63:30 p.m.KIN - YWG
2 stops25h 57mWestJet
Deal found 20/5C$ 606
Mon 2/63:45 p.m.YWG - KIN
2 stops20h 50mAir Canada
Mon 9/61:45 p.m.KIN - YWG
2 stops44h 25mAir Canada
Deal found 20/5C$ 629
Wed 4/67:00 p.m.YWG - KIN
1 stop17h 35mMultiple Airlines
Wed 11/63:30 p.m.KIN - YWG
1 stop18h 13mMultiple Airlines
Deal found 20/5C$ 729
Mon 27/1012:35 p.m.YWG - MBJ
1 stop21h 40mAir Transat
Fri 31/1011:35 a.m.MBJ - YWG
1 stop23h 10mAir Transat
Deal found 22/5C$ 774
Mon 9/65:10 p.m.YWG - MBJ
1 stop18h 32mMultiple Airlines
Sat 14/612:07 p.m.MBJ - YWG
2 stops34h 39mMultiple Airlines
Deal found 22/5C$ 805
Tue 3/610:00 a.m.YWG - MBJ
2 stops25h 42mWestJet
Sun 8/610:25 a.m.MBJ - YWG
2 stops22h 36mWestJet
Deal found 22/5C$ 821
Sun 6/75:00 a.m.YWG - MBJ
2 stops34h 10mUnited Airlines
Sun 13/74:33 p.m.MBJ - YWG
2 stops30h 00mUnited Airlines
Deal found 22/5C$ 932
Sun 26/107:20 p.m.YWG - MBJ
1 stop16h 45mAir Canada
Tue 4/112:40 p.m.MBJ - YWG
1 stop20h 03mAir Canada
Deal found 22/5C$ 1,054
Thu 5/66:30 a.m.YWG - KIN
2 stops13h 30mDelta
Thu 12/69:00 a.m.KIN - YWG
2 stops15h 13mDelta
Deal found 20/5C$ 1,407
Sun 26/1012:40 p.m.YWG - MBJ
2 stops26h 53mDelta
Thu 30/101:03 p.m.MBJ - YWG
2 stops22h 35mDelta
Deal found 22/5C$ 1,555

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 23 May 2025.
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

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Wed 4/6

6:15 p.m.-2:30 p.m.

2 stops44h 15m

Kingston Norman Manley

Wed 11/6

3:30 p.m.-5:27 p.m.

2 stops25h 57m

C$ 606

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 2/6

3:45 p.m.-12:35 p.m.

2 stops20h 50m

Kingston Norman Manley

Mon 9/6

1:45 p.m.-10:10 a.m.

2 stops44h 25m

C$ 629

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Wed 4/6

7:00 p.m.-12:35 p.m.

1 stop17h 35m

Kingston Norman Manley

Wed 11/6

3:30 p.m.-9:43 a.m.

1 stop18h 13m

C$ 729

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 27/10

12:35 p.m.-10:15 a.m.

1 stop21h 40m

Montego Bay Sangster Intl

Fri 31/10

11:35 a.m.-10:45 a.m.

1 stop23h 10m

C$ 774

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 9/6

5:10 p.m.-11:42 a.m.

1 stop18h 32m

Montego Bay Sangster Intl

Sat 14/6

12:07 p.m.-10:46 p.m.

2 stops34h 39m

C$ 805

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/6

10:00 a.m.-11:42 a.m.

2 stops25h 42m

Montego Bay Sangster Intl

Sun 8/6

10:25 a.m.-9:01 a.m.

2 stops22h 36m

C$ 821

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 6/7

5:00 a.m.-3:10 p.m.

2 stops34h 10m

Montego Bay Sangster Intl

Sun 13/7

4:33 p.m.-10:33 p.m.

2 stops30h 00m

C$ 932

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 26/10

7:20 p.m.-12:05 p.m.

1 stop16h 45m

Montego Bay Sangster Intl

Tue 4/11

2:40 p.m.-9:43 a.m.

1 stop20h 03m

C$ 1,054

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Thu 5/6

6:30 a.m.-8:00 p.m.

2 stops13h 30m

Kingston Norman Manley

Thu 12/6

9:00 a.m.-12:13 a.m.

2 stops15h 13m

C$ 1,407

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 26/10

12:40 p.m.-11:48 a.m.

2 stops23h 08m

Montego Bay Sangster Intl

Tue 4/11

2:03 p.m.-11:38 a.m.

2 stops22h 35m

C$ 1,555

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/5

Showing 1-10 of 17 results
1
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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, March is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 355). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 547). 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 23 May 2025.

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.

What is the cheapest day to fly from Winnipeg to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Jamaica. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 40.0 - 180.0 mm per month. October is typically the wettest month, when rainfall can reach 180.0 mm. February is typically the driest time to visit Jamaica when rainfall is around 40.0 mm.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

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 23 May 2025.
Read reviews from past customers who have flown Delta, Air Transat and United Airlines from Winnipeg to Jamaica. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,952 reviews
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Transat
7.8
Good
388 reviews
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,745 reviews
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,848 reviews
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,400 reviews
Delta
8.0
Very good
7,952 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 123 times in the past calendar month.

  • What are the cheapest airlines to fly from Winnipeg to Jamaica one-way?

    C$ 291 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and Air Transat, with prices starting from C$ 308 and C$ 369, respectively.

  • What are the cheapest flights from Winnipeg to Jamaica?

    The cheapest flight price from Winnipeg to Jamaica is C$ 736. On average you can expect to pay C$ 1,130. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 731.

  • 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$ 355). Flying from Winnipeg to Jamaica in December is currently the most expensive (average of C$ 547). 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 23 May 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 505AverageC$ 712FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 505AverageC$ 767FlexibilityNo 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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