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Cheap flights from Winnipeg to Jamaica from C$ 262

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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 520

One-way from

C$ 262

Popular in

November

Cheapest in

September

Average price

C$ 650

Good round-trip deal

C$ 1,006 or less
WestJet
  • WestJet
  • 27/10-3/11
  • 4 total stops
  • 36h 50m total
  • Winnipeg to Jamaica
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8/11
  • 8/11
  • 2 total stops
  • 17h 15m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 109 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 20 potential savings vs. average RT price).
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Average for round-trip flights in September 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 11 September 2025.

Mon 27/109:00 p.m.YWG - MBJ
2 stops15h 54mWestJet
Mon 3/117:25 p.m.MBJ - YWG
2 stops20h 56mWestJet
Deal found 11/9C$ 520
Wed 29/108:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Sun 2/111:25 p.m.MBJ - YWG
1 stop23h 10mWestJet
Deal found 10/9C$ 579
Fri 14/117:30 a.m.YWG - MBJ
1 stop30h 45mMultiple Airlines
Sat 29/112:50 p.m.MBJ - YWG
1 stop10h 51mMultiple Airlines
Deal found 10/9C$ 583
Sat 4/106:30 a.m.YWG - MBJ
2 stops30h 11mMultiple Airlines
Sat 11/1012:45 p.m.MBJ - YWG
1 stop11h 28mMultiple Airlines
Deal found 9/9C$ 635
Thu 2/109:05 p.m.YWG - MBJ
2 stops38h 36mWestJet
Fri 10/1012:45 p.m.MBJ - YWG
2 stops32h 40mWestJet
Deal found 10/9C$ 650
Sun 9/117:30 a.m.YWG - MBJ
1 stop30h 45mMultiple Airlines
Sun 16/118:25 p.m.MBJ - YWG
1 stop24h 10mMultiple Airlines
Deal found 10/9C$ 672
Fri 28/118:15 a.m.YWG - MBJ
1 stop8h 50mAir Canada
Fri 5/127:05 p.m.MBJ - YWG
1 stop16h 11mAir Canada
Deal found 11/9C$ 679
Fri 12/96:30 a.m.YWG - KIN
1 stop7h 58mWestJet
Fri 19/93:30 p.m.KIN - YWG
1 stop25h 28mWestJet
Deal found 10/9C$ 822
Fri 12/95:10 p.m.YWG - KIN
2 stops26h 55mMultiple Airlines
Fri 19/96:25 p.m.KIN - YWG
2 stops23h 50mMultiple Airlines
Deal found 10/9C$ 1,153

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 11 September 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

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 27/10

9:00 p.m.-12:54 p.m.

2 stops15h 54m

Montego Bay Sangster Intl

Mon 3/11

7:25 p.m.-3:21 p.m.

2 stops20h 56m

C$ 520

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 9/11

7:30 a.m.-3:15 p.m.

1 stop30h 45m

Montego Bay Sangster Intl

Sun 16/11

4:30 p.m.-12:39 a.m.

2 stops33h 09m

C$ 579

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 14/11

7:30 a.m.-3:15 p.m.

1 stop30h 45m

Montego Bay Sangster Intl

Sat 29/11

2:50 p.m.-12:41 a.m.

1 stop10h 51m

C$ 583

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 22/11

12:20 p.m.-12:29 p.m.

1 stop23h 09m

Montego Bay Sangster Intl

Sat 29/11

2:50 p.m.-11:53 a.m.

1 stop22h 03m

C$ 600

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

5:00 a.m.-12:54 p.m.

1 stop7h 54m

Montego Bay Sangster Intl

Sun 2/11

8:25 p.m.-3:21 p.m.

2 stops19h 56m

C$ 600

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 2/10

9:05 p.m.-11:41 a.m.

2 stops38h 36m

Montego Bay Sangster Intl

Fri 10/10

12:45 p.m.-9:25 p.m.

2 stops32h 40m

C$ 650

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 4/10

6:30 p.m.-12:41 p.m.

2 stops18h 11m

Montego Bay Sangster Intl

Sat 11/10

12:45 p.m.-12:13 a.m.

1 stop11h 28m

C$ 694

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 24/1

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

Nonstop5h 30m

Montego Bay Sangster Intl

Sat 7/2

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

Nonstop5h 53m

C$ 740

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 3/3

1:45 p.m.-1:45 p.m.

2 stops23h 00m

Kingston Norman Manley

Fri 6/3

2:55 p.m.-4:35 p.m.

2 stops26h 40m

C$ 852

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 14/2

12:20 p.m.-8:35 p.m.

2 stops31h 15m

Kingston Norman Manley

Sat 21/2

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

1 stop29h 05m

C$ 910

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 18 results
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

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 11 September 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.

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 11 September 2025.
Read reviews from past customers who have flown United Airlines,WestJet, andAir 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.
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
3,091 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 117 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like WestJet and Air Canada fly from Winnipeg to Jamaica in about 15h 54m. The time it takes to get you to your destination can typically vary by up to 7h 06m. 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$ 860. On average you can expect to pay C$ 1,031. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 579.

  • 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

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Top 3 airlines flying from Winnipeg to Jamaica

Discover the top 3 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 488AverageC$ 728FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 510AverageC$ 794FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 837AverageC$ 925FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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