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Cheap flights from Winnipeg to Jamaica from C$ 304

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 24/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

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 29 October 2025.

Round-trip from

C$ 646

One-way from

C$ 304

Popular in

November

Cheapest in

April

Average price

C$ 807

Good round-trip deal

C$ 796 or less

Good one-way deal

C$ 541 or less
Air Canada
  • Air Canada
  • 7/1-21/1
  • 3 total stops
  • 35h 13m total
  • Winnipeg to Jamaica
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Flair Airlines
  • Flair Airlines
  • 24/1
  • 1 total stop
  • 14h 10m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Winnipeg to Jamaica.
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Price to beat on a one-way flight from Winnipeg to Jamaica.
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Find 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 October 2025.

Tue 25/118:05 p.m.YWG - KIN
1 stop18h 28mWestJet
Tue 2/124:30 p.m.KIN - YWG
1 stop20h 05mWestJet
Deal found 28/10C$ 662
Wed 26/115:00 a.m.YWG - KIN
1 stop9h 33mWestJet
Wed 3/124:30 p.m.KIN - YWG
2 stops20h 39mWestJet
Deal found 29/10C$ 691
Tue 11/1112:40 p.m.YWG - KIN
2 stops25h 53mWestJet
Fri 14/114:30 p.m.KIN - YWG
1 stop9h 05mWestJet
Deal found 28/10C$ 694
Fri 28/118:15 a.m.YWG - MBJ
1 stop8h 50mAir Canada
Fri 5/127:05 p.m.MBJ - YWG
1 stop22h 30mAir Canada
Deal found 29/10C$ 697
Tue 30/128:05 p.m.YWG - KIN
1 stop18h 28mWestJet
Tue 20/14:30 p.m.KIN - YWG
2 stops26h 36mWestJet
Deal found 29/10C$ 698
Fri 28/118:40 a.m.YWG - MBJ
1 stop31h 10mUnited Airlines
Fri 5/121:25 p.m.MBJ - YWG
2 stops23h 32mUnited Airlines
Deal found 28/10C$ 701
Fri 5/125:00 a.m.YWG - KIN
1 stop9h 33mWestJet
Tue 16/124:30 p.m.KIN - YWG
2 stops44h 39mWestJet
Deal found 27/10C$ 743
Tue 25/1112:40 p.m.YWG - KIN
2 stops25h 53mMultiple Airlines
Tue 2/122:24 p.m.KIN - YWG
3 stops28h 42mMultiple Airlines
Deal found 28/10C$ 754
Fri 19/125:00 a.m.YWG - MBJ
1 stop13h 23mWestJet
Sat 3/13:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 28/10C$ 1,502
Fri 19/121:45 p.m.YWG - MBJ
2 stops48h 00mMultiple Airlines
Sat 3/13:25 p.m.MBJ - YWG
Nonstop5h 49mMultiple Airlines
Deal found 28/10C$ 1,520
Sat 20/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 29/10C$ 1,574
Sat 27/129:45 a.m.YWG - MBJ
2 stops31h 20mAir Canada
Sun 4/17:05 p.m.MBJ - YWG
1 stop22h 30mAir Canada
Deal found 29/10C$ 1,750

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 October 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

Tue 25/11

8:05 p.m.-3:33 p.m.

1 stop18h 28m

Kingston Norman Manley

Tue 2/12

4:30 p.m.-11:35 a.m.

1 stop20h 05m

C$ 662

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 11/11

12:40 p.m.-3:33 p.m.

2 stops25h 53m

Kingston Norman Manley

Fri 14/11

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

1 stop9h 05m

C$ 694

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 30/12

8:05 p.m.-3:33 p.m.

1 stop18h 28m

Kingston Norman Manley

Tue 20/1

4:30 p.m.-6:06 p.m.

2 stops26h 36m

C$ 698

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 30/12

8:05 p.m.-3:33 p.m.

1 stop18h 28m

Kingston Norman Manley

Mon 19/1

4:30 p.m.-3:21 p.m.

2 stops23h 51m

C$ 698

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

8:40 a.m.-4:50 p.m.

1 stop31h 10m

Montego Bay Sangster Intl

Fri 5/12

1:25 p.m.-11:57 a.m.

2 stops23h 32m

C$ 701

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Wed 26/11

5:00 a.m.-3:33 p.m.

1 stop9h 33m

Kingston Norman Manley

Wed 3/12

4:30 p.m.-11:35 a.m.

1 stop20h 05m

C$ 702

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 24/1

8:20 p.m.-11:30 a.m.

1 stop14h 10m

Montego Bay Sangster Intl

Sat 31/1

12:30 p.m.-11:35 p.m.

1 stop12h 05m

C$ 723

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Fri 5/12

5:00 a.m.-3:33 p.m.

1 stop9h 33m

Kingston Norman Manley

Tue 16/12

4:30 p.m.-12:09 p.m.

2 stops44h 39m

C$ 743

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/3

12:10 p.m.-1:15 p.m.

1 stop24h 05m

Montego Bay Sangster Intl

Tue 17/3

1:25 p.m.-3:30 p.m.

1 stop26h 05m

C$ 751

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 10/3

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

1 stop24h 05m

Montego Bay Sangster Intl

Tue 17/3

1:25 p.m.-3:30 p.m.

1 stop26h 05m

C$ 759

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

Showing 1-10 of 20 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, October is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 426). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 702). 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 October 2025.

It’s optimal to fly from Winnipeg to Jamaica in the evening. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight in the morning.

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 October 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
8,999 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,148 reviews
United Airlines
7.4
Good
8,999 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,372 reviews
United Airlines
7.4
Good
8,999 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 115 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 18h 28m. The time it takes to get you to your destination can typically vary by up to 12h 42m. There are 3993 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$ 406. On average you can expect to pay C$ 770. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 630.

  • 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$ 426). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 702). 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 29 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 490AverageC$ 752FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 514AverageC$ 821FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 842AverageC$ 930FlexibilityNo 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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