Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Jamaica from C$ 300

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 28/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
14 Jan — 21 Jan1
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 15 December 2025.

Sat 27/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sat 10/13:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 14/12C$ 744
Sat 27/128:00 a.m.YWG - MBJ
Nonstop5h 30mMultiple Airlines
Sat 10/14:36 p.m.MBJ - YWG
2 stops26h 30mMultiple Airlines
Deal found 15/12C$ 797
Sat 27/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 15/12C$ 912
Sat 20/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 15/12C$ 1,045
Sun 21/1211:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 28/121:25 p.m.MBJ - YWG
1 stop12h 10mWestJet
Deal found 14/12C$ 1,049
Sun 21/128:40 a.m.YWG - MBJ
2 stops28h 20mUnited Airlines
Sun 28/123:20 p.m.MBJ - YWG
2 stops30h 31mUnited Airlines
Deal found 14/12C$ 1,351

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 15 December 2025.

Round-trip from

C$ 595

One-way from

C$ 300

Popular in

December

Cheapest in

April

Average price

C$ 1,051

Good round-trip deal

C$ 681 or less

Good one-way deal

C$ 335 or less
27/2-7/3
  • 27/2-7/3
  • 2 total stops
  • 46h 57m total
  • Winnipeg to Jamaica
Search Deals
28/3
  • 28/3
  • 1 total stop
  • 15h 04m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 169 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Jamaica.
Search Deals
Price to beat on a one-way 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 15 December 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

Fri 6/3

8:05 p.m.-1:49 p.m.

1 stop16h 44m

Montego Bay Sangster Intl

Fri 13/3

1:55 p.m.-12:35 a.m.

1 stop10h 40m

C$ 632

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 17/1

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

2 stops30h 12m

Kingston Norman Manley

Thu 29/1

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

1 stop29h 05m

C$ 672

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/3

6:45 a.m.-11:24 a.m.

2 stops28h 39m

Montego Bay Sangster Intl

Sat 4/4

2:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 715

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 28/2

12:40 p.m.-12:24 p.m.

2 stops22h 44m

Montego Bay Sangster Intl

Sat 7/3

7:25 p.m.-10:32 a.m.

1 stop16h 07m

C$ 742

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 5/1

8:00 a.m.-12:05 p.m.

1 stop27h 05m

Montego Bay Sangster Intl

Sun 11/1

6:25 p.m.-11:14 p.m.

Nonstop5h 49m

C$ 749

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/3

5:00 a.m.-7:17 p.m.

1 stop13h 17m

Montego Bay Sangster Intl

Tue 17/3

7:25 p.m.-11:32 a.m.

1 stop16h 07m

C$ 766

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

6:55 p.m.-7:17 p.m.

2 stops23h 22m

Montego Bay Sangster Intl

Mon 9/3

6:25 p.m.-6:05 p.m.

2 stops23h 40m

C$ 766

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sun 18/1

2:20 p.m.-1:53 p.m.

2 stops46h 33m

Kingston Norman Manley

Thu 22/1

3:00 p.m.-11:57 a.m.

2 stops45h 57m

C$ 1,318

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sun 18/1

7:30 a.m.-8:00 p.m.

1 stop11h 30m

Kingston Norman Manley

Thu 22/1

9:00 a.m.-11:03 a.m.

2 stops27h 03m

C$ 1,765

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 17/1

6:00 a.m.-2:26 p.m.

3 stops31h 26m

Kingston Norman Manley

Thu 29/1

3:32 p.m.-11:35 p.m.

3 stops33h 03m

C$ 4,019

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Showing 1-10 of 19 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$ 421). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 694). 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 15 December 2025.

It’s optimal to fly from Winnipeg to Jamaica in the evening. By choosing this option you can save up to 17% 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 15 December 2025.
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
3,202 reviews
Check prices

Comfort

7.1

Crew

7.9

Boarding

7.4

Food

6.2

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Nov 2025

YQU - YYC

After first flight cancelled they barely accommodated our flight to get to our destination, after 36 hours of travel and long layovers we arrived but the worst experience ever! I will definitely put claims in of the lost upgrades and lost time and money we had!!!
WestJet
7.2
Good
3,202 reviews
WestJet
7.2
Good
3,202 reviews
Check prices

Comfort

7.1

Crew

7.9

Boarding

7.4

Food

6.2

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Nov 2025

YQU - YYC

After first flight cancelled they barely accommodated our flight to get to our destination, after 36 hours of travel and long layovers we arrived but the worst experience ever! I will definitely put claims in of the lost upgrades and lost time and money we had!!!
Air Canada
7.1
Good
10,525 reviews
WestJet
7.2
Good
3,202 reviews
Check prices

Comfort

7.1

Crew

7.9

Boarding

7.4

Food

6.2

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Nov 2025

YQU - YYC

After first flight cancelled they barely accommodated our flight to get to our destination, after 36 hours of travel and long layovers we arrived but the worst experience ever! I will definitely put claims in of the lost upgrades and lost time and money we had!!!

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 92 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 16h 44m. The time it takes to get you to your destination can typically vary by up to 29h 49m. 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 airlines to fly from Winnipeg to Jamaica one-way?

    C$ 253 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$ 276 and C$ 361, respectively.

  • What are the cheapest flights from Winnipeg to Jamaica?

    The cheapest flight price from Winnipeg to Jamaica is C$ 334. On average you can expect to pay C$ 530. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 614.

  • 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$ 421). Flying from Winnipeg to Jamaica in August is currently the most expensive (average of C$ 694). 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 15 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 485AverageC$ 777FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 505AverageC$ 793FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.