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Cheap flights from Jamaica to Winnipeg from C$ 828

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — YWG
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Jamaica to Winnipeg

Enter your travel dates to find the best prices.

Best flights from Jamaica to Winnipeg
Discover carefully curated flight deals from Jamaica to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 3 November 2025.

Fri 6/34:30 p.m.KIN - YWG
2 stops41h 37mWestJet
Mon 9/36:45 a.m.YWG - KIN
2 stops31h 45mWestJet
Deal found 1/11C$ 828
Fri 6/32:55 p.m.KIN - YWG
1 stop9h 59mAir Canada
Mon 9/37:05 p.m.YWG - KIN
1 stop17h 40mAir Canada
Deal found 1/11C$ 831

Cheap flight deals from Jamaica to Winnipeg

Keep the following information in mind while searching for Jamaica to Winnipeg flight deals. Data was last updated 3 November 2025.

Round-trip from

C$ 828

Popular in

August

Cheapest in

February

Average price

C$ 1,124

Good round-trip deal

C$ 753 or less
WestJet
  • WestJet
  • 6/3-9/3
  • 4 total stops
  • 73h 22m total
  • Jamaica to Winnipeg
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Jamaica to Winnipeg.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Winnipeg 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 3 November 2025.
Use the filters below to find and compare flights from Jamaica to Winnipeg that are best for you.

Fly from

Jamaica

Fly to

Winnipeg

Route

Depart

Return

Price

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 6/3

4:30 p.m.-9:07 a.m.

2 stops41h 37m

Winnipeg

Mon 9/3

6:45 a.m.-2:30 p.m.

2 stops31h 45m

C$ 828

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 6/3

2:55 p.m.-11:54 p.m.

1 stop9h 59m

Winnipeg

Mon 9/3

7:05 p.m.-12:45 p.m.

1 stop17h 40m

C$ 831

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Best time to book a flight from Jamaica to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Jamaica 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 Jamaica to Winnipeg

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

Currently, May is the cheapest month in which you can book a flight from Jamaica to Winnipeg (average of C$ 379). Flying from Jamaica to Winnipeg in August is currently the most expensive (average of C$ 1,092). 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 JM to YWG?

Find hourly flight availability from Jamaica to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 November 2025.

A simple way to save on the total cost of your ticket is to fly from Jamaica to Winnipeg in the evening. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated 3 November 2025.
Get a feel of what it's like to fly with WestJet and Air Canada from Jamaica to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,153 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Crew

7.9

Food

6.2

Overall

7.2

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.
WestJet
7.2
Good
3,153 reviews
WestJet
7.2
Good
3,153 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Crew

7.9

Food

6.2

Overall

7.2

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.
Air Canada
7.1
Good
10,398 reviews
WestJet
7.2
Good
3,153 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Crew

7.9

Food

6.2

Overall

7.2

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Winnipeg. 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 into for flights to Winnipeg from Jamaica?

    For a flight from Jamaica to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 7.3 km from the centre of the city.

  • How popular is this Jamaica to Winnipeg flight route?

    The Jamaica to Winnipeg flight path was viewed by 5 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Jamaica to Winnipeg?

    WestJet and Air Canada can get you from Jamaica to Winnipeg in just under 9h 59m. Your travel time can differ by up to 31h 38m. Jamaica and Winnipeg are separated by a distance of 3993 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest flights from Jamaica to Winnipeg?

    Looking at all options, your cheapest flight can be booked for C$ 753. While the most popular route (Kingston Norman Manley - Winnipeg) can be booked for C$ 907 on average, our data indicates C$ 755 when flying from Jamaica to Winnipeg.

  • Can I find deals for flights from Jamaica to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Jamaica to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Winnipeg.

  • Can I find deals for business class flights from Jamaica to Winnipeg?

    Yes. Cheapflights offers flight deals from Jamaica to Winnipeg 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 Jamaica to Winnipeg?

    Currently, May is the cheapest month in which you can book a flight from Jamaica to Winnipeg (average of C$ 379). Flying from Jamaica to Winnipeg in August is currently the most expensive (average of C$ 1,092). 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Alternative routes for Jamaica to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
George Town to Winnipeg flights
Kingston to Winnipeg flights
Nassau to Winnipeg flights

Top 2 airlines flying from Jamaica to Winnipeg

Discover the top 2 airlines that operate flights from Jamaica to Winnipeg. 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 3 November 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 500AverageC$ 790FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 835AverageC$ 1,052FlexibilityNo cancel feeOn-time67%
Search Air Canada 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 Jamaica to Winnipeg?

Deals for Jamaica to Winnipeg flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Jamaica to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Jamaica.

Can Cheapflights find flights from Jamaica to Winnipeg with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Jamaica to Winnipeg flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Jamaica to Winnipeg become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Winnipeg from Jamaica today and book when prices fit your budget.

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