Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Jamaica from C$ 326

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
18 Apr — 25 Apr1
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 19 March 2026.

Tue 19/56:05 p.m.
YWG
-
MBJ
1 stop17h 40m
WestJet
Thu 4/612:45 p.m.
MBJ
-
YWG
2 stops25h 30m
WestJet
Deal found 15/3C$ 477
Sun 24/56:05 p.m.
YWG
-
MBJ
1 stop17h 40m
WestJet
Sun 14/67:30 p.m.
MBJ
-
YWG
1 stop29h 25m
WestJet
Deal found 15/3C$ 488
Thu 21/56:05 p.m.
YWG
-
MBJ
1 stop17h 40m
WestJet
Thu 11/612:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 15/3C$ 496
Mon 18/59:05 p.m.
YWG
-
MBJ
2 stops14h 40m
WestJet
Thu 4/612:45 p.m.
MBJ
-
YWG
2 stops23h 30m
WestJet
Deal found 15/3C$ 498
Tue 19/54:55 p.m.
YWG
-
MBJ
2 stops18h 50m
WestJet
Wed 3/612:45 p.m.
MBJ
-
YWG
2 stops22h 25m
WestJet
Deal found 15/3C$ 502
Mon 18/54:55 p.m.
YWG
-
MBJ
2 stops18h 50m
WestJet
Wed 3/612:45 p.m.
MBJ
-
YWG
1 stop12h 10m
WestJet
Deal found 15/3C$ 503
Fri 10/79:05 p.m.
YWG
-
MBJ
2 stops21h 25m
WestJet
Tue 14/712:45 p.m.
MBJ
-
YWG
2 stops25h 30m
WestJet
Deal found 17/3C$ 506
Tue 19/512:50 p.m.
YWG
-
KIN
2 stops25h 40m
WestJet
Fri 5/63:30 p.m.
KIN
-
YWG
2 stops19h 40m
WestJet
Deal found 15/3C$ 696
Tue 19/56:05 p.m.
YWG
-
KIN
1 stop20h 25m
WestJet
Wed 3/63:30 p.m.
KIN
-
YWG
2 stops22h 45m
WestJet
Deal found 15/3C$ 702
Wed 20/56:15 a.m.
YWG
-
KIN
1 stop8h 15m
WestJet
Wed 3/63:30 p.m.
KIN
-
YWG
2 stops46h 45m
WestJet
Deal found 15/3C$ 703
Fri 15/56:05 p.m.
YWG
-
KIN
1 stop20h 25m
WestJet
Sat 30/53:30 p.m.
KIN
-
YWG
2 stops46h 45m
WestJet
Deal found 16/3C$ 710
Thu 21/52:55 p.m.
YWG
-
KIN
2 stops23h 35m
WestJet
Wed 3/63:30 p.m.
KIN
-
YWG
2 stops20h 30m
WestJet
Deal found 15/3C$ 717

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 19 March 2026.

Round-trip from

C$ 477

One-way from

C$ 326

Popular in

December

Cheapest in

April

Average price

C$ 836

Good round-trip deal

C$ 650 or less
WestJet
  • WestJet
  • 19/5-4/6
  • 3 total stops
  • 43h 10m total
  • Winnipeg to Jamaica
Search Deals
WestJet
  • WestJet
  • 30/4
  • 1 total stop
  • 19h 20m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip 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 19 March 2026.
Use the filters below to find and compare flights from Winnipeg to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 30/5

2:00 p.m.-11:20 a.m.

1 stop21h 20m

Montego Bay Sangster Intl

Tue 2/6

12:30 p.m.-11:18 p.m.

1 stop10h 48m

C$ 580

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 5/5

2:00 p.m.-1:30 p.m.

2 stops23h 30m

Montego Bay Sangster Intl

Sat 9/5

4:12 p.m.-11:52 a.m.

2 stops19h 40m

C$ 667

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 30/5

8:45 a.m.-3:26 p.m.

2 stops30h 41m

Montego Bay Sangster Intl

Tue 2/6

4:12 p.m.-10:33 p.m.

2 stops30h 21m

C$ 667

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Fri 15/5

4:15 p.m.-2:30 p.m.

2 stops22h 15m

Kingston Norman Manley

Sat 30/5

3:30 p.m.-2:15 p.m.

2 stops22h 45m

C$ 710

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 2/5

2:00 p.m.-1:30 p.m.

2 stops23h 30m

Montego Bay Sangster Intl

Fri 8/5

2:40 p.m.-11:52 a.m.

2 stops21h 12m

C$ 735

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Sat 9/5

4:05 p.m.-1:55 p.m.

2 stops45h 50m

Kingston Norman Manley

Tue 19/5

3:05 p.m.-10:03 a.m.

1 stop18h 58m

C$ 746

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Mon 13/4

8:05 p.m.-3:24 p.m.

1 stop19h 19m

Kingston Norman Manley

Mon 20/4

3:30 p.m.-10:07 a.m.

2 stops18h 37m

C$ 750

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 3/5

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

2 stops12h 30m

Montego Bay Sangster Intl

Sun 10/5

7:30 p.m.-2:05 p.m.

2 stops18h 35m

C$ 789

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 30/4

2:00 p.m.-3:10 p.m.

2 stops25h 10m

Montego Bay Sangster Intl

Sun 3/5

2:40 p.m.-11:52 a.m.

2 stops21h 12m

C$ 802

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 14/4

5:00 a.m.-6:17 p.m.

1 stop13h 17m

Montego Bay Sangster Intl

Tue 21/4

1:21 p.m.-7:25 p.m.

2 stops30h 04m

C$ 826

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/3

Showing 1-10 of 34 resultsSorted by cheapest first
1
2
3
4

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$ 419). Flying from Winnipeg to Jamaica in February is currently the most expensive (average of C$ 752). 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 19 March 2026.

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 19 March 2026.
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
3,297 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,297 reviews
WestJet
7.2
Good
3,297 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
Air Canada
7.1
Good
10,815 reviews
WestJet
7.2
Good
3,297 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 46 times in the past calendar month.

  • How long is the flight from Winnipeg to Jamaica?

    Airlines like Air Canada, United Airlines, and WestJet fly from Winnipeg to Jamaica in about 21h 20m. The time it takes to get you to your destination can typically vary by up to 2h 10m. 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$ 508. On average you can expect to pay C$ 670. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 644.

  • 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$ 419). Flying from Winnipeg to Jamaica in February is currently the most expensive (average of C$ 752). 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 19 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 385AverageC$ 810FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 505AverageC$ 796FlexibilityNo 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.