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Montego Bay

$286+ Cheap flights from Winnipeg (YWG) to Montego Bay (MBJ)

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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Montego Bay Sangster Intl are usually found in April or June, booked 60 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from Winnipeg to Montego Bay

Cheapest flights from Winnipeg to Montego Bay
Explore the most affordable flight options available from Winnipeg to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.

This Air Canada deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:45 pm
YWG
-
MBJ
1 stop22h 05m
Air Canada
Fri 12/181:50 pm
MBJ
-
YWG
1 stop21h 26m
Air Canada
Deal found 5/29$498
This Air Canada deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:20 pm
YWG
-
MBJ
1 stop16h 20m
Air Canada
Fri 11/271:50 pm
MBJ
-
YWG
1 stop21h 26m
Air Canada
Deal found 5/29$525
This oojo deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:00 am
YWG
-
MBJ
2 stops27h 45m
WestJet
Sun 6/712:45 pm
MBJ
-
YWG
1 stop21h 00m
WestJet
Deal found 5/26$552
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:05 pm
YWG
-
MBJ
1 stop22h 24m
WestJet
Fri 12/182:55 pm
MBJ
-
YWG
1 stop10h 50m
WestJet
Deal found 5/25$558
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:00 am
YWG
-
MBJ
2 stops30h 30m
United Airlines
Sat 7/114:33 pm
MBJ
-
YWG
2 stops19h 19m
United Airlines
Deal found 5/28$577
This Justfly.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:00 am
YWG
-
MBJ
Nonstop5h 30m
WestJet
Sun 12/273:25 pm
MBJ
-
YWG
Nonstop5h 53m
WestJet
Deal found 5/28$603

Find flight deals from Winnipeg to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Montego Bay (MBJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$525
(Air Canada)

One-way from

$286
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$608

Good round-trip deal

$669 or less
Provider with most accurate pricing for Winnipeg-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Montego Bay Sangster Intl flights.
Search Deals
From Winnipeg to Montego Bay Sangster Intl
Search Deals
One-way flight from Winnipeg to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Montego Bay Sangster Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Montego Bay 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 2,558,603 searches. Data last updated May 30, 2026.
Use the filters below to find and compare flights from Winnipeg to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 11/23

7:20 pm-12:40 pm

1 stop16h 20m

Montego Bay Sangster Intl

Fri 11/27

1:50 pm-10:16 am

1 stop21h 26m

$525

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/27

7:00 am-1:30 pm

2 stops30h 30m

Montego Bay Sangster Intl

Sat 7/11

4:33 pm-11:52 am

2 stops19h 19m

$577

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 6/30

12:50 pm-11:45 am

2 stops22h 55m

Montego Bay Sangster Intl

Sun 7/5

7:30 pm-2:05 pm

2 stops18h 35m

$681

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/27

7:10 pm-11:45 am

2 stops40h 35m

Montego Bay Sangster Intl

Sat 7/11

7:30 pm-9:45 am

1 stop14h 15m

$685

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 6/18

2:05 pm-12:50 pm

2 stops46h 45m

Montego Bay Sangster Intl

Wed 6/24

2:40 pm-10:00 am

3 stops43h 20m

$706
Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 6/27

5:10 pm-11:45 am

1 stop18h 35m

Montego Bay Sangster Intl

Sat 7/11

7:30 pm-9:45 am

1 stop14h 15m

$784

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 9/10

2:00 pm-11:43 am

2 stops21h 43m

Montego Bay Sangster Intl

Sun 9/20

12:52 pm-9:57 am

3 stops21h 05m

$2,970

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 11/23

12:10 pm-2:14 pm

3 stops25h 04m

Montego Bay Sangster Intl

Fri 11/27

3:50 pm-11:35 pm

3 stops32h 45m

$3,284
Cheapest one-way
Quickest one-way

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 7/13

7:00 am-3:10 pm

2 stops32h 10m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/28

Sorted by cheapest first

Compare providers for flights from Winnipeg to Montego Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Montego Bay in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Montego Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Winnipeg to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay 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 Montego Bay

How far ahead should I book a flight from Winnipeg to Montego Bay?

The best time to book flights from Winnipeg to Montego Bay is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, April is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $502). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of $854). 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.

How much does it cost to fly round-trip from Winnipeg to Montego Bay?

Reviews of airlines servicing Montego Bay

Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated May 30, 2026.
Read through reviews of airlines operating flights from Winnipeg to Montego Bay, such as WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,350 reviews

Boarding

7.4

Crew

7.9

Entertainment

6.1

Overall

7.2

Food

6.2

Comfort

7.0

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
3,350 reviews
WestJet
7.2
Good
3,350 reviews

Boarding

7.4

Crew

7.9

Entertainment

6.1

Overall

7.2

Food

6.2

Comfort

7.0

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 Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Winnipeg to Montego Bay flight route?

    The Winnipeg to Montego Bay Sangster Intl flight path was viewed by 6 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 Winnipeg to Montego Bay?

    Departing from Winnipeg to Montego Bay will take you 16h 20m. Airlines will cover a distance of 2417 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Winnipeg to Montego Bay round-trip?

    Cheapflights users have booked flights from Winnipeg to Montego Bay round-trip from $487. WestJet is currently priced 22% below the average price you’ll pay for this route.

  • What are the cheapest flights from Winnipeg to Montego Bay?

    Looking for the cheapest flight from Winnipeg to Montego Bay? While on average our users pay $670, our data indicates the cheapest price to be $624. The most popular route (Winnipeg - Montego Bay Sangster Intl), is priced around $556.

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

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

  • How can I find direct flights from Winnipeg to Montego Bay?

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Montego Bay 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 Montego Bay?

    Currently, April is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $502). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of $854). 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

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Lucea

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Winnipeg to Montego Bay

Discover the top airline that operate flights from Winnipeg to Montego Bay. 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 2,558,603 searches. Data last updated May 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$487Average$719FlexibilityNo cancel feeOn-time60%

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