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Montego Bay

$229+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 March, booked 31 days in advance, depart on a Monday or Thursday and return on a Thursday

Find 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 October 22, 2025.

This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sun 10/262:20 pmYWG - MBJ
2 stops23h 09mUnited Airlines
Sun 11/23:20 pmMBJ - YWG
2 stops45h 37mUnited Airlines
Deal found 10/21$457
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:10 pmYWG - MBJ
2 stops26h 13mWestJet
Mon 12/87:25 pmMBJ - YWG
1 stop17h 10mWestJet
Deal found 10/22$471
This FlightHub deal was found by Cheapflights users on 10/20. 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.
Mon 12/88:45 pmYWG - MBJ
1 stop21h 38mWestJet
Tue 3/37:25 pmMBJ - YWG
1 stop30h 14mWestJet
Deal found 10/20$514
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 11/282:20 pmYWG - MBJ
2 stops24h 52mUnited Airlines
Fri 12/51:25 pmMBJ - YWG
2 stops23h 32mUnited Airlines
Deal found 10/21$534
This Air Canada deal was found by Cheapflights users on 10/20. 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.
Fri 11/148:15 amYWG - MBJ
1 stop8h 50mAir Canada
Mon 11/175:45 pmMBJ - YWG
2 stops17h 31mAir Canada
Deal found 10/20$611
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Fri 11/142:20 pmYWG - MBJ
2 stops24h 52mUnited Airlines
Mon 11/171:25 pmMBJ - YWG
2 stops32h 31mUnited Airlines
Deal found 10/20$686
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:30 amYWG - MBJ
3 stops27h 32mMultiple Airlines
Mon 11/177:25 pmMBJ - YWG
2 stops16h 43mMultiple Airlines
Deal found 10/20$711

Cheap 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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$509
(United Airlines)

One-way from

$229
(Mytrip)

Popular in

November

Cheapest in

April

Average price

$579
Provider with most accurate pricing for Winnipeg-Montego Bay Sangster Intl flight deals.
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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. 13% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 22, 2025.
Use the filters below to find and compare flights from Winnipeg to Montego Bay that are best for you.

Fly from

Winnipeg

Fly to

Montego Bay

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 12/1

4:10 pm-7:23 pm

2 stops26h 13m

Montego Bay Sangster Intl

Mon 12/8

7:25 pm-11:35 am

1 stop17h 10m

$471

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 2/28

2:20 pm-1:46 pm

1 stop22h 26m

Montego Bay Sangster Intl

Sat 3/7

3:20 pm-10:39 am

2 stops20h 19m

$509

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 2/23

2:20 pm-2:37 pm

2 stops23h 17m

Montego Bay Sangster Intl

Mon 3/9

2:20 pm-11:39 am

2 stops45h 19m

$510

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 12/8

12:40 pm-7:23 pm

2 stops29h 43m

Montego Bay Sangster Intl

Tue 3/3

8:25 pm-11:32 am

1 stop16h 07m

$514

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 2/23

4:10 pm-7:17 pm

2 stops26h 07m

Montego Bay Sangster Intl

Mon 3/9

6:25 pm-3:20 pm

2 stops20h 55m

$514

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 2/21

12:20 pm-12:24 pm

1 stop23h 04m

Montego Bay Sangster Intl

Sat 2/28

7:25 pm-11:32 am

1 stop17h 07m

$532

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/3

9:00 pm-7:17 pm

2 stops21h 17m

Montego Bay Sangster Intl

Tue 3/17

6:25 pm-11:32 am

1 stop17h 07m

$532

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 1/31

8:20 pm-11:30 am

1 stop14h 10m

$229

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 1/7

7:30 am-12:05 pm

2 stops27h 35m

$251

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 1/6

8:05 pm-7:23 pm

1 stop22h 18m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 15 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
AranGrantPrice Accuracy3 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust 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?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Montego Bay. Price data was last updated on October 17, 2025.

The best time to book flights from Winnipeg to Montego Bay is 31 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $306). Flying from Winnipeg to Montego Bay in August is currently the most expensive (average of $504). 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 MBJ?

Find hourly flight availability from Winnipeg to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 22, 2025.

It’s optimal to fly from Winnipeg to Montego Bay at noon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the afternoon.

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 October 22, 2025.
Read through reviews of airlines operating flights from Winnipeg to Montego Bay, such as WestJet and Air Canada. 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
3,133 reviews

Overall

7.2

Boarding

7.4

Food

6.2

Entertainment

6.1

Crew

7.9

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
WestJet
7.2
Good
3,133 reviews
WestJet
7.2
Good
3,133 reviews

Overall

7.2

Boarding

7.4

Food

6.2

Entertainment

6.1

Crew

7.9

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
Air Canada
7.1
Good
10,344 reviews
WestJet
7.2
Good
3,133 reviews

Overall

7.2

Boarding

7.4

Food

6.2

Entertainment

6.1

Crew

7.9

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon

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 22h 26m. 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 are the cheapest airlines flying from Winnipeg to Montego Bay round-trip?

    Cheapflights users have booked flights from Winnipeg to Montego Bay round-trip from $363. Another airline that can offer you cheap pricing is Air Canada. WestJet is currently priced 39% below the average price you’ll pay for this route.

  • 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $306). Flying from Winnipeg to Montego Bay in August is currently the most expensive (average of $504). 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
Whitehouse
Lucea

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Top 2 airlines flying from Winnipeg to Montego Bay

Discover the top 2 airlines 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$363Average$663FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$475Average$660FlexibilityNo cancel feeOn-time67%

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