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Montego Bay

$265+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 September, booked 61 days in advance, depart on a Tuesday or Monday and return on a Monday

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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$475
(United Airlines)

One-way from

$265
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$591
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.
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From Winnipeg to Montego Bay Sangster Intl
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One-way flight from Winnipeg to Montego Bay Sangster Intl
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Highest demand for flights based on searches. 15% potential increase in price ($115 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This United Airlines deal was found by Cheapflights users on 1/8. 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.
Tue 3/32:20 pmYWG - MBJ
2 stops46h 45mUnited Airlines
Tue 3/172:20 pmMBJ - YWG
2 stops45h 37mUnited Airlines
Deal found 1/8$506
This Air Canada deal was found by Cheapflights users on 1/6. 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 3/246:00 amYWG - MBJ
2 stops29h 30mAir Canada
Sun 3/296:05 pmMBJ - YWG
1 stop22h 22mAir Canada
Deal found 1/6$532
This WestJet deal was found by Cheapflights users on 1/8. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/234:10 pmYWG - MBJ
2 stops26h 07mWestJet
Mon 3/96:25 pmMBJ - YWG
2 stops28h 15mWestJet
Deal found 1/8$559
This United Airlines deal was found by Cheapflights users on 1/8. 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 3/12:20 pmYWG - MBJ
2 stops22h 40mUnited Airlines
Sun 3/81:48 pmMBJ - YWG
1 stop22h 09mUnited Airlines
Deal found 1/8$577
This WestJet deal was found by Cheapflights users on 1/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:45 amYWG - MBJ
2 stops54h 04mWestJet
Sun 4/512:25 pmMBJ - YWG
2 stops29h 40mWestJet
Deal found 1/7$609
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/149:00 pmYWG - MBJ
2 stops35h 00mMultiple Airlines
Sat 2/2110:40 amMBJ - YWG
1 stop29h 29mMultiple Airlines
Deal found 1/7$658
This Trip.com deal was found by Cheapflights users on 1/7. 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.
Sat 2/148:00 amYWG - MBJ
Nonstop5h 25mWestJet
Sat 2/213:25 pmMBJ - YWG
Nonstop5h 53mWestJet
Deal found 1/7$666

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 January 8, 2026.
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

Tue 3/3

2:20 pm-2:05 pm

2 stops46h 45m

Montego Bay Sangster Intl

Tue 3/17

2:20 pm-11:57 am

2 stops45h 37m

$506

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/24

6:00 am-11:30 am

2 stops29h 30m

Montego Bay Sangster Intl

Sun 3/29

6:05 pm-4:27 pm

1 stop22h 22m

$532

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-10:40 pm

2 stops28h 15m

$559

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 3/1

2:20 pm-2:00 pm

2 stops22h 40m

Montego Bay Sangster Intl

Sun 3/8

1:48 pm-11:57 am

1 stop22h 09m

$577

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 2/22

2:20 pm-2:00 pm

2 stops22h 40m

$265

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 1/18

8:20 pm-1:53 pm

1 stop16h 33m

$272

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 1/18

12:40 pm-7:23 pm

2 stops53h 43m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Montego Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 January 2, 2026.

The best time to book flights from Winnipeg to Montego Bay is 61 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 January 8, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Montego Bay as you normally would.

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 January 8, 2026.
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
3,235 reviews

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Crew

7.9

Overall

7.2

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,235 reviews
WestJet
7.2
Good
3,235 reviews

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Crew

7.9

Overall

7.2

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
Air Canada
7.1
Good
10,603 reviews
WestJet
7.2
Good
3,235 reviews

Comfort

7.0

Entertainment

6.1

Boarding

7.4

Crew

7.9

Overall

7.2

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

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 7 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 50m. Airlines will cover a distance of 2417 mi.

  • 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 $323. Another airline that can offer you cheap pricing is WestJet. Air Canada is currently priced 47% 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$363Average$663FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$475Average$660FlexibilityNo cancel feeOn-time67%

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