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Montego Bay

$402+ Cheap flights from Winnipeg (YWG) to Montego Bay (MBJ)

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 Tuesday and return on a Thursday

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 September 16, 2025.

Round-trip from

$402
(oojo)

Popular in

November

Cheapest in

April

Average price

$504

Good round-trip deal

$719 or less
From Winnipeg to Montego Bay Sangster Intl
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Highest demand for flights based on searches. 14% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Winnipeg to Montego Bay Sangster Intl.
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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 September 16, 2025.

This oojo deal was found by Cheapflights users on 9/15. 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.
Wed 10/298:05 pmYWG - MBJ
1 stop16h 49mWestJet
Sun 11/21:25 pmMBJ - YWG
1 stop23h 10mWestJet
Deal found 9/15$402
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/19:00 pmYWG - MBJ
2 stops18h 15mMultiple Airlines
Sat 11/84:20 pmMBJ - YWG
1 stop23h 47mMultiple Airlines
Deal found 9/15$407
This oojo deal was found by Cheapflights users on 9/15. 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.
Sat 11/16:15 amYWG - MBJ
2 stops37h 08mWestJet
Sat 11/87:25 pmMBJ - YWG
2 stops20h 56mWestJet
Deal found 9/15$420
This WestJet deal was found by Cheapflights users on 9/15. 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.
Fri 11/145:00 amYWG - MBJ
1 stop7h 54mWestJet
Sun 11/238:25 pmMBJ - YWG
1 stop23h 47mWestJet
Deal found 9/15$440
This WestJet deal was found by Cheapflights users on 9/16. 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.
Fri 10/249:05 pmYWG - MBJ
2 stops38h 24mWestJet
Fri 10/311:55 pmMBJ - YWG
2 stops34h 46mWestJet
Deal found 9/16$447
This WestJet deal was found by Cheapflights users on 9/14. 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.
Sun 12/2111:00 amYWG - MBJ
Nonstop5h 30mWestJet
Tue 12/308:25 pmMBJ - YWG
1 stop16h 10mWestJet
Deal found 9/14$520
This WestJet deal was found by Cheapflights users on 9/16. 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 12/206:55 pmYWG - MBJ
2 stops16h 34mWestJet
Sun 1/46:25 pmMBJ - YWG
Nonstop5h 49mWestJet
Deal found 9/16$647

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 September 16, 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

Wed 10/29

9:00 pm-12:54 pm

2 stops15h 54m

Montego Bay Sangster Intl

Sun 11/2

1:25 pm-11:35 am

1 stop23h 10m

$405

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 10/24

9:05 pm-11:29 am

2 stops38h 24m

Montego Bay Sangster Intl

Fri 10/31

1:55 pm-12:41 am

2 stops34h 46m

$447

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 2/23

12:10 pm-11:15 am

1 stop22h 05m

Montego Bay Sangster Intl

Wed 3/11

1:25 pm-11:35 pm

1 stop10h 10m

$522

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 2/3

6:00 am-1:15 pm

1 stop30h 15m

Montego Bay Sangster Intl

Tue 2/17

12:25 pm-11:35 pm

1 stop12h 10m

$536

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 2/24

6:00 am-1:15 pm

1 stop30h 15m

Montego Bay Sangster Intl

Tue 3/10

1:25 pm-11:35 pm

1 stop10h 10m

$536

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 2/9

6:00 am-11:15 am

1 stop28h 15m

Montego Bay Sangster Intl

Tue 2/17

12:25 pm-3:30 pm

1 stop28h 05m

$551

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 2/3

6:00 am-1:15 pm

1 stop30h 15m

Montego Bay Sangster Intl

Wed 2/18

2:25 pm-11:35 pm

1 stop10h 10m

$551

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 2/8

6:00 am-6:50 pm

1 stop11h 50m

Montego Bay Sangster Intl

Tue 2/17

12:25 pm-11:35 pm

1 stop12h 10m

$554

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 2/26

6:00 am-11:15 am

1 stop28h 15m

Montego Bay Sangster Intl

Wed 3/11

1:25 pm-11:35 pm

1 stop10h 10m

$555

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 2/23

2:20 pm-1:46 pm

1 stop22h 26m

Montego Bay Sangster Intl

Wed 3/11

2:20 pm-11:39 am

2 stops21h 19m

$562

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 12 results
1
2

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 September 12, 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, January is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $403). Flying from Winnipeg to Montego Bay in July is currently the most expensive (average of $561). 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 September 16, 2025.

It’s optimal to fly from Winnipeg to Montego Bay at noon. By choosing this option you can save up to 42% 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 September 16, 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
3,093 reviews

Boarding

7.4

Crew

7.9

Food

6.2

Comfort

7.1

Entertainment

6.1

Overall

7.2

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
3,093 reviews
WestJet
7.2
Good
3,093 reviews

Boarding

7.4

Crew

7.9

Food

6.2

Comfort

7.1

Entertainment

6.1

Overall

7.2

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
10,000 reviews
WestJet
7.2
Good
3,093 reviews

Boarding

7.4

Crew

7.9

Food

6.2

Comfort

7.1

Entertainment

6.1

Overall

7.2

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 15h 54m. 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 38% 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 $740, our data indicates the cheapest price to be $719. The most popular route (Winnipeg - Montego Bay Sangster Intl), is priced around $548.

  • 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, January is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $403). Flying from Winnipeg to Montego Bay in July is currently the most expensive (average of $561). 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$363Average$645FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$475Average$657FlexibilityNo cancel feeOn-time67%

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