$249+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Montego Bay with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Winnipeg to Montego Bay Sangster Intl are usually found in September or April, booked 79 days in advance, depart on a Monday or Tuesday and return on a Monday
Cheap flight deals from Winnipeg to Montego Bay
Cheapest
Best
Last-minute
One-way
Cheapest flights from Winnipeg to Montego BayExplore 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, 2026.
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, 2026.
This Air Canada deal was found by Cheapflights users on 9/13. 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 12/83:05 pm -
1 stop25h 15m
Fri 12/182:20 pm -
1 stop27h 18m
Deal found 9/13![Air Canada logo]()
$481
This FlightHub deal was found by Cheapflights users on 9/12. 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.
Sun 12/206:10 am -
Nonstop5h 35m
Sun 12/271:45 pm -
Nonstop6h 00m
Deal found 9/12![WestJet logo]()
$515
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Sun 12/208:20 am -
Nonstop5h 20m
Sun 1/103:40 pm -
Nonstop5h 40m
Deal found 9/13![Air Canada logo]()
$540
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:20 am -
Nonstop5h 20m
Sun 12/273:40 pm -
Nonstop5h 40m
Deal found 9/16![Air Canada logo]()
$567
Best flights from Winnipeg to Montego BayDiscover carefully curated flight deals from Winnipeg to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Winnipeg to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/166:00 am -
2 stops12h 35m
Fri 1/228:35 pm -
2 stops28h 24m
Deal found 9/15![WestJet logo]()
$479
This Air Canada deal was found by Cheapflights users on 9/11. 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 12/83:05 pm -
1 stop25h 15m
Fri 12/182:20 pm -
2 stops29h 05m
Deal found 9/11![Air Canada logo]()
$482
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 1/1612:10 pm -
2 stops24h 25m
Tue 2/166:20 pm -
2 stops30h 39m
Deal found 9/15![WestJet logo]()
$485
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:00 am -
2 stops12h 35m
Sat 3/203:50 pm -
Nonstop6h 00m
Deal found 9/14![WestJet logo]()
$496
This Justfly.com deal was found by Cheapflights users on 9/13. 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 1/106:00 am -
2 stops30h 35m
Sun 1/315:35 pm -
2 stops23h 50m
Deal found 9/13![WestJet logo]()
$566
Last-minute flights from Winnipeg to Montego BayDiscover last-minute flight deals from Winnipeg to Montego Bay. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated September 16, 2026 and is based on user searches.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:00 pm -
2 stops47h 30m
Mon 9/2812:52 pm -
2 stops32h 05m
Deal found 9/15![United Airlines logo]()
$980
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.
Thu 9/249:25 am -
1 stop26h 20m
Mon 9/283:42 pm -
2 stops23h 43m
Deal found 9/15![Multiple Airlines logo]()
$1,050
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:20 pm -
1 stop20h 00m
Mon 9/2812:30 pm -
1 stop8h 57m
Deal found 9/15![Air Canada logo]()
$1,623
One-way flights from Winnipeg to Montego BaySearch for one-way flight options from Winnipeg to Montego Bay. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Winnipeg to Montego Bay. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/176:00 am -
2 stops30h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![WestJet logo]()
$249
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Sun 1/178:20 am -
Nonstop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 10/58:45 am -
2 stops26h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![United Airlines logo]()
$317
This Trip.com deal was found by Cheapflights users on 9/13. 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 11/712:10 pm -
2 stops24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![WestJet logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 1/173:45 pm -
3 stops24h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$370
This Air Canada deal was found by Cheapflights users on 9/13. 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 10/55:25 pm -
1 stop17h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Air Canada logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Mon 10/511:15 am -
3 stops48h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$510
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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $476 (CheapOair) |
One-way from | $249 (Booking.com) |
Popular in | December |
Cheapest in | September |
Average price | $364 |
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 7,457,451 searches. Data last updated September 16, 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
Cheapest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/17
6:00 am-1:35 pm
2 stops30h 35m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/17
8:20 am-2:40 pm
Nonstop5h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$265
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 10/5
8:45 am-11:43 am
2 stops26h 58m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$317
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 11/7
9:35 am-1:35 pm
1 stop27h 00m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$342
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 10/5
5:25 pm-11:20 am
1 stop17h 55m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$476
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
6:00 am-7:35 pm
2 stops12h 35m
Montego Bay Sangster Intl
Fri 1/22
8:35 pm-11:59 pm
2 stops28h 24m
$479
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 12/8
3:05 pm-5:20 pm
1 stop25h 15m
Montego Bay Sangster Intl
Fri 12/18
2:20 pm-6:25 pm
2 stops29h 05m
$482
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
12:10 pm-1:35 pm
2 stops24h 25m
Montego Bay Sangster Intl
Tue 2/16
6:20 pm-11:59 pm
2 stops30h 39m
$485
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 2/20
6:00 am-7:35 pm
2 stops12h 35m
Montego Bay Sangster Intl
Sat 3/20
3:50 pm-9:50 pm
Nonstop6h 00m
$496
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/10
6:00 am-1:35 pm
2 stops30h 35m
Montego Bay Sangster Intl
Sun 1/31
5:35 pm-4:25 pm
2 stops23h 50m
$566
Sorted by cheapest first
- 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.
YWG-MBJ
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 77 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, September is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $364). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of $847). 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?
Airfare is typical for this route at the moment.
Winnipeg to Montego Bay flights typically cost between $330 and $1,087 in January.The cheapest round-trip price found within the last 5 days was $476 on WestJet (Jan 16-Jan 22).
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, 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.
Boarding
7.4
Crew
7.9
Comfort
7.1
Entertainment
6.1
Food
6.2
Overall
7.2
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
Boarding
7.4
Crew
7.9
Comfort
7.1
Entertainment
6.1
Food
6.2
Overall
7.2
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
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.
Traveling to a place near Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsLucea
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Other flights to Montego Bay
Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 16, 2026.
Winnipeg and Montego Bay flights
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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 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$472 | Average$670 | FlexibilityNo cancel fee | On-time60% |