$311+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Nov 12 — Nov 191
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 October 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 October 13, 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 October 13, 2026.
This Air Canada deal was found by Cheapflights users on 10/9. 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 12/69:20 am -
Nonstop4h 20m
Sun 12/133:40 pm -
Nonstop6h 40m
Deal found 10/9![Air Canada logo]()
$411
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:05 pm -
1 stop21h 30m
Thu 12/32:40 pm -
1 stop31h 10m
Deal found 10/12![WestJet logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 12/511:00 am -
2 stops30h 54m
Sat 12/122:30 pm -
1 stop20h 45m
Deal found 10/9![Multiple Airlines logo]()
$438
This FlightHub deal was found by Cheapflights users on 10/9. 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 12/69:05 pm -
1 stop15h 30m
Sun 12/1312:45 pm -
Nonstop7h 00m
Deal found 10/9![WestJet logo]()
$445
This WestJet deal was found by Cheapflights users on 10/9. 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 12/58:00 am -
Nonstop4h 35m
Sat 12/126:20 pm -
1 stop18h 45m
Deal found 10/9![WestJet logo]()
$464
This oojo deal was found by Cheapflights users on 10/9. 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.
Tue 12/810:35 am -
1 stop26h 00m
Fri 12/181:35 pm -
1 stop13h 09m
Deal found 10/9![WestJet logo]()
$498
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 October 13, 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 October 13, 2026.
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/159:05 pm -
1 stop21h 30m
Thu 2/42:40 pm -
1 stop22h 25m
Deal found 10/12![WestJet logo]()
$486
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/158:00 am -
2 stops31h 19m
Tue 2/22:54 pm -
1 stop29h 34m
Deal found 10/12![United Airlines logo]()
$513
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:00 am -
1 stop12h 35m
Sat 3/203:50 pm -
Nonstop6h 00m
Deal found 10/11![WestJet logo]()
$565
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 1/167:55 pm -
2 stops39h 18m
Fri 1/221:25 pm -
2 stops22h 44m
Deal found 10/8![United Airlines logo]()
$610
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:40 am -
2 stops25h 33m
Fri 12/113:20 pm -
2 stops47h 03m
Deal found 10/11![United Airlines logo]()
$660
This United Airlines deal was found by Cheapflights users on 10/8. 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 12/82:15 pm -
2 stops20h 58m
Fri 12/182:54 pm -
1 stop22h 58m
Deal found 10/8![United Airlines logo]()
$697
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/77:55 pm -
2 stops16h 53m
Fri 11/131:25 pm -
2 stops22h 59m
Deal found 10/9![United Airlines logo]()
$702
Last-minute flights from Winnipeg to Montego BayDiscover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 13, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/67:55 pm -
2 stops19h 24m
Fri 11/131:25 pm -
2 stops22h 59m
Deal found 10/9![United Airlines logo]()
$839
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/77:55 pm -
2 stops16h 53m
Fri 11/131:25 pm -
2 stops22h 59m
Deal found 10/9![United Airlines logo]()
$702
This United Airlines deal was found by Cheapflights users on 10/10. 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 11/77:55 pm -
2 stops40h 53m
Sat 11/143:45 pm -
2 stops46h 38m
Deal found 10/10![United Airlines logo]()
$811
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/87:55 pm -
2 stops16h 53m
Sat 11/142:54 pm -
2 stops45h 30m
Deal found 10/9![United Airlines logo]()
$812
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/93:15 pm -
2 stops19h 58m
Fri 11/131:25 pm -
2 stops22h 59m
Deal found 10/9![United Airlines logo]()
$694
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:55 pm -
2 stops16h 53m
Mon 11/161:25 pm -
2 stops33h 32m
Deal found 10/12![United Airlines logo]()
$729
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/93:15 pm -
2 stops19h 58m
Sun 11/153:45 pm -
2 stops22h 38m
Deal found 10/9![United Airlines logo]()
$852
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/1012:20 pm -
2 stops24h 28m
Fri 11/131:25 pm -
2 stops22h 59m
Deal found 10/9![United Airlines logo]()
$778
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:05 pm -
1 stop21h 30m
Thu 12/32:40 pm -
1 stop31h 10m
Deal found 10/12![WestJet logo]()
$422
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:40 am -
2 stops25h 33m
Fri 12/113:20 pm -
2 stops47h 03m
Deal found 10/11![United Airlines logo]()
$660
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 October 13, 2026.
Search for one-way flight options from Winnipeg to Montego Bay. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:40 am -
2 stops49h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![United Airlines logo]()
$311
This United deal was found by Cheapflights users on 10/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:55 pm -
2 stops16h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:40 am -
2 stops25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:30 am -
3 stops51h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$740
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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $411 (Air Canada) |
One-way from | $311 (United Airlines) |
Popular in | July |
Cheapest in | October |
Average price | $457 |
Good round-trip deal | $634 or less |
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 October 13, 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 12/6
9:40 am-1:14 pm
2 stops27h 34m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$311
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Wed 11/25
9:40 am-11:13 am
2 stops49h 33m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$311
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 11/7
7:55 pm-12:48 pm
2 stops16h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$349
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 12/13
9:40 am-11:13 am
2 stops25h 33m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$364
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 1/15
9:05 pm-6:35 pm
1 stop21h 30m
Montego Bay Sangster Intl
Thu 2/4
2:40 pm-1:05 pm
1 stop22h 25m
$486
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 1/15
8:00 am-3:19 pm
2 stops31h 19m
Montego Bay Sangster Intl
Tue 2/2
2:54 pm-8:28 pm
1 stop29h 34m
$513
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 2/20
6:00 am-6:35 pm
1 stop12h 35m
Montego Bay Sangster Intl
Sat 3/20
3:50 pm-9:50 pm
Nonstop6h 00m
$565
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
7:55 pm-11:13 am
2 stops39h 18m
Montego Bay Sangster Intl
Fri 1/22
1:25 pm-12:09 pm
2 stops22h 44m
$610
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 11/30
9:40 am-11:13 am
2 stops25h 33m
Montego Bay Sangster Intl
Fri 12/11
3:20 pm-2:23 pm
2 stops47h 03m
$660
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 12/8
2:15 pm-11:13 am
2 stops20h 58m
Montego Bay Sangster Intl
Fri 12/18
2:54 pm-1:52 pm
1 stop22h 58m
$697
Showing 1-10 of 12 resultsSorted 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of $457). Flying from Winnipeg to Montego Bay in July is currently the most expensive (average of $821). 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.
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 13, 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.
Overall
7.2
Boarding
7.4
Comfort
7.1
Entertainment
6.1
Food
6.2
Crew
7.9
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
Overall
7.2
Boarding
7.4
Comfort
7.1
Entertainment
6.1
Food
6.2
Crew
7.9
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.
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Book flights to Montego Bay if you plan to visit one of these locationsLucea
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Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 13, 2026.
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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 October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$472 | Average$670 | FlexibilityNo cancel fee | On-time60% |