$271+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Nov 21 — Nov 281
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 78 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 22, 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 22, 2026.
This Air Canada deal was found by Cheapflights users on 10/19. 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 12/139:20 am -
Nonstop4h 20m
Sun 12/203:40 pm -
Nonstop6h 40m
Deal found 10/19![Air Canada logo]()
$380
This Booking.com deal was found by Cheapflights users on 10/19. 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 12/136:10 am -
Nonstop4h 35m
Sun 12/208:35 pm -
1 stop16h 30m
Deal found 10/19![WestJet logo]()
$398
This Air Canada deal was found by Cheapflights users on 10/19. 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 12/87:55 pm -
1 stop21h 25m
Fri 12/182:20 pm -
1 stop20h 40m
Deal found 10/19![Air Canada logo]()
$399
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 22, 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 22, 2026.
This Air Canada deal was found by Cheapflights users on 10/19. 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 12/139:20 am -
Nonstop4h 20m
Sun 12/203:40 pm -
Nonstop6h 40m
Deal found 10/19![Air Canada logo]()
$380
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/309:35 pm -
2 stops15h 55m
Tue 2/162:30 pm -
1 stop19h 45m
Deal found 10/21![Multiple Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 10/17. 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 1/159:40 am -
2 stops27h 59m
Thu 2/42:54 pm -
1 stop29h 34m
Deal found 10/17![United Airlines logo]()
$558
This Air Canada deal was found by Cheapflights users on 10/18. 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 4/206:00 am -
2 stops29h 30m
Tue 4/2712:35 pm -
2 stops21h 19m
Deal found 10/18![Air Canada logo]()
$565
This United Airlines deal was found by Cheapflights users on 10/19. 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 stops40h 53m
Fri 1/221:25 pm -
2 stops22h 44m
Deal found 10/19![United Airlines logo]()
$580
This Air Canada deal was found by Cheapflights users on 10/18. 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 1/107:00 am -
2 stops28h 50m
Sun 1/313:40 pm -
Nonstop6h 40m
Deal found 10/18![Air Canada logo]()
$577
This United Airlines deal was found by Cheapflights users on 10/18. 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 2/19:40 am -
2 stops25h 33m
Sat 2/62:54 pm -
1 stop29h 34m
Deal found 10/18![United Airlines logo]()
$609
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 12/139:40 am -
2 stops26h 33m
Sat 1/233:20 pm -
2 stops28h 08m
Deal found 10/21![United Airlines logo]()
$610
This United Airlines deal was found by Cheapflights users on 10/18. 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 12/83:15 pm -
2 stops19h 58m
Fri 12/183:45 pm -
2 stops23h 07m
Deal found 10/18![United Airlines logo]()
$626
Last-minute flights from Winnipeg to Montego BayDiscover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 22, 2026 and is based on user searches.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:30 am -
2 stops26h 45m
Mon 11/22:40 pm -
1 stop21h 25m
Deal found 10/21![Multiple Airlines logo]()
$1,075
This United Airlines deal was found by Cheapflights users on 10/19. 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 11/123:15 pm -
2 stops47h 24m
Sun 11/153:45 pm -
2 stops54h 12m
Deal found 10/19![United Airlines logo]()
$701
This Air Canada deal was found by Cheapflights users on 10/19. 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 11/123:05 pm -
1 stop22h 20m
Sun 11/152:20 pm -
1 stop20h 40m
Deal found 10/19![Air Canada logo]()
$837
This Mytrip deal was found by Cheapflights users on 10/19. 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.
Thu 11/126:55 pm -
3 stops20h 13m
Sun 11/155:35 pm -
2 stops17h 45m
Deal found 10/19![Multiple Airlines logo]()
$2,898
This Booking.com deal was found by Cheapflights users on 10/18. 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 11/159:05 pm -
1 stop15h 30m
Sat 11/288:35 pm -
1 stop16h 30m
Deal found 10/18![WestJet logo]()
$676
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/159:35 pm -
2 stops16h 33m
Sat 11/285:35 pm -
1 stop17h 40m
Deal found 10/18![Multiple Airlines logo]()
$784
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 22, 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 22, 2026.
This Air Canada deal was found by Cheapflights users on 10/18. 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 1/39:20 am -
Nonstop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$271
This Expedia deal was found by Cheapflights users on 10/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/35:00 am -
1 stop13h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![WestJet logo]()
$286
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.
Sun 12/63:15 pm -
2 stops22h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/33:15 pm -
2 stops49h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 10/18. 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 1/33:15 pm -
2 stops24h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/18. 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 12/209:40 am -
2 stops27h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 1/34:45 pm -
3 stops22h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$528
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $380 (Air Canada) |
One-way from | $271 (Air Canada) |
Popular in | July |
Cheapest in | October |
Average price | $457 |
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 22, 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
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/3
9:20 am-2:40 pm
Nonstop4h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$271
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 12/6
3:15 pm-3:14 pm
2 stops22h 59m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$293
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Thu 12/3
3:15 pm-5:19 pm
2 stops49h 04m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$298
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/3
3:15 pm-4:19 pm
2 stops24h 04m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$324
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 12/13
9:20 am-2:40 pm
Nonstop4h 20m
Montego Bay Sangster Intl
Sun 12/20
3:40 pm-9:20 pm
Nonstop6h 40m
$380
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 12/20
9:40 am-2:39 pm
2 stops27h 59m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$430
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/30
9:35 pm-2:30 pm
2 stops15h 55m
Montego Bay Sangster Intl
Tue 2/16
2:30 pm-9:15 am
1 stop19h 45m
$490
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 1/15
9:40 am-2:39 pm
2 stops27h 59m
Montego Bay Sangster Intl
Thu 2/4
2:54 pm-7:28 pm
1 stop29h 34m
$558
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 4/20
6:00 am-11:30 am
2 stops29h 30m
Montego Bay Sangster Intl
Tue 4/27
12:35 pm-9:54 am
2 stops21h 19m
$565
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/10
7:00 am-12:50 pm
2 stops28h 50m
Montego Bay Sangster Intl
Sun 1/31
3:40 pm-9:20 pm
Nonstop6h 40m
$577
Showing 1-10 of 14 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.
How much does it cost to fly round-trip from Winnipeg to Montego Bay?
Airfare is below average for this route at the moment.
Winnipeg to Montego Bay flights typically cost between $478 and $548 in December.The cheapest round-trip price found within the last 5 days was $380 on Air Canada (Dec 13-Dec 20).
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, 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
Entertainment
6.1
Crew
7.9
Boarding
7.4
Comfort
7.1
Food
6.2
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
Overall
7.2
Entertainment
6.1
Crew
7.9
Boarding
7.4
Comfort
7.1
Food
6.2
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 October 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$472 | Average$670 | FlexibilityNo cancel fee | On-time60% |