$375+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Nov 2 — Nov 91
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 3, 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 3, 2026.
This Air Canada deal was found by Cheapflights users on 9/30. 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 stop20h 25m
Fri 12/182:20 pm -
2 stops30h 05m
Deal found 9/30![Air Canada logo]()
$539
This United Airlines deal was found by Cheapflights users on 10/1. 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 12/183:45 pm -
2 stops22h 07m
Deal found 10/1![United Airlines logo]()
$657
This WestJet deal was found by Cheapflights users on 9/29. 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 -
Nonstop5h 35m
Sat 1/234:50 pm -
Nonstop6h 00m
Deal found 9/29![WestJet logo]()
$719
This Air Canada deal was found by Cheapflights users on 9/29. 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 9/29![Air Canada logo]()
$743
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 3, 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 3, 2026.
This United Airlines deal was found by Cheapflights users on 9/28. 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 1/57:00 am -
2 stops54h 14m
Thu 2/42:54 pm -
1 stop8h 39m
Deal found 9/28![United Airlines logo]()
$535
This FlightHub deal was found by Cheapflights users on 9/29. 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 2/209:35 am -
1 stop9h 00m
Sat 3/203:50 pm -
Nonstop6h 00m
Deal found 9/29![WestJet logo]()
$615
This Mytrip deal was found by Cheapflights users on 9/28. 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.
Tue 1/55:55 pm -
3 stops18h 35m
Thu 2/41:15 pm -
2 stops23h 05m
Deal found 9/28![Multiple Airlines logo]()
$725
This United Airlines deal was found by Cheapflights users on 10/2. 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 1/163:40 pm -
2 stops45h 08m
Fri 1/221:25 pm -
2 stops22h 44m
Deal found 10/2![United Airlines logo]()
$555
This Justfly.com deal was found by Cheapflights users on 10/3. 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.
Sat 1/169:15 am -
Nonstop5h 35m
Fri 1/228:35 pm -
1 stop15h 30m
Deal found 10/3![WestJet logo]()
$620
This United Airlines deal was found by Cheapflights users on 10/3. 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 3/277:00 am -
2 stops32h 10m
Wed 4/74:12 pm -
2 stops28h 43m
Deal found 10/3![United Airlines logo]()
$699
This United Airlines deal was found by Cheapflights users on 9/30. 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 1/107:00 am -
1 stop29h 48m
Sun 1/312:54 pm -
1 stop8h 39m
Deal found 9/30![United Airlines logo]()
$715
Last-minute flights from Winnipeg to Montego BayDiscover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/28:45 am -
2 stops50h 58m
Fri 10/912:52 pm -
2 stops56h 05m
Deal found 10/1![United Airlines logo]()
$929
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/98:45 am -
2 stops52h 45m
Fri 10/1612:52 pm -
2 stops32h 05m
Deal found 10/3![United Airlines logo]()
$896
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/98:45 am -
1 stop31h 00m
Wed 10/1412:52 pm -
2 stops32h 05m
Deal found 9/30![United Airlines logo]()
$975
This Air Canada deal was found by Cheapflights users on 9/30. 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.
Fri 10/95:25 pm -
1 stop17h 55m
Wed 10/1412:30 pm -
1 stop8h 57m
Deal found 9/30![Air Canada logo]()
$1,334
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 3, 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 3, 2026.
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/152:15 pm -
2 stops44h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 9/30. 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 11/167:15 am -
2 stops27h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$383
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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $427 (United Airlines) |
One-way from | $375 (United Airlines) |
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 3, 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 11/15
2:15 pm-11:13 am
2 stops44h 58m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$375
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 11/16
7:15 am-11:13 am
2 stops27h 58m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$383
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 1/5
7:00 am-1:14 pm
2 stops54h 14m
Montego Bay Sangster Intl
Thu 2/4
2:54 pm-11:33 pm
1 stop8h 39m
$535
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
3:40 pm-12:48 pm
2 stops45h 08m
Montego Bay Sangster Intl
Fri 1/22
1:25 pm-12:09 pm
2 stops22h 44m
$555
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 2/20
9:35 am-6:35 pm
1 stop9h 00m
Montego Bay Sangster Intl
Sat 3/20
3:50 pm-9:50 pm
Nonstop6h 00m
$615
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
9:15 am-2:50 pm
Nonstop5h 35m
Montego Bay Sangster Intl
Fri 1/22
8:35 pm-12:05 pm
1 stop15h 30m
$620
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 3/27
7:00 am-3:10 pm
2 stops32h 10m
Montego Bay Sangster Intl
Wed 4/7
4:12 pm-8:55 pm
2 stops28h 43m
$699
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/10
7:00 am-12:48 pm
1 stop29h 48m
Montego Bay Sangster Intl
Sun 1/31
2:54 pm-11:33 pm
1 stop8h 39m
$715
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 1/5
5:55 pm-12:30 pm
3 stops18h 35m
Montego Bay Sangster Intl
Thu 2/4
1:15 pm-12:20 pm
2 stops23h 05m
$725
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, 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 typical for this route at the moment.
Winnipeg to Montego Bay flights typically cost between $426 and $457 in January.The cheapest round-trip price found within the last 5 days was $427 on United Airlines (Jan 16-Jan 30).
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 3, 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
Food
6.2
Comfort
7.1
Entertainment
6.1
Boarding
7.4
Crew
7.9
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
Overall
7.2
Food
6.2
Comfort
7.1
Entertainment
6.1
Boarding
7.4
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.
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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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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$472 | Average$670 | FlexibilityNo cancel fee | On-time60% |