$258+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
Nov 29 — Dec 61
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 30, 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 30, 2026.
This FlightHub deal was found by Cheapflights users on 10/29. 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.
Sun 12/136:10 am -
Nonstop5h 35m
Sun 12/202:50 pm -
1 stop10h 54m
Deal found 10/29![WestJet logo]()
$451
This Air Canada deal was found by Cheapflights users on 10/29. 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 12/139:20 am -
Nonstop5h 20m
Sun 12/203:40 pm -
Nonstop5h 40m
Deal found 10/29![Air Canada logo]()
$458
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:35 am -
1 stop27h 10m
Fri 12/181:35 pm -
1 stop12h 09m
Deal found 10/29![WestJet logo]()
$502
This FlightHub deal was found by Cheapflights users on 10/29. 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.
Wed 12/96:00 am -
1 stop7h 45m
Fri 12/189:20 pm -
1 stop13h 45m
Deal found 10/29![WestJet logo]()
$533
This Porter Airlines deal was found by Cheapflights users on 10/29. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop9h 42m
Thu 12/101:15 pm -
1 stop9h 42m
Deal found 10/29![Porter Airlines logo]()
$535
This Air Canada deal was found by Cheapflights users on 10/30. 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 12/87:00 am -
2 stops34h 20m
Fri 12/181:50 pm -
1 stop21h 19m
Deal found 10/30![Air Canada logo]()
$565
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/139:40 am -
2 stops30h 39m
Tue 11/241:25 pm -
2 stops23h 58m
Deal found 10/27![United Airlines logo]()
$578
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/153:15 pm -
2 stops22h 59m
Wed 11/253:20 pm -
2 stops22h 03m
Deal found 10/27![United Airlines logo]()
$580
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 30, 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 30, 2026.
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/208:05 pm -
1 stop22h 30m
Tue 4/2712:45 pm -
1 stop21h 00m
Deal found 10/30![WestJet logo]()
$476
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 1/248:00 am -
2 stops28h 13m
Sun 1/311:25 pm -
2 stops56h 30m
Deal found 10/28![United Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 10/27. 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 1/169:40 am -
2 stops50h 33m
Sat 1/305:21 pm -
2 stops26h 07m
Deal found 10/27![United Airlines logo]()
$493
This FlightHub deal was found by Cheapflights users on 10/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:00 am -
1 stop13h 35m
Sat 3/203:50 pm -
Nonstop6h 00m
Deal found 10/30![WestJet logo]()
$528
This United Airlines deal was found by Cheapflights users on 10/25. 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 1/178:00 am -
2 stops30h 14m
Sun 1/243:20 pm -
2 stops52h 08m
Deal found 10/25![United Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 1/169:40 am -
2 stops50h 33m
Sat 1/233:45 pm -
2 stops27h 43m
Deal found 10/30![United Airlines logo]()
$531
This United Airlines deal was found by Cheapflights users on 10/27. 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 2/228:00 am -
2 stops28h 13m
Sat 2/273:45 pm -
2 stops30h 12m
Deal found 10/27![United Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:15 pm -
2 stops23h 24m
Sat 12/123:45 pm -
2 stops30h 10m
Deal found 10/29![United Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:40 am -
2 stops28h 34m
Thu 12/103:20 pm -
2 stops22h 03m
Deal found 10/29![United Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:40 am -
2 stops26h 33m
Thu 12/101:25 pm -
2 stops23h 58m
Deal found 10/29![United Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:15 pm -
2 stops44h 58m
Wed 11/251:25 pm -
2 stops23h 58m
Deal found 10/29![United Airlines logo]()
$618
Last-minute flights from Winnipeg to Montego BayDiscover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated October 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/139:40 am -
2 stops30h 39m
Tue 11/241:25 pm -
2 stops23h 58m
Deal found 10/27![United Airlines logo]()
$578
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/139:40 am -
2 stops30h 39m
Sun 11/223:45 pm -
2 stops21h 38m
Deal found 10/27![United Airlines logo]()
$650
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/153:15 pm -
2 stops22h 59m
Wed 11/253:20 pm -
2 stops22h 03m
Deal found 10/27![United Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/159:40 am -
2 stops28h 34m
Mon 11/232:54 pm -
1 stop22h 29m
Deal found 10/27![United Airlines logo]()
$622
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/259:40 am -
2 stops50h 33m
Wed 12/21:25 pm -
2 stops23h 58m
Deal found 10/28![United Airlines logo]()
$652
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 30, 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 30, 2026.
This United Airlines deal was found by Cheapflights users on 10/27. 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 2/39:40 am -
2 stops28h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![United Airlines logo]()
$258
This Porter Airlines deal was found by Cheapflights users on 10/30. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop9h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Porter Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 10/27. 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 10/27![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/30. 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 11/139:40 am -
2 stops28h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/129:40 am -
2 stops28h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 12/209:40 am -
2 stops28h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/113:15 pm -
2 stops25h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$436
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $443 (Kiwi.com) |
One-way from | $258 (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 30, 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
Wed 2/3
9:40 am-2:14 pm
2 stops28h 34m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$258
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 12/7
7:00 am-4:42 pm
1 stop9h 42m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$295
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 12/7
9:40 am-12:13 pm
2 stops26h 33m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$321
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 12/12
9:40 am-2:39 pm
2 stops28h 59m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$371
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 12/20
9:40 am-2:39 pm
2 stops28h 59m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$435
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 12/14
9:40 am-2:14 pm
2 stops28h 34m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$436
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 12/11
3:15 pm-4:19 pm
2 stops25h 04m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$436
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 4/20
8:05 pm-6:35 pm
1 stop22h 30m
Montego Bay Sangster Intl
Tue 4/27
12:45 pm-9:45 am
1 stop21h 00m
$476
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 1/24
8:00 am-12:13 pm
2 stops28h 13m
Montego Bay Sangster Intl
Sun 1/31
1:25 pm-9:55 pm
2 stops56h 30m
$493
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 1/16
9:40 am-12:13 pm
2 stops50h 33m
Montego Bay Sangster Intl
Sat 1/30
5:21 pm-7:28 pm
2 stops26h 07m
$493
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Winnipeg to Montego Bay
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Montego Bay in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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 $531 and $639 in January.The cheapest round-trip price found within the last 5 days was $443 on Multiple Airlines (Jan 17-Jan 24).
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 30, 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.
Comfort
7.1
Crew
7.9
Boarding
7.4
Entertainment
6.1
Overall
7.2
Food
6.2
Reviews
1 / 20
8.0
ExcellentSeth,Sep 2026
YVR - YYC
Comfort
7.1
Crew
7.9
Boarding
7.4
Entertainment
6.1
Overall
7.2
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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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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$472 | Average$670 | FlexibilityNo cancel fee | On-time60% |