Cheap flights from Winnipeg to Montego Bay from C$ 233
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 13/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
10 Oct — 17 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
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
Enter your travel dates to find the best prices.
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Direct
Last-minute
One-way
Cheapest flights from Winnipeg to Montego Bay
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 10 September 2026.
Sat 21/116:00 a.m. -
2 stops12h 35m
Sat 28/113:35 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 444
Fri 20/1112:10 p.m. -
2 stops30h 25m
Sat 28/113:35 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 451
Fri 4/129:35 a.m. -
1 stop9h 00m
Fri 11/128:35 p.m. -
2 stops28h 24m
Deal found 6/9C$ 465
Best flights from Winnipeg to Montego Bay
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 10 September 2026.
Fri 4/129:35 a.m. -
1 stop9h 00m
Fri 11/128:35 p.m. -
2 stops28h 24m
Deal found 6/9C$ 465
Sat 16/17:00 a.m. -
2 stops54h 14m
Fri 22/13:20 p.m. -
2 stops56h 13m
Deal found 7/9C$ 609
Sun 13/128:30 p.m. -
1 stop19h 15m
Tue 22/122:30 p.m. -
2 stops23h 50m
Deal found 5/9C$ 678
Mon 26/1012:45 p.m. -
1 stop23h 05m
Thu 29/1012:50 p.m. -
1 stop21h 34m
Deal found 6/9C$ 689
Sat 20/29:35 a.m. -
1 stop9h 00m
Sat 20/33:50 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 659
Sun 7/36:10 a.m. -
Nonstop5h 35m
Mon 29/31:40 p.m. -
2 stops35h 20m
Deal found 9/9C$ 666
Sat 12/128:30 a.m. -
2 stops29h 09m
Mon 14/123:20 p.m. -
2 stops22h 03m
Deal found 8/9C$ 826
Sun 20/126:10 a.m. -
Nonstop5h 35m
Sun 27/128:35 p.m. -
2 stops50h 40m
Deal found 6/9C$ 837
Sun 29/116:10 a.m. -
2 stops54h 25m
Thu 31/128:35 p.m. -
1 stop24h 15m
Deal found 5/9C$ 842
Direct flights from Winnipeg to Montego Bay
Explore direct flight options from Winnipeg to Montego Bay based on user searches, and compare prices and availability for your desired travel dates. Data last updated 10 September 2026.
Sun 13/126:10 a.m. -
Nonstop5h 35m
Sun 20/121:45 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 586
Sun 13/126:10 a.m. -
Nonstop5h 35m
Sun 27/121:45 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 600
Sun 7/38:20 a.m. -
Nonstop5h 20m
Sun 14/32:40 p.m. -
Nonstop5h 40m
Deal found 9/9C$ 648
Sat 20/29:15 a.m. -
Nonstop5h 35m
Sat 20/33:50 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 654
Sun 20/126:10 a.m. -
Nonstop5h 35m
Sun 27/121:45 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 707
Sun 20/128:20 a.m. -
Nonstop5h 20m
Sun 27/123:40 p.m. -
Nonstop5h 40m
Deal found 9/9C$ 783
Sun 10/18:20 a.m. -
Nonstop5h 20m
Sun 31/13:40 p.m. -
Nonstop5h 40m
Deal found 6/9C$ 786
Sun 6/128:20 a.m. -
Nonstop5h 20m
Sun 3/13:40 p.m. -
Nonstop5h 40m
Deal found 9/9C$ 794
Sat 12/128:00 a.m. -
Nonstop5h 35m
Sun 20/121:45 p.m. -
Nonstop6h 00m
Deal found 8/9C$ 844
Last-minute flights from Winnipeg to Montego Bay
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated 10 September 2026 and is based on user searches.
Sat 3/101:30 p.m. -
2 stops21h 50m
Sat 10/1012:30 p.m. -
1 stop21h 27m
Deal found 5/9C$ 756
Sat 3/106:15 a.m. -
1 stop12h 15m
Sat 10/107:30 p.m. -
1 stop21h 45m
Deal found 5/9C$ 807
Fri 9/104:15 p.m. -
2 stops26h 15m
Fri 16/1012:45 p.m. -
2 stops20h 35m
Deal found 6/9C$ 677
Sun 25/106:55 p.m. -
1 stop21h 25m
Thu 29/1012:50 p.m. -
1 stop8h 24m
Deal found 9/9C$ 551
Sun 25/102:15 p.m. -
2 stops22h 59m
Thu 29/102:20 p.m. -
2 stops22h 03m
Deal found 7/9C$ 853
Sun 25/107:00 a.m. -
2 stops29h 35m
Thu 29/101:40 p.m. -
2 stops47h 05m
Deal found 8/9C$ 895
Mon 26/1012:45 p.m. -
1 stop23h 05m
Thu 29/1012:50 p.m. -
2 stops29h 35m
Deal found 5/9C$ 689
One-way flights from Winnipeg to Montego Bay
Search for one-way flight options from Winnipeg to Montego Bay. Find affordable one-way fares based on user searches. Data last updated 10 September 2026.
Sun 13/128:20 a.m. -
Nonstop5h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 233
Sun 13/1210:00 a.m. -
1 stop29h 45m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 316
Mon 2/116:00 a.m. -
2 stops29h 50m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 383
Wed 21/106:05 p.m. -
1 stop17h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 393
Mon 2/118:05 p.m. -
1 stop16h 30m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 423
Tue 3/118:40 a.m. -
2 stops28h 34m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 458
Sun 20/128:20 a.m. -
Nonstop5h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/9C$ 489
Sat 19/122:05 p.m. -
1 stop22h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/9C$ 517
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 10 September 2026.
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 10 September 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
Price
Cheapest round-trip
Quickest round-trip
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 13/12
8:20 a.m.-2:40 p.m.
Nonstop5h 20m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 233
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 2/11
6:00 a.m.-12:50 p.m.
2 stops29h 50m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 383
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Wed 21/10
7:00 a.m.-11:45 a.m.
2 stops28h 45m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 400
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 2/11
8:05 p.m.-1:35 p.m.
1 stop16h 30m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 423
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Tue 3/11
8:40 a.m.-2:14 p.m.
2 stops28h 34m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 458
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 4/12
9:35 a.m.-7:35 p.m.
1 stop9h 00m
Montego Bay Sangster Intl
Fri 11/12
8:35 p.m.-11:59 p.m.
2 stops28h 24m
C$ 465
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 13/12
12:10 p.m.-4:45 p.m.
3 stops27h 35m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 521
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 19/12
3:45 p.m.-6:55 p.m.
3 stops26h 10m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 557
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 16/1
7:00 a.m.-2:14 p.m.
2 stops54h 14m
Montego Bay Sangster Intl
Fri 22/1
3:20 p.m.-10:33 p.m.
2 stops56h 13m
C$ 609
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 20/2
9:35 a.m.-7:35 p.m.
1 stop9h 00m
Montego Bay Sangster Intl
Sat 20/3
3:50 p.m.-9:50 p.m.
Nonstop6h 00m
C$ 659
Flights are sorted by cheapest round-trip flights first.
Deals found on 10/9
Showing 1-10 of 16 resultsSorted by cheapest first
1
2
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?
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Winnipeg to Montego Bay. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 C$ 502). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,168). 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 C$ 455 and C$ 1,499 in November.The cheapest round-trip price found within the last 5 days was C$ 444 on WestJet (21 Nov-28 Nov).
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 10 September 2026.
Check out reviews from past customers who have flown with WestJet and Air Canada from Winnipeg to Montego Bay to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Better snacks I also flew Delta much better with movies and entertainment
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.
How popular is this Winnipeg to Montego Bay flight route?
This flight path from Winnipeg to Montego Bay Sangster Intl was viewed by 35 users in the past month. Keep an eye out for changes in search interest prior to high and low season.
How long is the flight from Winnipeg to Montego Bay?
A quick flight from Winnipeg to Montego Bay can take about 9h. WestJet provides one of the quickest options available for as low as C$ 465. There are 3890 km between Winnipeg and Montego Bay. Both multi-stop and direct flights can be found to your destination and back.
What are the cheapest airlines flying from Winnipeg to Montego Bay round-trip?
Flying on Air Canada is currently your cheapest option to Montego Bay, with prices starting at C$ 456. Another option worth looking into is WestJet, starting at C$ 536 round trip. These flights start at 45% lower than the current average price 3 months from now.
What are the cheapest flights from Winnipeg to Montego Bay?
Looking at all options, your cheapest flight can be booked for C$ 618. While the most popular route (Winnipeg - Montego Bay Sangster Intl) can be booked for C$ 512 on average, our data indicates C$ 670 when flying from Winnipeg to Montego Bay.
Can I find deals for business class flights from Winnipeg to Montego Bay?
Yes. Cheapflights offers flight deals from Winnipeg to Montego Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
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 C$ 502). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,168). 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.
Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 10 September 2026.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 10 September 2026.
Top 2 airlines flying from Winnipeg to Montego Bay
Discover the top 2 airlines 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 10 September 2026.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Winnipeg to Montego Bay?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Montego Bay. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Montego Bay?
Cheapflights helps you find that perfect flight to Montego Bay from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Winnipeg to Montego Bay with no change fees?
Yes, we can. To see specific flights from Winnipeg to Montego Bay with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Can Cheapflights notify me if prices for flights from Winnipeg to Montego Bay become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!
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