Cheap flights from Winnipeg to Montego Bay from C$ 300
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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
22 Nov — 29 Nov1
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 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
Enter your travel dates to find the best prices.
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Best
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 23 October 2026.
Sun 13/129:20 a.m. -
Nonstop4h 20m
Sun 20/123:40 p.m. -
Nonstop6h 40m
Deal found 19/10C$ 533
Sun 13/126:10 a.m. -
Nonstop4h 35m
Sun 20/128:35 p.m. -
1 stop16h 30m
Deal found 19/10C$ 558
Tue 8/127:55 p.m. -
1 stop21h 25m
Fri 18/122:20 p.m. -
1 stop20h 40m
Deal found 19/10C$ 560
Sun 6/129:20 a.m. -
Nonstop5h 20m
Sun 13/123:40 p.m. -
Nonstop5h 40m
Deal found 23/10C$ 574
Sun 6/126:00 a.m. -
1 stop7h 45m
Sun 13/1212:45 p.m. -
Nonstop6h 00m
Deal found 23/10C$ 659
Sun 6/127:55 p.m. -
1 stop17h 50m
Sun 13/122:50 p.m. -
1 stop19h 25m
Deal found 23/10C$ 686
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 23 October 2026.
Sun 13/129:20 a.m. -
Nonstop4h 20m
Sun 20/123:40 p.m. -
Nonstop6h 40m
Deal found 19/10C$ 533
Sat 16/19:40 a.m. -
2 stops49h 33m
Sat 23/16:00 p.m. -
2 stops26h 28m
Deal found 19/10C$ 670
Sat 20/26:00 a.m. -
1 stop13h 35m
Sat 20/33:50 p.m. -
Nonstop6h 00m
Deal found 21/10C$ 875
Sun 14/310:00 a.m. -
1 stop31h 05m
Sat 20/38:50 p.m. -
1 stop12h 25m
Deal found 20/10C$ 935
Tue 20/46:00 a.m. -
2 stops29h 30m
Tue 27/412:35 p.m. -
2 stops21h 19m
Deal found 22/10C$ 801
Sat 16/17:55 p.m. -
2 stops41h 53m
Fri 22/11:25 p.m. -
2 stops21h 44m
Deal found 20/10C$ 818
Sun 13/129:40 a.m. -
2 stops26h 33m
Sat 23/13:20 p.m. -
2 stops28h 08m
Deal found 21/10C$ 855
Tue 20/48:40 a.m. -
2 stops28h 30m
Tue 27/44:12 p.m. -
2 stops19h 27m
Deal found 23/10C$ 903
Thu 10/123:15 p.m. -
2 stops49h 04m
Thu 17/123:45 p.m. -
2 stops46h 07m
Deal found 21/10C$ 959
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 23 October 2026.
Sun 13/129:20 a.m. -
Nonstop4h 20m
Sun 20/123:40 p.m. -
Nonstop6h 40m
Deal found 19/10C$ 533
Sun 6/129:20 a.m. -
Nonstop5h 20m
Sun 13/123:40 p.m. -
Nonstop5h 40m
Deal found 23/10C$ 574
Sun 10/19:20 a.m. -
Nonstop4h 20m
Sun 31/13:40 p.m. -
Nonstop6h 40m
Deal found 19/10C$ 700
Sun 13/126:10 a.m. -
Nonstop5h 35m
Sat 23/13:50 p.m. -
Nonstop6h 00m
Deal found 21/10C$ 722
Sat 16/19:15 a.m. -
Nonstop4h 35m
Sat 23/13:50 p.m. -
Nonstop7h 00m
Deal found 19/10C$ 743
Sat 3/48:00 a.m. -
Nonstop5h 35m
Sat 10/42:35 p.m. -
Nonstop6h 00m
Deal found 23/10C$ 834
Sun 7/29:20 a.m. -
Nonstop5h 20m
Sun 14/23:40 p.m. -
Nonstop5h 40m
Deal found 23/10C$ 843
Sat 20/29:15 a.m. -
Nonstop5h 35m
Sat 20/33:50 p.m. -
Nonstop6h 00m
Deal found 22/10C$ 858
Last-minute flights from Winnipeg to Montego Bay
Discover last-minute flight deals from Winnipeg to Montego Bay. Data last updated 23 October 2026 and is based on user searches.
Fri 30/108:40 a.m. -
2 stops28h 59m
Fri 6/112:54 p.m. -
1 stop22h 29m
Deal found 23/10C$ 912
Sun 15/119:05 p.m. -
1 stop15h 30m
Sat 28/118:35 p.m. -
1 stop16h 30m
Deal found 18/10C$ 948
Fri 20/117:55 p.m. -
1 stop17h 35m
Tue 24/116:20 p.m. -
1 stop15h 55m
Deal found 19/10C$ 885
Sun 29/117:55 p.m. -
1 stop21h 25m
Thu 3/121:50 p.m. -
1 stop30h 19m
Deal found 19/10C$ 724
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 23 October 2026.
Sun 6/129:20 a.m. -
Nonstop5h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 20/10C$ 300
Sun 24/111:00 a.m. -
1 stop26h 30m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 335
Sat 14/117:00 a.m. -
2 stops30h 25m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 338
Sun 24/19:20 a.m. -
Nonstop5h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 349
Sun 24/111:40 a.m. -
2 stops25h 50m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 358
Sun 6/127:55 p.m. -
1 stop20h 47m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 20/10C$ 360
Sun 15/119:05 p.m. -
1 stop16h 30m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 363
Mon 16/117:55 p.m. -
1 stop17h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 370
Fri 20/117:55 p.m. -
1 stop23h 40m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 376
Wed 18/118:00 p.m. -
1 stop17h 35m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 387
Sun 6/127:00 a.m. -
1 stop8h 12m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 391
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 23 October 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 23 October 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 6/12
9:20 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$ 300
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 6/12
7:55 p.m.-4:42 p.m.
1 stop20h 47m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 360
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 6/12
7:00 a.m.-3:12 p.m.
1 stop8h 12m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 391
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 6/12
3:15 p.m.-2:14 p.m.
2 stops22h 59m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 411
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Thu 3/12
3:15 p.m.-4:19 p.m.
2 stops49h 04m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 418
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 4/12
9:40 a.m.-2:39 p.m.
2 stops28h 59m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 421
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Fri 13/11
9:40 a.m.-2:39 p.m.
2 stops28h 59m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 422
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sun 22/11
9:40 a.m.-12:13 p.m.
2 stops26h 33m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 452
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Mon 16/11
3:15 p.m.-12:13 p.m.
2 stops20h 58m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 453
WinnipegMontego Bay
YWG Winnipeg - MBJ Montego Bay Sangster Intl
YWGMBJ
Winnipeg
Sat 21/11
3:15 p.m.-12:13 p.m.
2 stops44h 58m
Montego Bay Sangster Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 461
Flights are sorted by cheapest round-trip flights first.
Deals found on 20/10
Showing 1-10 of 20 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 641). Flying from Winnipeg to Montego Bay in July is currently the most expensive (average of C$ 1,151). 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$ 671 and C$ 768 in December.The cheapest round-trip price found within the last 5 days was C$ 533 on Air Canada (13 Dec-20 Dec).
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 23 October 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.
The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.
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 26 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 4h 20m. Air Canada provides one of the quickest options available for as low as C$ 533. 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$ 463. Another option worth looking into is WestJet, starting at C$ 528 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$ 500. While the most popular route (Winnipeg - Montego Bay Sangster Intl) can be booked for C$ 611 on average, our data indicates C$ 944 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 641). Flying from Winnipeg to Montego Bay in July is currently the most expensive (average of C$ 1,151). 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 23 October 2026.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 23 October 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 23 October 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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