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Cheap flights from Winnipeg to Montego Bay from C$ 359

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
12 Jul — 19 Jul1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Montego Bay Sangster Intl are usually found in April or October, booked 61 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.

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 12 June 2026.

Fri 16/1010:30 p.m.
YWG
-
MBJ
2 stops20h 00m
WestJet
Mon 26/101:55 p.m.
MBJ
-
YWG
2 stops22h 10m
WestJet
Deal found 8/6C$ 627
Tue 8/121:45 p.m.
YWG
-
MBJ
1 stop22h 05m
Air Canada
Fri 18/121:50 p.m.
MBJ
-
YWG
2 stops31h 38m
Air Canada
Deal found 8/6C$ 675
Sat 12/121:45 p.m.
YWG
-
MBJ
2 stops24h 00m
Air Canada
Sat 19/126:20 p.m.
MBJ
-
YWG
1 stop16h 24m
Air Canada
Deal found 8/6C$ 679
Thu 3/95:15 p.m.
YWG
-
MBJ
1 stop18h 05m
Air Canada
Sat 5/912:30 p.m.
MBJ
-
YWG
2 stops31h 31m
Air Canada
Deal found 8/6C$ 691
Tue 8/1212:00 p.m.
YWG
-
MBJ
2 stops30h 29m
WestJet
Fri 18/122:55 p.m.
MBJ
-
YWG
2 stops31h 10m
WestJet
Deal found 9/6C$ 693
Mon 5/108:15 a.m.
YWG
-
MBJ
1 stop27h 05m
Air Canada
Thu 8/1012:30 p.m.
MBJ
-
YWG
1 stop21h 27m
Air Canada
Deal found 9/6C$ 698

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 12 June 2026.

Round-trip from

C$ 627

One-way from

C$ 359

Popular in

December

Cheapest in

April

Average price

C$ 902
WestJet
  • WestJet
  • 16/10-26/10
  • 4 total stops
  • 42h 10m total
  • Winnipeg to Montego Bay
Search Deals
WestJet
  • WestJet
  • 3/9
  • 1 total stop
  • 15h 25m total
  • Winnipeg to Montego Bay
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

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 629,999 searches. Data last updated 12 June 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 - MBJ

YWGMBJ

Winnipeg

Fri 16/10

6:05 p.m.-6:30 p.m.

1 stop24h 25m

Montego Bay Sangster Intl

Mon 26/10

1:55 p.m.-12:45 a.m.

1 stop10h 50m

C$ 627

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

1:45 p.m.-12:50 p.m.

1 stop22h 05m

Montego Bay Sangster Intl

Fri 18/12

1:50 p.m.-10:16 a.m.

1 stop21h 26m

C$ 675

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 5/10

8:15 a.m.-11:20 a.m.

1 stop27h 05m

Montego Bay Sangster Intl

Thu 8/10

12:30 p.m.-9:57 a.m.

1 stop21h 27m

C$ 698

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 22/9

1:25 p.m.-11:20 a.m.

2 stops21h 55m

Montego Bay Sangster Intl

Sat 26/9

12:30 p.m.-9:57 a.m.

1 stop21h 27m

C$ 732

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 22/9

8:45 a.m.-11:43 a.m.

2 stops26h 58m

Montego Bay Sangster Intl

Sat 26/9

2:40 p.m.-10:33 p.m.

2 stops31h 53m

C$ 768
Cheapest one-way
Quickest one-way

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 17/6

4:25 p.m.-11:45 a.m.

1 stop19h 20m

C$ 366

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 7/7

10:30 p.m.-11:45 a.m.

2 stops37h 15m

C$ 384

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 7/7

8:45 a.m.-3:10 p.m.

2 stops30h 25m

C$ 397

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 7/7

3:20 p.m.-11:20 a.m.

1 stop20h 00m

C$ 415

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 3/9

8:00 a.m.-11:20 a.m.

3 stops27h 20m

C$ 518

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Showing 1-10 of 11 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.
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 60 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, April is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 701). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,203). 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?

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 12 June 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.
WestJet
7.2
Good
3,356 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Comfort

7.0

Overall

7.2

Food

6.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,356 reviews
WestJet
7.2
Good
3,356 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Comfort

7.0

Overall

7.2

Food

6.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
Air Canada
7.1
Good
11,164 reviews
WestJet
7.2
Good
3,356 reviews
Check prices

Entertainment

6.1

Crew

7.9

Boarding

7.4

Comfort

7.0

Overall

7.2

Food

6.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 44 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 22h 05m. WestJet provides one of the quickest options available for as low as C$ 675. 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$ 393. Another option worth looking into is WestJet, starting at C$ 511 round trip. These flights start at 55% lower than the current average price 3 months from now.

  • Can I find deals for flights from Winnipeg to Montego Bay that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Montego Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Montego Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights 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, April is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 701). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,203). 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.

See more FAQs

Travelling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Lucea
Treasure Beach

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Alternative routes for Winnipeg to Montego Bay

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Kingston flights

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 629,999 searches. Data last updated 12 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 393AverageC$ 942FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 511AverageC$ 860FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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