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Cheap flights from Winnipeg to Montego Bay from C$ 375

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 16/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
22 Aug — 29 Aug1
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 86 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 23 July 2026.

Tue 8/126:15 a.m.
YWG
-
MBJ
1 stop10h 09m
WestJet
Fri 18/128:25 p.m.
MBJ
-
YWG
1 stop16h 10m
WestJet
Deal found 20/7C$ 600
Sun 16/88:00 a.m.
YWG
-
MBJ
2 stops27h 45m
WestJet
Sun 13/912:45 p.m.
MBJ
-
YWG
2 stops27h 15m
WestJet
Deal found 19/7C$ 710
Mon 24/81:30 p.m.
YWG
-
MBJ
2 stops45h 50m
Air Canada
Tue 8/912:30 p.m.
MBJ
-
YWG
1 stop25h 52m
Air Canada
Deal found 20/7C$ 713

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 July 2026.

Round-trip from

C$ 600

One-way from

C$ 375

Popular in

December

Cheapest in

April

Average price

C$ 922

Good round-trip deal

C$ 679 or less
Air Canada
  • Air Canada
  • 10/1-31/1
  • Nonstop
  • 11h 00m total
  • Winnipeg to Montego Bay
Search Deals
Air Canada
  • Air Canada
  • 16/10
  • 2 total stops
  • 21h 55m total
  • Winnipeg to Montego Bay
Search Deals
Highest demand for flights based on searches. 8% 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 July 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Montego Bay Sangster Intl.
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 23 July 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

Tue 8/12

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:35 a.m.

1 stop16h 10m

C$ 616

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 22/1

2:55 p.m.-9:05 p.m.

2 stops31h 10m

C$ 647

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 16/1

2:05 p.m.-1:25 p.m.

1 stop22h 20m

Montego Bay Sangster Intl

Fri 22/1

2:20 p.m.-10:00 a.m.

1 stop20h 40m

C$ 660

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 24/8

7:45 p.m.-11:20 a.m.

1 stop15h 35m

Montego Bay Sangster Intl

Tue 8/9

12:30 p.m.-11:17 p.m.

1 stop10h 47m

C$ 746

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 20/12

8:00 a.m.-2:30 p.m.

Nonstop5h 30m

Montego Bay Sangster Intl

Sun 27/12

11:55 a.m.-11:35 a.m.

1 stop24h 40m

C$ 896

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 18/8

12:25 p.m.-11:45 a.m.

2 stops47h 20m

Montego Bay Sangster Intl

Sat 29/8

7:30 p.m.-2:15 p.m.

2 stops42h 45m

C$ 965

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 17/8

7:45 p.m.-11:20 a.m.

1 stop15h 35m

Montego Bay Sangster Intl

Mon 24/8

12:30 p.m.-10:05 a.m.

2 stops21h 35m

C$ 985

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 23/12

12:55 p.m.-7:29 p.m.

2 stops53h 34m

Montego Bay Sangster Intl

Sun 27/12

3:25 p.m.-8:18 p.m.

Nonstop5h 53m

C$ 996

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 23/12

12:55 p.m.-7:29 p.m.

2 stops53h 34m

Montego Bay Sangster Intl

Wed 6/1

5:35 p.m.-3:40 p.m.

2 stops23h 05m

C$ 1,058
Cheapest one-way

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 31/7

12:56 p.m.-3:26 p.m.

2 stops26h 30m

C$ 437

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/7

Showing 1-10 of 15 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 85 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$ 707). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,225). 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$ 886 and C$ 1,114 in January.
The cheapest round-trip price found within the last 5 days was C$ 600 on Air Canada (10 Jan-31 Jan).

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 July 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
3,411 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Entertainment

6.1

Boarding

7.4

Overall

7.2

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
3,411 reviews
WestJet
7.2
Good
3,411 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Entertainment

6.1

Boarding

7.4

Overall

7.2

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
11,373 reviews
WestJet
7.2
Good
3,411 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Entertainment

6.1

Boarding

7.4

Overall

7.2

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 40 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 10h 09m. WestJet provides one of the quickest options available for as low as C$ 616. 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 WestJet is currently your cheapest option to Montego Bay, with prices starting at C$ 585. Another option worth looking into is Air Canada, starting at C$ 675 round trip. These flights start at 35% 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$ 635. While the most popular route (Winnipeg - Montego Bay Sangster Intl) can be booked for C$ 665 on average, our data indicates C$ 774 when flying from Winnipeg to Montego Bay.

  • 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$ 707). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 1,225). 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 23 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 585AverageC$ 865FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 675AverageC$ 1,049FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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