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Cheap flights from Winnipeg to Montego Bay from C$ 311

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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Montego Bay Sangster Intl are usually found in September or March, booked 25 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Cheap 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 29 July 2025.

Round-trip from

C$ 630

One-way from

C$ 311

Popular in

November

Cheapest in

September

Average price

C$ 893

Good round-trip deal

C$ 809 or less
Air Canada
  • Air Canada
  • 9/9-23/9
  • 4 total stops
  • 65h 55m total
  • Winnipeg to Montego Bay
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WestJet
  • WestJet
  • 11/9
  • 1 total stop
  • 21h 06m total
  • Winnipeg to Montego Bay
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Highest demand for flights based on searches. 7% potential increase in price (C$ 89 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 21 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Winnipeg to Montego Bay Sangster Intl.
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Find flight deals from Winnipeg to Montego Bay

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 29 July 2025.

Tue 9/93:45 p.m.YWG - MBJ
2 stops43h 25mAir Canada
Tue 23/912:10 p.m.MBJ - YWG
2 stops22h 30mAir Canada
Deal found 29/7C$ 630
Fri 29/86:30 a.m.YWG - MBJ
1 stop11h 56mWestJet
Fri 5/912:45 p.m.MBJ - YWG
1 stop11h 28mWestJet
Deal found 28/7C$ 652
Fri 1/84:25 p.m.YWG - MBJ
2 stops23h 01mUnited Airlines
Sat 16/84:33 p.m.MBJ - YWG
2 stops30h 00mUnited Airlines
Deal found 27/7C$ 668
Wed 29/107:30 a.m.YWG - MBJ
1 stop24h 23mMultiple Airlines
Sun 2/111:25 p.m.MBJ - YWG
1 stop12h 17mMultiple Airlines
Deal found 29/7C$ 716
Tue 2/1212:10 p.m.YWG - MBJ
1 stop24h 05mAir Transat
Tue 9/1212:25 p.m.MBJ - YWG
1 stop12h 10mAir Transat
Deal found 27/7C$ 759

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 29 July 2025.
Use the filters below to find and compare flights from Winnipeg to Montego Bay that are best for you.

Fly from

Winnipeg

Fly to

Montego Bay

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/9

3:45 p.m.-11:10 a.m.

2 stops43h 25m

Montego Bay Sangster Intl

Tue 23/9

12:10 p.m.-10:40 a.m.

2 stops22h 30m

C$ 630

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 29/8

6:30 a.m.-6:26 p.m.

1 stop11h 56m

Montego Bay Sangster Intl

Fri 5/9

12:45 p.m.-12:13 a.m.

1 stop11h 28m

C$ 652

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 29/10

7:30 a.m.-7:53 a.m.

1 stop24h 23m

Montego Bay Sangster Intl

Sun 2/11

1:25 p.m.-12:42 a.m.

1 stop12h 17m

C$ 716

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 15/9

4:25 p.m.-11:43 a.m.

2 stops19h 18m

Montego Bay Sangster Intl

Fri 17/10

12:52 p.m.-3:31 p.m.

2 stops26h 39m

C$ 735

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 2/12

12:10 p.m.-1:15 p.m.

1 stop24h 05m

Montego Bay Sangster Intl

Tue 9/12

12:25 p.m.-11:35 p.m.

1 stop12h 10m

C$ 759

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 11/9

2:35 p.m.-11:41 a.m.

1 stop21h 06m

C$ 311

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 4/8

7:00 a.m.-3:10 p.m.

2 stops32h 10m

C$ 316

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 5/8

9:15 p.m.-11:42 a.m.

3 stops38h 27m

C$ 519

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 3/8

6:10 a.m.-3:50 p.m.

1 stop9h 40m

C$ 824

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 4/8

6:35 p.m.-11:05 a.m.

1 stop16h 30m

C$ 1,004

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Montego Bay. Price data was last updated on 25 July 2025.

Booking 25 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, March is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 355). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 547). 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.

What is the cheapest time of day to fly from YWG to MBJ?

Find hourly flight availability from Winnipeg to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 July 2025.

One of the essential ways to save on airfare from Winnipeg to Montego Bay is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 24% on airfare.

What’s the top layover airport for flights from Winnipeg to Montego Bay?

Share of one-stop round-trip flights from Winnipeg to Montego Bay chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 99% of one-stop itineraries from Winnipeg to Montego Bay on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Montego Bay?

Average round-trip fare for 1-stop flights from Winnipeg to Montego Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 879.

What’s the fastest layover option from Winnipeg to Montego Bay?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Montego Bay, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 9h 18m.

Which airport typically offers the quickest layover for flights from Winnipeg to Montego Bay?

Average layover duration for 1-stop one-way flights from Winnipeg to Montego Bay, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 5h 32m.

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 29 July 2025.
Check out reviews from past customers who have flown with Air Transat,United Airlines, andWestJet 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.
Air Transat
7.7
Good
424 reviews
Check prices

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Food

6.7

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
Air Transat
7.7
Good
424 reviews
Air Transat
7.7
Good
424 reviews
Check prices

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Food

6.7

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
United Airlines
7.4
Good
8,899 reviews
Air Transat
7.7
Good
424 reviews
Check prices

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Food

6.7

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
WestJet
7.2
Good
2,973 reviews
Air Transat
7.7
Good
424 reviews
Check prices

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Food

6.7

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.
Air Canada
7.1
Good
9,822 reviews
Air Transat
7.7
Good
424 reviews
Check prices

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Food

6.7

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Liam,Jun 2025

GLA - YYZ

To and from Glasgow with Air Transat. Excellent flights, food, service. Nothing but praise.

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 128 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • 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$ 630. Additional round-trip tickets that might be worth considering are offered by WestJet and United Airlines, with the lowest prices starting at C$ 652 and C$ 735, respectively. These flights start at 18% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Winnipeg to Montego Bay one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 311. However, be on the lookout for offers from United Airlines and Air Transat, as they are both options that can get you from Winnipeg to Montego Bay for a low price.

  • What are the cheapest flights from Winnipeg to Montego Bay?

    Looking at all options, your cheapest flight can be booked for C$ 363. While the most popular route (Winnipeg - Montego Bay Sangster Intl) can be booked for C$ 668 on average our data indicates C$ 979 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, March is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 355). Flying from Winnipeg to Montego Bay in December is currently the most expensive (average of C$ 547). 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 3 airlines flying from Winnipeg to Montego Bay

Discover the top 3 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 483AverageC$ 672FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 498AverageC$ 789FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 812AverageC$ 915FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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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.

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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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