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Cheap flights from Winnipeg to Montego Bay from C$ 354

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MBJ
27 Nov — 4 Dec1
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 March, booked 31 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Find 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 28 October 2025.

Sat 1/117:05 p.m.YWG - MBJ
2 stops23h 00mMultiple Airlines
Mon 3/117:25 p.m.MBJ - YWG
2 stops20h 56mMultiple Airlines
Deal found 27/10C$ 632
Sat 1/115:30 p.m.YWG - MBJ
2 stops20h 59mUnited Airlines
Mon 3/112:48 p.m.MBJ - YWG
1 stop22h 09mUnited Airlines
Deal found 27/10C$ 683
Fri 28/118:40 a.m.YWG - MBJ
1 stop31h 10mUnited Airlines
Fri 5/123:36 p.m.MBJ - YWG
2 stops21h 21mUnited Airlines
Deal found 27/10C$ 704
Fri 28/118:15 a.m.YWG - MBJ
1 stop8h 50mAir Canada
Fri 5/127:05 p.m.MBJ - YWG
1 stop16h 11mAir Canada
Deal found 26/10C$ 733
Mon 10/117:05 a.m.YWG - MBJ
1 stop8h 30mAir Canada
Fri 28/117:05 p.m.MBJ - YWG
1 stop22h 30mAir Canada
Deal found 26/10C$ 877
Mon 10/115:00 a.m.YWG - MBJ
1 stop10h 35mMultiple Airlines
Fri 28/117:05 p.m.MBJ - YWG
3 stops30h 37mMultiple Airlines
Deal found 26/10C$ 951

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 28 October 2025.

Round-trip from

C$ 649

One-way from

C$ 354

Popular in

November

Cheapest in

April

Average price

C$ 810

Good round-trip deal

C$ 799 or less

Good one-way deal

C$ 543 or less
Air Canada
  • Air Canada
  • 7/1-21/1
  • 4 total stops
  • 37h 28m total
  • Winnipeg to Montego Bay
Search Deals
Air Canada
  • Air Canada
  • 1/11
  • 2 total stops
  • 23h 00m total
  • Winnipeg to Montego Bay
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 170 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Montego Bay Sangster Intl.
Search Deals
Price to beat on a one-way flight from Winnipeg to Montego Bay Sangster Intl.
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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 28 October 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

Sat 1/11

7:05 p.m.-6:05 p.m.

2 stops23h 00m

Montego Bay Sangster Intl

Mon 3/11

7:25 p.m.-3:21 p.m.

2 stops20h 56m

C$ 632

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Wed 7/1

8:15 a.m.-6:05 p.m.

1 stop8h 50m

Montego Bay Sangster Intl

Wed 21/1

7:05 p.m.-8:28 p.m.

2 stops26h 23m

C$ 649

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 1/11

7:05 p.m.-2:29 p.m.

2 stops19h 24m

Montego Bay Sangster Intl

Mon 3/11

2:48 p.m.-11:57 a.m.

1 stop22h 09m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

8:40 a.m.-4:50 p.m.

1 stop31h 10m

Montego Bay Sangster Intl

Fri 5/12

1:25 p.m.-11:57 a.m.

2 stops23h 32m

C$ 704

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 28/11

8:15 a.m.-6:05 p.m.

1 stop8h 50m

Montego Bay Sangster Intl

Fri 5/12

7:05 p.m.-10:16 a.m.

1 stop16h 11m

C$ 733

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 1/11

7:05 p.m.-6:05 p.m.

2 stops23h 00m

C$ 354

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 1/11

8:20 p.m.-7:23 p.m.

1 stop23h 03m

C$ 614

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 21/12

12:10 p.m.-1:57 p.m.

2 stops24h 47m

C$ 757

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 20/12

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

Nonstop5h 30m

C$ 813

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 20/12

11:05 a.m.-2:37 p.m.

2 stops26h 32m

C$ 815

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 11 results
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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 24 October 2025.

Booking 31 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$ 428). Flying from Winnipeg to Montego Bay in August is currently the most expensive (average of C$ 705). 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 28 October 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.

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 28 October 2025.
Check out reviews from past customers who have flown with United Airlines,WestJet, andAir 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.
United Airlines
7.4
Good
9,001 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,001 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,148 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,371 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 115 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 8h 50m. Air Canada provides one of the quickest options available for as low as C$ 649. There are 3890 km between Winnipeg and Montego Bay.

  • 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$ 492. Additional round-trip tickets that might be worth considering are offered by WestJet and United Airlines, with the lowest prices starting at C$ 516 and C$ 845, respectively. These flights start at 41% 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$ 408. While the most popular route (Winnipeg - Montego Bay Sangster Intl) can be booked for C$ 624 on average, our data indicates C$ 773 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, October is the cheapest month in which you can book a flight from Winnipeg to Montego Bay (average of C$ 428). Flying from Winnipeg to Montego Bay in August is currently the most expensive (average of C$ 705). 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 28 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 492AverageC$ 748FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 517AverageC$ 853FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 845AverageC$ 933FlexibilityNo 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!

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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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