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Cheap flights from Winnipeg to Jamaica from C$ 313

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
4 Aug — 11 Aug1
1 adult

Cheap flight deals from Winnipeg to Jamaica

Keep the following information in mind while searching for Winnipeg to Jamaica flight deals. Data was last updated 30 July 2025.

Round-trip from

C$ 633

One-way from

C$ 313

Popular in

November

Cheapest in

September

Average price

C$ 898

Good round-trip deal

C$ 814 or less
Air Canada
  • Air Canada
  • 9/9-23/9
  • 4 total stops
  • 65h 55m total
  • Winnipeg to Jamaica
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WestJet
  • WestJet
  • 11/9
  • 1 total stop
  • 21h 06m total
  • Winnipeg to Jamaica
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 90 potential increase over avg. RT price).
Search Deals
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 Jamaica.
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Find flight deals from Winnipeg to Jamaica

Cheapest flights from Winnipeg to Jamaica
Explore the most affordable flight options available from Winnipeg to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 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$ 633
Mon 4/82:20 p.m.YWG - MBJ
2 stops24h 50mUnited Airlines
Fri 15/82:40 p.m.MBJ - YWG
2 stops22h 29mUnited Airlines
Deal found 30/7C$ 650
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$ 655
Wed 29/107:30 a.m.YWG - MBJ
1 stop24h 23mMultiple Airlines
Sun 2/118:25 p.m.MBJ - YWG
1 stop16h 10mMultiple Airlines
Deal found 30/7C$ 717
Tue 12/89:05 p.m.YWG - KIN
3 stops23h 00mMultiple Airlines
Fri 22/812:32 p.m.KIN - YWG
3 stops29h 08mMultiple Airlines
Deal found 29/7C$ 941
Tue 12/82:35 p.m.YWG - KIN
1 stop23h 55mWestJet
Fri 22/83:30 p.m.KIN - YWG
1 stop18h 13mWestJet
Deal found 29/7C$ 1,035

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Jamaica 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 30 July 2025.
Use the filters below to find and compare flights from Winnipeg to Jamaica that are best for you.

Fly from

Winnipeg

Fly to

Jamaica

Route

Depart

Return

Price

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 9/9

11:40 a.m.-11:10 a.m.

2 stops47h 30m

Montego Bay Sangster Intl

Tue 23/9

12:10 p.m.-10:38 a.m.

1 stop22h 28m

C$ 633

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$ 655

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

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

1 stop16h 10m

C$ 717

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.-1:09 p.m.

2 stops24h 17m

C$ 737

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 12/8

9:05 p.m.-8:05 p.m.

3 stops23h 00m

Kingston Norman Manley

Fri 22/8

12:32 p.m.-5:40 p.m.

3 stops29h 08m

C$ 941

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Tue 12/8

2:35 p.m.-2:30 p.m.

1 stop23h 55m

Kingston Norman Manley

Fri 22/8

3:30 p.m.-9:43 a.m.

1 stop18h 13m

C$ 1,035

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 27/12

6:55 p.m.-2:13 p.m.

2 stops18h 18m

Montego Bay Sangster Intl

Sun 4/1

8:00 a.m.-3:07 p.m.

1 stop8h 07m

C$ 1,152

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 11/9

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

1 stop21h 06m

C$ 313

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 4/8

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

2 stops32h 10m

C$ 317

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 15/1

6:00 a.m.-11:15 a.m.

1 stop28h 15m

C$ 400

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

Showing 1-10 of 14 results
1
2

Best time to book a flight from Winnipeg to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica 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 Jamaica

What is the cheapest month to book a flight from Winnipeg to Jamaica?

Currently, March is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 355). Flying from Winnipeg to Jamaica 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 JM?

Find hourly flight availability from Winnipeg to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 July 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Jamaica as you normally would.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated 30 July 2025.
Read reviews from past customers who have flown Delta,Air Transat, andUnited Airlines from Winnipeg to Jamaica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Transat
7.7
Good
424 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.1
Good
9,837 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Jamaica?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Jamaica.

  • How popular is this Winnipeg to Jamaica flight route?

    Flights from Winnipeg to Jamaica have been viewed 128 times in the past calendar month.

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

    C$ 313 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Transat, with prices starting from C$ 317 and C$ 400, respectively.

  • What are the cheapest flights from Winnipeg to Jamaica?

    The cheapest flight price from Winnipeg to Jamaica is C$ 365. On average you can expect to pay C$ 985. The most popular route, (Winnipeg - Montego Bay Sangster Intl), can usually be booked for C$ 670.

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

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

  • How can I find direct flights from Winnipeg to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Jamaica.

  • Can I find deals for business class flights from Winnipeg to Jamaica?

    Yes. Cheapflights offers flight deals from Winnipeg to Jamaica 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 Jamaica?

    Currently, March is the cheapest month in which you can book a flight from Winnipeg to Jamaica (average of C$ 355). Flying from Winnipeg to Jamaica 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Winnipeg to Jamaica

Discover the top 3 airlines that operate flights from Winnipeg to Jamaica. 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 30 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 486AverageC$ 715FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 501AverageC$ 774FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 817AverageC$ 920FlexibilityNo cancel feeOn-time69%
Search United Airlines 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 Jamaica?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Jamaica. 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 Jamaica?

Cheapflights helps you find that perfect flight to Jamaica 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 Jamaica with no change fees?

Yes, we can. To see specific flights from Winnipeg to Jamaica 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 Jamaica 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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