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Cheap flights from Caribbean Islands to Winnipeg from C$ 309

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 24/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Caribbean Islands to Winnipeg

Enter your travel dates to find the best prices.

Best flights from Caribbean Islands to Winnipeg
Discover carefully curated flight deals from Caribbean Islands to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 18 December 2025.

Thu 15/11:30 p.m.GCM - YWG
2 stops31h 58mAir Canada
Sun 18/17:05 p.m.YWG - GCM
1 stop16h 20mAir Canada
Deal found 15/12C$ 616
Thu 15/12:50 p.m.GCM - YWG
2 stops46h 19mWestJet
Sun 18/16:15 a.m.YWG - GCM
2 stops30h 29mWestJet
Deal found 15/12C$ 639
Wed 7/14:30 p.m.KIN - YWG
1 stop20h 05mMultiple Airlines
Sun 18/17:30 a.m.YWG - KIN
2 stops27h 42mMultiple Airlines
Deal found 15/12C$ 1,057
Fri 23/111:15 a.m.NAS - YWG
1 stop10h 13mAir Canada
Sun 25/18:15 a.m.YWG - NAS
1 stop27h 10mAir Canada
Deal found 15/12C$ 732
Fri 23/14:30 p.m.KIN - YWG
1 stop20h 05mWestJet
Mon 26/18:05 p.m.YWG - KIN
1 stop18h 28mWestJet
Deal found 14/12C$ 842
Fri 23/12:55 p.m.KIN - YWG
1 stop29h 39mAir Canada
Mon 26/18:15 a.m.YWG - KIN
2 stops52h 30mAir Canada
Deal found 15/12C$ 805
Wed 7/17:10 p.m.KIN - YWG
2 stops30h 25mMultiple Airlines
Fri 16/15:00 a.m.YWG - KIN
1 stop9h 33mMultiple Airlines
Deal found 14/12C$ 1,578
Wed 7/14:30 p.m.KIN - YWG
1 stop9h 12mWestJet
Fri 16/15:00 a.m.YWG - KIN
1 stop9h 33mWestJet
Deal found 14/12C$ 1,678
Wed 7/14:30 p.m.KIN - YWG
1 stop20h 05mWestJet
Sun 18/110:55 a.m.YWG - KIN
2 stops27h 38mWestJet
Deal found 15/12C$ 1,711

Find flight deals from Caribbean Islands to Winnipeg

Keep the following information in mind while searching for Caribbean Islands to Winnipeg flight deals. Data was last updated 18 December 2025.

Round-trip from

C$ 616

One-way from

C$ 309
Air Canada
  • Air Canada
  • 15/1-18/1
  • 2 total stops
  • 39h 44m total
  • Caribbean Islands to Winnipeg
Search Deals
24/3
  • 24/3
  • 2 total stops
  • 31h 35m total
  • Caribbean Islands to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Winnipeg 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 18 December 2025.
Use the filters below to find and compare flights from Caribbean Islands to Winnipeg that are best for you.

Fly from

Caribbean Islands

Fly to

Winnipeg

Route

Depart

Return

Price

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 15/1

1:30 p.m.-8:28 p.m.

2 stops31h 58m

Winnipeg

Sun 18/1

7:05 p.m.-12:25 p.m.

1 stop16h 20m

C$ 616

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 15/1

2:50 p.m.-12:09 p.m.

2 stops46h 19m

Winnipeg

Sun 18/1

6:15 a.m.-1:44 p.m.

2 stops30h 29m

C$ 639

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 23/1

11:15 a.m.-8:28 p.m.

1 stop10h 13m

Winnipeg

Sun 25/1

8:15 a.m.-12:25 p.m.

1 stop27h 10m

C$ 732

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 23/1

2:55 p.m.-7:34 p.m.

1 stop29h 39m

Winnipeg

Mon 26/1

8:15 a.m.-1:45 p.m.

2 stops52h 30m

C$ 805

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 23/1

4:30 p.m.-11:35 a.m.

1 stop20h 05m

Winnipeg

Mon 26/1

8:05 p.m.-3:33 p.m.

1 stop18h 28m

C$ 842

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 7/1

4:30 p.m.-11:35 a.m.

1 stop20h 05m

Winnipeg

Sun 18/1

7:30 a.m.-12:12 p.m.

2 stops27h 42m

C$ 1,057

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 7/1

7:10 p.m.-12:35 a.m.

2 stops30h 25m

Winnipeg

Fri 16/1

5:00 a.m.-3:33 p.m.

1 stop9h 33m

C$ 1,578

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 7/1

4:30 p.m.-12:42 a.m.

1 stop9h 12m

Winnipeg

Fri 16/1

5:00 a.m.-3:33 p.m.

1 stop9h 33m

C$ 1,678

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 7/1

4:30 p.m.-11:35 a.m.

1 stop20h 05m

Winnipeg

Sun 18/1

10:55 a.m.-3:33 p.m.

2 stops27h 38m

C$ 1,711

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Tue 24/3

1:00 p.m.-7:35 p.m.

2 stops31h 35m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Showing 1-10 of 17 results
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Best time to book a flight from Caribbean Islands to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Caribbean Islands 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 Caribbean Islands to Winnipeg

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

Currently, May is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 372). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,084). 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 EPX to YWG?

Find hourly flight availability from Caribbean Islands to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 18 December 2025.

It’s typically best to fly out from Caribbean Islands to Winnipeg at noon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated 18 December 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Winnipeg, such as WestJet. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,204 reviews
Check prices

Overall

7.2

Crew

7.9

Comfort

7.1

Entertainment

6.1

Food

6.2

Boarding

7.4

Reviews

1 / 20
6.0
Good

Anne,Dec 2025

HUX - YYC

Travel on airplanes sucks now. My legs are cramped because i cant stretch them out, if i drop anything theres not enough room to bend and reach to pick it up, the trays if down crowd my middle, the pocket on the seat in front is so small i cant even put my water bottle in it, because the seats are so close, the recline function is pretty irrelevant, but the staff are great and doing their best.
WestJet
7.2
Good
3,204 reviews
WestJet
7.2
Good
3,204 reviews
Check prices

Overall

7.2

Crew

7.9

Comfort

7.1

Entertainment

6.1

Food

6.2

Boarding

7.4

Reviews

1 / 20
6.0
Good

Anne,Dec 2025

HUX - YYC

Travel on airplanes sucks now. My legs are cramped because i cant stretch them out, if i drop anything theres not enough room to bend and reach to pick it up, the trays if down crowd my middle, the pocket on the seat in front is so small i cant even put my water bottle in it, because the seats are so close, the recline function is pretty irrelevant, but the staff are great and doing their best.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Winnipeg. 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 into for flights to Winnipeg from Caribbean Islands?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Caribbean Islands to Winnipeg. It is only a 7.3 km journey from Winnipeg (YWG) to Winnipeg’s city centre.

  • How long is the flight from Caribbean Islands to Winnipeg?

    Departing from Caribbean Islands to Winnipeg will take you 31h 58m. Caribbean Islands and Winnipeg are separated by a distance of 3681 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the most popular routes from Caribbean Islands to Winnipeg?

    When deciding which route to take from Caribbean Islands to Winnipeg consider Kingston Norman Manley - Winnipeg, George Town Owen Roberts Intl - Winnipeg or Havana Jose Marti Intl - Winnipeg as they are the most popular.

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

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

  • How can I find direct flights from Caribbean Islands to Winnipeg?

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Winnipeg 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 Caribbean Islands to Winnipeg?

    Currently, May is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 372). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,084). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Top airline flying from Caribbean Islands to Winnipeg

Discover the top airline that operate flights from Caribbean Islands to Winnipeg. 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 491AverageC$ 789FlexibilityNo 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 Caribbean Islands to Winnipeg?

When you search for this flight from Caribbean Islands to Winnipeg, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Caribbean Islands to Winnipeg?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Caribbean Islands to Winnipeg.

Can Cheapflights find flights from Caribbean Islands to Winnipeg with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Caribbean Islands to Winnipeg, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Caribbean Islands to Winnipeg become cheaper?

Not ready to book yet? You can track prices for flights from Caribbean Islands to Winnipeg on Cheapflights with our Price Alert feature and get notified when better prices are available.

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