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Cheap flights from Caribbean Islands to Winnipeg from C$ 377

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 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
16 Oct — 23 Oct1
1 adult
1 adult, Economy

Cheap 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 16 September 2025.

Round-trip from

C$ 960

One-way from

C$ 377
WestJet
  • WestJet
  • 6/3-9/3
  • 4 total stops
  • 74h 17m total
  • Caribbean Islands to Winnipeg
Search Deals
31/10
  • 31/10
  • 3 total stops
  • 36h 27m total
  • Caribbean Islands to Winnipeg
Search Deals

Find flight deals from Caribbean Islands to Winnipeg

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 16 September 2025.

Fri 6/34:30 p.m.KIN - YWG
2 stops43h 37mWestJet
Mon 9/37:50 a.m.YWG - KIN
2 stops30h 40mWestJet
Deal found 13/9C$ 960

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 16 September 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

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 6/3

4:30 p.m.-11:07 a.m.

2 stops43h 37m

Winnipeg

Mon 9/3

7:50 a.m.-2:30 p.m.

2 stops30h 40m

C$ 960

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 31/10

12:14 p.m.-12:41 a.m.

3 stops36h 27m

C$ 377

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 23/9

1:45 p.m.-10:35 a.m.

1 stop20h 50m

C$ 441

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 23/9

12:08 p.m.-3:00 p.m.

3 stops26h 52m

C$ 492

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sun 21/9

8:05 a.m.-8:55 a.m.

1 stop24h 50m

C$ 529

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 9/10

12:55 p.m.-11:27 p.m.

2 stops10h 32m

C$ 634

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 9/10

12:50 p.m.-11:25 p.m.

1 stop10h 35m

C$ 927

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 123). Flying from Caribbean Islands to Winnipeg in July is currently the most expensive (average of C$ 232). 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 16 September 2025.

When flying from Caribbean Islands to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 16 September 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Winnipeg, such as WestJet and Air Canada. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,093 reviews
Check prices

Food

6.2

Comfort

7.1

Entertainment

6.1

Boarding

7.4

Overall

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
WestJet
7.2
Good
3,093 reviews
WestJet
7.2
Good
3,093 reviews
Check prices

Food

6.2

Comfort

7.1

Entertainment

6.1

Boarding

7.4

Overall

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
Air Canada
7.1
Good
10,000 reviews
WestJet
7.2
Good
3,093 reviews
Check prices

Food

6.2

Comfort

7.1

Entertainment

6.1

Boarding

7.4

Overall

7.2

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon

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 43h 37m. Caribbean Islands and Winnipeg are separated by a distance of 3993 km.

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

    When deciding which route to take from Caribbean Islands to Winnipeg consider George Town Owen Roberts Intl - Winnipeg, Havana Jose Marti Intl - Winnipeg or Kingston Norman Manley - 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 123). Flying from Caribbean Islands to Winnipeg in July is currently the most expensive (average of C$ 232). 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 2 airlines flying from Caribbean Islands to Winnipeg

Discover the top 2 airlines 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 492AverageC$ 838FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 679AverageC$ 1,036FlexibilityNo 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 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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