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Cheap flights from Caribbean Islands to Winnipeg from C$ 357

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 18/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Caribbean Islands to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Caribbean Islands to Winnipeg
Explore the most affordable flight options available from Caribbean Islands to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 November 2025.

Tue 16/125:50 p.m.GCM - YWG
1 stop18h 45mMultiple Airlines
Tue 23/124:25 p.m.YWG - GCM
1 stop20h 35mMultiple Airlines
Deal found 1/11C$ 820
Mon 22/122:50 p.m.GCM - YWG
2 stops44h 18mWestJet
Thu 1/15:00 a.m.YWG - GCM
1 stop7h 44mWestJet
Deal found 2/11C$ 827
Sun 21/122:50 p.m.GCM - YWG
2 stops20h 18mWestJet
Thu 1/15:00 a.m.YWG - GCM
1 stop7h 44mWestJet
Deal found 2/11C$ 835
Tue 16/125:45 p.m.GCM - YWG
2 stops19h 12mUnited Airlines
Tue 23/127:05 p.m.YWG - GCM
2 stops17h 40mUnited Airlines
Deal found 1/11C$ 905
Sun 21/125:10 p.m.GCM - YWG
2 stops19h 47mUnited Airlines
Fri 2/18:40 a.m.YWG - GCM
2 stops30h 55mUnited Airlines
Deal found 2/11C$ 983
Sun 21/125:45 p.m.GCM - YWG
2 stops19h 12mUnited Airlines
Thu 1/15:30 a.m.YWG - GCM
2 stops31h 15mUnited Airlines
Deal found 2/11C$ 985
Mon 22/122:50 p.m.GCM - YWG
1 stop10h 52mMultiple Airlines
Thu 1/14:25 p.m.YWG - GCM
1 stop20h 35mMultiple Airlines
Deal found 2/11C$ 1,002
Sun 21/122:50 p.m.GCM - YWG
1 stop9h 45mMultiple Airlines
Thu 1/15:00 a.m.YWG - GCM
1 stop7h 44mMultiple Airlines
Deal found 2/11C$ 1,018
Sun 21/122:50 p.m.GCM - YWG
1 stop10h 52mMultiple Airlines
Fri 2/17:30 a.m.YWG - GCM
2 stops51h 05mMultiple Airlines
Deal found 2/11C$ 1,028
Wed 24/121:50 p.m.NAS - YWG
1 stop22h 23mPorter Airlines
Sat 27/126:00 a.m.YWG - NAS
1 stop7h 15mPorter Airlines
Deal found 3/11C$ 1,031
Fri 19/123:15 p.m.NAS - YWG
2 stops20h 58mPorter Airlines
Fri 26/1212:10 p.m.YWG - NAS
2 stops29h 40mPorter Airlines
Deal found 3/11C$ 1,038
Fri 19/124:50 p.m.NAS - YWG
1 stop8h 45mMultiple Airlines
Fri 26/124:25 p.m.YWG - NAS
1 stop25h 25mMultiple Airlines
Deal found 3/11C$ 1,058

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 3 November 2025.

Round-trip from

C$ 820

One-way from

C$ 357
Porter Airlines
  • Porter Airlines
  • 16/12-23/12
  • 2 total stops
  • 39h 20m total
  • Caribbean Islands to Winnipeg
Search Deals
Porter Airlines
  • Porter Airlines
  • 18/12
  • 1 total stop
  • 9h 20m 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 3 November 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

Tue 16/12

5:50 p.m.-11:35 a.m.

1 stop18h 45m

Winnipeg

Tue 23/12

4:25 p.m.-2:00 p.m.

1 stop20h 35m

C$ 820

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Mon 22/12

2:50 p.m.-10:08 a.m.

2 stops44h 18m

Winnipeg

Thu 1/1

5:00 a.m.-1:44 p.m.

1 stop7h 44m

C$ 827

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 6/3

4:30 p.m.-9:07 a.m.

2 stops41h 37m

Winnipeg

Mon 9/3

6:45 a.m.-2:30 p.m.

2 stops31h 45m

C$ 827

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 6/3

2:55 p.m.-11:54 p.m.

1 stop9h 59m

Winnipeg

Mon 9/3

7:05 p.m.-12:45 p.m.

1 stop17h 40m

C$ 829

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sun 21/12

2:50 p.m.-10:08 a.m.

2 stops20h 18m

Winnipeg

Thu 1/1

5:00 a.m.-1:44 p.m.

1 stop7h 44m

C$ 835

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Tue 16/12

5:45 p.m.-11:57 a.m.

2 stops19h 12m

Winnipeg

Tue 23/12

7:05 p.m.-1:45 p.m.

2 stops17h 40m

C$ 905

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Thu 26/3

11:20 a.m.-12:35 a.m.

1 stop14h 15m

Winnipeg

Mon 30/3

10:55 a.m.-3:40 p.m.

2 stops27h 45m

C$ 911

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sun 21/12

5:10 p.m.-11:57 a.m.

2 stops19h 47m

Winnipeg

Fri 2/1

8:40 a.m.-4:35 p.m.

2 stops30h 55m

C$ 983

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sun 21/12

5:45 p.m.-11:57 a.m.

2 stops19h 12m

Winnipeg

Thu 1/1

5:30 a.m.-1:45 p.m.

2 stops31h 15m

C$ 985

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Mon 22/12

2:50 p.m.-12:42 a.m.

1 stop10h 52m

Winnipeg

Thu 1/1

4:25 p.m.-2:00 p.m.

1 stop20h 35m

C$ 1,002

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 19 results
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2

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$ 378). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,090). 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 3 November 2025.

It’s typically best to fly out from Caribbean Islands to Winnipeg at noon. Doing so could potentially save you 29% 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 3 November 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
3,153 reviews
Check prices

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.1

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.
WestJet
7.2
Good
3,153 reviews
WestJet
7.2
Good
3,153 reviews
Check prices

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.1

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.
Air Canada
7.1
Good
10,398 reviews
WestJet
7.2
Good
3,153 reviews
Check prices

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.1

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.

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 9h 59m. Caribbean Islands and Winnipeg are separated by a distance of 3993 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 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, May is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 378). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,090). 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 3 November 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 499AverageC$ 800FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 833AverageC$ 1,050FlexibilityNo 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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