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Cheap flights from Caribbean Islands to Winnipeg from C$ 442

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 18/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
21 Apr — 28 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 22 March 2026.

Wed 8/43:30 p.m.
KIN
-
YWG
2 stops23h 50m
WestJet
Wed 27/56:15 a.m.
YWG
-
KIN
1 stop8h 15m
WestJet
Deal found 19/3C$ 855
Wed 19/83:05 p.m.
KIN
-
YWG
1 stop20h 10m
Multiple Airlines
Wed 16/96:15 a.m.
YWG
-
KIN
1 stop8h 15m
Multiple Airlines
Deal found 20/3C$ 920
Wed 19/83:05 p.m.
KIN
-
YWG
1 stop18h 55m
Air Canada
Wed 16/95:10 a.m.
YWG
-
KIN
1 stop8h 45m
Air Canada
Deal found 19/3C$ 930
Wed 19/83:30 p.m.
KIN
-
YWG
1 stop9h 25m
WestJet
Wed 16/96:15 a.m.
YWG
-
KIN
1 stop8h 15m
WestJet
Deal found 18/3C$ 1,001

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 22 March 2026.

Round-trip from

C$ 855

One-way from

C$ 442
WestJet
  • WestJet
  • 8/4-27/5
  • 3 total stops
  • 32h 05m total
  • Caribbean Islands to Winnipeg
Search Deals
Flair Airlines
  • Flair Airlines
  • 18/5
  • 1 total stop
  • 14h 15m 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 22 March 2026.
Use the filters below to find and compare flights from Caribbean Islands to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 19/8

3:05 p.m.-11:15 a.m.

1 stop20h 10m

Winnipeg

Wed 16/9

6:15 a.m.-2:30 p.m.

1 stop8h 15m

C$ 920

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 19/8

3:05 p.m.-10:00 a.m.

1 stop18h 55m

Winnipeg

Wed 16/9

5:10 a.m.-1:55 p.m.

1 stop8h 45m

C$ 930
Quickest round-trip

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 19/8

3:30 p.m.-12:55 a.m.

1 stop9h 25m

Winnipeg

Wed 16/9

6:15 a.m.-2:30 p.m.

1 stop8h 15m

C$ 1,001

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sat 18/4

2:59 p.m.-11:52 a.m.

2 stops20h 53m

Winnipeg

Sat 25/4

2:00 p.m.-1:52 p.m.

2 stops47h 52m

C$ 1,598

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 8/4

2:59 p.m.-12:33 p.m.

3 stops21h 34m

Winnipeg

Wed 27/5

2:00 p.m.-1:54 p.m.

3 stops23h 54m

C$ 1,659

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 19/8

2:56 p.m.-2:25 p.m.

3 stops23h 29m

Winnipeg

Wed 16/9

2:00 p.m.-1:54 p.m.

3 stops23h 54m

C$ 2,399

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sat 18/4

2:27 p.m.-11:35 p.m.

3 stops33h 08m

Winnipeg

Sat 25/4

6:00 a.m.-6:54 p.m.

3 stops12h 54m

C$ 4,467
Cheapest one-way
Quickest one-way

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 18/5

6:25 p.m.-8:40 a.m.

1 stop14h 15m

C$ 442

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 18/5

6:25 p.m.-12:00 p.m.

2 stops17h 35m

C$ 468

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sat 4/4

1:15 p.m.-11:13 a.m.

2 stops21h 58m

C$ 973

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/3

Sorted by cheapest first

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$ 370). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,080). 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 22 March 2026.

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 22 March 2026.
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
3,300 reviews
Check prices

Food

6.2

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2026

TQO - YYZ

I had a very happy experience with fast boarding, an early flight and landing, and a quick baggage claim.
WestJet
7.2
Good
3,300 reviews
WestJet
7.2
Good
3,300 reviews
Check prices

Food

6.2

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2026

TQO - YYZ

I had a very happy experience with fast boarding, an early flight and landing, and a quick baggage claim.

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 25m. 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 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$ 370). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,080). 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 22 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 370AverageC$ 784FlexibilityNo 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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