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Cheap flights from Caribbean Islands to Winnipeg from C$ 718

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
7 Mar — 14 Mar1
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 5 February 2026.

Thu 21/51:35 p.m.
NAS
-
YWG
1 stop8h 44m
Air Canada
Fri 22/58:10 a.m.
YWG
-
NAS
1 stop8h 20m
Air Canada
Deal found 2/2C$ 718
Thu 21/51:35 p.m.
NAS
-
YWG
1 stop8h 44m
Air Canada
Mon 25/58:10 a.m.
YWG
-
NAS
1 stop8h 20m
Air Canada
Deal found 2/2C$ 720
Fri 19/63:05 p.m.
KIN
-
YWG
2 stops28h 56m
Air Canada
Fri 10/75:10 a.m.
YWG
-
KIN
1 stop8h 45m
Air Canada
Deal found 4/2C$ 804
Tue 17/25:30 p.m.
KIN
-
YWG
2 stops41h 37m
WestJet
Sat 21/26:45 a.m.
YWG
-
KIN
2 stops55h 45m
WestJet
Deal found 2/2C$ 814
Sat 23/53:59 p.m.
NAS
-
YWG
1 stop7h 25m
United Airlines
Mon 25/57:00 a.m.
YWG
-
NAS
1 stop6h 57m
United Airlines
Deal found 2/2C$ 866
Fri 19/63:30 p.m.
KIN
-
YWG
2 stops17h 50m
WestJet
Fri 10/75:30 p.m.
YWG
-
KIN
2 stops21h 00m
WestJet
Deal found 4/2C$ 995
Fri 19/63:30 p.m.
KIN
-
YWG
2 stops17h 50m
Multiple Airlines
Fri 10/75:10 p.m.
YWG
-
KIN
3 stops18h 45m
Multiple Airlines
Deal found 4/2C$ 1,110
Fri 22/53:59 p.m.
NAS
-
YWG
1 stop7h 25m
United Airlines
Mon 25/57:00 a.m.
YWG
-
NAS
1 stop6h 57m
United Airlines
Deal found 2/2C$ 1,113
Sat 23/53:59 p.m.
NAS
-
YWG
1 stop7h 25m
United Airlines
Thu 28/57:00 a.m.
YWG
-
NAS
1 stop6h 57m
United Airlines
Deal found 2/2C$ 1,159
Sat 21/32:30 p.m.
KIN
-
YWG
1 stop29h 05m
Multiple Airlines
Sat 28/35:00 p.m.
YWG
-
KIN
2 stops45h 30m
Multiple Airlines
Deal found 4/2C$ 1,214
Fri 22/53:59 p.m.
NAS
-
YWG
1 stop7h 25m
United Airlines
Sun 24/57:00 a.m.
YWG
-
NAS
1 stop6h 57m
United Airlines
Deal found 2/2C$ 1,406
Sun 24/53:59 p.m.
NAS
-
YWG
1 stop7h 25m
United Airlines
Tue 26/57:00 a.m.
YWG
-
NAS
1 stop6h 57m
United Airlines
Deal found 2/2C$ 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 5 February 2026.

Round-trip from

C$ 718
Air Canada
  • Air Canada
  • 21/5-22/5
  • 2 total stops
  • 17h 04m 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 5 February 2026.
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

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Thu 21/5

1:35 p.m.-9:19 p.m.

1 stop8h 44m

Winnipeg

Fri 22/5

8:10 a.m.-5:30 p.m.

1 stop8h 20m

C$ 718

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Thu 21/5

1:35 p.m.-9:19 p.m.

1 stop8h 44m

Winnipeg

Wed 27/5

8:10 a.m.-5:30 p.m.

1 stop8h 20m

C$ 720

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Thu 21/5

1:35 p.m.-9:19 p.m.

1 stop8h 44m

Winnipeg

Mon 25/5

8:10 a.m.-5:30 p.m.

1 stop8h 20m

C$ 720

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 19/6

3:05 p.m.-2:25 p.m.

1 stop23h 20m

Winnipeg

Fri 10/7

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

1 stop8h 45m

C$ 804

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 17/2

5:30 p.m.-10:07 a.m.

2 stops41h 37m

Winnipeg

Sat 21/2

6:45 a.m.-3:30 p.m.

2 stops55h 45m

C$ 814

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Sat 23/5

3:59 p.m.-10:24 p.m.

1 stop7h 25m

Winnipeg

Tue 26/5

7:00 a.m.-2:57 p.m.

1 stop6h 57m

C$ 866

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Sat 23/5

3:59 p.m.-10:24 p.m.

1 stop7h 25m

Winnipeg

Wed 27/5

7:00 a.m.-2:57 p.m.

1 stop6h 57m

C$ 866

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Sat 23/5

3:59 p.m.-10:24 p.m.

1 stop7h 25m

Winnipeg

Mon 25/5

7:00 a.m.-2:57 p.m.

1 stop6h 57m

C$ 866

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 19/6

3:30 p.m.-9:20 a.m.

2 stops17h 50m

Winnipeg

Fri 10/7

5:30 p.m.-2:30 p.m.

2 stops21h 00m

C$ 995

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 19/6

3:30 p.m.-9:20 a.m.

2 stops17h 50m

Winnipeg

Fri 10/7

5:10 p.m.-11:55 a.m.

3 stops18h 45m

C$ 1,110

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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$ 369). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,075). 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 5 February 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 5 February 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
3,255 reviews
Check prices

Crew

7.9

Overall

7.2

Boarding

7.4

Entertainment

6.1

Comfort

7.0

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,255 reviews
WestJet
7.2
Good
3,255 reviews
Check prices

Crew

7.9

Overall

7.2

Boarding

7.4

Entertainment

6.1

Comfort

7.0

Food

6.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

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 7h 25m. Caribbean Islands and Winnipeg are separated by a distance of 3244 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, Nassau 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$ 369). Flying from Caribbean Islands to Winnipeg in August is currently the most expensive (average of C$ 1,075). 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 5 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 368AverageC$ 780FlexibilityNo 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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