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Cheap flights from Caribbean to Winnipeg from C$ 446

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 23/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
15 Oct — 22 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Caribbean to Winnipeg

Keep the following information in mind while searching for Caribbean to Winnipeg flight deals. Data was last updated 15 September 2025.

Round-trip from

C$ 962

One-way from

C$ 446

Popular in

January

Cheapest in

February

Average price

C$ 965
WestJet
  • WestJet
  • 6/3-9/3
  • 4 total stops
  • 73h 22m total
  • Caribbean to Winnipeg
Search Deals
23/12
  • 23/12
  • 2 total stops
  • 30h 44m total
  • Caribbean to Winnipeg
Search Deals
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Caribbean to Winnipeg

Best flights from Caribbean to Winnipeg
Discover carefully curated flight deals from Caribbean to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 September 2025.

Fri 6/34:30 p.m.KIN - YWG
2 stops41h 37mWestJet
Mon 9/36:45 a.m.YWG - KIN
2 stops31h 45mWestJet
Deal found 12/9C$ 962

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 15 September 2025.
Use the filters below to find and compare flights from Caribbean to Winnipeg that are best for you.

Fly from

Caribbean

Fly to

Winnipeg

Route

Depart

Return

Price

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$ 962

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 23/12

1:28 p.m.-7:12 p.m.

2 stops30h 44m

C$ 446

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 23/12

4:30 p.m.-12:35 a.m.

1 stop9h 05m

C$ 476

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$ 635

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$ 929

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Best time to book a flight from Caribbean to Winnipeg

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Winnipeg (average of C$ 123). Flying from Caribbean 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 CB to YWG?

Find hourly flight availability from Caribbean 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 15 September 2025.

When flying from Caribbean 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 15 September 2025.
Read through reviews of airlines operating flights from Caribbean to Winnipeg, such as WestJet and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Overall

7.2

Crew

7.9

Food

6.2

Boarding

7.4

Comfort

7.1

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
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Overall

7.2

Crew

7.9

Food

6.2

Boarding

7.4

Comfort

7.1

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
3,091 reviews
Check prices

Entertainment

6.1

Overall

7.2

Crew

7.9

Food

6.2

Boarding

7.4

Comfort

7.1

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 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?

    If you book a flight to Winnipeg from Caribbean, you will be flying to Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • How long is the flight from Caribbean to Winnipeg?

    There are many flights that can get you from Caribbean to Winnipeg in 41h 37m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 3993 km.

  • What are the cheapest airlines to fly from Caribbean to Winnipeg one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 476. Delta flights start at C$ 635 while deals on Air Canada start at C$ 929 one-way.

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

    The most popular flight routes from Caribbean to Winnipeg are George Town Owen Roberts Intl - Winnipeg, Havana Jose Marti Intl - Winnipeg and Kingston Norman Manley - Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Winnipeg (average of C$ 123). Flying from Caribbean 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 to Winnipeg

Discover the top 2 airlines that operate flights from Caribbean 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 15 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 493AverageC$ 840FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 680AverageC$ 1,038FlexibilityNo 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 to Winnipeg?

When you search for this flight from Caribbean 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 to Winnipeg?

Millions of users choose and trust Cheapflights to book the best flight deals from Caribbean to Winnipeg for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Yes, we can. To see specific flights from Caribbean to Winnipeg with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Winnipeg from Caribbean today and book when prices fit your budget.

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