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Cheap flights from Caribbean to Winnipeg from C$ 452

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
23 Apr — 30 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Caribbean to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Caribbean to Winnipeg
Explore the most affordable flight options available from Caribbean to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 March 2026.

Mon 4/53:05 p.m.
KIN
-
YWG
1 stop20h 03m
Multiple Airlines
Fri 22/54:15 p.m.
YWG
-
KIN
2 stops22h 15m
Multiple Airlines
Deal found 22/3C$ 785
Mon 4/53:05 p.m.
KIN
-
YWG
1 stop20h 03m
Air Canada
Fri 22/55:10 a.m.
YWG
-
KIN
1 stop8h 45m
Air Canada
Deal found 22/3C$ 795
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$ 857
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$ 923
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$ 932
Tue 21/41:50 p.m.
GCM
-
YWG
1 stop22h 02m
United Airlines
Tue 28/45:30 p.m.
YWG
-
GCM
2 stops19h 15m
United Airlines
Deal found 23/3C$ 1,015

Find flight deals from Caribbean to Winnipeg

Keep the following information in mind while searching for Caribbean to Winnipeg flight deals. Data was last updated 24 March 2026.

Round-trip from

C$ 785

One-way from

C$ 452

Popular in

August

Cheapest in

February

Average price

C$ 1,052

Good one-way deal

C$ 639 or less
WestJet
  • WestJet
  • 4/5-22/5
  • 3 total stops
  • 42h 18m total
  • Caribbean to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 9/5
  • 2 total stops
  • 43h 37m total
  • Caribbean to Winnipeg
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from Caribbean to Winnipeg.
Search Deals

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 24 March 2026.
Use the filters below to find and compare flights from Caribbean 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 8/4

3:30 p.m.-9:42 p.m.

2 stops30h 12m

Winnipeg

Wed 27/5

9:05 p.m.-2:30 p.m.

2 stops41h 25m

C$ 893

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 4/5

4:50 p.m.-12:55 a.m.

2 stops32h 05m

Winnipeg

Fri 22/5

4:55 p.m.-2:30 p.m.

2 stops21h 35m

C$ 998
Quickest round-trip

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Tue 21/4

1:35 p.m.-11:52 a.m.

2 stops22h 17m

Winnipeg

Tue 28/4

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

2 stops17h 40m

C$ 1,015

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 4/5

2:59 p.m.-2:18 p.m.

3 stops23h 19m

Winnipeg

Fri 22/5

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

3 stops23h 54m

C$ 1,473

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$ 1,602

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$ 1,663

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$ 4,478
Cheapest one-way

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sat 9/5

4:15 p.m.-11:52 a.m.

2 stops43h 37m

C$ 452

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Tue 21/4

12:55 p.m.-11:52 a.m.

2 stops22h 57m

C$ 503

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Sat 9/5

1:45 p.m.-5:15 p.m.

1 stop27h 30m

C$ 585

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/3

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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, May is the cheapest month in which you can book a flight from Caribbean to Winnipeg (average of C$ 371). Flying from Caribbean to Winnipeg in August is currently the most expensive (average of C$ 1,082). 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 24 March 2026.

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 24 March 2026.
Read through reviews of airlines operating flights from Caribbean to Winnipeg, such as WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,301 reviews
Check prices

Boarding

7.4

Food

6.2

Overall

7.2

Comfort

7.0

Crew

7.9

Entertainment

6.1

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
3,301 reviews
WestJet
7.2
Good
3,301 reviews
Check prices

Boarding

7.4

Food

6.2

Overall

7.2

Comfort

7.0

Crew

7.9

Entertainment

6.1

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 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 22h 17m. Fly via WestJet or United Airlines to get the fastest option. Airlines will cover a distance of 3681 km. This flight may include one or multiple stops.

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

    The most popular flight routes from Caribbean to Winnipeg are Kingston Norman Manley - Winnipeg, George Town Owen Roberts Intl - Winnipeg and Havana Jose Marti Intl - 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, May is the cheapest month in which you can book a flight from Caribbean to Winnipeg (average of C$ 371). Flying from Caribbean to Winnipeg in August is currently the most expensive (average of C$ 1,082). 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

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Top airline flying from Caribbean to Winnipeg

Discover the top airline 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 24 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 371AverageC$ 786FlexibilityNo 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 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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