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Cheap flights from Caribbean to Winnipeg from C$ 588

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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
8 Aug — 15 Aug1
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 9 July 2026.

Thu 6/811:35 a.m.
KIN
-
YWG
2 stops22h 30m
Multiple Airlines
Mon 10/84:05 p.m.
YWG
-
KIN
2 stops46h 25m
Multiple Airlines
Deal found 7/7C$ 950
Fri 10/71:35 p.m.
GCM
-
YWG
2 stops20h 25m
Air Canada
Fri 17/73:20 p.m.
YWG
-
GCM
1 stop18h 40m
Air Canada
Deal found 9/7C$ 1,001
Mon 27/76:25 p.m.
KIN
-
YWG
1 stop14h 15m
Multiple Airlines
Sat 15/810:30 p.m.
YWG
-
KIN
2 stops40h 00m
Multiple Airlines
Deal found 8/7C$ 1,004
Wed 29/76:25 p.m.
KIN
-
YWG
1 stop15h 20m
Multiple Airlines
Sun 16/88:00 a.m.
YWG
-
KIN
2 stops30h 30m
Multiple Airlines
Deal found 8/7C$ 1,086
Sat 22/81:50 p.m.
KIN
-
YWG
3 stops24h 35m
Multiple Airlines
Sat 29/81:10 p.m.
YWG
-
KIN
2 stops49h 20m
Multiple Airlines
Deal found 7/7C$ 1,092
Wed 29/76:25 p.m.
KIN
-
YWG
1 stop15h 20m
Multiple Airlines
Wed 12/88:30 p.m.
YWG
-
KIN
2 stops42h 00m
Multiple Airlines
Deal found 7/7C$ 1,126
Wed 29/76:25 p.m.
KIN
-
YWG
1 stop15h 20m
Multiple Airlines
Fri 14/86:15 a.m.
YWG
-
KIN
1 stop8h 15m
Multiple Airlines
Deal found 8/7C$ 1,170
Fri 10/710:45 a.m.
GCM
-
YWG
3 stops29h 40m
Multiple Airlines
Fri 17/79:05 p.m.
YWG
-
GCM
2 stops15h 40m
Multiple Airlines
Deal found 9/7C$ 2,073

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 9 July 2026.

Round-trip from

C$ 950

One-way from

C$ 588

Popular in

January

Cheapest in

March

Average price

C$ 764

Good one-way deal

C$ 659 or less
WestJet
  • WestJet
  • 6/8-10/8
  • 4 total stops
  • 68h 55m total
  • Caribbean to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 3/8
  • 2 total stops
  • 24h 09m total
  • Caribbean to Winnipeg
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 9 July 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

Thu 6/8

11:35 a.m.-10:05 a.m.

2 stops22h 30m

Winnipeg

Mon 10/8

4:05 p.m.-2:30 p.m.

2 stops46h 25m

C$ 950

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sat 22/8

1:50 p.m.-2:25 p.m.

3 stops24h 35m

Winnipeg

Sat 29/8

1:10 p.m.-2:30 p.m.

2 stops49h 20m

C$ 1,092
Quickest round-trip

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sat 22/8

3:30 p.m.-8:20 p.m.

1 stop28h 50m

Winnipeg

Sat 29/8

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

1 stop8h 15m

C$ 1,249

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

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

3 stops23h 29m

Winnipeg

Wed 12/8

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

3 stops23h 54m

C$ 1,979

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

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

3 stops23h 29m

Winnipeg

Sun 16/8

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

3 stops23h 54m

C$ 2,319
Cheapest one-way

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 3/8

3:05 p.m.-3:14 p.m.

2 stops24h 09m

C$ 588
Quickest one-way

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 3/8

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

1 stop14h 15m

C$ 659

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sun 23/8

8:05 a.m.-12:55 a.m.

1 stop16h 50m

C$ 723

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 3/8

5:03 p.m.-7:49 p.m.

3 stops26h 46m

C$ 1,552

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Sorted by cheapest first

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
No data available for this route at this time. Please check back soon.

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 9 July 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
3,404 reviews
Check prices

Food

6.2

Comfort

7.0

Boarding

7.4

Crew

7.9

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
6.0
Good

Anonymous,Jun 2026

FRA - YYC

There was no vegetarian option in business section and needed to be pre-ordered. This was my first experience where for business section I needed to pre order it. And I did not learn that until I was already boarded.
WestJet
7.2
Good
3,404 reviews
WestJet
7.2
Good
3,404 reviews
Check prices

Food

6.2

Comfort

7.0

Boarding

7.4

Crew

7.9

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
6.0
Good

Anonymous,Jun 2026

FRA - YYC

There was no vegetarian option in business section and needed to be pre-ordered. This was my first experience where for business section I needed to pre order it. And I did not learn that until I was already boarded.

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.

  • 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.

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 9 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 505AverageC$ 770FlexibilityNo 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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