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Cheap flights from Caribbean 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 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 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 to Winnipeg

Keep the following information in mind while searching for Caribbean to Winnipeg flight deals. Data was last updated 5 February 2026.

Round-trip from

C$ 718

Popular in

August

Cheapest in

February

Average price

C$ 590

Good one-way deal

C$ 634 or less
Air Canada
  • Air Canada
  • 21/5-22/5
  • 2 total stops
  • 17h 04m total
  • Caribbean to Winnipeg
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 183 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 5 February 2026.
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

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
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$ 369). Flying from Caribbean 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 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 5 February 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 5 February 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
3,255 reviews
Check prices

Comfort

7.0

Food

6.2

Crew

7.9

Entertainment

6.1

Boarding

7.4

Overall

7.2

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

Comfort

7.0

Food

6.2

Crew

7.9

Entertainment

6.1

Boarding

7.4

Overall

7.2

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 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 7h 25m. Fly via Air Canada, WestJet, or United Airlines to get the fastest option. Airlines will cover a distance of 3244 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 George Town Owen Roberts Intl - Winnipeg, Nassau 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$ 369). Flying from Caribbean 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 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 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 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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