Find flights
When to book
Airlines
FAQs

Cheap flights from Caribbean Islands to Winnipeg from C$ 394

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YWG
17 Jun — 24 Jun1
1 adult

Cheap 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 12 June 2025.

Round-trip from

C$ 749

One-way from

C$ 394
Air Canada
  • Air Canada
  • 15/7-22/7
  • 2 total stops
  • 45h 23m total
  • Caribbean Islands to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 9/10
  • 2 total stops
  • 21h 20m total
  • Caribbean Islands to Winnipeg
Search Deals

Find flight deals from Caribbean Islands to Winnipeg

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 12 June 2025.

Wed 11/63:30 p.m.KIN - YWG
2 stops32h 12mWestJet
Wed 10/99:05 p.m.YWG - KIN
2 stops41h 23mWestJet
Deal found 11/6C$ 721
Tue 15/711:15 a.m.NAS - YWG
1 stop23h 28mMultiple Airlines
Tue 22/76:35 p.m.YWG - NAS
1 stop21h 55mMultiple Airlines
Deal found 11/6C$ 749
Thu 3/71:37 p.m.KIN - YWG
2 stops26h 18mMultiple Airlines
Thu 10/76:55 p.m.YWG - KIN
1 stop22h 15mMultiple Airlines
Deal found 11/6C$ 793
Tue 15/75:00 p.m.NAS - YWG
2 stops21h 09mUnited Airlines
Tue 22/72:20 p.m.YWG - NAS
2 stops22h 11mUnited Airlines
Deal found 11/6C$ 837
Mon 28/71:45 p.m.KIN - YWG
2 stops20h 29mAir Canada
Sun 31/811:50 a.m.YWG - KIN
2 stops24h 45mAir Canada
Deal found 9/6C$ 976
Thu 10/71:35 p.m.GCM - YWG
2 stops25h 56mUnited Airlines
Wed 16/77:00 a.m.YWG - GCM
2 stops29h 30mUnited Airlines
Deal found 11/6C$ 1,072
Thu 10/712:50 p.m.GCM - YWG
2 stops21h 24mAir Canada
Wed 16/76:35 p.m.YWG - GCM
1 stop17h 20mAir Canada
Deal found 12/6C$ 1,344
Tue 1/72:54 p.m.KIN - YWG
3 stops23h 09mUnited Airlines
Tue 8/72:20 p.m.YWG - KIN
3 stops23h 33mUnited Airlines
Deal found 11/6C$ 1,749

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 12 June 2025.
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

Tue 15/7

11:15 a.m.-9:43 a.m.

1 stop23h 28m

Winnipeg

Tue 22/7

6:35 p.m.-5:30 p.m.

1 stop21h 55m

C$ 749

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Thu 3/7

1:37 p.m.-3:55 p.m.

2 stops26h 18m

Winnipeg

Thu 10/7

6:55 p.m.-5:10 p.m.

1 stop22h 15m

C$ 793

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Tue 15/7

5:00 p.m.-1:09 p.m.

2 stops21h 09m

Winnipeg

Tue 22/7

2:20 p.m.-1:31 p.m.

2 stops22h 11m

C$ 837

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 1/7

3:30 p.m.-9:43 a.m.

1 stop18h 13m

Winnipeg

Tue 8/7

8:15 p.m.-2:30 p.m.

2 stops18h 15m

C$ 855

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Mon 28/7

1:45 p.m.-10:14 a.m.

2 stops20h 29m

Winnipeg

Sun 31/8

11:50 a.m.-12:35 p.m.

2 stops24h 45m

C$ 976

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 10/7

1:35 p.m.-3:31 p.m.

2 stops25h 56m

Winnipeg

Wed 16/7

7:00 a.m.-12:30 p.m.

2 stops29h 30m

C$ 1,072

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 10/7

12:50 p.m.-10:14 a.m.

2 stops21h 24m

Winnipeg

Wed 16/7

6:35 p.m.-11:55 a.m.

1 stop17h 20m

C$ 1,344

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Tue 1/7

2:54 p.m.-2:03 p.m.

3 stops23h 09m

Winnipeg

Tue 8/7

2:20 p.m.-1:53 p.m.

3 stops23h 33m

C$ 1,749

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 9/10

12:50 p.m.-10:10 a.m.

2 stops21h 20m

C$ 394

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Sat 26/7

6:25 p.m.-9:26 p.m.

2 stops27h 01m

C$ 431

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 12 results
1
2

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 123). Flying from Caribbean Islands to Winnipeg in July is currently the most expensive (average of C$ 229). 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 12 June 2025.

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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

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 12 June 2025.
Read reviews from past customers who have flown United Airlines, WestJet and Air Canada from Caribbean Islands to Winnipeg. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,790 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Momny,Jun 2025

HND - BKK

I very love and happy with ANA and Sevice very super good .Thank you ANA
United Airlines
7.4
Good
8,790 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Momny,Jun 2025

HND - BKK

I very love and happy with ANA and Sevice very super good .Thank you ANA
WestJet
7.2
Good
2,868 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Momny,Jun 2025

HND - BKK

I very love and happy with ANA and Sevice very super good .Thank you ANA
Air Canada
7.1
Good
9,531 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Momny,Jun 2025

HND - BKK

I very love and happy with ANA and Sevice very super good .Thank you ANA
Flair Airlines
6.0
Okay
242 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Momny,Jun 2025

HND - BKK

I very love and happy with ANA and Sevice very super good .Thank you ANA

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.

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

    When deciding which route to take from Caribbean Islands to Winnipeg consider Kingston Norman Manley - Winnipeg, Nassau Intl - Winnipeg or George Town Owen Roberts 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Winnipeg (average of C$ 123). Flying from Caribbean Islands to Winnipeg in July is currently the most expensive (average of C$ 229). 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Selkirk
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Winnipeg flights
Vancouver Intl to Winnipeg flights
Toronto Island to Winnipeg flights
Hamilton to Winnipeg flights
Ottawa to Winnipeg flights
Pierre Elliott Trudeau Intl to Winnipeg flights
Calgary to Winnipeg flights
Abbotsford to Winnipeg flights
Edmonton to Winnipeg flights
Halifax to Winnipeg flights
Region of Waterloo Intl to Winnipeg flights
Thunder Bay to Winnipeg flights
Hobby to Winnipeg flights
Kelowna to Winnipeg flights
George Bush Intcntl to Winnipeg flights
John F Kennedy Intl to Winnipeg flights
Saskatoon to Winnipeg flights
Victoria to Winnipeg flights
Los Angeles to Winnipeg flights
O'Hare Intl to Winnipeg flights
Dulles Intl to Winnipeg flights
Newark to Winnipeg flights
Nanaimo to Winnipeg flights
Regina to Winnipeg flights
Baltimore to Winnipeg flights
Québec City to Winnipeg flights
LaGuardia to Winnipeg flights
San Francisco to Winnipeg flights
Denver to Winnipeg flights
Dallas/Fort Worth to Winnipeg flights
Fredericton to Winnipeg flights
Detroit to Winnipeg flights
Minneapolis to Winnipeg flights
Atlanta to Winnipeg flights
Ontario to Winnipeg flights
Philadelphia to Winnipeg flights
Windsor to Winnipeg flights
Tampa to Winnipeg flights
Winnipeg to Churchill flights
Reagan-National to Winnipeg flights
Orlando to Winnipeg flights
Cancún to Winnipeg flights
Boston to Winnipeg flights
London to Winnipeg flights
Sky Harbor Intl to Winnipeg flights
Portland to Winnipeg flights
St. John's to Winnipeg flights
Kamloops to Winnipeg flights
Fort Lauderdale to Winnipeg flights

Top 2 airlines flying from Caribbean Islands to Winnipeg

Discover the top 2 airlines 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 545AverageC$ 839FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 672AverageC$ 1,025FlexibilityNo 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 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.