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Cheap flights from Winnipeg to Caribbean from C$ 286

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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
22 Jan — 29 Jan1
1 adult

Cheap flight deals from Winnipeg to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 17 January 2025.

Round-trip from

C$ 536

One-way from

C$ 286
WestJet
  • WestJet
  • 16/3-6/4
  • 3 total stops
  • 41h 25m total
  • Winnipeg to Caribbean
Search Deals
8/2
  • 8/2
  • 1 total stop
  • 20h 50m total
  • Winnipeg to Caribbean
Search Deals

Find flight deals from Winnipeg to Caribbean

Cheapest flights from Winnipeg to Caribbean
Explore the most affordable flight options available from Winnipeg to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 January 2025.

Sun 16/35:00 a.m.YWG - GCM
1 stop7h 43mWestJet
Sun 6/41:50 p.m.GCM - YWG
2 stops33h 42mWestJet
Deal found 16/1C$ 536
Tue 8/46:45 a.m.YWG - MBJ
2 stops29h 30mAir Canada
Tue 15/412:45 p.m.MBJ - YWG
2 stops31h 00mAir Canada
Deal found 15/1C$ 546
Sun 2/28:00 a.m.YWG - MBJ
Nonstop5h 27mWestJet
Sun 16/23:30 p.m.MBJ - YWG
Nonstop5h 55mWestJet
Deal found 15/1C$ 550
Wed 2/45:00 a.m.YWG - ANU
1 stop8h 21mWestJet
Wed 9/43:20 p.m.ANU - YWG
1 stop10h 14mWestJet
Deal found 15/1C$ 563
Sun 16/35:00 a.m.YWG - PUJ
1 stop11h 50mMultiple Airlines
Sat 22/36:00 a.m.PUJ - YWG
1 stop19h 34mMultiple Airlines
Deal found 15/1C$ 571
Tue 8/412:20 p.m.YWG - AUA
1 stop25h 15mWestJet
Tue 15/43:25 p.m.AUA - YWG
1 stop10h 09mWestJet
Deal found 15/1C$ 589
Wed 19/35:00 a.m.YWG - POP
1 stop8h 41mWestJet
Wed 26/33:40 p.m.POP - YWG
2 stops34h 04mWestJet
Deal found 16/1C$ 602
Sun 16/36:45 a.m.YWG - GCM
2 stops31h 15mAir Canada
Sun 6/42:40 p.m.GCM - YWG
2 stops43h 17mAir Canada
Deal found 16/1C$ 609
Sat 5/41:00 p.m.YWG - SXM
2 stops24h 16mWestJet
Tue 15/43:10 p.m.SXM - YWG
2 stops21h 58mWestJet
Deal found 14/1C$ 609
Wed 29/18:25 p.m.YWG - MBJ
2 stops22h 01mMultiple Airlines
Fri 31/12:45 p.m.MBJ - YWG
2 stops30h 13mMultiple Airlines
Deal found 15/1C$ 632
Mon 27/11:45 p.m.YWG - PUJ
1 stop22h 00mAir Canada
Tue 4/23:20 p.m.PUJ - YWG
1 stop20h 47mAir Canada
Deal found 16/1C$ 658
Mon 27/15:00 a.m.YWG - KIN
1 stop9h 41mWestJet
Tue 28/14:35 p.m.KIN - YWG
1 stop27h 35mWestJet
Deal found 16/1C$ 668

Find flights from Winnipeg to Caribbean within your budget

Customize your flight search to find flights from Winnipeg to Caribbean 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 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 16/3

5:00 a.m.-12:43 p.m.

1 stop7h 43m

George Town Owen Roberts Intl

Sun 6/4

1:50 p.m.-11:32 p.m.

2 stops33h 42m

C$ 536

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/4

1:45 p.m.-12:15 p.m.

1 stop22h 30m

Montego Bay Sangster Intl

Tue 15/4

12:45 p.m.-9:57 a.m.

2 stops21h 12m

C$ 546

WinnipegSt. John's

YWG - ANU

YWGANU

Winnipeg

Wed 2/4

5:00 a.m.-2:21 p.m.

1 stop8h 21m

St. John's V.C. Bird Intl

Wed 9/4

3:20 p.m.-12:34 a.m.

1 stop10h 14m

C$ 563

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 1/2

6:00 a.m.-7:23 p.m.

2 stops36h 23m

Montego Bay Sangster Intl

Sat 8/2

3:30 p.m.-8:25 p.m.

Nonstop5h 55m

C$ 566

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 16/3

5:00 a.m.-5:50 p.m.

1 stop11h 50m

Punta Cana

Sat 22/3

6:00 a.m.-12:34 a.m.

1 stop19h 34m

C$ 591

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 19/3

5:00 a.m.-2:41 p.m.

1 stop8h 41m

Puerto Plata La Union

Wed 26/3

3:40 p.m.-12:44 a.m.

2 stops34h 04m

C$ 602

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 16/3

6:45 a.m.-2:00 p.m.

2 stops31h 15m

George Town Owen Roberts Intl

Sun 6/4

2:40 p.m.-9:57 a.m.

2 stops43h 17m

C$ 609

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 5/4

1:00 p.m.-2:16 p.m.

2 stops24h 16m

Simpson Bay Princess Juliana

Tue 15/4

3:10 p.m.-12:08 p.m.

2 stops21h 58m

C$ 609

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 23/2

8:00 a.m.-2:27 p.m.

Nonstop5h 27m

Montego Bay Sangster Intl

Mon 3/3

1:45 p.m.-5:18 p.m.

1 stop28h 33m

C$ 621

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 27/1

1:45 p.m.-1:45 p.m.

1 stop22h 00m

Punta Cana

Tue 4/2

3:20 p.m.-10:07 a.m.

1 stop20h 47m

C$ 658

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

Showing 1-10 of 45 results
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Best time to book a flight from Winnipeg to Caribbean

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

Travel insights for flights from Winnipeg to Caribbean

Get recent, data-driven insights about flights from Winnipeg to Caribbean including ideal travel times, pricing trends, and more.

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

Currently, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 254). Flying from Winnipeg to Caribbean in May is currently the most expensive (average of C$ 580). 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 YWG to CB?

Find hourly flight availability from Winnipeg to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 January 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Caribbean as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 40.0 - 180.0 mm per month. October is typically the wettest month, when rainfall can reach 180.0 mm. February is typically the driest time to visit Caribbean when rainfall is around 40.0 mm.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated 17 January 2025.
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,511 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,965 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,824 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada
7.0
Good
8,587 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.3

Overall

8.0

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Caribbean. 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 from for flights from Winnipeg to Caribbean?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Caribbean.

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

    The cheapest airlines for a one-way flight from Winnipeg to Caribbean are Flair Airlines (C$ 302), WestJet (C$ 303), and United Airlines (C$ 354).

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

    The most popular route from Winnipeg to Caribbean is Winnipeg - Punta Cana. You may also consider Winnipeg - Montego Bay Sangster Intl or Winnipeg - Kingston Norman Manley.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Caribbean 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 Winnipeg to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 254). Flying from Winnipeg to Caribbean in May is currently the most expensive (average of C$ 580). 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

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Alternative routes for Winnipeg to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Winnipeg to Caribbean

Discover the top 5 airlines that operate flights from Winnipeg to Caribbean. 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 17 January 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 435AverageC$ 823FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 489AverageC$ 801FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 530AverageC$ 814FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 736AverageC$ 1,238FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 843AverageC$ 1,108FlexibilityNo cancel feeOn-time50%
Search Air Transat 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 Winnipeg to Caribbean?

When you search for this flight from Winnipeg to Caribbean, 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 Winnipeg to Caribbean?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Caribbean for you. Better yet — we are completely free to use.

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

Yes! Cheapflights helps users easily find flights from Winnipeg to Caribbean with no change fees.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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