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Cheap flights from Winnipeg to Caribbean from C$ 309

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 23/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 12 June 2025.

Round-trip from

C$ 546

One-way from

C$ 309

Popular in

December

Cheapest in

September

Average price

C$ 805
WestJet
  • WestJet
  • 4/7-12/7
  • 4 total stops
  • 64h 16m total
  • Winnipeg to Caribbean
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WestJet
  • WestJet
  • 23/7
  • 2 total stops
  • 39h 38m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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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 12 June 2025.

Fri 4/76:30 a.m.YWG - AUA
2 stops30h 25mWestJet
Sat 12/72:50 p.m.AUA - YWG
2 stops33h 51mWestJet
Deal found 10/6C$ 546
Tue 1/79:05 p.m.YWG - PUJ
2 stops40h 18mWestJet
Tue 15/73:35 p.m.PUJ - YWG
2 stops29h 41mWestJet
Deal found 11/6C$ 562
Fri 11/79:00 a.m.YWG - SJU
1 stop29h 25mMultiple Airlines
Thu 17/72:40 a.m.SJU - YWG
2 stops14h 43mMultiple Airlines
Deal found 11/6C$ 572
Sat 20/93:45 p.m.YWG - NAS
2 stops48h 45mAir Canada
Sat 27/96:30 p.m.NAS - YWG
2 stops17h 10mAir Canada
Deal found 12/6C$ 625
Fri 11/78:35 a.m.YWG - SJU
2 stops14h 24mDelta
Fri 18/76:15 a.m.SJU - YWG
2 stops14h 55mDelta
Deal found 11/6C$ 630
Wed 29/108:00 p.m.YWG - POP
1 stop17h 45mWestJet
Mon 15/124:40 p.m.POP - YWG
2 stops28h 55mWestJet
Deal found 10/6C$ 649
Tue 1/76:35 p.m.YWG - PUJ
2 stops17h 50mAir Canada
Wed 9/72:45 p.m.PUJ - YWG
2 stops20h 29mAir Canada
Deal found 10/6C$ 659
Sat 18/107:55 a.m.YWG - SJU
2 stops27h 39mAir Canada
Sun 26/102:45 p.m.SJU - YWG
2 stops25h 28mAir Canada
Deal found 10/6C$ 660
Sat 27/95:45 p.m.YWG - PUJ
1 stop18h 59mMultiple Airlines
Sat 4/106:10 a.m.PUJ - YWG
1 stop11h 15mMultiple Airlines
Deal found 10/6C$ 664
Sun 13/79:05 p.m.YWG - MBJ
2 stops17h 40mMultiple Airlines
Wed 16/79:05 a.m.MBJ - YWG
2 stops34h 19mMultiple Airlines
Deal found 12/6C$ 675
Wed 9/77:00 a.m.YWG - NAS
2 stops31h 58mUnited Airlines
Tue 15/72:53 p.m.NAS - YWG
2 stops23h 16mUnited Airlines
Deal found 10/6C$ 721
Thu 7/89:05 p.m.YWG - MBJ
2 stops21h 21mWestJet
Thu 14/812:45 p.m.MBJ - YWG
2 stops28h 56mWestJet
Deal found 11/6C$ 725

Cheapflights Fare Finder

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 12 June 2025.
Use the filters below to find and compare flights from Winnipeg to Caribbean that are best for you.

Fly from

Winnipeg

Fly to

Caribbean

Route

Depart

Return

Price

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Fri 4/7

6:30 a.m.-1:55 p.m.

2 stops30h 25m

Oranjestad Reina Beatrix

Sat 12/7

2:50 p.m.-11:41 p.m.

2 stops33h 51m

C$ 546

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 1/7

9:05 p.m.-2:23 p.m.

2 stops40h 18m

Punta Cana

Tue 15/7

3:35 p.m.-8:16 p.m.

2 stops29h 41m

C$ 562

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 11/7

9:00 a.m.-3:25 p.m.

1 stop29h 25m

San Juan Luis Munoz Marin Intl

Thu 17/7

2:40 a.m.-4:23 p.m.

2 stops14h 43m

C$ 572

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sat 20/9

3:45 p.m.-5:30 p.m.

2 stops48h 45m

Nassau Intl

Sat 27/9

6:30 p.m.-10:40 a.m.

2 stops17h 10m

C$ 625

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 11/7

8:35 a.m.-11:59 p.m.

2 stops14h 24m

San Juan Luis Munoz Marin Intl

Fri 18/7

6:15 a.m.-8:10 p.m.

2 stops14h 55m

C$ 630

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 29/10

8:00 p.m.-2:45 p.m.

1 stop17h 45m

Puerto Plata La Union

Mon 15/12

4:40 p.m.-7:35 p.m.

2 stops28h 55m

C$ 649

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 1/7

6:35 p.m.-1:25 p.m.

2 stops17h 50m

Punta Cana

Wed 9/7

2:45 p.m.-10:14 a.m.

2 stops20h 29m

C$ 659

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 18/10

7:55 a.m.-12:34 p.m.

2 stops27h 39m

San Juan Luis Munoz Marin Intl

Sun 26/10

2:45 p.m.-3:13 p.m.

2 stops25h 28m

C$ 660

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 27/9

5:45 p.m.-1:44 p.m.

1 stop18h 59m

Punta Cana

Sat 4/10

6:10 a.m.-4:25 p.m.

1 stop11h 15m

C$ 664

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 13/7

9:05 p.m.-2:45 p.m.

2 stops17h 40m

Montego Bay Sangster Intl

Wed 16/7

9:05 a.m.-7:24 p.m.

2 stops34h 19m

C$ 675

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 41 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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Caribbean

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 July 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 12 June 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 12 June 2025.
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Air Transat
7.8
Good
396 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kade,Sep 2023

LHR - SLC

It was weird that we had to check after security and go to a corral which had no bathroom or other services about an hour before boarding. Had to check out of the corral to leave and check back in.

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 WestJet (C$ 309), Air Canada (C$ 372), and United Airlines (C$ 401).

  • 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 - San Juan Luis Munoz Marin Intl or Winnipeg - Oranjestad Reina Beatrix.

  • 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 July 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

Browse thousands of different options on Cheapflights for your next trip

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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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 460AverageC$ 788FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 465AverageC$ 785FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 481AverageC$ 912FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 700AverageC$ 1,132FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 795AverageC$ 865FlexibilityNo 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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