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Cheap flights from Winnipeg to Caribbean from C$ 264

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
5 May — 12 May1
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 30 April 2025.

Round-trip from

C$ 592

One-way from

C$ 264

Popular in

July

Cheapest in

October

Average price

C$ 662

Good round-trip deal

C$ 677 or less
WestJet
  • WestJet
  • 3/6-8/6
  • 3 total stops
  • 45h 13m total
  • Winnipeg to Caribbean
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WestJet
  • WestJet
  • 3/6
  • 2 total stops
  • 39h 08m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from 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 30 April 2025.

Tue 3/610:45 a.m.YWG - MBJ
1 stop24h 57mWestJet
Sun 8/612:45 p.m.MBJ - YWG
2 stops20h 16mWestJet
Deal found 28/4C$ 592
Sun 1/66:30 a.m.YWG - PUJ
1 stop30h 13mWestJet
Fri 6/611:45 a.m.PUJ - YWG
2 stops27h 26mWestJet
Deal found 29/4C$ 633
Fri 6/66:55 p.m.YWG - NAS
1 stop14h 28mMultiple Airlines
Thu 12/611:15 a.m.NAS - YWG
1 stop22h 40mMultiple Airlines
Deal found 29/4C$ 642
Fri 6/69:05 p.m.YWG - NAS
2 stops12h 18mWestJet
Thu 12/611:15 a.m.NAS - YWG
2 stops31h 11mWestJet
Deal found 29/4C$ 662
Mon 12/511:25 a.m.YWG - PUJ
2 stops23h 22mMultiple Airlines
Fri 6/612:42 p.m.PUJ - YWG
2 stops35h 04mMultiple Airlines
Deal found 28/4C$ 687
Tue 27/52:20 p.m.YWG - NAS
2 stops22h 11mUnited Airlines
Tue 3/62:53 p.m.NAS - YWG
2 stops25h 38mUnited Airlines
Deal found 29/4C$ 692
Sun 8/67:00 p.m.YWG - NAS
1 stop21h 30mAir Canada
Thu 12/66:30 p.m.NAS - YWG
1 stop16h 10mAir Canada
Deal found 29/4C$ 693
Thu 12/66:55 p.m.YWG - MBJ
1 stop16h 47mMultiple Airlines
Tue 24/612:07 p.m.MBJ - YWG
2 stops28h 21mMultiple Airlines
Deal found 28/4C$ 716
Mon 11/84:25 p.m.YWG - PUJ
2 stops46h 00mUnited Airlines
Sun 17/812:10 p.m.PUJ - YWG
2 stops25h 59mUnited Airlines
Deal found 28/4C$ 783
Wed 30/44:25 p.m.YWG - MBJ
2 stops46h 45mUnited Airlines
Wed 7/52:40 p.m.MBJ - YWG
2 stops22h 29mUnited Airlines
Deal found 29/4C$ 785
Sat 28/65:00 a.m.YWG - PLS
2 stops10h 40mAir Canada
Sat 5/77:05 p.m.PLS - YWG
1 stop15h 35mAir Canada
Deal found 29/4C$ 862
Sun 24/85:10 p.m.YWG - MBJ
1 stop18h 05mAir Canada
Fri 29/812:10 p.m.MBJ - YWG
2 stops29h 40mAir Canada
Deal found 28/4C$ 871

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 30 April 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

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/6

10:45 a.m.-11:42 a.m.

1 stop24h 57m

Montego Bay Sangster Intl

Sun 8/6

12:45 p.m.-9:01 a.m.

2 stops20h 16m

C$ 592

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 1/6

6:30 a.m.-1:43 p.m.

1 stop30h 13m

Punta Cana

Fri 6/6

11:45 a.m.-2:11 p.m.

2 stops27h 26m

C$ 633

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 6/6

6:55 p.m.-10:23 a.m.

1 stop14h 28m

Nassau Intl

Thu 12/6

11:15 a.m.-8:55 a.m.

1 stop22h 40m

C$ 642

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 6/6

9:05 p.m.-10:23 a.m.

2 stops12h 18m

Nassau Intl

Thu 12/6

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

1 stop23h 28m

C$ 662

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 12/5

11:25 a.m.-11:47 a.m.

2 stops23h 22m

Punta Cana

Fri 6/6

12:42 p.m.-10:46 p.m.

2 stops35h 04m

C$ 687

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 27/5

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

2 stops22h 11m

Nassau Intl

Tue 3/6

2:53 p.m.-3:31 p.m.

2 stops25h 38m

C$ 692

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 8/6

7:00 p.m.-5:30 p.m.

1 stop21h 30m

Nassau Intl

Thu 12/6

6:30 p.m.-9:40 a.m.

1 stop16h 10m

C$ 693

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 12/6

6:55 p.m.-11:42 a.m.

1 stop16h 47m

Montego Bay Sangster Intl

Tue 24/6

12:07 p.m.-4:28 p.m.

2 stops28h 21m

C$ 716

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 11/8

4:25 p.m.-3:25 p.m.

2 stops46h 00m

Punta Cana

Sun 17/8

12:10 p.m.-1:09 p.m.

2 stops25h 59m

C$ 783

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Sat 28/6

5:00 a.m.-4:40 p.m.

2 stops10h 40m

Providenciales

Sat 5/7

7:05 p.m.-9:40 a.m.

1 stop15h 35m

C$ 862

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

Showing 1-10 of 25 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 30 April 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 30 April 2025.
Air Transat
7.8
Good
385 reviews
Check prices

Overall

7.8

Food

6.7

Entertainment

7.1

Crew

8.5

Boarding

7.9

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Transat
7.8
Good
385 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Overall

7.8

Food

6.7

Entertainment

7.1

Crew

8.5

Boarding

7.9

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
United Airlines
7.4
Good
8,696 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Overall

7.8

Food

6.7

Entertainment

7.1

Crew

8.5

Boarding

7.9

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
WestJet
7.2
Good
2,823 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Overall

7.8

Food

6.7

Entertainment

7.1

Crew

8.5

Boarding

7.9

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Canada
7.0
Good
9,242 reviews
Air Transat
7.8
Good
385 reviews
Check prices

Overall

7.8

Food

6.7

Entertainment

7.1

Crew

8.5

Boarding

7.9

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.

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$ 264), Air Canada (C$ 305), and Air Transat (C$ 393).

  • 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 - Simpson Bay Princess Juliana.

  • 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

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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 30 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 464AverageC$ 806FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 471AverageC$ 731FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 504AverageC$ 924FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Sunwing AirlinesCheapestC$ 709AverageC$ 1,188FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 805AverageC$ 965FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

Fly with Cheapflights

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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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