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Cheap flights from Windsor, ON to Caribbean from C$ 380

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
1 Jul — 8 Jul1
1 adult

Cheap flight deals from Windsor to Caribbean

Keep the following information in mind while searching for Windsor to Caribbean flight deals. Data was last updated 26 June 2025.

Round-trip from

C$ 885

One-way from

C$ 380
24/7-31/7
  • 24/7-31/7
  • 4 total stops
  • 94h 00m total
  • Windsor to Caribbean
Search Deals
Air Transat
  • Air Transat
  • 9/8
  • 2 total stops
  • 47h 15m total
  • Windsor to Caribbean
Search Deals

Find flight deals from Windsor to Caribbean

Cheapest flights from Windsor to Caribbean
Explore the most affordable flight options available from Windsor to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 June 2025.

Thu 24/72:30 p.m.YQG - PUJ
2 stops47h 15mMultiple Airlines
Thu 31/73:05 p.m.PUJ - YQG
2 stops46h 45mMultiple Airlines
Deal found 24/6C$ 885
Mon 28/710:05 a.m.YQG - PUJ
1 stop27h 40mAir Canada
Fri 1/84:25 p.m.PUJ - YQG
1 stop22h 57mAir Canada
Deal found 24/6C$ 890
Wed 30/77:45 p.m.YQG - MBJ
2 stops38h 42mWestJet
Tue 12/81:40 p.m.MBJ - YQG
2 stops28h 15mWestJet
Deal found 26/6C$ 1,288
Wed 30/74:00 p.m.YQG - MBJ
1 stop20h 05mAir Canada
Tue 12/812:00 p.m.MBJ - YQG
1 stop20h 27mAir Canada
Deal found 25/6C$ 1,565

Cheapflights Fare Finder

Customize your flight search to find flights from Windsor 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 26 June 2025.
Use the filters below to find and compare flights from Windsor to Caribbean that are best for you.

Fly from

Windsor

Fly to

Caribbean

Route

Depart

Return

Price

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 24/7

2:30 p.m.-1:45 p.m.

2 stops47h 15m

Punta Cana

Thu 31/7

3:05 p.m.-1:50 p.m.

2 stops46h 45m

C$ 885

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 28/7

10:05 a.m.-1:45 p.m.

1 stop27h 40m

Punta Cana

Fri 1/8

4:25 p.m.-3:22 p.m.

1 stop22h 57m

C$ 890

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 30/7

7:45 p.m.-9:27 a.m.

2 stops38h 42m

Montego Bay Sangster Intl

Tue 12/8

1:40 p.m.-6:55 p.m.

2 stops28h 15m

C$ 1,288

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 30/7

4:00 p.m.-11:05 a.m.

1 stop20h 05m

Montego Bay Sangster Intl

Tue 12/8

12:00 p.m.-9:27 a.m.

1 stop20h 27m

C$ 1,565

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 9/8

2:30 p.m.-1:45 p.m.

2 stops47h 15m

C$ 380

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 9/8

4:00 p.m.-3:20 p.m.

1 stop23h 20m

C$ 406

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 9/8

10:05 a.m.-11:45 a.m.

3 stops25h 40m

C$ 479

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/6

Best time to book a flight from Windsor to Caribbean

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

What is the cheapest month to book a flight from Windsor, Ontario to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Windsor, Ontario to Caribbean (average of C$ 254). Flying from Windsor, Ontario 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.

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 26 June 2025.
Get a feel of what it's like to fly with Air Transat,WestJet, andAir Canada from Windsor to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
401 reviews
Check prices

Food

6.8

Crew

8.5

Comfort

7.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YYZ

first time flying with porter airlines - it was a good experience. good friendly service from the crew. good choice of complimentary snacks and drinks. great seating. just lack of onboard entertainment
Air Transat
7.8
Good
401 reviews
Air Transat
7.8
Good
401 reviews
Check prices

Food

6.8

Crew

8.5

Comfort

7.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YYZ

first time flying with porter airlines - it was a good experience. good friendly service from the crew. good choice of complimentary snacks and drinks. great seating. just lack of onboard entertainment
WestJet
7.2
Good
2,893 reviews
Air Transat
7.8
Good
401 reviews
Check prices

Food

6.8

Crew

8.5

Comfort

7.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YYZ

first time flying with porter airlines - it was a good experience. good friendly service from the crew. good choice of complimentary snacks and drinks. great seating. just lack of onboard entertainment
Air Canada
7.1
Good
9,637 reviews
Air Transat
7.8
Good
401 reviews
Check prices

Food

6.8

Crew

8.5

Comfort

7.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Jun 2025

YVR - YYZ

first time flying with porter airlines - it was a good experience. good friendly service from the crew. good choice of complimentary snacks and drinks. great seating. just lack of onboard entertainment

Related info for your journey

Find useful and relevant information for your journey from Windsor 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 Windsor to Caribbean?

    For a flight from Windsor to Caribbean, you will be flying from Windsor. Windsor (YQG) is just 8.0 km from the centre of the city.

  • What are the most popular routes from Windsor, Ontario to Caribbean?

    When deciding which route to take from Windsor, Ontario to Caribbean consider Windsor - Punta Cana, Windsor - Montego Bay Sangster Intl or Windsor - San Juan Luis Munoz Marin Intl as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Windsor 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 Windsor, Ontario to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Windsor, Ontario to Caribbean (average of C$ 254). Flying from Windsor, Ontario 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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Top airline flying from Windsor to Caribbean

Discover the top airline that operate flights from Windsor 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 26 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 481AverageC$ 725FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Windsor to Caribbean?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Windsor to Caribbean. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Windsor to Caribbean?

Millions of users choose and trust Cheapflights to book the best flight deals from Windsor to Caribbean 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 Windsor to Caribbean with no change fees?

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

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

Yes! Start tracking prices for Windsor to Caribbean flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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