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Cheap flights from Windsor, ON to Caribbean from C$ 480

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 19/12. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
19 Aug — 26 Aug1
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 14 August 2025.

Round-trip from

C$ 542

One-way from

C$ 480
Air Canada
  • Air Canada
  • 12/11-3/12
  • 3 total stops
  • 39h 29m total
  • Windsor to Caribbean
Search Deals
Air Transat
  • Air Transat
  • 19/12
  • Nonstop
  • 4h 10m 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 14 August 2025.

Wed 12/119:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
Wed 3/123:35 p.m.PUJ - YQG
2 stops28h 39mAir Canada
Deal found 14/8C$ 542
Sun 7/93:55 p.m.YQG - PUJ
2 stops21h 30mAir Canada
Sat 13/94:25 p.m.PUJ - YQG
1 stop16h 57mAir Canada
Deal found 14/8C$ 576
Sun 7/99:55 a.m.YQG - PUJ
1 stop29h 25mAir Canada
Sun 14/92:25 p.m.PUJ - YQG
2 stops18h 47mAir Canada
Deal found 14/8C$ 580
Mon 8/94:00 p.m.YQG - PUJ
1 stop23h 20mAir Canada
Sun 14/92:25 p.m.PUJ - YQG
2 stops18h 47mAir Canada
Deal found 14/8C$ 622
Sat 6/93:55 p.m.YQG - PUJ
2 stops21h 30mAir Canada
Fri 12/92:25 p.m.PUJ - YQG
2 stops25h 02mAir Canada
Deal found 14/8C$ 636
Tue 16/99:55 a.m.YQG - PUJ
2 stops26h 45mMultiple Airlines
Tue 23/91:50 p.m.PUJ - YQG
2 stops25h 27mMultiple Airlines
Deal found 11/8C$ 638
Tue 16/94:00 p.m.YQG - PUJ
2 stops21h 25mAir Canada
Tue 23/94:25 p.m.PUJ - YQG
1 stop16h 57mAir Canada
Deal found 11/8C$ 709
Sat 6/98:50 a.m.YQG - PUJ
1 stop28h 54mMultiple Airlines
Sat 13/96:10 a.m.PUJ - YQG
1 stop14h 40mMultiple Airlines
Deal found 14/8C$ 794
Sat 6/98:50 a.m.YQG - PUJ
1 stop28h 54mMultiple Airlines
Sun 14/92:45 p.m.PUJ - YQG
1 stop30h 05mMultiple Airlines
Deal found 14/8C$ 882
Tue 19/84:00 p.m.YQG - PUJ
2 stops21h 25mAir Canada
Tue 26/82:25 p.m.PUJ - YQG
2 stops19h 02mAir Canada
Deal found 12/8C$ 922

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 14 August 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

Wed 12/11

9:45 a.m.-9:35 p.m.

1 stop10h 50m

Punta Cana

Wed 3/12

3:35 p.m.-7:14 p.m.

2 stops28h 39m

C$ 542

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/9

3:55 p.m.-3:20 p.m.

1 stop23h 25m

Punta Cana

Sat 13/9

4:25 p.m.-9:22 a.m.

1 stop16h 57m

C$ 576

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/9

9:55 a.m.-3:20 p.m.

1 stop29h 25m

Punta Cana

Fri 12/9

4:25 p.m.-3:27 p.m.

1 stop23h 02m

C$ 580

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/9

3:55 p.m.-3:20 p.m.

1 stop23h 25m

Punta Cana

Sun 14/9

4:25 p.m.-9:12 a.m.

1 stop16h 47m

C$ 580

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 8/9

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

1 stop23h 20m

Punta Cana

Fri 12/9

2:25 p.m.-3:27 p.m.

2 stops25h 02m

C$ 622

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 19/12

5:35 p.m.-10:45 p.m.

Nonstop4h 10m

C$ 480

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 19/12

7:35 a.m.-7:55 p.m.

2 stops11h 20m

C$ 1,115

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 19/12

9:45 a.m.-12:05 p.m.

1 stop25h 20m

C$ 2,109

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

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 14 August 2025.
Get a feel of what it's like to fly with Air 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 Canada
7.1
Good
9,949 reviews
Check prices

Overall

7.1

Entertainment

6.8

Crew

7.8

Comfort

7.1

Boarding

7.3

Food

6.3

Reviews

1 / 20
8.0
Excellent

Jadi-Ann,Jun 2025

YYZ - KIN

The flight was smooth with minor turbulence. The staff was courteous. Since I have an aeroplan account I was able to use the inflight wifi. I wanted extra space and the window seat and I had to pay for that. At first, I was okay with that, however, I felt that it was the same distance between for everyone. Maybe I could be wrong.
Air Canada
7.1
Good
9,949 reviews
Air Canada
7.1
Good
9,949 reviews
Check prices

Overall

7.1

Entertainment

6.8

Crew

7.8

Comfort

7.1

Boarding

7.3

Food

6.3

Reviews

1 / 20
8.0
Excellent

Jadi-Ann,Jun 2025

YYZ - KIN

The flight was smooth with minor turbulence. The staff was courteous. Since I have an aeroplan account I was able to use the inflight wifi. I wanted extra space and the window seat and I had to pay for that. At first, I was okay with that, however, I felt that it was the same distance between for everyone. Maybe I could be wrong.

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 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 485AverageC$ 728FlexibilityNo 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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