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Cheap flights from Windsor, ON to Caribbean from C$ 327

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 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 537

One-way from

C$ 327
Air Canada
  • Air Canada
  • 29/10-5/11
  • 2 total stops
  • 22h 29m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 30/10
  • 2 total stops
  • 17h 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 16 September 2025.

Wed 29/109:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
Wed 5/1110:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 14/9C$ 537
Sat 22/117:50 p.m.YQG - PUJ
2 stops51h 55mAir Canada
Sat 29/114:35 p.m.PUJ - YQG
2 stops27h 39mAir Canada
Deal found 15/9C$ 594
Sun 7/127:50 p.m.YQG - PUJ
1 stop16h 55mAir Canada
Sun 14/1210:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 14/9C$ 619
Fri 21/117:50 p.m.YQG - PUJ
2 stops44h 30mAir Canada
Sat 29/114:35 p.m.PUJ - YQG
2 stops27h 39mAir Canada
Deal found 15/9C$ 624
Mon 3/117:50 p.m.YQG - MBJ
2 stops18h 39mMultiple Airlines
Fri 7/112:48 p.m.MBJ - YQG
2 stops28h 26mMultiple Airlines
Deal found 15/9C$ 641
Wed 10/129:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
Wed 17/127:40 p.m.PUJ - YQG
2 stops24h 34mAir Canada
Deal found 14/9C$ 645
Thu 11/127:50 p.m.YQG - PUJ
2 stops24h 55mAir Canada
Sun 14/1210:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 14/9C$ 649
Sun 7/127:50 p.m.YQG - PUJ
1 stop16h 55mAir Canada
Tue 16/121:05 p.m.PUJ - YQG
1 stop7h 09mAir Canada
Deal found 14/9C$ 695
Sun 14/127:50 p.m.YQG - PUJ
2 stops17h 10mAir Canada
Sun 21/127:40 p.m.PUJ - YQG
2 stops24h 34mAir Canada
Deal found 14/9C$ 717
Sun 7/127:50 p.m.YQG - PUJ
1 stop16h 55mAir Canada
Sat 20/121:05 p.m.PUJ - YQG
1 stop7h 09mAir Canada
Deal found 14/9C$ 724
Mon 3/119:45 a.m.YQG - MBJ
1 stop6h 50mAir Canada
Fri 7/112:45 p.m.MBJ - YQG
1 stop18h 19mAir Canada
Deal found 15/9C$ 728
Wed 3/127:50 p.m.YQG - MBJ
1 stop17h 20mAir Canada
Sun 7/125:45 p.m.MBJ - YQG
1 stop15h 19mAir Canada
Deal found 15/9C$ 898

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 16 September 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 29/10

9:45 a.m.-8:35 p.m.

1 stop10h 50m

Punta Cana

Wed 5/11

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

2 stops28h 39m

C$ 537

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 22/11

7:50 p.m.-12:45 a.m.

2 stops51h 55m

Punta Cana

Sat 29/11

4:35 p.m.-7:14 p.m.

2 stops27h 39m

C$ 594

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 10/12

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

1 stop10h 50m

Punta Cana

Sun 14/12

3:15 p.m.-7:14 p.m.

1 stop28h 59m

C$ 619

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 8/12

7:50 p.m.-12:05 p.m.

1 stop15h 15m

Punta Cana

Sun 14/12

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

2 stops28h 39m

C$ 619

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 9/12

7:50 p.m.-12:05 p.m.

1 stop15h 15m

Punta Cana

Sun 14/12

3:15 p.m.-7:14 p.m.

1 stop28h 59m

C$ 619

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/12

7:50 p.m.-12:45 a.m.

2 stops51h 55m

Punta Cana

Sun 14/12

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

2 stops28h 39m

C$ 619

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 21/11

7:50 p.m.-5:20 p.m.

2 stops44h 30m

Punta Cana

Sat 29/11

4:35 p.m.-7:14 p.m.

2 stops27h 39m

C$ 624

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 3/11

7:50 p.m.-2:29 p.m.

2 stops18h 39m

Montego Bay Sangster Intl

Fri 7/11

2:48 p.m.-7:14 p.m.

2 stops28h 26m

C$ 641

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 11/12

7:50 p.m.-9:45 p.m.

2 stops24h 55m

Punta Cana

Sun 14/12

10:25 p.m.-9:04 a.m.

1 stop11h 39m

C$ 649

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 1/2

7:50 p.m.-4:35 p.m.

1 stop20h 45m

Montego Bay Sangster Intl

Wed 4/2

7:05 p.m.-9:04 a.m.

2 stops13h 59m

C$ 653

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 30 results
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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 16 September 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
10,000 reviews
Check prices

Food

6.3

Comfort

7.1

Entertainment

6.8

Boarding

7.3

Overall

7.1

Crew

7.8

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Food

6.3

Comfort

7.1

Entertainment

6.8

Boarding

7.3

Overall

7.1

Crew

7.8

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.

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.

  • How long is the flight from Windsor, Ontario to Caribbean?

    Departing from Windsor, Ontario to Caribbean will take you 10h 50m. The distance between Windsor, Ontario and Caribbean is about 2972 km.

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

    When deciding which route to take from Windsor, Ontario to Caribbean consider Windsor - Montego Bay Sangster Intl, Windsor - Punta Cana 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 565AverageC$ 739FlexibilityNo cancel feeOn-time67%
Search Air Canada 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 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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