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Cheap flights from Windsor, ON to Caribbean from C$ 302

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

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 6 November 2025.

Round-trip from

C$ 563

One-way from

C$ 302
Air Canada
  • Air Canada
  • 22/2-24/2
  • 2 total stops
  • 38h 29m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 10/2
  • 2 total stops
  • 32h 20m total
  • Windsor to Caribbean
Search Deals

Find flight deals from Windsor to Caribbean

Enter your travel dates to find the best prices.

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 6 November 2025.

Wed 12/117:50 p.m.YQG - PUJ
1 stop24h 45mAir Canada
Wed 19/111:05 p.m.PUJ - YQG
1 stop20h 59mAir Canada
Deal found 4/11C$ 566
Wed 12/117:35 a.m.YQG - PUJ
3 stops29h 25mMultiple Airlines
Wed 19/113:35 p.m.PUJ - YQG
2 stops28h 58mMultiple Airlines
Deal found 4/11C$ 991
Fri 26/127:50 p.m.YQG - MBJ
2 stops42h 55mAir Canada
Wed 31/127:05 p.m.MBJ - YQG
2 stops37h 59mAir Canada
Deal found 4/11C$ 1,029
Fri 19/125:35 p.m.YQG - PUJ
Nonstop4h 10mAir Transat
Fri 26/1212:40 p.m.PUJ - YQG
Nonstop4h 35mAir Transat
Deal found 4/11C$ 1,055
Fri 19/129:45 a.m.YQG - PUJ
2 stops14h 00mAir Canada
Fri 26/126:20 p.m.PUJ - YQG
2 stops25h 54mAir Canada
Deal found 4/11C$ 3,197

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 6 November 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

Sun 22/2

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

1 stop15h 15m

Punta Cana

Wed 25/2

1:05 p.m.-7:14 p.m.

1 stop7h 09m

C$ 563

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 23/2

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

2 stops38h 00m

Punta Cana

Wed 25/2

1:05 p.m.-7:14 p.m.

1 stop7h 09m

C$ 563

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 16/1

7:50 p.m.-10:10 p.m.

1 stop25h 20m

Punta Cana

Fri 23/1

1:05 p.m.-7:14 p.m.

1 stop7h 09m

C$ 573

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 1/1

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

1 stop15h 15m

Punta Cana

Thu 15/1

7:40 p.m.-7:14 p.m.

2 stops24h 34m

C$ 579

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 29/3

7:50 p.m.-1:00 p.m.

2 stops17h 10m

Punta Cana

Fri 3/4

2:35 p.m.-9:04 a.m.

2 stops18h 29m

C$ 584

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 21/2

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

2 stops14h 00m

Punta Cana

Tue 24/2

7:40 p.m.-7:14 p.m.

2 stops24h 34m

C$ 594

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 7/2

9:45 a.m.-2:37 p.m.

2 stops28h 52m

Montego Bay Sangster Intl

Sat 14/2

6:00 p.m.-7:14 p.m.

2 stops25h 14m

C$ 661

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 7/2

9:45 a.m.-6:05 p.m.

2 stops32h 20m

Montego Bay Sangster Intl

Sat 14/2

2:40 p.m.-9:04 a.m.

1 stop18h 24m

C$ 738

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 26/12

7:50 p.m.-2:45 p.m.

2 stops42h 55m

Montego Bay Sangster Intl

Wed 31/12

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

2 stops37h 59m

C$ 1,029

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sun 26/4

9:45 a.m.-11:54 p.m.

2 stops38h 09m

San Juan Luis Munoz Marin Intl

Tue 28/4

1:05 a.m.-7:14 p.m.

2 stops18h 09m

C$ 1,276

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

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
No data available for this route at this time. Please check back soon.

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 6 November 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
10,410 reviews
Check prices

Overall

7.1

Crew

7.8

Entertainment

6.8

Boarding

7.3

Food

6.3

Comfort

7.1

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
10,410 reviews
Air Canada
7.1
Good
10,410 reviews
Check prices

Overall

7.1

Crew

7.8

Entertainment

6.8

Boarding

7.3

Food

6.3

Comfort

7.1

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 15h 15m. 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 - 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.

See more FAQs

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Alternative routes for Windsor to Caribbean

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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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 569AverageC$ 773FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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

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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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