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Cheap flights from Windsor, ON to Caribbean from C$ 287

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 30/11. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
12 Dec — 19 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 12 November 2025.

Round-trip from

C$ 631

One-way from

C$ 287
Air Canada
  • Air Canada
  • 15/2-7/3
  • 3 total stops
  • 35h 44m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 30/11
  • 1 total stop
  • 17h 25m 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 12 November 2025.

Mon 17/117:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
Mon 24/111:05 p.m.PUJ - YQG
1 stop20h 59mAir Canada
Deal found 10/11C$ 552
Wed 19/117:50 p.m.YQG - PUJ
1 stop24h 45mAir Canada
Wed 3/1210:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 11/11C$ 585
Mon 17/117:50 p.m.YQG - MBJ
1 stop17h 25mAir Canada
Fri 21/117:05 p.m.MBJ - YQG
2 stops24h 09mAir Canada
Deal found 11/11C$ 592
Fri 19/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Fri 26/1210:25 p.m.PUJ - YQG
1 stop11h 39mMultiple Airlines
Deal found 10/11C$ 983
Fri 19/125:35 p.m.YQG - PUJ
Nonstop4h 10mAir Transat
Fri 26/1212:40 p.m.PUJ - YQG
Nonstop4h 35mAir Transat
Deal found 10/11C$ 1,042
Wed 19/117:50 p.m.YQG - PUJ
2 stops17h 10mMultiple Airlines
Wed 3/121:01 p.m.PUJ - YQG
3 stops31h 13mMultiple Airlines
Deal found 11/11C$ 1,098
Fri 19/129:45 a.m.YQG - PUJ
2 stops38h 00mAir Canada
Fri 26/124:55 p.m.PUJ - YQG
2 stops41h 09mAir Canada
Deal found 10/11C$ 1,169
Mon 17/119:45 a.m.YQG - MBJ
3 stops26h 17mMultiple Airlines
Fri 21/117:05 p.m.MBJ - YQG
2 stops24h 09mMultiple Airlines
Deal found 11/11C$ 1,598

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 12 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 15/2

7:50 p.m.-2:00 p.m.

2 stops17h 10m

Punta Cana

Sat 7/3

12:40 a.m.-6:14 p.m.

1 stop18h 34m

C$ 631

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 20/2

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

2 stops14h 00m

Punta Cana

Fri 6/3

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

1 stop11h 39m

C$ 637

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 9/2

9:45 a.m.-1:46 p.m.

2 stops28h 01m

Montego Bay Sangster Intl

Thu 12/2

3:55 p.m.-7:14 p.m.

2 stops27h 19m

C$ 663

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 5/2

7:50 p.m.-1:10 p.m.

1 stop17h 20m

Montego Bay Sangster Intl

Mon 16/2

5:45 p.m.-9:04 a.m.

1 stop15h 19m

C$ 707

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 20/2

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

Nonstop4h 10m

Punta Cana

Fri 27/2

12:40 p.m.-4:15 p.m.

Nonstop4h 35m

C$ 813

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 20/2

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

2 stops14h 00m

Punta Cana

Fri 27/2

3:35 p.m.-9:04 a.m.

2 stops18h 29m

C$ 823

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 20/2

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

Nonstop4h 10m

Punta Cana

Fri 6/3

12:40 p.m.-4:15 p.m.

Nonstop4h 35m

C$ 845

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 5/2

7:50 p.m.-2:37 p.m.

2 stops18h 47m

Montego Bay Sangster Intl

Mon 16/2

1:25 p.m.-9:04 a.m.

2 stops19h 39m

C$ 892

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 25/4

9:45 a.m.-9:24 p.m.

2 stops35h 39m

San Juan Luis Munoz Marin Intl

Wed 29/4

4:55 p.m.-7:14 p.m.

2 stops26h 19m

C$ 973

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 19/12

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

Nonstop4h 10m

Punta Cana

Fri 26/12

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

1 stop11h 39m

C$ 983

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 27 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 12 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
10,444 reviews
Check prices

Overall

7.1

Boarding

7.3

Comfort

7.1

Crew

7.8

Entertainment

6.8

Food

6.3

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
10,444 reviews
Air Canada
7.1
Good
10,444 reviews
Check prices

Overall

7.1

Boarding

7.3

Comfort

7.1

Crew

7.8

Entertainment

6.8

Food

6.3

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 4h 10m. The distance between Windsor, Ontario and Caribbean is about 2972 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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 12 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 565AverageC$ 768FlexibilityNo 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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