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Cheap flights from Windsor, ON to Caribbean from C$ 315

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 18/1. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
8 Jan — 15 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 9 December 2025.

Fri 26/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Tue 13/13:15 p.m.PUJ - YQG
1 stop18h 49mMultiple Airlines
Deal found 8/12C$ 819
Fri 12/129:45 a.m.YQG - PUJ
1 stop10h 50mMultiple Airlines
Fri 19/127:20 a.m.PUJ - YQG
1 stop13h 13mMultiple Airlines
Deal found 8/12C$ 852
Mon 15/127:50 p.m.YQG - PUJ
1 stop16h 55mMultiple Airlines
Mon 22/129:30 a.m.PUJ - YQG
1 stop11h 03mMultiple Airlines
Deal found 8/12C$ 867
Fri 19/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Tue 13/15:45 p.m.PUJ - YQG
1 stop16h 19mMultiple Airlines
Deal found 8/12C$ 899
Tue 30/127:50 p.m.YQG - SJU
2 stops27h 46mAir Canada
Sun 11/13:40 p.m.SJU - YQG
1 stop18h 24mAir Canada
Deal found 7/12C$ 922
Fri 26/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Sun 28/124:55 p.m.PUJ - YQG
2 stops41h 09mMultiple Airlines
Deal found 8/12C$ 954
Wed 31/127:35 a.m.YQG - SJU
2 stops14h 24mMultiple Airlines
Fri 9/16:01 a.m.SJU - YQG
2 stops14h 32mMultiple Airlines
Deal found 7/12C$ 1,001
Wed 31/127:35 a.m.YQG - SJU
2 stops14h 24mMultiple Airlines
Thu 8/16:01 a.m.SJU - YQG
2 stops14h 32mMultiple Airlines
Deal found 7/12C$ 1,057
Tue 16/127:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
Tue 23/126:20 p.m.PUJ - YQG
2 stops25h 54mAir Canada
Deal found 8/12C$ 1,088
Tue 30/127:50 p.m.YQG - SJU
2 stops27h 46mAir Canada
Sat 10/13:40 p.m.SJU - YQG
1 stop18h 24mAir Canada
Deal found 7/12C$ 1,091
Wed 31/129:45 a.m.YQG - SJU
2 stops19h 26mAir Canada
Sun 11/13:40 p.m.SJU - YQG
1 stop18h 24mAir Canada
Deal found 7/12C$ 1,142
Tue 30/127:35 a.m.YQG - SJU
2 stops15h 21mMultiple Airlines
Fri 9/16:01 a.m.SJU - YQG
2 stops14h 32mMultiple Airlines
Deal found 7/12C$ 1,220

Find flight deals from Windsor to Caribbean

Keep the following information in mind while searching for Windsor to Caribbean flight deals. Data was last updated 9 December 2025.

Round-trip from

C$ 548

One-way from

C$ 315

Good round-trip deal

C$ 804 or less
Air Canada
  • Air Canada
  • 6/1-13/1
  • 2 total stops
  • 46h 34m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 18/1
  • 1 total stop
  • 16h 55m total
  • Windsor to Caribbean
Search Deals
Price to beat on a round-trip flight from Windsor to Caribbean.
Search Deals

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 9 December 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

Tue 6/1

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

1 stop24h 55m

Punta Cana

Tue 13/1

10:35 p.m.-7:14 p.m.

1 stop21h 39m

C$ 548

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 4/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Fri 9/1

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

2 stops24h 09m

C$ 588

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 5/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Sun 11/1

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

2 stops24h 09m

C$ 588

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 4/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Sun 11/1

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

2 stops24h 09m

C$ 588

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 5/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Fri 9/1

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

2 stops24h 09m

C$ 588

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 5/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Wed 7/1

1:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 597

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 3/1

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

1 stop17h 20m

Montego Bay Sangster Intl

Sun 11/1

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

2 stops24h 09m

C$ 618

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 3/1

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

1 stop17h 20m

Montego Bay Sangster Intl

Fri 9/1

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

2 stops24h 09m

C$ 618

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 8/1

9:45 a.m.-12:30 p.m.

1 stop26h 45m

Montego Bay Sangster Intl

Tue 13/1

1:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 626

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 7/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

Montego Bay Sangster Intl

Tue 13/1

1:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 626

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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 9 December 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
10,514 reviews
Check prices

Crew

7.8

Comfort

7.1

Food

6.3

Entertainment

6.8

Overall

7.1

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,514 reviews
Air Canada
7.1
Good
10,514 reviews
Check prices

Crew

7.8

Comfort

7.1

Food

6.3

Entertainment

6.8

Overall

7.1

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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 24h 55m. 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 - San Juan Luis Munoz Marin Intl or Windsor - Montego Bay Sangster 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 9 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 558AverageC$ 772FlexibilityNo 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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