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Cheap flights from Windsor, ON to Caribbean from C$ 339

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 16/3. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
28 Feb — 7 Mar1
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 29 January 2026.

Thu 26/29:45 a.m.
YQG
-
PUJ
1 stop11h 00m
Air Canada
Thu 5/310:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 27/1C$ 620
Wed 4/27:50 p.m.
YQG
-
PUJ
1 stop24h 55m
Air Canada
Wed 11/210:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 28/1C$ 635
Sat 31/17:50 p.m.
YQG
-
PUJ
1 stop24h 55m
Air Canada
Wed 4/210:35 p.m.
PUJ
-
YQG
1 stop21h 40m
Air Canada
Deal found 28/1C$ 645
Fri 10/49:45 a.m.
YQG
-
PUJ
1 stop10h 55m
Air Canada
Sun 12/49:40 p.m.
PUJ
-
YQG
1 stop21h 29m
Air Canada
Deal found 28/1C$ 662
Fri 6/29:45 a.m.
YQG
-
PUJ
2 stops14h 00m
Air Canada
Fri 13/210:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 28/1C$ 669
Fri 10/49:45 a.m.
YQG
-
PUJ
2 stops13h 50m
Air Canada
Fri 17/42:25 p.m.
PUJ
-
YQG
2 stops28h 44m
Air Canada
Deal found 28/1C$ 675
Sun 8/27:50 p.m.
YQG
-
PUJ
2 stops48h 55m
Air Canada
Sun 15/210:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 29/1C$ 709
Mon 9/27:50 p.m.
YQG
-
SJU
2 stops25h 32m
Air Canada
Tue 10/22:05 a.m.
SJU
-
YQG
2 stops31h 59m
Air Canada
Deal found 26/1C$ 929
Sat 28/39:40 a.m.
YQG
-
MBJ
2 stops32h 10m
Air Canada
Tue 31/312:30 p.m.
MBJ
-
YQG
1 stop19h 34m
Air Canada
Deal found 26/1C$ 1,424

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 29 January 2026.

Round-trip from

C$ 620

One-way from

C$ 339
Air Canada
  • Air Canada
  • 26/2-5/3
  • 2 total stops
  • 22h 29m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 15/3
  • 1 total stop
  • 24h 45m total
  • 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 29 January 2026.
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

Thu 26/2

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

1 stop11h 00m

Punta Cana

Thu 5/3

10:35 p.m.-9:04 a.m.

1 stop11h 29m

C$ 620

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 8/2

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

2 stops48h 55m

Punta Cana

Sun 15/2

10:35 p.m.-9:04 a.m.

1 stop11h 29m

C$ 709

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 28/3

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

1 stop16h 55m

Punta Cana

Sat 4/4

6:40 p.m.-7:09 p.m.

2 stops24h 29m

C$ 715

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 10/4

9:45 a.m.-11:35 p.m.

2 stops13h 50m

Punta Cana

Sun 12/4

7:05 p.m.-7:09 p.m.

2 stops24h 04m

C$ 721

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 10/4

9:45 a.m.-8:40 p.m.

1 stop10h 55m

Punta Cana

Fri 17/4

2:10 p.m.-9:04 a.m.

1 stop18h 54m

C$ 785

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 30/3

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

1 stop17h 00m

Punta Cana

Sat 4/4

6:40 p.m.-7:09 p.m.

2 stops24h 29m

C$ 810

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 16/5

4:05 p.m.-3:20 p.m.

1 stop23h 15m

Punta Cana

Sat 23/5

2:55 p.m.-3:24 p.m.

2 stops24h 29m

C$ 869

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 26/2

7:35 a.m.-9:45 p.m.

2 stops13h 10m

Punta Cana

Thu 5/3

1:05 p.m.-9:04 a.m.

1 stop20h 59m

C$ 915

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 9/2

7:50 p.m.-10:22 p.m.

2 stops25h 32m

San Juan Luis Munoz Marin Intl

Tue 10/2

2:05 a.m.-9:04 a.m.

2 stops31h 59m

C$ 929

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 28/3

9:40 a.m.-4:50 p.m.

2 stops32h 10m

Montego Bay Sangster Intl

Tue 31/3

12:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 1,424

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

Showing 1-10 of 21 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 time of day to fly from YQG to CB?

Find hourly flight availability from Windsor to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 January 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Windsor, Ontario to Caribbean as you normally would.

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 29 January 2026.
Get a feel of what it's like to fly with Air Transat and 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 Transat
7.7
Good
501 reviews
Check prices

Boarding

7.9

Crew

8.4

Entertainment

7.0

Comfort

7.3

Food

6.8

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Transat
7.7
Good
501 reviews
Air Transat
7.7
Good
501 reviews
Check prices

Boarding

7.9

Crew

8.4

Entertainment

7.0

Comfort

7.3

Food

6.8

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Canada
7.1
Good
10,667 reviews
Air Transat
7.7
Good
501 reviews
Check prices

Boarding

7.9

Crew

8.4

Entertainment

7.0

Comfort

7.3

Food

6.8

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.

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 11h. 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Windsor to Caribbean

Discover the top 2 airlines 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 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 548AverageC$ 769FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 715AverageC$ 862FlexibilityNo cancel feeOn-time50%
Search Air Transat 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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