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Cheap flights from Windsor, ON to Caribbean from C$ 280

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
15 Apr — 22 Apr1
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 16 March 2026.

Sun 20/94:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Thu 24/912:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 14/3C$ 512
Fri 3/47:45 p.m.
YQG
-
PUJ
1 stop19h 45m
Air Canada
Fri 10/49:40 p.m.
PUJ
-
YQG
1 stop21h 29m
Air Canada
Deal found 12/3C$ 580
Tue 11/84:05 p.m.
YQG
-
PUJ
1 stop23h 20m
Air Canada
Thu 13/84:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 15/3C$ 630
Fri 27/37:50 p.m.
YQG
-
PUJ
2 stops16h 05m
Air Canada
Sat 28/36:40 p.m.
PUJ
-
YQG
2 stops24h 29m
Air Canada
Deal found 14/3C$ 735
Sun 15/37:50 p.m.
YQG
-
PUJ
2 stops48h 55m
Air Canada
Fri 20/32:35 p.m.
PUJ
-
YQG
2 stops18h 29m
Air Canada
Deal found 13/3C$ 798
Fri 3/45:35 p.m.
YQG
-
PUJ
Nonstop4h 10m
Multiple Airlines
Fri 10/47:05 p.m.
PUJ
-
YQG
2 stops24h 04m
Multiple Airlines
Deal found 14/3C$ 811
Sat 26/94:05 p.m.
YQG
-
SJU
2 stops22h 39m
Air Canada
Tue 29/91:05 a.m.
SJU
-
YQG
2 stops14h 17m
Air Canada
Deal found 14/3C$ 942
Wed 29/47:45 p.m.
YQG
-
MBJ
2 stops17h 31m
Multiple Airlines
Wed 6/512:30 p.m.
MBJ
-
YQG
1 stop19h 54m
Multiple Airlines
Deal found 15/3C$ 985
Thu 9/47:45 p.m.
YQG
-
MBJ
1 stop16h 50m
Multiple Airlines
Thu 16/41:21 p.m.
MBJ
-
YQG
3 stops29h 12m
Multiple Airlines
Deal found 11/3C$ 1,087
Sun 20/94:30 p.m.
YQG
-
MBJ
3 stops19h 50m
Multiple Airlines
Thu 24/912:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Multiple Airlines
Deal found 14/3C$ 1,309
Sat 14/37:50 p.m.
YQG
-
SJU
2 stops16h 40m
Multiple Airlines
Sun 22/34:06 p.m.
SJU
-
YQG
3 stops27h 27m
Multiple Airlines
Deal found 14/3C$ 2,312
Sat 14/37:50 p.m.
YQG
-
SJU
2 stops24h 10m
Air Canada
Sun 22/31:45 p.m.
SJU
-
YQG
2 stops19h 19m
Air Canada
Deal found 14/3C$ 2,361

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 16 March 2026.

Round-trip from

C$ 580

One-way from

C$ 280
Air Canada
  • Air Canada
  • 3/4-10/4
  • 2 total stops
  • 41h 14m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 26/4
  • 1 total stop
  • 16h 35m 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 16 March 2026.
Use the filters below to find and compare flights from Windsor to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 3/4

7:45 p.m.-3:30 p.m.

1 stop19h 45m

Punta Cana

Fri 10/4

9:40 p.m.-7:09 p.m.

1 stop21h 29m

C$ 580

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 11/8

4:05 p.m.-3:25 p.m.

1 stop23h 20m

Punta Cana

Thu 13/8

4:20 p.m.-7:07 p.m.

1 stop26h 47m

C$ 630
Quickest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 29/4

7:45 p.m.-12:16 p.m.

2 stops17h 31m

Montego Bay Sangster Intl

Wed 6/5

12:30 p.m.-9:24 a.m.

1 stop19h 54m

C$ 985

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 9/4

7:45 p.m.-11:35 a.m.

1 stop16h 50m

Montego Bay Sangster Intl

Thu 16/4

1:21 p.m.-7:33 p.m.

3 stops29h 12m

C$ 1,087
Cheapest one-way

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 26/4

7:45 p.m.-11:20 a.m.

1 stop16h 35m

C$ 280

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 26/4

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

1 stop17h 00m

C$ 316

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 25/4

7:45 p.m.-4:50 p.m.

2 stops22h 05m

C$ 386

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 28/4

7:35 a.m.-12:45 p.m.

3 stops29h 10m

C$ 482

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 25/4

9:45 a.m.-5:52 p.m.

1 stop9h 07m

C$ 499

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 28/4

9:45 a.m.-11:50 p.m.

2 stops14h 05m

C$ 510

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 16 March 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
521 reviews
Check prices

Boarding

7.9

Crew

8.5

Overall

7.7

Entertainment

7.0

Food

6.8

Comfort

7.3

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
521 reviews
Air Transat
7.7
Good
521 reviews
Check prices

Boarding

7.9

Crew

8.5

Overall

7.7

Entertainment

7.0

Food

6.8

Comfort

7.3

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
10,806 reviews
Air Transat
7.7
Good
521 reviews
Check prices

Boarding

7.9

Crew

8.5

Overall

7.7

Entertainment

7.0

Food

6.8

Comfort

7.3

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 19h 45m. 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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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 16 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 480AverageC$ 770FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 722AverageC$ 891FlexibilityNo 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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