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Cheap flights from Windsor, ON to Caribbean from C$ 341

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
14 Jun — 21 Jun1
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 15 May 2026.

Sat 23/510:05 a.m.
YQG
-
PUJ
2 stops27h 50m
Air Canada
Wed 27/52:55 p.m.
PUJ
-
YQG
2 stops24h 29m
Air Canada
Deal found 13/5C$ 566
Mon 18/57:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Mon 25/52:55 p.m.
PUJ
-
YQG
2 stops24h 29m
Air Canada
Deal found 11/5C$ 591
Mon 14/97:45 p.m.
YQG
-
PUJ
1 stop19h 45m
Air Canada
Fri 18/95:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 11/5C$ 605
Sat 6/67:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Wed 10/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 14/5C$ 609
Sat 19/94:05 p.m.
YQG
-
SJU
2 stops21h 40m
Air Canada
Tue 22/91:00 a.m.
SJU
-
YQG
2 stops14h 22m
Air Canada
Deal found 14/5C$ 632
Wed 18/117:50 p.m.
YQG
-
PUJ
1 stop15h 20m
Air Canada
Thu 26/119:35 p.m.
PUJ
-
YQG
1 stop22h 39m
Air Canada
Deal found 12/5C$ 638
Mon 16/117:50 p.m.
YQG
-
SJU
2 stops24h 10m
Air Canada
Fri 20/117:45 a.m.
SJU
-
YQG
2 stops36h 29m
Air Canada
Deal found 12/5C$ 753
Tue 2/64:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Fri 5/612:30 p.m.
MBJ
-
YQG
1 stop19h 54m
Air Canada
Deal found 12/5C$ 865
Tue 9/610:05 a.m.
YQG
-
SJU
2 stops11h 19m
Air Canada
Mon 15/61:00 a.m.
SJU
-
YQG
2 stops14h 24m
Air Canada
Deal found 12/5C$ 1,250
Tue 9/64:30 p.m.
YQG
-
SJU
3 stops22h 04m
Multiple Airlines
Tue 16/64:30 p.m.
SJU
-
YQG
3 stops23h 16m
Multiple Airlines
Deal found 12/5C$ 1,261
Wed 10/610:05 a.m.
YQG
-
SJU
2 stops11h 19m
Air Canada
Wed 17/67:40 a.m.
SJU
-
YQG
2 stops11h 29m
Air Canada
Deal found 13/5C$ 1,415
Mon 8/610:05 a.m.
YQG
-
SJU
2 stops11h 19m
Air Canada
Sun 14/62:05 a.m.
SJU
-
YQG
2 stops13h 20m
Air Canada
Deal found 10/5C$ 1,439

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 15 May 2026.

Round-trip from

C$ 605

One-way from

C$ 341
Air Canada
  • Air Canada
  • 14/9-18/9
  • 3 total stops
  • 42h 02m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 11/6
  • 1 total stop
  • 23h 20m 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 15 May 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

Sat 6/6

7:45 p.m.-4:30 p.m.

2 stops20h 45m

Punta Cana

Wed 10/6

5:25 p.m.-3:24 p.m.

2 stops21h 59m

C$ 619

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

4:05 p.m.-1:45 p.m.

2 stops21h 40m

San Juan Luis Munoz Marin Intl

Tue 22/9

1:00 a.m.-3:22 p.m.

2 stops14h 22m

C$ 632

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 2/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Fri 5/6

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

1 stop19h 54m

C$ 865

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 27/6

7:45 p.m.-4:05 p.m.

2 stops20h 20m

Punta Cana

Sat 4/7

5:05 p.m.-3:22 p.m.

2 stops22h 17m

C$ 898

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 6/6

10:05 a.m.-4:30 p.m.

2 stops30h 25m

Punta Cana

Wed 10/6

5:25 p.m.-3:46 p.m.

3 stops22h 21m

C$ 951

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 9/6

10:05 a.m.-9:24 p.m.

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Mon 15/6

1:00 a.m.-3:24 p.m.

2 stops14h 24m

C$ 1,250

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 9/6

4:30 p.m.-2:34 p.m.

3 stops22h 04m

San Juan Luis Munoz Marin Intl

Tue 16/6

4:30 p.m.-3:46 p.m.

3 stops23h 16m

C$ 1,261

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 27/6

7:45 p.m.-3:15 p.m.

1 stop19h 30m

Punta Cana

Wed 8/7

4:25 p.m.-7:02 p.m.

1 stop26h 37m

C$ 1,288

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Wed 10/6

10:05 a.m.-9:24 p.m.

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Wed 17/6

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

2 stops11h 29m

C$ 1,415

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 8/6

10:05 a.m.-9:24 p.m.

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Sun 14/6

2:05 a.m.-3:25 p.m.

2 stops13h 20m

C$ 1,439

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/5

Showing 1-10 of 17 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 15 May 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
7.8
Good
552 reviews
Check prices

Food

6.8

Crew

8.5

Overall

7.8

Entertainment

7.1

Boarding

7.9

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
7.8
Good
552 reviews
Air Transat
7.8
Good
552 reviews
Check prices

Food

6.8

Crew

8.5

Overall

7.8

Entertainment

7.1

Boarding

7.9

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
11,042 reviews
Air Transat
7.8
Good
552 reviews
Check prices

Food

6.8

Crew

8.5

Overall

7.8

Entertainment

7.1

Boarding

7.9

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 20h 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 - San Juan Luis Munoz Marin Intl, Windsor - Montego Bay Sangster Intl or Windsor - Punta Cana 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 15 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 581AverageC$ 988FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 724AverageC$ 892FlexibilityNo 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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