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Cheap flights from Windsor, ON to Caribbean Islands from C$ 294

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 31/5. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
16 May — 23 May1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Caribbean Islands
Explore the most affordable flight options available from Windsor to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 April 2026.

Mon 1/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Fri 5/612:30 p.m.
MBJ
-
YQG
1 stop25h 54m
Air Canada
Deal found 14/4C$ 484
Thu 28/57:45 p.m.
YQG
-
PUJ
2 stops18h 10m
Air Canada
Thu 4/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 15/4C$ 501
Sat 1/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 5/812:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 12/4C$ 523
Tue 2/64:05 p.m.
YQG
-
PUJ
1 stop23h 20m
Air Canada
Sun 7/64:25 p.m.
PUJ
-
YQG
1 stop16h 59m
Air Canada
Deal found 13/4C$ 528
Tue 16/610:05 a.m.
YQG
-
PUJ
1 stop29h 20m
Air Canada
Sat 20/64:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 13/4C$ 531
Tue 22/94:05 p.m.
YQG
-
SJU
2 stops23h 37m
Air Canada
Thu 24/91:05 a.m.
SJU
-
YQG
2 stops14h 17m
Air Canada
Deal found 12/4C$ 1,014
Sat 1/84:00 p.m.
YQG
-
MBJ
2 stops27h 30m
WestJet
Wed 5/812:45 p.m.
MBJ
-
YQG
2 stops49h 25m
WestJet
Deal found 12/4C$ 1,421
Sun 22/119:45 a.m.
YQG
-
SJU
2 stops26h 04m
Air Canada
Wed 25/112:05 a.m.
SJU
-
YQG
2 stops18h 09m
Air Canada
Deal found 14/4C$ 1,455
Fri 1/510:05 a.m.
YQG
-
SJU
2 stops11h 19m
Air Canada
Sun 3/51:00 a.m.
SJU
-
YQG
2 stops14h 24m
Air Canada
Deal found 15/4C$ 1,824

Find flight deals from Windsor to Caribbean Islands

Keep the following information in mind while searching for Windsor to Caribbean Islands flight deals. Data was last updated 16 April 2026.

Round-trip from

C$ 484

One-way from

C$ 294
Air Canada
  • Air Canada
  • 1/6-5/6
  • 2 total stops
  • 46h 09m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 31/5
  • 1 total stop
  • 19h 40m total
  • Windsor to Caribbean Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Windsor to Caribbean Islands 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 April 2026.
Use the filters below to find and compare flights from Windsor to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 1/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Fri 5/6

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 484

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 28/5

7:45 p.m.-1:55 p.m.

2 stops18h 10m

Punta Cana

Thu 4/6

4:25 p.m.-3:24 p.m.

1 stop22h 59m

C$ 501

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 1/8

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

1 stop16h 35m

Montego Bay Sangster Intl

Wed 5/8

12:30 p.m.-3:22 p.m.

1 stop25h 52m

C$ 523

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 16/6

10:05 a.m.-3:25 p.m.

1 stop29h 20m

Punta Cana

Sat 20/6

4:20 p.m.-9:22 a.m.

1 stop17h 02m

C$ 531

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 3/6

7:45 p.m.-3:25 p.m.

1 stop19h 40m

Punta Cana

Tue 9/6

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

2 stops21h 59m

C$ 534

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 2/6

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

2 stops20h 45m

Punta Cana

Sun 7/6

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

2 stops21h 59m

C$ 538

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 22/9

10:05 a.m.-12:54 p.m.

2 stops26h 49m

San Juan Luis Munoz Marin Intl

Thu 24/9

1:05 a.m.-3:22 p.m.

2 stops14h 17m

C$ 1,014

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 1/8

4:00 p.m.-6:30 p.m.

2 stops27h 30m

Montego Bay Sangster Intl

Wed 5/8

12:45 p.m.-3:10 p.m.

2 stops49h 25m

C$ 1,421
Quickest round-trip

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Fri 1/5

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

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Sun 3/5

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

2 stops14h 24m

C$ 1,824
Cheapest one-way

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 31/5

7:45 p.m.-3:25 p.m.

1 stop19h 40m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/4

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Windsor to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 16 April 2026.
Check out reviews from past customers who have flown with Air Transat and Air Canada from Windsor to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.7
Good
536 reviews
Check prices

Overall

7.7

Boarding

7.9

Entertainment

7.0

Food

6.8

Comfort

7.3

Crew

8.4

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
536 reviews
Air Transat
7.7
Good
536 reviews
Check prices

Overall

7.7

Boarding

7.9

Entertainment

7.0

Food

6.8

Comfort

7.3

Crew

8.4

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
10,932 reviews
Air Transat
7.7
Good
536 reviews
Check prices

Overall

7.7

Boarding

7.9

Entertainment

7.0

Food

6.8

Comfort

7.3

Crew

8.4

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 Islands. 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 Islands?

    Windsor (YQG), located 8.0 km from the city centre, is the airport you fly out of when you book flights from Windsor to Caribbean Islands.

  • How long is the flight from Windsor, Ontario to Caribbean Islands?

    For as low as C$ 484, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 16h 35m. Windsor, Ontario and Caribbean Islands are separated by a distance of 2683 km.

  • What are the most popular routes from Windsor, Ontario to Caribbean Islands?

    The most popular flight routes from Windsor, Ontario to Caribbean Islands are Windsor - Punta Cana, Windsor - Montego Bay Sangster Intl and Windsor - San Juan Luis Munoz Marin Intl.

  • Can I find deals for flights from Windsor to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Windsor to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Windsor to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Windsor to Caribbean Islands.

  • Can I find deals for business class flights from Windsor to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Windsor to Caribbean Islands 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 Islands

Discover the top 2 airlines that operate flights from Windsor to Caribbean Islands. 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 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 480AverageC$ 763FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 722AverageC$ 890FlexibilityNo 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 Islands?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Windsor to Caribbean Islands. 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 Islands?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean Islands from Windsor.

Can Cheapflights find flights from Windsor to Caribbean Islands with no change fees?

Certainly. Search results for flights to Caribbean Islands from Windsor shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Windsor to Caribbean Islands become cheaper?

Yes, Cheapflights offers price alerts on Windsor to Caribbean Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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