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Cheap flights from Windsor, ON to Caribbean Islands from C$ 319

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
28 Aug — 4 Sep1
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 29 July 2026.

Sun 22/1110:35 a.m.
YQG
-
PUJ
1 stop10h 05m
Air Canada
Sun 29/1110:40 p.m.
PUJ
-
YQG
1 stop21h 05m
Air Canada
Deal found 27/7C$ 494
Sat 21/117:20 p.m.
YQG
-
PUJ
2 stops17h 25m
Air Canada
Sun 29/1110:40 p.m.
PUJ
-
YQG
1 stop21h 05m
Air Canada
Deal found 27/7C$ 499
Sat 21/117:20 p.m.
YQG
-
PUJ
2 stops17h 25m
Air Canada
Sat 28/117:45 p.m.
PUJ
-
YQG
2 stops24h 00m
Air Canada
Deal found 27/7C$ 504
Tue 1/1210:35 a.m.
YQG
-
PUJ
1 stop7h 00m
Air Canada
Tue 8/1210:40 p.m.
PUJ
-
YQG
1 stop12h 15m
Air Canada
Deal found 24/7C$ 604
Thu 10/97:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 17/94:20 p.m.
PUJ
-
YQG
1 stop26h 42m
Air Canada
Deal found 27/7C$ 610
Sat 19/910:05 a.m.
YQG
-
SJU
2 stops25h 52m
Air Canada
Wed 23/93:00 p.m.
SJU
-
YQG
2 stops24h 22m
Air Canada
Deal found 27/7C$ 632
Mon 14/97:45 p.m.
YQG
-
SJU
2 stops28h 05m
Air Canada
Thu 17/92:55 p.m.
SJU
-
YQG
2 stops24h 27m
Air Canada
Deal found 25/7C$ 633
Sat 19/97:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 24/94:20 p.m.
PUJ
-
YQG
1 stop23h 02m
Air Canada
Deal found 25/7C$ 694
Sat 12/910:05 a.m.
YQG
-
MBJ
1 stop26h 15m
Air Canada
Sat 19/912:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 28/7C$ 828
Sat 12/94:00 p.m.
YQG
-
MBJ
2 stops20h 45m
WestJet
Sat 19/97:30 p.m.
MBJ
-
YQG
2 stops42h 40m
WestJet
Deal found 28/7C$ 1,414
Sat 12/94:00 p.m.
YQG
-
MBJ
2 stops24h 45m
Multiple Airlines
Sat 19/97:30 p.m.
MBJ
-
YQG
2 stops19h 16m
Multiple Airlines
Deal found 28/7C$ 1,457

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 29 July 2026.

Round-trip from

C$ 610

One-way from

C$ 319
Air Canada
  • Air Canada
  • 10/9-17/9
  • 2 total stops
  • 46h 22m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 10/9
  • 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 29 July 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

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 22/11

7:20 p.m.-12:10 p.m.

1 stop15h 50m

Punta Cana

Sun 29/11

3:15 p.m.-9:55 a.m.

2 stops19h 40m

C$ 499

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 21/11

7:20 p.m.-9:40 p.m.

1 stop25h 20m

Punta Cana

Sat 28/11

10:40 p.m.-6:45 p.m.

1 stop21h 05m

C$ 552

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 21/11

7:20 p.m.-1:45 p.m.

2 stops17h 25m

Punta Cana

Sun 29/11

7:45 p.m.-6:45 p.m.

2 stops24h 00m

C$ 562
Quickest round-trip

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 1/12

10:35 a.m.-6:35 p.m.

1 stop7h 00m

Punta Cana

Tue 8/12

10:40 p.m.-9:55 a.m.

1 stop12h 15m

C$ 604

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-11:57 a.m.

2 stops25h 52m

San Juan Luis Munoz Marin Intl

Wed 23/9

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

2 stops24h 22m

C$ 632

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 14/9

4:05 p.m.-1:53 p.m.

2 stops21h 48m

San Juan Luis Munoz Marin Intl

Thu 17/9

2:20 p.m.-7:02 p.m.

2 stops28h 42m

C$ 633

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 21/1

10:35 a.m.-9:40 p.m.

1 stop10h 05m

Punta Cana

Thu 28/1

10:40 p.m.-9:55 a.m.

1 stop12h 15m

C$ 666

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 15/1

7:20 p.m.-1:45 p.m.

2 stops17h 25m

Punta Cana

Fri 29/1

10:40 p.m.-9:55 a.m.

1 stop12h 15m

C$ 693

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 19/9

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

1 stop19h 40m

Punta Cana

Thu 24/9

4:20 p.m.-3:22 p.m.

1 stop23h 02m

C$ 694

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 12/9

4:00 p.m.-11:45 a.m.

2 stops20h 45m

Montego Bay Sangster Intl

Sat 19/9

7:30 p.m.-3:10 p.m.

2 stops42h 40m

C$ 1,414

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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 29 July 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
7.8
Good
568 reviews
Check prices

Crew

8.5

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Transat
7.8
Good
568 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Crew

8.5

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Canada
7.1
Good
11,404 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Crew

8.5

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus

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$ 494, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 10h 05m. Windsor, Ontario and Caribbean Islands are separated by a distance of 2972 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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 airline flying from Windsor to Caribbean Islands

Discover the top airline 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 29 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 743AverageC$ 944FlexibilityNo 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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