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Cheap flights from Windsor, ON to Caribbean from C$ 360

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
17 Sep — 24 Sep1
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 18 August 2026.

Mon 30/1110:35 a.m. -
1 stop26h 15m
Sat 5/121:05 p.m. -
1 stop21h 50m
Deal found 16/8C$ 509
Sat 31/1010:35 a.m. -
1 stop6h 45m
Tue 3/111:50 p.m. -
1 stop28h 55m
Deal found 16/8C$ 509
Sat 31/107:20 p.m. -
1 stop26h 20m
Tue 3/113:30 p.m. -
1 stop19h 25m
Deal found 16/8C$ 512
Mon 7/1210:35 a.m. -
2 stops24h 15m
Tue 8/122:05 a.m. -
2 stops17h 40m
Deal found 14/8C$ 650
Sat 15/87:45 p.m. -
2 stops20h 25m
Mon 31/812:52 p.m. -
2 stops25h 30m
Deal found 14/8C$ 2,217

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 18 August 2026.

Round-trip from

C$ 509

One-way from

C$ 360
Air Canada
  • Air Canada
  • 30/11-5/12
  • 2 total stops
  • 48h 05m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 12/9
  • 1 total stop
  • 27h 00m 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 18 August 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 Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Mon 30/11

10:35 a.m.-1:50 p.m.

1 stop26h 15m

Punta Cana

Sat 5/12

1:05 p.m.-9:55 a.m.

1 stop21h 50m

C$ 509
Quickest round-trip

WindsorMontego Bay

YQG Windsor - MBJ Montego Bay Sangster Intl

YQGMBJ

Windsor

Sat 31/10

10:35 a.m.-4:20 p.m.

1 stop6h 45m

Montego Bay Sangster Intl

Tue 3/11

1:50 p.m.-6:45 p.m.

1 stop28h 55m

C$ 509

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Sat 31/10

7:20 p.m.-1:50 p.m.

1 stop18h 30m

Punta Cana

Tue 3/11

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

1 stop21h 05m

C$ 513

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Thu 15/10

7:45 p.m.-3:20 p.m.

1 stop19h 35m

Punta Cana

Sat 24/10

5:05 p.m.-6:45 p.m.

2 stops25h 40m

C$ 623

WindsorSan Juan

YQG Windsor - SJU San Juan Luis Munoz Marin Intl

YQGSJU

Windsor

Mon 7/12

10:35 a.m.-11:50 a.m.

2 stops24h 15m

San Juan Luis Munoz Marin Intl

Tue 8/12

2:05 a.m.-6:45 p.m.

2 stops17h 40m

C$ 650

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Wed 30/9

7:45 p.m.-3:20 p.m.

1 stop19h 35m

Punta Cana

Wed 7/10

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

1 stop17h 02m

C$ 745

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Tue 15/9

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

1 stop23h 20m

Punta Cana

Tue 22/9

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

1 stop17h 02m

C$ 747

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Sat 31/10

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

2 stops12h 00m

Punta Cana

Tue 3/11

8:00 p.m.-6:51 p.m.

3 stops23h 51m

C$ 753
Cheapest one-way

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Sat 12/9

10:05 a.m.-1:05 p.m.

1 stop27h 00m

C$ 360

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Sun 20/9

7:45 p.m.-11:55 a.m.

1 stop16h 10m

C$ 384

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

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 18 August 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
572 reviews
Check prices

Comfort

7.3

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

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
572 reviews
Air Transat
7.8
Good
572 reviews
Check prices

Comfort

7.3

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

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
11,493 reviews
Air Transat
7.8
Good
572 reviews
Check prices

Comfort

7.3

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

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. 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 26h 15m. 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 - San Juan Luis Munoz Marin Intl or Windsor - Montego Bay Sangster 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 airline flying from Windsor to Caribbean

Discover the top airline 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 18 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 730AverageC$ 900FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

Fly with Cheapflights

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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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