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Cheap flights from Windsor, ON to Caribbean from C$ 354

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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
10 Aug — 17 Aug1
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 11 July 2026.

Fri 4/127:20 p.m.
YQG
-
SJU
2 stops18h 20m
Air Canada
Sat 12/123:35 p.m.
SJU
-
YQG
2 stops19h 20m
Air Canada
Deal found 10/7C$ 501
Tue 22/94:05 p.m.
YQG
-
SJU
2 stops28h 33m
Air Canada
Wed 23/91:00 a.m.
SJU
-
YQG
2 stops18h 02m
Air Canada
Deal found 8/7C$ 624
Mon 21/97:45 p.m.
YQG
-
SJU
2 stops18h 08m
Air Canada
Fri 25/96:45 p.m.
SJU
-
YQG
2 stops24h 17m
Air Canada
Deal found 7/7C$ 630
Fri 28/84:05 p.m.
YQG
-
PUJ
1 stop23h 20m
Air Canada
Tue 1/94:20 p.m.
PUJ
-
YQG
1 stop26h 42m
Air Canada
Deal found 6/7C$ 645
Fri 28/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Mon 31/85:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 6/7C$ 677
Wed 18/117:20 p.m.
YQG
-
PUJ
1 stop25h 20m
Air Canada
Wed 25/1110:40 p.m.
PUJ
-
YQG
1 stop21h 05m
Air Canada
Deal found 7/7C$ 678
Thu 6/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Wed 12/84:25 p.m.
PUJ
-
YQG
1 stop16h 57m
Air Canada
Deal found 9/7C$ 681
Thu 20/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 27/84:20 p.m.
PUJ
-
YQG
1 stop26h 42m
Air Canada
Deal found 7/7C$ 682
Tue 28/77:45 p.m.
YQG
-
PUJ
1 stop19h 30m
Air Canada
Mon 3/812:55 p.m.
PUJ
-
YQG
1 stop26h 27m
Air Canada
Deal found 7/7C$ 684
Sat 15/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sun 30/812:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 9/7C$ 1,155
Tue 4/87:45 p.m.
YQG
-
SJU
2 stops24h 49m
Air Canada
Sun 9/87:20 a.m.
SJU
-
YQG
2 stops26h 02m
Air Canada
Deal found 10/7C$ 1,257
Sat 15/84:30 p.m.
YQG
-
MBJ
2 stops24h 15m
Multiple Airlines
Sun 30/84:55 p.m.
MBJ
-
YQG
2 stops21h 51m
Multiple Airlines
Deal found 9/7C$ 1,737

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 11 July 2026.

Round-trip from

C$ 501

One-way from

C$ 354
Air Canada
  • Air Canada
  • 4/12-12/12
  • 4 total stops
  • 37h 40m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 6/8
  • 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 11 July 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

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Fri 4/12

7:20 p.m.-2:40 p.m.

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Sat 12/12

3:35 p.m.-9:55 a.m.

2 stops19h 20m

C$ 501

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 22/9

10:05 a.m.-1:53 p.m.

2 stops27h 48m

San Juan Luis Munoz Marin Intl

Wed 23/9

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

2 stops14h 22m

C$ 624

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 21/9

7:45 p.m.-1:53 p.m.

2 stops18h 08m

San Juan Luis Munoz Marin Intl

Fri 25/9

6:45 p.m.-7:02 p.m.

2 stops24h 17m

C$ 630

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 28/8

4:05 p.m.-4:05 p.m.

2 stops24h 00m

Punta Cana

Tue 1/9

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

1 stop17h 02m

C$ 650

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 28/8

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

1 stop19h 40m

Punta Cana

Mon 31/8

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

2 stops22h 17m

C$ 677

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 30/7

4:05 p.m.-3:15 p.m.

1 stop23h 10m

Punta Cana

Tue 4/8

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

1 stop23h 02m

C$ 684

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 28/7

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

1 stop19h 30m

Punta Cana

Mon 3/8

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

2 stops22h 17m

C$ 688

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 10/9

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

1 stop19h 40m

Punta Cana

Sun 13/9

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

2 stops22h 17m

C$ 719

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 18/11

7:20 p.m.-11:35 p.m.

2 stops27h 15m

Punta Cana

Wed 25/11

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

1 stop21h 50m

C$ 720

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 6/8

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

2 stops20h 20m

Punta Cana

Wed 12/8

5:05 p.m.-9:22 a.m.

2 stops16h 17m

C$ 747

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 11 July 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
563 reviews
Check prices

Food

6.8

Boarding

8.0

Comfort

7.3

Crew

8.5

Overall

7.8

Entertainment

7.1

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
563 reviews
Air Transat
7.8
Good
563 reviews
Check prices

Food

6.8

Boarding

8.0

Comfort

7.3

Crew

8.5

Overall

7.8

Entertainment

7.1

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
11,327 reviews
Air Transat
7.8
Good
563 reviews
Check prices

Food

6.8

Boarding

8.0

Comfort

7.3

Crew

8.5

Overall

7.8

Entertainment

7.1

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 18h 20m. The distance between Windsor, Ontario and Caribbean is about 3095 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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Alternative routes for Windsor to Caribbean

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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 11 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 745AverageC$ 947FlexibilityNo 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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