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Cheap flights from Windsor, ON to Caribbean from C$ 363

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
30 Jul — 6 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 30 June 2026.

Fri 11/127:20 p.m.
YQG
-
SJU
2 stops18h 20m
Air Canada
Sat 19/123:35 p.m.
SJU
-
YQG
2 stops19h 20m
Air Canada
Deal found 28/6C$ 503
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 25/6C$ 632
Sat 10/104:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sat 7/116:20 p.m.
MBJ
-
YQG
1 stop24h 25m
Air Canada
Deal found 27/6C$ 662
Mon 6/74:05 p.m.
YQG
-
PUJ
1 stop23h 10m
Air Canada
Mon 13/712:55 p.m.
PUJ
-
YQG
1 stop26h 27m
Air Canada
Deal found 29/6C$ 697
Wed 15/77:45 p.m.
YQG
-
PUJ
2 stops20h 20m
Air Canada
Sun 19/74:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 28/6C$ 699
Wed 22/74:05 p.m.
YQG
-
PUJ
1 stop23h 10m
Air Canada
Sun 26/74:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 27/6C$ 700
Tue 4/84:05 p.m.
YQG
-
PUJ
2 stops24h 00m
Air Canada
Sun 9/85:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 29/6C$ 708
Fri 4/97:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Mon 7/94:20 p.m.
PUJ
-
YQG
1 stop23h 02m
Air Canada
Deal found 28/6C$ 718
Wed 12/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Wed 19/84:25 p.m.
PUJ
-
YQG
1 stop22h 57m
Air Canada
Deal found 27/6C$ 745
Sat 4/77:45 p.m.
YQG
-
PUJ
1 stop19h 30m
Air Canada
Sun 11/49:40 p.m.
PUJ
-
YQG
1 stop20h 59m
Air Canada
Deal found 27/6C$ 748
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 29/6C$ 1,085
Tue 7/77:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 22/712:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 27/6C$ 1,163

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 30 June 2026.

Round-trip from

C$ 503

One-way from

C$ 363
Air Canada
  • Air Canada
  • 11/12-19/12
  • 4 total stops
  • 37h 40m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 12/8
  • 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 30 June 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 11/12

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

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Sat 19/12

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

2 stops19h 20m

C$ 503

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$ 632

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 10/10

4:05 p.m.-11:20 a.m.

1 stop20h 15m

Montego Bay Sangster Intl

Sat 7/11

6:20 p.m.-6:45 p.m.

1 stop24h 25m

C$ 662

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 6/7

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

1 stop23h 10m

Punta Cana

Mon 13/7

12:55 p.m.-3:22 p.m.

1 stop26h 27m

C$ 697

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 22/7

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

1 stop19h 30m

Punta Cana

Sun 26/7

4:20 p.m.-7:02 p.m.

1 stop26h 42m

C$ 699

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 3/8

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

2 stops20h 20m

Punta Cana

Sun 9/8

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

1 stop17h 02m

C$ 701

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 4/9

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

1 stop19h 40m

Punta Cana

Mon 7/9

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

1 stop23h 02m

C$ 718

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 4/7

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

1 stop19h 30m

Punta Cana

Sun 11/4

9:40 p.m.-6:39 p.m.

1 stop20h 59m

C$ 748
Quickest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 15/8

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

1 stop16h 35m

Montego Bay Sangster Intl

Sun 30/8

12:30 p.m.-9:22 a.m.

1 stop19h 52m

C$ 1,085

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 15/8

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

2 stops27h 30m

Montego Bay Sangster Intl

Sun 30/8

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

2 stops18h 40m

C$ 1,674

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/6

Showing 1-10 of 14 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 30 June 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
559 reviews
Check prices

Overall

7.8

Comfort

7.3

Entertainment

7.1

Crew

8.5

Boarding

8.0

Food

6.8

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
559 reviews
Air Transat
7.8
Good
559 reviews
Check prices

Overall

7.8

Comfort

7.3

Entertainment

7.1

Crew

8.5

Boarding

8.0

Food

6.8

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
11,271 reviews
Air Transat
7.8
Good
559 reviews
Check prices

Overall

7.8

Comfort

7.3

Entertainment

7.1

Crew

8.5

Boarding

8.0

Food

6.8

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 18h 20m. The distance between Windsor, Ontario and Caribbean is about 3095 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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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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 30 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 748AverageC$ 950FlexibilityNo 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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