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Cheap flights from Windsor, ON to Caribbean from C$ 289

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 19/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
5 Jul — 12 Jul1
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 5 June 2026.

Sun 19/74:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Fri 24/712:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 4/6C$ 569
Mon 15/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Fri 19/612:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 1/6C$ 589
Wed 9/129:45 a.m.
YQG
-
MBJ
2 stops51h 05m
Air Canada
Sun 13/123:55 p.m.
MBJ
-
YQG
2 stops27h 19m
Air Canada
Deal found 3/6C$ 612
Sat 21/119:45 a.m.
YQG
-
PUJ
1 stop10h 55m
Air Canada
Sat 28/117:35 p.m.
PUJ
-
YQG
1 stop24h 39m
Air Canada
Deal found 1/6C$ 621
Mon 26/107:50 p.m.
YQG
-
SJU
2 stops27h 46m
Air Canada
Fri 30/107:30 a.m.
SJU
-
YQG
2 stops25h 39m
Air Canada
Deal found 4/6C$ 631
Tue 22/910:05 a.m.
YQG
-
SJU
2 stops25h 52m
Air Canada
Fri 25/91:00 a.m.
SJU
-
YQG
2 stops14h 22m
Air Canada
Deal found 2/6C$ 634
Fri 14/84:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sat 29/812:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 2/6C$ 652
Wed 9/129:45 a.m.
YQG
-
PUJ
1 stop10h 55m
Air Canada
Sun 13/123:30 p.m.
PUJ
-
YQG
1 stop28h 44m
Air Canada
Deal found 3/6C$ 673
Sat 12/910:05 a.m.
YQG
-
PUJ
1 stop29h 20m
Air Canada
Tue 15/94:20 p.m.
PUJ
-
YQG
1 stop23h 02m
Air Canada
Deal found 1/6C$ 687
Sun 19/77:45 p.m.
YQG
-
MBJ
2 stops37h 40m
Multiple Airlines
Fri 24/712:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Multiple Airlines
Deal found 4/6C$ 695
Mon 19/107:45 p.m.
YQG
-
PUJ
1 stop19h 35m
Air Canada
Thu 22/104:20 p.m.
PUJ
-
YQG
1 stop23h 02m
Air Canada
Deal found 4/6C$ 720
Sun 19/74:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sun 26/712:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 3/6C$ 780

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 5 June 2026.

Round-trip from

C$ 569

One-way from

C$ 289
Air Canada
  • Air Canada
  • 19/7-24/7
  • 2 total stops
  • 40h 07m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 19/7
  • 1 total stop
  • 16h 35m 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 5 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
Quickest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 15/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Fri 19/6

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

1 stop19h 52m

C$ 589

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 21/11

9:45 a.m.-11:35 p.m.

2 stops12h 50m

Punta Cana

Sat 28/11

7:35 p.m.-7:14 p.m.

1 stop24h 39m

C$ 626

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 26/10

7:50 p.m.-11:36 p.m.

2 stops27h 46m

San Juan Luis Munoz Marin Intl

Fri 30/10

7:30 a.m.-9:09 a.m.

2 stops25h 39m

C$ 631

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 22/9

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

2 stops25h 52m

San Juan Luis Munoz Marin Intl

Fri 25/9

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

2 stops14h 22m

C$ 634

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 14/8

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

1 stop20h 15m

Montego Bay Sangster Intl

Sat 29/8

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

1 stop19h 52m

C$ 652

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 12/9

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

1 stop29h 20m

Punta Cana

Tue 15/9

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

1 stop23h 02m

C$ 687

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 19/7

7:45 p.m.-8:25 a.m.

2 stops37h 40m

Montego Bay Sangster Intl

Fri 24/7

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

1 stop19h 52m

C$ 695

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 19/10

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

1 stop19h 35m

Punta Cana

Thu 22/10

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

1 stop23h 02m

C$ 720

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 15/6

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

2 stops20h 45m

Punta Cana

Fri 19/6

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

2 stops22h 17m

C$ 778

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 19/7

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

1 stop20h 15m

Montego Bay Sangster Intl

Sun 26/7

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

1 stop19h 52m

C$ 780

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 22 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 5 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
554 reviews
Check prices

Crew

8.5

Overall

7.8

Entertainment

7.1

Food

6.8

Boarding

7.9

Comfort

7.3

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
554 reviews
Air Transat
7.8
Good
554 reviews
Check prices

Crew

8.5

Overall

7.8

Entertainment

7.1

Food

6.8

Boarding

7.9

Comfort

7.3

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
11,127 reviews
Air Transat
7.8
Good
554 reviews
Check prices

Crew

8.5

Overall

7.8

Entertainment

7.1

Food

6.8

Boarding

7.9

Comfort

7.3

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 20h 15m. The distance between Windsor, Ontario and Caribbean is about 2683 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 - Montego Bay Sangster Intl, Windsor - Punta Cana 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 2 airlines flying from Windsor to Caribbean

Discover the top 2 airlines 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 5 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 587AverageC$ 999FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 732AverageC$ 930FlexibilityNo 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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