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Cheap flights from Windsor, ON to Caribbean from C$ 304

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 25/5. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
10 May — 17 May1
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 10 April 2026.

Fri 17/47:45 p.m.
YQG
-
PUJ
1 stop19h 45m
Air Canada
Fri 24/42:35 p.m.
PUJ
-
YQG
2 stops28h 34m
Air Canada
Deal found 10/4C$ 552
Tue 2/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sat 6/612:30 p.m.
MBJ
-
YQG
1 stop25h 54m
Air Canada
Deal found 5/4C$ 553
Mon 25/57:45 p.m.
YQG
-
PUJ
2 stops18h 10m
Air Canada
Mon 1/65:25 p.m.
PUJ
-
YQG
2 stops21h 59m
Air Canada
Deal found 10/4C$ 561
Mon 1/64:05 p.m.
YQG
-
PUJ
1 stop23h 20m
Air Canada
Mon 8/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 10/4C$ 563
Sat 1/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 5/812:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 9/4C$ 586
Tue 9/67:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 11/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 6/4C$ 608
Sun 7/67:45 p.m.
YQG
-
PUJ
1 stop16h 10m
Air Canada
Thu 11/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 5/4C$ 611
Sun 29/119:45 a.m.
YQG
-
MBJ
1 stop6h 50m
Air Canada
Fri 4/122:40 p.m.
MBJ
-
YQG
1 stop18h 29m
Air Canada
Deal found 7/4C$ 697
Thu 26/119:45 a.m.
YQG
-
MBJ
1 stop26h 55m
Air Canada
Thu 3/122:15 p.m.
MBJ
-
YQG
1 stop18h 54m
Air Canada
Deal found 8/4C$ 701
Thu 7/57:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Thu 14/512:30 p.m.
MBJ
-
YQG
1 stop19h 54m
Air Canada
Deal found 9/4C$ 754
Sat 9/57:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Thu 14/512:30 p.m.
MBJ
-
YQG
1 stop25h 54m
Air Canada
Deal found 9/4C$ 803
Sun 10/57:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 13/512:30 p.m.
MBJ
-
YQG
1 stop19h 54m
Air Canada
Deal found 9/4C$ 832

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 10 April 2026.

Round-trip from

C$ 553

One-way from

C$ 304
Air Canada
  • Air Canada
  • 2/6-6/6
  • 2 total stops
  • 42h 29m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 25/5
  • 2 total stops
  • 18h 10m 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 10 April 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

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 2/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Sat 6/6

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 553

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 1/6

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

1 stop23h 20m

Punta Cana

Mon 8/6

4:25 p.m.-3:24 p.m.

1 stop22h 59m

C$ 563

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 1/8

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

1 stop16h 35m

Montego Bay Sangster Intl

Wed 5/8

12:30 p.m.-3:22 p.m.

1 stop25h 52m

C$ 586

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/6

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

1 stop16h 10m

Punta Cana

Thu 11/6

4:25 p.m.-3:24 p.m.

1 stop22h 59m

C$ 611

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 9/6

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

2 stops20h 45m

Punta Cana

Thu 11/6

5:25 p.m.-3:24 p.m.

2 stops21h 59m

C$ 617

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 16/6

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

1 stop29h 20m

Punta Cana

Sat 20/6

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

1 stop17h 02m

C$ 636

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 12/5

10:05 a.m.-11:20 a.m.

1 stop26h 15m

Montego Bay Sangster Intl

Thu 14/5

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 754

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 12/5

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

1 stop20h 15m

Montego Bay Sangster Intl

Fri 15/5

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 925

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

Thu 24/9

1:05 a.m.-7:07 p.m.

2 stops18h 02m

C$ 1,005

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 8/5

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

1 stop20h 15m

Montego Bay Sangster Intl

Sat 16/5

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 1,169

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 18 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 10 April 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
7.7
Good
534 reviews
Check prices

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

Food

6.8

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
7.7
Good
534 reviews
Air Transat
7.7
Good
534 reviews
Check prices

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

Food

6.8

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
10,916 reviews
Air Transat
7.7
Good
534 reviews
Check prices

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

Food

6.8

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 16h 35m. 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 10 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 484AverageC$ 769FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 728AverageC$ 898FlexibilityNo 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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