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Cheap flights from Windsor, ON to Caribbean from C$ 369

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
21 Jul — 28 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 21 June 2026.

Sat 19/97:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Tue 22/912:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 19/6C$ 624
Sat 26/94:05 p.m.
YQG
-
SJU
2 stops21h 40m
Air Canada
Mon 28/91:00 a.m.
SJU
-
YQG
2 stops18h 02m
Air Canada
Deal found 20/6C$ 633
Sun 27/97:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Thu 1/1012:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 16/6C$ 634
Sat 19/910:05 a.m.
YQG
-
SJU
2 stops26h 49m
Air Canada
Mon 21/91:00 a.m.
SJU
-
YQG
2 stops18h 07m
Air Canada
Deal found 17/6C$ 637
Mon 3/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Mon 10/84:20 p.m.
PUJ
-
YQG
1 stop26h 42m
Air Canada
Deal found 19/6C$ 698
Sat 4/77:45 p.m.
YQG
-
PUJ
1 stop19h 30m
Air Canada
Mon 13/74:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 16/6C$ 700
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 19/6C$ 703
Sun 25/109:45 a.m.
YQG
-
PUJ
1 stop28h 05m
Air Canada
Thu 29/106:35 p.m.
PUJ
-
YQG
1 stop14h 34m
Air Canada
Deal found 16/6C$ 747
Tue 23/64:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sat 27/612:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 18/6C$ 971
Sat 19/94:00 p.m.
YQG
-
MBJ
2 stops20h 45m
Multiple Airlines
Tue 22/912:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Multiple Airlines
Deal found 19/6C$ 1,020
Mon 3/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Mon 10/812:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 18/6C$ 1,043
Sat 18/77:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sat 25/712:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 19/6C$ 1,084

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 21 June 2026.

Round-trip from

C$ 624

One-way from

C$ 369
Air Canada
  • Air Canada
  • 19/9-22/9
  • 2 total stops
  • 36h 27m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 15/7
  • 1 total stop
  • 19h 30m 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 21 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

Sat 26/9

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

2 stops25h 52m

San Juan Luis Munoz Marin Intl

Mon 28/9

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

2 stops14h 22m

C$ 633

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 27/9

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

1 stop16h 35m

Montego Bay Sangster Intl

Thu 1/10

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

1 stop19h 52m

C$ 634

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-12:54 p.m.

2 stops26h 49m

San Juan Luis Munoz Marin Intl

Mon 21/9

1:00 a.m.-7:07 p.m.

2 stops18h 07m

C$ 637

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 4/7

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

1 stop19h 30m

Punta Cana

Mon 13/7

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

1 stop17h 02m

C$ 700

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 3/8

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

2 stops20h 20m

Punta Cana

Mon 10/8

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

1 stop17h 02m

C$ 702

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$ 705

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 15/9

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

1 stop23h 20m

Punta Cana

Tue 29/9

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

1 stop23h 02m

C$ 709

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 25/10

9:45 a.m.-1:50 p.m.

1 stop28h 05m

Punta Cana

Thu 29/10

6:35 p.m.-9:09 a.m.

1 stop14h 34m

C$ 747

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 19/9

4:00 p.m.-11:45 a.m.

2 stops20h 45m

Montego Bay Sangster Intl

Tue 22/9

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

1 stop25h 52m

C$ 1,020

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 3/8

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

1 stop16h 35m

Montego Bay Sangster Intl

Mon 10/8

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

1 stop25h 52m

C$ 1,043

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/6

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 21 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
556 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Overall

7.8

Food

6.8

Boarding

7.9

Crew

8.5

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
556 reviews
Air Transat
7.8
Good
556 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Overall

7.8

Food

6.8

Boarding

7.9

Crew

8.5

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
11,238 reviews
Air Transat
7.8
Good
556 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Overall

7.8

Food

6.8

Boarding

7.9

Crew

8.5

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 25h 52m. 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 - 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 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 21 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 745AverageC$ 946FlexibilityNo 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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