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Cheap flights from Windsor, ON to Caribbean from C$ 392

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
28 Apr — 5 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 29 March 2026.

Mon 15/610:05 a.m.
YQG
-
MBJ
1 stop26h 15m
Air Canada
Wed 17/612:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 28/3C$ 552
Tue 23/610:05 a.m.
YQG
-
MBJ
1 stop26h 15m
Air Canada
Sat 4/712:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 26/3C$ 588
Sat 15/810:05 a.m.
YQG
-
MBJ
1 stop26h 15m
Air Canada
Sun 30/812:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 25/3C$ 599
Tue 29/94:05 p.m.
YQG
-
PUJ
1 stop23h 25m
Air Canada
Sat 3/104:20 p.m.
PUJ
-
YQG
1 stop26h 47m
Air Canada
Deal found 28/3C$ 624
Thu 15/104:05 p.m.
YQG
-
PUJ
1 stop23h 15m
Air Canada
Tue 20/104:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 24/3C$ 667
Thu 15/107:45 p.m.
YQG
-
PUJ
1 stop19h 35m
Air Canada
Wed 21/105:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 24/3C$ 671
Thu 24/97:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sun 4/1012:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 25/3C$ 684
Mon 4/57:45 p.m.
YQG
-
SJU
2 stops24h 53m
Air Canada
Fri 8/56:45 p.m.
SJU
-
YQG
2 stops24h 24m
Air Canada
Deal found 28/3C$ 902
Sun 18/107:45 p.m.
YQG
-
SJU
2 stops28h 12m
Air Canada
Wed 28/101:05 a.m.
SJU
-
YQG
2 stops18h 09m
Air Canada
Deal found 25/3C$ 953
Sat 11/47:35 a.m.
YQG
-
SJU
2 stops15h 29m
Multiple Airlines
Tue 14/45:01 a.m.
SJU
-
YQG
2 stops14h 32m
Multiple Airlines
Deal found 28/3C$ 954
Mon 15/64:00 p.m.
YQG
-
MBJ
2 stops20h 45m
WestJet
Wed 17/612:45 p.m.
MBJ
-
YQG
2 stops25h 25m
WestJet
Deal found 28/3C$ 1,071
Sat 11/47:45 p.m.
YQG
-
SJU
1 stop17h 40m
Air Canada
Tue 14/43:56 p.m.
SJU
-
YQG
2 stops17h 08m
Air Canada
Deal found 28/3C$ 1,510

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 29 March 2026.

Round-trip from

C$ 552

One-way from

C$ 392
Air Canada
  • Air Canada
  • 15/6-17/6
  • 2 total stops
  • 52h 07m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 9/5
  • 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 29 March 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

Mon 15/6

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

1 stop26h 15m

Montego Bay Sangster Intl

Wed 17/6

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

1 stop25h 52m

C$ 552

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 23/6

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

1 stop26h 15m

Montego Bay Sangster Intl

Sat 4/7

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

1 stop19h 52m

C$ 588

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 24/9

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

1 stop16h 35m

Montego Bay Sangster Intl

Sun 4/10

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

1 stop19h 52m

C$ 684

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 10/7

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

2 stops20h 20m

Punta Cana

Fri 17/7

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

2 stops22h 17m

C$ 775

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 4/5

7:45 p.m.-8:38 p.m.

2 stops24h 53m

San Juan Luis Munoz Marin Intl

Fri 8/5

6:45 p.m.-7:09 p.m.

2 stops24h 24m

C$ 902

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 7/5

10:05 a.m.-1:55 p.m.

2 stops27h 50m

Punta Cana

Sun 10/5

2:55 p.m.-3:24 p.m.

2 stops24h 29m

C$ 1,009

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 24/4

7:45 p.m.-8:40 p.m.

1 stop24h 55m

Punta Cana

Fri 1/5

1:01 p.m.-3:24 p.m.

3 stops26h 23m

C$ 1,034

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 15/6

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

2 stops20h 45m

Montego Bay Sangster Intl

Wed 17/6

12:45 p.m.-3:10 p.m.

2 stops25h 25m

C$ 1,071

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 23/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Sat 4/7

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

2 stops42h 40m

C$ 1,342

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 11/4

7:45 p.m.-1:25 p.m.

1 stop17h 40m

San Juan Luis Munoz Marin Intl

Tue 14/4

3:56 p.m.-9:04 a.m.

2 stops17h 08m

C$ 1,510

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

Showing 1-10 of 25 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

What is the cheapest time of day to fly from YQG to CB?

Find hourly flight availability from Windsor to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 March 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Windsor, Ontario to Caribbean as you normally would.

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 29 March 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
527 reviews
Check prices

Food

6.8

Comfort

7.3

Crew

8.4

Overall

7.7

Boarding

7.9

Entertainment

7.0

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
527 reviews
Air Transat
7.7
Good
527 reviews
Check prices

Food

6.8

Comfort

7.3

Crew

8.4

Overall

7.7

Boarding

7.9

Entertainment

7.0

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
10,856 reviews
Air Transat
7.7
Good
527 reviews
Check prices

Food

6.8

Comfort

7.3

Crew

8.4

Overall

7.7

Boarding

7.9

Entertainment

7.0

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 26h 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 29 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 486AverageC$ 773FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 732AverageC$ 902FlexibilityNo 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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