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Cheap flights from Windsor, ON to Caribbean from C$ 371

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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
25 Mar — 1 Apr1
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 23 February 2026.

Thu 27/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Tue 1/912:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 21/2C$ 659
Sat 28/39:40 a.m.
YQG
-
MBJ
2 stops32h 10m
Air Canada
Tue 31/32:30 p.m.
MBJ
-
YQG
1 stop17h 34m
Air Canada
Deal found 20/2C$ 788
Tue 24/37:50 p.m.
YQG
-
MBJ
1 stop16h 40m
Air Canada
Tue 7/412:30 p.m.
MBJ
-
YQG
1 stop19h 34m
Air Canada
Deal found 22/2C$ 806
Sat 21/39:40 a.m.
YQG
-
MBJ
2 stops32h 25m
Air Canada
Sat 28/32:05 p.m.
MBJ
-
YQG
1 stop17h 59m
Air Canada
Deal found 21/2C$ 812
Thu 5/39:40 a.m.
YQG
-
PUJ
1 stop11h 05m
Air Canada
Thu 12/39:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 20/2C$ 833
Sat 7/39:40 a.m.
YQG
-
PUJ
1 stop24h 25m
Air Canada
Wed 11/39:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 20/2C$ 834
Thu 26/27:50 p.m.
YQG
-
PUJ
1 stop15h 25m
Air Canada
Thu 5/310:35 p.m.
PUJ
-
YQG
1 stop21h 39m
Air Canada
Deal found 19/2C$ 847
Mon 23/37:50 p.m.
YQG
-
PUJ
1 stop15h 15m
Air Canada
Tue 31/34:45 p.m.
PUJ
-
YQG
1 stop26h 24m
Air Canada
Deal found 19/2C$ 873
Wed 3/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 10/612:15 p.m.
MBJ
-
YQG
1 stop26h 09m
Air Canada
Deal found 20/2C$ 889
Sat 21/39:40 a.m.
YQG
-
PUJ
1 stop27h 05m
Air Canada
Sat 28/311:50 a.m.
PUJ
-
YQG
2 stops21h 14m
Air Canada
Deal found 21/2C$ 889
Fri 27/29:45 a.m.
YQG
-
PUJ
1 stop11h 00m
Air Canada
Fri 6/310:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 22/2C$ 905
Mon 2/37:50 p.m.
YQG
-
SJU
2 stops24h 10m
Air Canada
Tue 3/32:05 a.m.
SJU
-
YQG
2 stops31h 59m
Air Canada
Deal found 19/2C$ 997

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 23 February 2026.

Round-trip from

C$ 788

One-way from

C$ 371
Air Canada
  • Air Canada
  • 28/3-31/3
  • 3 total stops
  • 49h 44m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 6/4
  • 1 total stop
  • 18h 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 23 February 2026.
Use the filters below to find and compare flights from Windsor to Caribbean that are best for you.

Fly from

Windsor

Fly to

Caribbean

Route

Depart

Return

Price

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 28/3

7:50 p.m.-4:50 p.m.

2 stops22h 00m

Montego Bay Sangster Intl

Tue 31/3

12:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 789

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 24/3

7:50 p.m.-11:30 a.m.

1 stop16h 40m

Montego Bay Sangster Intl

Tue 7/4

12:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 806

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 5/3

9:40 a.m.-9:45 p.m.

1 stop11h 05m

Punta Cana

Thu 12/3

9:35 p.m.-9:04 a.m.

1 stop11h 29m

C$ 833

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 23/3

7:50 p.m.-11:05 a.m.

1 stop15h 15m

Punta Cana

Tue 31/3

4:45 p.m.-7:09 p.m.

1 stop26h 24m

C$ 873

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 7/3

7:50 p.m.-8:35 p.m.

1 stop23h 45m

Punta Cana

Wed 11/3

12:05 p.m.-9:04 a.m.

1 stop20h 59m

C$ 884

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 3/6

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

1 stop16h 35m

Montego Bay Sangster Intl

Wed 10/6

12:15 p.m.-3:24 p.m.

1 stop26h 09m

C$ 889

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 9/4

7:45 p.m.-8:30 p.m.

1 stop24h 45m

Punta Cana

Thu 16/4

9:40 p.m.-9:04 a.m.

1 stop11h 24m

C$ 971

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 23/3

7:35 a.m.-6:55 p.m.

2 stops11h 20m

Punta Cana

Tue 31/3

7:10 p.m.-7:09 p.m.

3 stops23h 59m

C$ 1,003

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 9/3

7:50 p.m.-1:30 p.m.

1 stop18h 40m

Montego Bay Sangster Intl

Mon 16/3

12:40 p.m.-9:04 a.m.

1 stop19h 24m

C$ 1,100

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sat 21/3

7:35 a.m.-11:05 a.m.

3 stops28h 30m

Montego Bay Sangster Intl

Sat 28/3

2:05 p.m.-7:09 p.m.

1 stop28h 04m

C$ 1,124

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 24 results
1
2
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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 23 February 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 23 February 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
511 reviews
Check prices

Food

6.8

Comfort

7.3

Boarding

7.9

Crew

8.4

Entertainment

7.0

Overall

7.7

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
511 reviews
Air Transat
7.7
Good
511 reviews
Check prices

Food

6.8

Comfort

7.3

Boarding

7.9

Crew

8.4

Entertainment

7.0

Overall

7.7

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
10,739 reviews
Air Transat
7.7
Good
511 reviews
Check prices

Food

6.8

Comfort

7.3

Boarding

7.9

Crew

8.4

Entertainment

7.0

Overall

7.7

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 32h 10m. 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 - 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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Alternative routes for Windsor to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 23 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 478AverageC$ 758FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 720AverageC$ 888FlexibilityNo 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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