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Cheap flights from Windsor, ON to Caribbean from C$ 361

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

Mon 15/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 17/612:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 19/3C$ 573
Tue 11/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 13/85:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 18/3C$ 663
Fri 27/37:50 p.m.
YQG
-
PUJ
2 stops17h 10m
Air Canada
Tue 31/310:00 p.m.
PUJ
-
YQG
2 stops21h 09m
Air Canada
Deal found 19/3C$ 731
Sun 12/74:05 p.m.
YQG
-
PUJ
1 stop23h 10m
Air Canada
Thu 13/85:05 p.m.
PUJ
-
YQG
2 stops16h 17m
Air Canada
Deal found 20/3C$ 748
Sun 12/77:45 p.m.
YQG
-
PUJ
1 stop19h 30m
Air Canada
Thu 16/74:20 p.m.
PUJ
-
YQG
1 stop26h 47m
Air Canada
Deal found 20/3C$ 753
Sun 29/37:45 p.m.
YQG
-
PUJ
1 stop17h 00m
Air Canada
Sun 5/47:05 p.m.
PUJ
-
YQG
2 stops37h 59m
Air Canada
Deal found 22/3C$ 816
Fri 27/37:50 p.m.
YQG
-
PUJ
1 stop15h 00m
Air Canada
Wed 1/49:40 p.m.
PUJ
-
YQG
1 stop21h 29m
Air Canada
Deal found 21/3C$ 835
Mon 4/54:05 p.m.
YQG
-
SJU
2 stops21h 40m
Air Canada
Thu 7/51:00 a.m.
SJU
-
YQG
2 stops18h 09m
Air Canada
Deal found 22/3C$ 901
Sat 26/94:05 p.m.
YQG
-
SJU
2 stops19h 52m
Air Canada
Wed 30/96:40 p.m.
SJU
-
YQG
2 stops20h 42m
Air Canada
Deal found 19/3C$ 942
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 19/3C$ 1,077
Sun 20/910:05 a.m.
YQG
-
MBJ
1 stop26h 15m
Air Canada
Thu 24/912:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 18/3C$ 1,247
Fri 19/610:05 a.m.
YQG
-
SJU
2 stops11h 19m
Air Canada
Thu 25/62:05 a.m.
SJU
-
YQG
2 stops13h 17m
Air Canada
Deal found 18/3C$ 2,002

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 March 2026.

Round-trip from

C$ 573

One-way from

C$ 361
Air Canada
  • Air Canada
  • 15/6-17/6
  • 2 total stops
  • 42h 27m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 5/5
  • 1 total stop
  • 20h 15m 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 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

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

1 stop16h 35m

Montego Bay Sangster Intl

Wed 17/6

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

1 stop25h 52m

C$ 573

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 11/8

7:45 p.m.-3:25 p.m.

1 stop19h 40m

Punta Cana

Thu 13/8

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

2 stops22h 17m

C$ 663

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 12/7

4:05 p.m.-3:15 p.m.

1 stop23h 10m

Punta Cana

Thu 13/8

5:05 p.m.-9:22 a.m.

2 stops16h 17m

C$ 748

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 12/7

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

1 stop19h 30m

Punta Cana

Thu 16/7

4:20 p.m.-7:07 p.m.

1 stop26h 47m

C$ 753

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 23/5

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

2 stops27h 50m

Punta Cana

Tue 26/5

2:55 p.m.-7:09 p.m.

2 stops28h 14m

C$ 848

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 4/5

10:05 a.m.-8:34 p.m.

2 stops34h 29m

San Juan Luis Munoz Marin Intl

Thu 7/5

1:00 a.m.-9:24 a.m.

2 stops32h 24m

C$ 901

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 11/4

7:45 p.m.-11:10 a.m.

1 stop15h 25m

Punta Cana

Sat 18/4

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

1 stop11h 59m

C$ 938

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$ 1,077

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 19/4

7:45 p.m.-11:35 p.m.

2 stops27h 50m

Punta Cana

Sun 26/4

12:50 p.m.-7:09 p.m.

3 stops30h 19m

C$ 1,364
Quickest round-trip

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Fri 19/6

10:05 a.m.-9:24 p.m.

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Thu 25/6

2:05 a.m.-3:22 p.m.

2 stops13h 17m

C$ 2,002

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 17 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

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 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 23 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
521 reviews
Check prices

Boarding

7.9

Comfort

7.3

Food

6.8

Crew

8.5

Overall

7.7

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
521 reviews
Air Transat
7.7
Good
521 reviews
Check prices

Boarding

7.9

Comfort

7.3

Food

6.8

Crew

8.5

Overall

7.7

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
10,835 reviews
Air Transat
7.7
Good
521 reviews
Check prices

Boarding

7.9

Comfort

7.3

Food

6.8

Crew

8.5

Overall

7.7

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 16h 35m. The distance between Windsor, Ontario and Caribbean is about 2683 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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

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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 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 480AverageC$ 763FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 722AverageC$ 891FlexibilityNo 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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