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Cheap flights from Windsor, ON to Caribbean Islands from C$ 296

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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
31 Mar — 7 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Caribbean Islands
Explore the most affordable flight options available from Windsor to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 1 March 2026.

Tue 22/97:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sun 27/912:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 28/2C$ 503
Thu 2/47:45 p.m.
YQG
-
PUJ
2 stops24h 55m
Air Canada
Tue 7/49:40 p.m.
PUJ
-
YQG
1 stop11h 24m
Air Canada
Deal found 26/2C$ 667
Mon 27/47:45 p.m.
YQG
-
MBJ
1 stop16h 50m
Air Canada
Mon 11/512:30 p.m.
MBJ
-
YQG
1 stop25h 54m
Air Canada
Deal found 27/2C$ 672
Sat 4/47:45 p.m.
YQG
-
PUJ
2 stops17h 00m
Air Canada
Tue 7/42:25 p.m.
PUJ
-
YQG
2 stops18h 39m
Air Canada
Deal found 26/2C$ 676
Sat 2/510:05 a.m.
YQG
-
PUJ
2 stops27h 50m
Air Canada
Sat 9/52:55 p.m.
PUJ
-
YQG
2 stops24h 29m
Air Canada
Deal found 27/2C$ 678
Sat 28/37:50 p.m.
YQG
-
MBJ
2 stops22h 00m
Air Canada
Tue 31/312:30 p.m.
MBJ
-
YQG
1 stop19h 34m
Air Canada
Deal found 26/2C$ 696
Thu 2/47:45 p.m.
YQG
-
PUJ
2 stops24h 55m
Air Canada
Thu 9/49:40 p.m.
PUJ
-
YQG
1 stop11h 24m
Air Canada
Deal found 26/2C$ 716
Sun 1/37:50 p.m.
YQG
-
PUJ
1 stop24h 55m
Air Canada
Fri 13/37:05 p.m.
PUJ
-
YQG
2 stops24h 09m
Air Canada
Deal found 27/2C$ 719
Sat 7/37:50 p.m.
YQG
-
PUJ
1 stop23h 45m
Air Canada
Wed 11/39:35 p.m.
PUJ
-
YQG
1 stop11h 29m
Air Canada
Deal found 28/2C$ 720
Sat 4/47:45 p.m.
YQG
-
PUJ
2 stops17h 00m
Air Canada
Thu 9/49:40 p.m.
PUJ
-
YQG
1 stop11h 24m
Air Canada
Deal found 26/2C$ 721
Fri 27/37:50 p.m.
YQG
-
PUJ
2 stops16h 05m
Air Canada
Fri 3/43:55 p.m.
PUJ
-
YQG
2 stops17h 09m
Air Canada
Deal found 25/2C$ 723
Fri 20/119:45 a.m.
YQG
-
PUJ
1 stop10h 50m
Air Canada
Thu 26/1110:35 p.m.
PUJ
-
YQG
1 stop11h 34m
Air Canada
Deal found 27/2C$ 762

Find flight deals from Windsor to Caribbean Islands

Keep the following information in mind while searching for Windsor to Caribbean Islands flight deals. Data was last updated 1 March 2026.

Round-trip from

C$ 667

One-way from

C$ 296
Air Canada
  • Air Canada
  • 2/4-7/4
  • 3 total stops
  • 36h 19m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 7/6
  • 1 total stop
  • 16h 10m total
  • Windsor to Caribbean Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Windsor to Caribbean Islands 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 1 March 2026.
Use the filters below to find and compare flights from Windsor to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 2/4

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

1 stop15h 25m

Punta Cana

Tue 7/4

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

1 stop11h 24m

C$ 667

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 27/4

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

1 stop16h 50m

Montego Bay Sangster Intl

Mon 11/5

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

1 stop25h 54m

C$ 672

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 28/4

9:45 a.m.-11:35 a.m.

1 stop26h 50m

Montego Bay Sangster Intl

Tue 12/5

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

1 stop25h 54m

C$ 672

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 2/5

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

2 stops27h 50m

Punta Cana

Sat 9/5

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

2 stops24h 29m

C$ 678

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$ 696

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 27/3

7:50 p.m.-10:50 a.m.

1 stop15h 00m

Punta Cana

Fri 3/4

3:55 p.m.-9:04 a.m.

2 stops17h 09m

C$ 768

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 18/3

9:40 a.m.-8:35 p.m.

1 stop10h 55m

Punta Cana

Wed 25/3

7:05 p.m.-9:04 a.m.

2 stops37h 59m

C$ 791

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 28/4

9:45 a.m.-11:35 a.m.

1 stop26h 50m

Montego Bay Sangster Intl

Tue 12/5

4:55 p.m.-3:46 p.m.

2 stops21h 51m

C$ 877

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 28/3

7:50 p.m.-12:45 p.m.

2 stops16h 55m

Punta Cana

Sat 4/4

12:55 p.m.-9:04 a.m.

2 stops20h 09m

C$ 922

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 27/3

7:50 p.m.-10:50 a.m.

1 stop15h 00m

Punta Cana

Fri 3/4

3:35 p.m.-9:04 a.m.

1 stop17h 29m

C$ 1,002

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/2

Showing 1-10 of 26 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Windsor to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Find hourly flight availability from Windsor to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 1 March 2026.

When flying from Windsor, Ontario to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 1 March 2026.
Check out reviews from past customers who have flown with Air Transat and Air Canada from Windsor to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.7
Good
515 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.5

Boarding

7.9

Food

6.8

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
515 reviews
Air Transat
7.7
Good
515 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.5

Boarding

7.9

Food

6.8

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
10,760 reviews
Air Transat
7.7
Good
515 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.5

Boarding

7.9

Food

6.8

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 Islands. 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 Islands?

    Windsor (YQG), located 8.0 km from the city centre, is the airport you fly out of when you book flights from Windsor to Caribbean Islands.

  • How long is the flight from Windsor, Ontario to Caribbean Islands?

    For as low as C$ 667, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 15h 25m. Windsor, Ontario and Caribbean Islands are separated by a distance of 2972 km.

  • What are the most popular routes from Windsor, Ontario to Caribbean Islands?

    The most popular flight routes from Windsor, Ontario to Caribbean Islands are Windsor - Punta Cana, Windsor - San Juan Luis Munoz Marin Intl and Windsor - Montego Bay Sangster Intl.

  • Can I find deals for flights from Windsor to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Windsor to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Windsor to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Windsor to Caribbean Islands.

  • Can I find deals for business class flights from Windsor to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Windsor to Caribbean Islands 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 Islands

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 Islands

Discover the top 2 airlines that operate flights from Windsor to Caribbean Islands. 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 1 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 477AverageC$ 756FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 718AverageC$ 885FlexibilityNo 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 Islands?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Windsor to Caribbean Islands. 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 Islands?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean Islands from Windsor.

Can Cheapflights find flights from Windsor to Caribbean Islands with no change fees?

Certainly. Search results for flights to Caribbean Islands from Windsor shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Windsor to Caribbean Islands become cheaper?

Yes, Cheapflights offers price alerts on Windsor to Caribbean Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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