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Cheap flights from Windsor, ON to Caribbean Islands from C$ 315

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 27/1. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
14 Jan — 21 Jan1
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 15 December 2025.

Sun 14/127:50 p.m.YQG - PUJ
1 stop15h 15mMultiple Airlines
Sun 21/1211:55 p.m.PUJ - YQG
2 stops20h 38mMultiple Airlines
Deal found 13/12C$ 847
Sun 21/127:50 p.m.YQG - PUJ
2 stops17h 10mMultiple Airlines
Sun 28/124:55 p.m.PUJ - YQG
2 stops27h 38mMultiple Airlines
Deal found 13/12C$ 1,008

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 15 December 2025.

Round-trip from

C$ 515

One-way from

C$ 315
Air Canada
  • Air Canada
  • 11/1-18/1
  • 2 total stops
  • 44h 09m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 27/1
  • 1 total stop
  • 11h 00m 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 15 December 2025.
Use the filters below to find and compare flights from Windsor to Caribbean Islands that are best for you.

Fly from

Windsor

Fly to

Caribbean Islands

Route

Depart

Return

Price

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 11/1

7:50 p.m.-9:45 p.m.

1 stop24h 55m

Punta Cana

Sun 18/1

7:40 p.m.-7:14 p.m.

2 stops24h 34m

C$ 520

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 13/1

9:45 a.m.-12:05 p.m.

1 stop25h 20m

Punta Cana

Mon 19/1

10:35 p.m.-9:04 a.m.

1 stop11h 29m

C$ 551

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 28/1

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

1 stop11h 00m

Punta Cana

Wed 4/2

10:35 p.m.-7:14 p.m.

1 stop21h 39m

C$ 574

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 18/1

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

1 stop27h 00m

Punta Cana

Sat 24/1

11:00 p.m.-9:04 a.m.

1 stop11h 04m

C$ 580

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 30/3

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

1 stop16h 55m

Punta Cana

Sat 4/4

9:35 p.m.-7:14 p.m.

1 stop21h 39m

C$ 591

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sun 8/2

7:50 p.m.-4:36 p.m.

2 stops43h 46m

San Juan Luis Munoz Marin Intl

Thu 12/2

7:35 p.m.-9:04 a.m.

2 stops38h 29m

C$ 912

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sun 1/2

9:45 a.m.-1:17 p.m.

2 stops26h 32m

San Juan Luis Munoz Marin Intl

Tue 10/2

2:05 a.m.-7:14 p.m.

2 stops18h 09m

C$ 914

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sun 1/2

7:50 p.m.-3:35 p.m.

3 stops18h 45m

San Juan Luis Munoz Marin Intl

Wed 11/2

4:40 p.m.-7:14 p.m.

3 stops27h 34m

C$ 1,038

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 27/1

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

1 stop11h 00m

C$ 315

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Thu 29/1

7:35 a.m.-9:47 a.m.

3 stops25h 12m

C$ 395

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/12

Showing 1-10 of 13 results
1
2

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
No data available for this route at this time. Please check back soon.

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 15 December 2025.
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
7.8
Good
482 reviews
Check prices

Crew

8.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Comfort

7.4

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Transat
7.8
Good
482 reviews
Air Transat
7.8
Good
482 reviews
Check prices

Crew

8.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Comfort

7.4

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Canada
7.1
Good
10,525 reviews
Air Transat
7.8
Good
482 reviews
Check prices

Crew

8.4

Boarding

7.9

Overall

7.8

Entertainment

7.1

Comfort

7.4

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.

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$ 520, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 24h 55m. 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 - Montego Bay Sangster Intl and Windsor - San Juan Luis Munoz Marin 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

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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 15 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 555AverageC$ 785FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 725AverageC$ 874FlexibilityNo 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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