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Cheap flights from Windsor, ON to Caribbean from C$ 318

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 30/1. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
16 Jan — 23 Jan1
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 17 December 2025.

Tue 23/127:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
Tue 30/1211:00 p.m.PUJ - YQG
2 stops35h 04mAir Canada
Deal found 17/12C$ 856
Tue 23/127:50 p.m.YQG - PUJ
1 stop15h 15mMultiple Airlines
Tue 30/128:05 p.m.PUJ - YQG
1 stop13h 59mMultiple Airlines
Deal found 17/12C$ 1,080
Fri 26/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Sun 4/111:55 p.m.PUJ - YQG
2 stops20h 38mMultiple Airlines
Deal found 16/12C$ 1,266
Wed 24/127:35 a.m.YQG - SJU
2 stops18h 24mMultiple Airlines
Sun 28/126:01 a.m.SJU - YQG
2 stops14h 32mMultiple Airlines
Deal found 16/12C$ 1,616
Fri 26/127:50 p.m.YQG - PUJ
2 stops44h 30mAir Canada
Sun 4/110:35 p.m.PUJ - YQG
1 stop11h 29mAir Canada
Deal found 16/12C$ 2,204
Wed 24/129:45 a.m.YQG - SJU
2 stops9h 24mAir Canada
Sun 28/123:40 p.m.SJU - YQG
1 stop18h 24mAir Canada
Deal found 16/12C$ 2,686

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 17 December 2025.

Round-trip from

C$ 515

One-way from

C$ 318

Good round-trip deal

C$ 800 or less
Air Canada
  • Air Canada
  • 11/1-18/1
  • 2 total stops
  • 44h 09m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 30/1
  • 1 total stop
  • 11h 00m total
  • Windsor to Caribbean
Search Deals
Price to beat on a round-trip flight from 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 17 December 2025.
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

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 9/1

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

1 stop11h 00m

Punta Cana

Fri 16/1

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

1 stop11h 29m

C$ 516

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 14/4

7:50 p.m.-11:00 a.m.

1 stop15h 10m

Punta Cana

Thu 16/4

4:45 p.m.-9:04 a.m.

1 stop16h 19m

C$ 517

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

Sun 11/1

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

1 stop24h 55m

Punta Cana

Mon 19/1

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

1 stop11h 29m

C$ 526

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sun 8/2

9:45 a.m.-9:26 p.m.

2 stops34h 41m

San Juan Luis Munoz Marin Intl

Thu 12/2

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

2 stops38h 29m

C$ 911

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 30/1

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

1 stop11h 00m

C$ 318

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 15/1

7:50 p.m.-12:30 p.m.

1 stop16h 40m

C$ 322

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 30/1

5:35 p.m.-10:45 p.m.

Nonstop4h 10m

C$ 365

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 30/1

9:45 a.m.-5:12 p.m.

3 stops30h 27m

C$ 500

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 15/1

7:35 a.m.-12:02 p.m.

3 stops28h 27m

C$ 578

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/12

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

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 17 December 2025.
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
7.8
Good
483 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Crew

8.4

Overall

7.8

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
483 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Crew

8.4

Overall

7.8

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
10,531 reviews
Air Transat
7.8
Good
483 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Crew

8.4

Overall

7.8

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. 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 11h. The distance between Windsor, Ontario and Caribbean is about 2972 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 - San Juan Luis Munoz Marin Intl or Windsor - Montego Bay Sangster 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 17 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?

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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