Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean from C$ 308

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 15/1. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
26 Dec — 2 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean

Keep the following information in mind while searching for Windsor to Caribbean flight deals. Data was last updated 26 November 2025.

Round-trip from

C$ 543

One-way from

C$ 308
Air Canada
  • Air Canada
  • 6/12-9/12
  • 2 total stops
  • 48h 44m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 15/1
  • 1 total stop
  • 25h 20m total
  • Windsor to Caribbean
Search Deals

Find 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 26 November 2025.

Thu 27/117:50 p.m.YQG - PUJ
1 stop16h 55mAir Canada
Sun 30/1110:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 24/11C$ 540
Sat 6/127:50 p.m.YQG - PUJ
2 stops42h 55mAir Canada
Tue 9/1210:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 23/11C$ 557
Fri 26/127:50 p.m.YQG - PUJ
2 stops42h 55mAir Canada
Fri 9/13:35 p.m.PUJ - YQG
2 stops28h 39mAir Canada
Deal found 26/11C$ 631
Fri 26/125:35 p.m.YQG - PUJ
Nonstop4h 10mMultiple Airlines
Fri 9/14:55 p.m.PUJ - YQG
2 stops17h 09mMultiple Airlines
Deal found 26/11C$ 810
Fri 26/125:35 p.m.YQG - PUJ
Nonstop4h 10mAir Transat
Fri 9/112:40 p.m.PUJ - YQG
Nonstop4h 35mAir Transat
Deal found 26/11C$ 830
Sun 14/129:45 a.m.YQG - PUJ
1 stop25h 20mAir Canada
Thu 18/121:00 p.m.PUJ - YQG
1 stop21h 04mAir Canada
Deal found 24/11C$ 847

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 26 November 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

Sat 6/12

7:50 p.m.-4:35 p.m.

1 stop19h 45m

Punta Cana

Tue 9/12

3:15 p.m.-7:14 p.m.

1 stop28h 59m

C$ 543

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 23/1

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

1 stop16h 40m

Montego Bay Sangster Intl

Mon 26/1

1:30 p.m.-9:04 a.m.

1 stop19h 34m

C$ 570

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 7/3

9:45 a.m.-10:00 p.m.

1 stop11h 15m

Punta Cana

Wed 11/3

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

2 stops24h 09m

C$ 578

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 29/3

7:50 p.m.-10:55 a.m.

1 stop15h 05m

Punta Cana

Thu 2/4

9:20 p.m.-7:14 p.m.

1 stop21h 54m

C$ 583

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 29/3

7:50 p.m.-1:00 p.m.

2 stops17h 10m

Punta Cana

Sun 5/4

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

2 stops24h 09m

C$ 583

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 26/1

7:50 p.m.-10:22 p.m.

2 stops25h 32m

San Juan Luis Munoz Marin Intl

Thu 29/1

4:52 p.m.-9:04 a.m.

2 stops17h 12m

C$ 893

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 15/1

7:50 p.m.-2:00 p.m.

2 stops17h 10m

C$ 308

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Wed 7/1

7:50 p.m.-1:45 p.m.

1 stop16h 55m

C$ 309

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 13/2

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

2 stops46h 15m

C$ 415

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 15/1

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

3 stops26h 30m

C$ 567

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/11

Showing 1-10 of 12 results
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
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 26 November 2025.
Get a feel of what it's like to fly with 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 Canada
7.1
Good
10,481 reviews
Check prices

Comfort

7.1

Crew

7.8

Entertainment

6.8

Overall

7.1

Boarding

7.3

Food

6.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,481 reviews
Air Canada
7.1
Good
10,481 reviews
Check prices

Comfort

7.1

Crew

7.8

Entertainment

6.8

Overall

7.1

Boarding

7.3

Food

6.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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 19h 45m. 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 - 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Windsor to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Vancouver Intl flights
Pierre Elliott Trudeau Intl to Cancún flights
Pearson Intl to New Delhi flights
Pearson Intl to Cancún flights
Hamilton to Vancouver Intl flights
Toronto Island to Vancouver Intl flights
Pearson Intl to Abbotsford flights
Pierre Elliott Trudeau Intl to Charles de Gaulle flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Pierre Elliott Trudeau Intl to Fort Lauderdale flights
Pearson Intl to John F Kennedy Intl flights
Pearson Intl to Fort Lauderdale flights
Pearson Intl to Calgary flights
Pearson Intl to Heathrow flights
Toronto Island to Newark flights
Toronto Island to New Delhi flights
Pearson Intl to Las Vegas flights
Pierre Elliott Trudeau Intl to Miami flights
Pearson Intl to Newark flights
Pierre Elliott Trudeau Intl to Mexico City flights
Pearson Intl to Mumbai flights
Pearson Intl to Haneda flights
Pierre Elliott Trudeau Intl to Suvarnabhumi flights
Pearson Intl to LaGuardia flights
Pearson Intl to Narita flights
Pearson Intl to Hong Kong flights
Pierre Elliott Trudeau Intl to Puerto Vallarta flights
Pearson Intl to Gatwick flights
Pearson Intl to Istanbul flights
Pearson Intl to Miami flights
Toronto Island to Cancún flights
Pierre Elliott Trudeau Intl to Punta Cana flights
Pierre Elliott Trudeau Intl to Narita flights
Pearson Intl to Mexico City flights
Pearson Intl to Dubai flights
Pearson Intl to Lisbon flights
Pearson Intl to Punta Cana flights
Pearson Intl to Edmonton flights
Pearson Intl to Orlando flights
Pearson Intl to Cozumel flights
Pearson Intl to Suvarnabhumi flights
Pearson Intl to Los Angeles flights
Pierre Elliott Trudeau Intl to Calgary flights
Pearson Intl to Charles de Gaulle flights
Pierre Elliott Trudeau Intl to Casablanca flights
Pierre Elliott Trudeau Intl to Fort-de-France flights
Pierre Elliott Trudeau Intl to Cozumel flights
Ottawa to Cancún flights
Pierre Elliott Trudeau Intl to John F Kennedy Intl flights
Pierre Elliott Trudeau Intl to Newark flights

Top airline flying from Windsor to Caribbean

Discover the top airline 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 26 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 569AverageC$ 787FlexibilityNo cancel feeOn-time67%
Search Air Canada 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.