Find flights
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean from C$ 272

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 18/10. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
6 Sep — 13 Sep1
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 7 August 2026.

Thu 22/107:45 p.m. -
1 stop19h 35m
Sun 25/1012:05 p.m. -
1 stop21h 50m
Deal found 4/8C$ 506
Sun 25/1010:35 a.m. -
1 stop26h 15m
Thu 29/1012:50 p.m. -
1 stop20h 05m
Deal found 3/8C$ 507
Mon 23/1110:35 a.m. -
1 stop24h 35m
Thu 26/1110:40 p.m. -
1 stop12h 15m
Deal found 6/8C$ 556
Mon 2/1110:35 a.m. -
1 stop6h 45m
Thu 5/111:50 p.m. -
1 stop20h 05m
Deal found 6/8C$ 587
Fri 4/97:45 p.m. -
2 stops20h 20m
Thu 10/94:20 p.m. -
1 stop17h 02m
Deal found 6/8C$ 597
Sat 19/910:05 a.m. -
2 stops25h 52m
Wed 23/93:00 p.m. -
2 stops24h 22m
Deal found 3/8C$ 631
Fri 11/127:20 p.m. -
1 stop17h 30m
Fri 18/1210:40 p.m. -
1 stop21h 05m
Deal found 4/8C$ 632
Sun 13/94:05 p.m. -
1 stop23h 20m
Sat 19/94:20 p.m. -
1 stop17h 02m
Deal found 5/8C$ 653
Sat 19/1210:35 a.m. -
1 stop6h 45m
Thu 24/121:50 p.m. -
1 stop20h 05m
Deal found 6/8C$ 785
Wed 9/94:05 p.m. -
1 stop20h 15m
Tue 29/912:30 p.m. -
1 stop25h 52m
Deal found 4/8C$ 867
Fri 9/104:05 p.m. -
1 stop20h 15m
Fri 16/1012:30 p.m. -
1 stop19h 52m
Deal found 2/8C$ 939
Wed 9/910:05 a.m. -
1 stop26h 15m
Tue 29/912:22 p.m. -
2 stops20h 00m
Deal found 4/8C$ 1,103

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 7 August 2026.

Round-trip from

C$ 506

One-way from

C$ 272
Air Canada
  • Air Canada
  • 22/10-25/10
  • 2 total stops
  • 41h 25m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 18/10
  • 2 total stops
  • 20h 20m 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 7 August 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 Windsor - MBJ Montego Bay Sangster Intl

YQGMBJ

Windsor

Sun 25/10

10:35 a.m.-11:50 a.m.

1 stop26h 15m

Montego Bay Sangster Intl

Thu 29/10

12:50 p.m.-9:55 a.m.

1 stop20h 05m

C$ 507

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Thu 22/10

7:45 p.m.-4:05 p.m.

2 stops20h 20m

Punta Cana

Sun 25/10

3:30 p.m.-6:45 p.m.

1 stop27h 15m

C$ 510

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Mon 23/11

10:35 a.m.-11:35 p.m.

2 stops36h 00m

Punta Cana

Thu 26/11

10:40 p.m.-9:55 a.m.

1 stop12h 15m

C$ 560
Quickest round-trip

WindsorMontego Bay

YQG Windsor - MBJ Montego Bay Sangster Intl

YQGMBJ

Windsor

Mon 2/11

10:35 a.m.-5:20 p.m.

1 stop6h 45m

Montego Bay Sangster Intl

Thu 5/11

1:50 p.m.-9:55 a.m.

1 stop20h 05m

C$ 587

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Fri 4/9

7:45 p.m.-4:05 p.m.

2 stops20h 20m

Punta Cana

Thu 10/9

4:20 p.m.-9:22 a.m.

1 stop17h 02m

C$ 597

WindsorSan Juan

YQG Windsor - SJU San Juan Luis Munoz Marin Intl

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-11:57 a.m.

2 stops25h 52m

San Juan Luis Munoz Marin Intl

Wed 23/9

3:00 p.m.-3:22 p.m.

2 stops24h 22m

C$ 631

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Fri 11/12

10:35 a.m.-1:50 p.m.

1 stop26h 15m

Punta Cana

Fri 18/12

7:45 p.m.-6:45 p.m.

2 stops24h 00m

C$ 636

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Tue 12/1

7:20 p.m.-1:45 p.m.

2 stops17h 25m

Punta Cana

Tue 19/1

3:15 p.m.-9:55 a.m.

2 stops19h 40m

C$ 670

WindsorPunta Cana

YQG Windsor - PUJ Punta Cana

YQGPUJ

Windsor

Sat 23/1

7:20 p.m.-1:50 p.m.

1 stop17h 30m

Punta Cana

Tue 26/1

7:35 p.m.-9:55 a.m.

1 stop15h 20m

C$ 738

WindsorMontego Bay

YQG Windsor - MBJ Montego Bay Sangster Intl

YQGMBJ

Windsor

Sat 19/12

10:35 a.m.-5:20 p.m.

1 stop6h 45m

Montego Bay Sangster Intl

Thu 24/12

1:50 p.m.-9:55 a.m.

1 stop20h 05m

C$ 785

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 27 resultsSorted by cheapest first
1
2
3

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 7 August 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
7.8
Good
572 reviews
Check prices

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Transat
7.8
Good
572 reviews
Air Transat
7.8
Good
572 reviews
Check prices

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Canada
7.1
Good
11,431 reviews
Air Transat
7.8
Good
572 reviews
Check prices

Boarding

8.0

Crew

8.5

Food

6.8

Entertainment

7.1

Overall

7.8

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus

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 26h 15m. The distance between Windsor, Ontario and Caribbean is about 2683 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 Cancún flights
Toronto Island to Cancún flights
Pearson Intl to Vancouver Intl flights
Pearson Intl to Cozumel flights
Hamilton to Cancún flights
Hamilton to Vancouver Intl flights
Pearson Intl to Calgary flights
Region of Waterloo Intl to Cancún flights
Toronto Island to Vancouver Intl flights
Pearson Intl to Abbotsford flights
Pearson Intl to New Delhi flights
Hamilton to Calgary flights
Toronto Island to Newark flights
Pearson Intl to Newark flights
Pierre Elliott Trudeau Intl to Charles de Gaulle flights
Pearson Intl to Edmonton flights
Region of Waterloo Intl to Vancouver Intl flights
Pearson Intl to LaGuardia flights
Pierre Elliott Trudeau Intl to Cancún flights
Hamilton to Halifax flights
Pearson Intl to John F Kennedy Intl flights
Pearson Intl to Heathrow flights
Toronto Island to LaGuardia flights
Toronto Island to Calgary flights
Pearson Intl to Mexico City flights
Region of Waterloo Intl to Calgary flights
Pearson Intl to Istanbul flights
Hamilton to Edmonton flights
Ottawa to Vancouver Intl flights
Toronto Island to Halifax flights
Pierre Elliott Trudeau Intl to LaGuardia flights
Pearson Intl to Halifax flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Toronto Island to New Delhi flights
Pearson Intl to Fort Lauderdale flights
Pearson Intl to Gatwick flights
Pearson Intl to Pierre Elliott Trudeau Intl flights
Toronto Island to John F Kennedy Intl flights
Pearson Intl to Orlando flights
Pierre Elliott Trudeau Intl to Fort Lauderdale flights
Pierre Elliott Trudeau Intl to Pearson Intl flights
Toronto Island to Pierre Elliott Trudeau Intl flights
Pierre Elliott Trudeau Intl to Calgary flights
Pearson Intl to Hong Kong flights
Pearson Intl to Winnipeg flights
Pearson Intl to Mumbai flights
Pierre Elliott Trudeau Intl to Miami flights
Pearson Intl to Los Angeles flights
Pearson Intl to Las Vegas flights
Pearson Intl to Charles de Gaulle 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 7 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 738AverageC$ 937FlexibilityNo 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.

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.