Find flights
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean from C$ 460

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 26/2. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
30 Jan — 6 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean

Enter your travel dates to find the best prices.

Best flights from Windsor to Caribbean
Discover carefully curated flight deals from Windsor to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 31 December 2025.

Tue 13/19:45 a.m.YQG - PUJ
1 stop11h 00mAir Canada
Wed 28/11:05 p.m.PUJ - YQG
1 stop7h 09mAir Canada
Deal found 28/12C$ 550
Thu 29/17:50 p.m.YQG - MBJ
1 stop16h 40mMultiple Airlines
Tue 17/21:00 p.m.MBJ - YQG
3 stops30h 33mMultiple Airlines
Deal found 28/12C$ 999
Tue 13/17:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
Tue 20/110:35 p.m.PUJ - YQG
1 stop21h 39mAir Canada
Deal found 29/12C$ 550
Mon 19/17:50 p.m.YQG - PUJ
1 stop16h 45mAir Canada
Thu 22/110:35 p.m.PUJ - YQG
1 stop21h 39mAir Canada
Deal found 29/12C$ 580
Mon 30/39:45 a.m.YQG - MBJ
1 stop26h 50mAir Canada
Sun 5/46:05 p.m.MBJ - YQG
2 stops24h 09mAir Canada
Deal found 28/12C$ 649
Fri 30/17:50 p.m.YQG - MBJ
1 stop15h 40mMultiple Airlines
Wed 18/21:30 p.m.MBJ - YQG
1 stop19h 34mMultiple Airlines
Deal found 28/12C$ 1,019
Fri 30/17:50 p.m.YQG - MBJ
2 stops46h 15mAir Canada
Wed 18/21:30 p.m.MBJ - YQG
1 stop19h 34mAir Canada
Deal found 28/12C$ 854
Mon 26/17:50 p.m.YQG - SJU
2 stops25h 32mAir Canada
Tue 27/12:05 a.m.SJU - YQG
2 stops31h 59mAir Canada
Deal found 29/12C$ 856
Thu 19/27:35 a.m.YQG - SJU
2 stops17h 00mMultiple Airlines
Sun 22/26:10 a.m.SJU - YQG
2 stops14h 23mMultiple Airlines
Deal found 30/12C$ 1,778
Mon 30/37:50 p.m.YQG - SJU
2 stops19h 52mAir Canada
Sun 5/41:00 a.m.SJU - YQG
2 stops18h 14mAir Canada
Deal found 29/12C$ 1,428
Thu 19/29:45 a.m.YQG - SJU
2 stops13h 51mAir Canada
Sun 22/23:40 p.m.SJU - YQG
1 stop18h 24mAir Canada
Deal found 30/12C$ 2,738

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 31 December 2025.

Round-trip from

C$ 550

One-way from

C$ 460

Good round-trip deal

C$ 796 or less
Air Canada
  • Air Canada
  • 13/1-20/1
  • 2 total stops
  • 36h 54m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 26/2
  • 1 total stop
  • 16h 50m 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 31 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

Tue 13/1

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

1 stop11h 00m

Punta Cana

Wed 28/1

1:05 p.m.-7:14 p.m.

1 stop7h 09m

C$ 550

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 13/1

7:50 p.m.-12:05 p.m.

1 stop15h 15m

Punta Cana

Tue 20/1

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

1 stop21h 39m

C$ 550

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 19/1

7:50 p.m.-1:35 p.m.

1 stop16h 45m

Punta Cana

Thu 22/1

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

1 stop21h 39m

C$ 580

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 30/3

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

1 stop26h 50m

Montego Bay Sangster Intl

Sun 5/4

6:05 p.m.-7:14 p.m.

2 stops24h 09m

C$ 649

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 30/1

7:50 p.m.-6:05 p.m.

2 stops46h 15m

Montego Bay Sangster Intl

Wed 18/2

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

1 stop19h 34m

C$ 854

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

Tue 27/1

2:05 a.m.-9:04 a.m.

2 stops31h 59m

C$ 856

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Thu 29/1

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

1 stop16h 40m

Montego Bay Sangster Intl

Tue 17/2

1:00 p.m.-7:33 p.m.

3 stops30h 33m

C$ 999

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 30/1

7:50 p.m.-11:30 a.m.

1 stop15h 40m

Montego Bay Sangster Intl

Wed 18/2

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

1 stop19h 34m

C$ 1,019

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 30/3

7:50 p.m.-3:42 p.m.

2 stops19h 52m

San Juan Luis Munoz Marin Intl

Sun 5/4

1:00 a.m.-7:14 p.m.

2 stops18h 14m

C$ 1,428

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Thu 19/2

7:35 a.m.-1:35 a.m.

2 stops17h 00m

San Juan Luis Munoz Marin Intl

Sun 22/2

6:10 a.m.-7:33 p.m.

2 stops14h 23m

C$ 1,778

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/12

Showing 1-10 of 16 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

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

Find hourly flight availability from Windsor to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 31 December 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Windsor, Ontario to Caribbean as you normally would.

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 31 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
7.7
Good
489 reviews
Check prices

Food

6.7

Comfort

7.3

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

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
489 reviews
Air Transat
7.7
Good
489 reviews
Check prices

Food

6.7

Comfort

7.3

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

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
10,571 reviews
Air Transat
7.7
Good
489 reviews
Check prices

Food

6.7

Comfort

7.3

Overall

7.7

Boarding

7.9

Crew

8.4

Entertainment

7.0

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. 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 - 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
Pierre Elliott Trudeau Intl to Fort Lauderdale flights
Pearson Intl to Cancún flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Pierre Elliott Trudeau Intl to Charles de Gaulle flights
Pearson Intl to Miami flights
Pearson Intl to John F Kennedy Intl flights
Toronto Island to Vancouver Intl flights
Pearson Intl to Heathrow flights
Pearson Intl to Narita flights
Pearson Intl to Haneda flights
Hamilton to Vancouver Intl flights
Pearson Intl to Newark flights
Pearson Intl to Abbotsford flights
Pearson Intl to Las Vegas flights
Pearson Intl to Fort Lauderdale flights
Toronto Island to Newark flights
Pierre Elliott Trudeau Intl to Narita flights
Pearson Intl to LaGuardia flights
Pierre Elliott Trudeau Intl to Suvarnabhumi flights
Pierre Elliott Trudeau Intl to Mexico City flights
Pearson Intl to Orlando flights
Pierre Elliott Trudeau Intl to Miami flights
Pearson Intl to Calgary flights
Pierre Elliott Trudeau Intl to Lisbon flights
Toronto Island to New Delhi flights
Pearson Intl to Lisbon flights
Pearson Intl to Gatwick flights
Pierre Elliott Trudeau Intl to Puerto Vallarta flights
Pearson Intl to Hong Kong flights
Pearson Intl to Istanbul flights
Toronto Island to Cancún flights
Pearson Intl to Dallas/Fort Worth flights
Pearson Intl to Suvarnabhumi flights
Pierre Elliott Trudeau Intl to Calgary flights
Pearson Intl to Charles de Gaulle flights
Pearson Intl to Cozumel flights
Pierre Elliott Trudeau Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to Mexico City flights
Ottawa to Vancouver Intl flights
Pearson Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to Los Angeles flights
Pierre Elliott Trudeau Intl to Heathrow flights
Pierre Elliott Trudeau Intl to Punta Cana flights
Pierre Elliott Trudeau Intl to Casablanca flights
Pearson Intl to Mumbai flights
Pierre Elliott Trudeau Intl to Liberia flights
Pierre Elliott Trudeau Intl to LaGuardia flights

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 31 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 552AverageC$ 797FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 721AverageC$ 889FlexibilityNo 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.