HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$328+ Cheap flights from Watertown, NY (ART) to Caribbean

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Watertown to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Watertown to Caribbean

Keep the following information in mind while searching for Watertown to Caribbean flight deals. Data was last updated August 11, 2025.

Round-trip from

$759
(American Airlines)

One-way from

$328
(American Airlines)
From Watertown to Caribbean
Search Deals
One-way flight from Watertown to Caribbean
Search Deals

Find flight deals from Watertown to Caribbean

Cheapest flights from Watertown to Caribbean
Explore the most affordable flight options available from Watertown to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2025.

This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amART - SJU
2 stops32h 25mAmerican Airlines
Thu 8/217:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$666
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amART - SJU
2 stops32h 25mAmerican Airlines
Tue 8/197:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$705
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amART - SJU
2 stops32h 25mAmerican Airlines
Fri 8/157:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$735
This American Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:28 pmART - SKB
2 stops20h 47mAmerican Airlines
Thu 12/113:30 pmSKB - ART
2 stops31h 55mAmerican Airlines
Deal found 8/9$759
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amART - SJU
2 stops32h 25mAmerican Airlines
Sat 8/167:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$775
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/124:09 pmART - SJU
2 stops22h 16mAmerican Airlines
Wed 8/207:05 pmSJU - ART
2 stops27h 38mAmerican Airlines
Deal found 8/11$776
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/124:09 pmART - SJU
2 stops22h 16mAmerican Airlines
Tue 8/197:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$815
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:19 amART - SJU
1 stop12h 42mAmerican Airlines
Sat 1/106:30 amSJU - ART
1 stop9h 29mAmerican Airlines
Deal found 8/8$823
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/113:14 pmART - SJU
2 stops23h 11mAmerican Airlines
Wed 8/207:05 pmSJU - ART
2 stops27h 38mAmerican Airlines
Deal found 8/11$833
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/124:09 pmART - SJU
1 stop6h 40mAmerican Airlines
Fri 8/157:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$845
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/113:14 pmART - SJU
2 stops23h 11mAmerican Airlines
Tue 8/197:05 pmSJU - ART
2 stops19h 44mAmerican Airlines
Deal found 8/11$872
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/124:09 pmART - SJU
2 stops22h 16mAmerican Airlines
Mon 8/187:05 pmSJU - ART
2 stops27h 38mAmerican Airlines
Deal found 8/11$880

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown 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 2,558,603 searches. Data last updated August 11, 2025.
Use the filters below to find and compare flights from Watertown to Caribbean that are best for you.

Fly from

Watertown

Fly to

Caribbean

Route

Depart

Return

Price

WatertownBasseterre

ART - SKB

ARTSKB

Watertown

Tue 12/9

4:28 pm-2:15 pm

2 stops20h 47m

Basseterre Robert Bradshaw Intl

Thu 12/11

3:30 pm-10:25 pm

2 stops31h 55m

$759

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sat 12/20

6:19 am-8:01 pm

1 stop12h 42m

San Juan Luis Munoz Marin Intl

Sat 1/10

6:30 am-2:59 pm

1 stop9h 29m

$823

WatertownSt. George's

ART - GND

ARTGND

Watertown

Sat 12/6

4:28 pm-2:55 pm

2 stops21h 27m

St. George's Point Saline Intl

Wed 12/10

4:20 pm-10:25 pm

2 stops31h 05m

$940

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Mon 12/1

6:00 am-11:47 pm

1 stop16h 47m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Best time to book a flight from Watertown to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Watertown 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 Watertown to Caribbean

What is the cheapest month to book a flight from Watertown, New York to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $254). Flying from Watertown, New York to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 August 11, 2025.
Read through reviews of airlines operating flights from Watertown to Caribbean, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Watertown 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 Watertown to Caribbean?

    Watertown (ART) is the airport you will fly out of if you book a flight from Watertown to Caribbean. It is only a 5.6 mi journey to Watertown (ART) from Watertown’s city center.

  • What are the most popular routes from Watertown, New York to Caribbean?

    When deciding which route to take from Watertown, New York to Caribbean consider Watertown - Varadero Juan Gualberto Gomez, Watertown - Freeport Grand Bahama Intl or Watertown - St. George's Point Saline Intl as they are the most popular.

  • Can I find deals for flights from Watertown to Caribbean that include hotel bookings?

    Yes. In addition to deals on Watertown to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Watertown to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Watertown to Caribbean.

  • Can I find deals for business class flights from Watertown to Caribbean?

    Yes. Cheapflights offers flight deals from Watertown 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.

  • What is the cheapest month to book a flight from Watertown, New York to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $254). Flying from Watertown, New York to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 Watertown to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Heathrow flights
Newark to Heathrow flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Cancún flights
Newark to Cancún flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Miami flights
Newark to O'Hare Intl flights
Newark to Luis Munoz Marin Intl flights
LaGuardia to O'Hare Intl flights
Newark to Los Angeles flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to O'Hare Intl flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Mexico City flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to San Francisco flights
Newark to Las Vegas flights
LaGuardia to Miami flights
John F Kennedy Intl to Haneda flights
Newark to Gatwick flights
John F Kennedy Intl to London City flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Newark to Orlando flights
John F Kennedy Intl to Gatwick flights
LaGuardia to Heathrow flights
John F Kennedy Intl to Seattle flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Orlando flights
Newark to Charles de Gaulle flights
LaGuardia to Atlanta flights
Newark to San Francisco flights
Newark to Mexico City flights
Newark to Leonardo da Vinci/Fiumicino flights
Newark to Haneda flights
LaGuardia to Cancún flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Atlanta flights
Newark to Dallas/Fort Worth flights
Newark to London City flights
LaGuardia to Gatwick flights
Newark to Seattle flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Stansted flights
Newark to Narita flights

Top airline flying from Watertown to Caribbean

Discover the top airline that operate flights from Watertown 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 2,558,603 searches. Data last updated August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$493Average$537FlexibilityNo cancel feeOn-time71%

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.