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Caribbean Islands

$245+ Cheap flights from Watertown, NY (ART) to Caribbean Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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Cheap flight deals from Watertown to Caribbean Islands

Keep the following information in mind while searching for Watertown to Caribbean Islands flight deals. Data was last updated August 1, 2025.

Round-trip from

$245
(American Airlines)
From Watertown to Caribbean Islands
Search Deals

Find flight deals from Watertown to Caribbean Islands

Cheapest flights from Watertown to Caribbean Islands
Explore the most affordable flight options available from Watertown to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 10/36:00 amART - SJU
2 stops17h 37mAmerican Airlines
Sun 10/57:05 pmSJU - ART
2 stops19h 15mAmerican Airlines
Deal found 7/31$245
This American Airlines deal was found by Cheapflights users on 7/31. 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 12/84:28 pmART - SKB
2 stops20h 47mAmerican Airlines
Wed 12/103:30 pmSKB - ART
2 stops24h 32mAmerican Airlines
Deal found 7/31$759
This American Airlines deal was found by Cheapflights users on 7/30. 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 12/64:28 pmART - GND
2 stops21h 27mAmerican Airlines
Wed 12/104:20 pmGND - ART
2 stops23h 42mAmerican Airlines
Deal found 7/30$940

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown to Caribbean Islands 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 1, 2025.
Use the filters below to find and compare flights from Watertown to Caribbean Islands that are best for you.

Fly from

Watertown

Fly to

Caribbean Islands

Route

Depart

Return

Price

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Fri 10/3

6:00 am-11:37 pm

2 stops17h 37m

San Juan Luis Munoz Marin Intl

Sun 10/5

7:05 pm-2:20 pm

2 stops19h 15m

$245

WatertownBasseterre

ART - SKB

ARTSKB

Watertown

Mon 12/8

4:28 pm-2:15 pm

2 stops20h 47m

Basseterre Robert Bradshaw Intl

Wed 12/10

3:30 pm-3:02 pm

2 stops24h 32m

$759

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-3:02 pm

2 stops23h 42m

$940

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Best time to book a flight from Watertown to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Watertown, New York to Caribbean Islands (average of $254). Flying from Watertown, New York to Caribbean Islands 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated August 1, 2025.
See what other customers who have flown with American Airlines from Watertown to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

Related info for your journey

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

    Watertown (ART), located 5.6 mi from the city center, is the airport you fly out of when you book flights from Watertown to Caribbean Islands.

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

    While some choose either Watertown - Varadero Juan Gualberto Gomez or Watertown - Freeport Grand Bahama Intl, Watertown - San Juan Luis Munoz Marin Intl is the most popular route from Watertown, New York to Caribbean Islands.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Watertown to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Watertown, New York to Caribbean Islands (average of $254). Flying from Watertown, New York to Caribbean Islands 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

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Top airline flying from Watertown to Caribbean Islands

Discover the top airline that operate flights from Watertown to Caribbean Islands. 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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$396Average$564FlexibilityNo cancel feeOn-time71%

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