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$295+ Cheap flights from Watertown, NY (ART) to Caribbean

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
nov. 15 — nov. 221
sam. 11/15
sam. 11/22
1 adult, Economy
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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 octobre 16, 2025.

This American Airlines deal was found by Cheapflights users on 10/16. 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.
mer. 12/172:30 pmART - SJU
2 stops18h 05mAmerican Airlines
sam. 12/277:00 amSJU - ART
1 stop17h 04mAmerican Airlines
Deal found 10/16$600
This American Airlines deal was found by Cheapflights users on 10/16. 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.
ven. 11/2810:00 amART - SJU
2 stops24h 12mAmerican Airlines
lun. 12/15:09 pmSJU - ART
1 stop7h 00mAmerican Airlines
Deal found 10/16$655
This American Airlines deal was found by Cheapflights users on 10/15. 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.
lun. 12/82:30 pmART - SKB
2 stops22h 57mAmerican Airlines
mer. 12/103:27 pmSKB - ART
2 stops23h 38mAmerican Airlines
Deal found 10/15$743
This American Airlines deal was found by Cheapflights users on 10/14. 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.
mer. 11/266:00 amART - SJU
2 stops17h 44mAmerican Airlines
sam. 11/291:59 amSJU - ART
1 stop13h 09mAmerican Airlines
Deal found 10/14$868
This American Airlines deal was found by Cheapflights users on 10/15. 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.
sam. 12/62:30 pmART - GND
2 stops23h 32mAmerican Airlines
mer. 12/104:04 pmGND - ART
2 stops23h 01mAmerican Airlines
Deal found 10/15$1,167

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 octobre 16, 2025.

Round-trip from

$295
(American Airlines)
From Watertown to Caribbean
Search Deals

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 octobre 16, 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

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

mar. 3/3

6:19 am-11:30 pm

1 stop16h 11m

San Juan Luis Munoz Marin Intl

jeu. 3/5

6:50 pm-10:23 pm

2 stops28h 33m

$295

WatertownMontego Bay

ART - MBJ

ARTMBJ

Watertown

dim. 3/29

4:37 pm-9:15 am

2 stops41h 38m

Montego Bay Sangster Intl

jeu. 4/2

3:00 pm-10:20 pm

1 stop6h 20m

$468

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

ven. 11/28

10:00 am-11:12 am

2 stops24h 12m

San Juan Luis Munoz Marin Intl

lun. 12/1

5:09 pm-11:09 pm

1 stop7h 00m

$655

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

ven. 1/16

6:50 pm-2:59 pm

2 stops19h 09m

San Juan Luis Munoz Marin Intl

dim. 1/18

7:00 am-9:23 pm

1 stop15h 23m

$655

WatertownFreeport

ART - FPO

ARTFPO

Watertown

mar. 3/10

6:22 am-4:25 pm

2 stops10h 03m

Freeport Grand Bahama Intl

mer. 3/11

6:59 pm-10:20 pm

2 stops27h 21m

$702

WatertownBasseterre

ART - SKB

ARTSKB

Watertown

lun. 12/8

2:30 pm-2:27 pm

2 stops22h 57m

Basseterre Robert Bradshaw Intl

mer. 12/10

3:27 pm-2:05 pm

2 stops23h 38m

$743

WatertownSt. George's

ART - GND

ARTGND

Watertown

sam. 12/6

2:30 pm-3:02 pm

2 stops23h 32m

St. George's Point Saline Intl

mer. 12/10

4:04 pm-2:05 pm

2 stops23h 01m

$1,167

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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, February is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $130). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $286). 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 octobre 16, 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
11,043 reviews

Food

6.4

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,043 reviews
American Airlines
7.2
Good
11,043 reviews

Food

6.4

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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.

  • How long is the flight from Watertown, New York to Caribbean?

    American Airlines can get you from Watertown, New York to Caribbean in just under 16h 11m. Your travel time can differ by up to . Watertown, New York and Caribbean are separated by a distance of 1857 mi.

  • 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 - San Juan Luis Munoz Marin Intl, Watertown - Varadero Juan Gualberto Gomez or Watertown - Montego Bay Sangster 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, February is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $130). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $286). 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

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 octobre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$493Average$537FlexibilityNo cancel feeOn-time71%

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