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Caribbean

$199+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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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 January 15, 2026.

Round-trip from

$312
(American Airlines)

One-way from

$199
(American Airlines)
From Watertown to Caribbean
Search Deals
One-way flight from Watertown to Caribbean
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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 January 15, 2026.

This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 3/256:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Wed 4/81:31 pm
SJU
-
ART
2 stops21h 28m
American Airlines
Deal found 1/14$312
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Tue 3/314:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Wed 4/81:31 pm
SJU
-
ART
2 stops21h 28m
American Airlines
Deal found 1/14$337
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sun 3/294:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Wed 4/81:31 pm
SJU
-
ART
2 stops21h 28m
American Airlines
Deal found 1/14$392
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Mon 1/196:50 pm
ART
-
SJU
2 stops21h 11m
American Airlines
Wed 1/288:20 am
SJU
-
ART
2 stops14h 03m
American Airlines
Deal found 1/14$403
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Mon 3/304:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Wed 4/81:31 pm
SJU
-
ART
2 stops21h 28m
American Airlines
Deal found 1/14$434
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 2/184:06 pm
ART
-
MBJ
1 stop20h 15m
American Airlines
Sat 2/281:22 pm
MBJ
-
ART
2 stops26h 19m
American Airlines
Deal found 1/14$452
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 3/256:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Thu 4/26:00 am
SJU
-
ART
2 stops33h 19m
American Airlines
Deal found 1/14$458
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Tue 3/314:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Tue 4/76:00 am
SJU
-
ART
1 stop17h 23m
American Airlines
Deal found 1/14$459
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Thu 3/266:00 am
ART
-
SJU
2 stops28h 40m
American Airlines
Wed 4/81:31 pm
SJU
-
ART
2 stops21h 28m
American Airlines
Deal found 1/14$474
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Tue 3/314:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Thu 4/26:00 am
SJU
-
ART
2 stops33h 19m
American Airlines
Deal found 1/14$483
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 3/256:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Mon 4/64:02 pm
SJU
-
ART
1 stop6h 53m
American Airlines
Deal found 1/14$554
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 3/256:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Fri 4/31:30 am
SJU
-
ART
2 stops21h 25m
American Airlines
Deal found 1/14$555

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 January 15, 2026.
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

Wed 3/25

6:00 am-10:56 am

2 stops28h 56m

San Juan Luis Munoz Marin Intl

Wed 4/8

1:31 pm-10:59 am

2 stops21h 28m

$312

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Tue 3/31

4:01 pm-11:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Wed 4/8

1:31 pm-10:59 am

2 stops21h 28m

$337

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sun 3/29

4:01 pm-8:50 pm

2 stops28h 49m

San Juan Luis Munoz Marin Intl

Tue 4/7

5:45 am-11:23 pm

2 stops17h 38m

$434

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Mon 3/30

4:01 pm-5:11 pm

2 stops25h 10m

San Juan Luis Munoz Marin Intl

Tue 4/7

6:00 am-11:23 pm

1 stop17h 23m

$434

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Tue 3/31

6:00 am-10:31 pm

2 stops16h 31m

San Juan Luis Munoz Marin Intl

Tue 4/7

6:00 am-11:23 pm

1 stop17h 23m

$434

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Mon 3/30

4:01 pm-11:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Wed 4/8

1:31 pm-10:59 am

2 stops21h 28m

$434

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sat 3/28

4:01 pm-10:31 pm

2 stops30h 30m

San Juan Luis Munoz Marin Intl

Wed 4/8

1:31 pm-10:59 am

2 stops21h 28m

$434

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Fri 3/27

4:01 pm-11:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Wed 4/8

1:31 pm-10:59 am

2 stops21h 28m

$434

WatertownMontego Bay

ART - MBJ

ARTMBJ

Watertown

Wed 2/18

4:06 pm-12:21 pm

1 stop20h 15m

Montego Bay Sangster Intl

Sat 2/28

1:22 pm-3:41 pm

2 stops26h 19m

$452

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Wed 3/25

6:00 am-10:56 am

2 stops28h 56m

San Juan Luis Munoz Marin Intl

Thu 4/2

6:00 am-3:19 pm

2 stops33h 19m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 15 results
1
2

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, August is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $140). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $285). 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 January 15, 2026.
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
11,129 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,129 reviews
American Airlines
7.2
Good
11,129 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 28h 56m. 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 - Freeport Grand Bahama 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, August is the cheapest month in which you can book a flight from Watertown, New York to Caribbean (average of $140). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $285). 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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Alternative routes for Watertown to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$493Average$498FlexibilityNo cancel feeOn-time71%

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