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Caribbean

$289+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
Apr 5 — Apr 121
Sun 4/5
Sun 4/12
1 adult, Economy
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Cheap 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 March 6, 2026.

This American Airlines deal was found by Cheapflights users on 3/4. 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 4/1611:25 am
ART
-
SJU
2 stops21h 48m
American Airlines
Sat 4/256:02 pm
SJU
-
ART
2 stops16h 57m
American Airlines
Deal found 3/4$289
This American Airlines deal was found by Cheapflights users on 3/3. 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 3/306:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Tue 3/316:01 pm
SJU
-
ART
2 stops21h 18m
American Airlines
Deal found 3/3$332
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/1111:25 am
ART
-
MBJ
2 stops25h 26m
American Airlines
Thu 4/1612:56 pm
MBJ
-
ART
2 stops21h 03m
American Airlines
Deal found 3/5$337
This American Airlines deal was found by Cheapflights users on 3/6. 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 3/214:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Wed 3/259:20 am
SJU
-
ART
1 stop13h 35m
American Airlines
Deal found 3/6$392
This American Airlines deal was found by Cheapflights users on 3/3. 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 3/306:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Wed 4/13:40 pm
SJU
-
ART
2 stops31h 15m
American Airlines
Deal found 3/3$395
This American Airlines deal was found by Cheapflights users on 3/6. 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 7/246:00 am
ART
-
SJU
2 stops18h 17m
American Airlines
Mon 7/2712:39 am
SJU
-
ART
2 stops23h 13m
American Airlines
Deal found 3/6$442
This American Airlines deal was found by Cheapflights users on 3/4. 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 4/1611:25 am
ART
-
SJU
2 stops21h 48m
American Airlines
Sun 4/266:00 am
SJU
-
ART
1 stop17h 23m
American Airlines
Deal found 3/4$444
This American Airlines deal was found by Cheapflights users on 3/4. 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 3/194:01 pm
ART
-
SJU
1 stop7h 51m
American Airlines
Mon 3/235:00 am
SJU
-
ART
1 stop10h 19m
American Airlines
Deal found 3/4$514
This American Airlines deal was found by Cheapflights users on 3/3. 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 3/306:00 am
ART
-
SJU
2 stops28h 56m
American Airlines
Thu 4/26:00 am
SJU
-
ART
2 stops33h 19m
American Airlines
Deal found 3/3$517
This American Airlines deal was found by Cheapflights users on 3/5. 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 4/1911:25 am
ART
-
GND
2 stops26h 53m
American Airlines
Sun 4/263:18 pm
GND
-
ART
2 stops32h 05m
American Airlines
Deal found 3/5$703

Find flight deals from Watertown to Caribbean

Keep the following information in mind while searching for Watertown to Caribbean flight deals. Data was last updated March 6, 2026.

Round-trip from

$289
(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 March 6, 2026.
Use the filters below to find and compare flights from Watertown to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WatertownMontego Bay

ART - MBJ

ARTMBJ

Watertown

Sat 4/11

11:25 am-11:51 am

2 stops25h 26m

Montego Bay Sangster Intl

Thu 4/16

12:56 pm-10:59 am

2 stops21h 03m

$337

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sat 3/21

4:01 pm-11:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Wed 3/25

7:40 am-10:55 pm

2 stops15h 15m

$392

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Mon 3/30

6:00 am-10:56 am

2 stops28h 56m

San Juan Luis Munoz Marin Intl

Thu 4/2

5:00 am-3:19 pm

1 stop10h 19m

$489

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Tue 3/31

6:00 am-5:03 pm

2 stops35h 03m

San Juan Luis Munoz Marin Intl

Thu 4/2

5:00 am-3:19 pm

1 stop10h 19m

$552

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Mon 3/30

6:00 am-10:56 am

2 stops28h 56m

San Juan Luis Munoz Marin Intl

Mon 4/6

1:44 pm-10:59 am

2 stops21h 15m

$564

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Thu 7/23

4:00 pm-11:41 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Mon 7/27

12:39 am-11:52 pm

2 stops23h 13m

$609

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Tue 3/31

6:00 am-5:03 pm

2 stops35h 03m

San Juan Luis Munoz Marin Intl

Fri 4/3

5:00 am-3:19 pm

1 stop10h 19m

$627

WatertownSt. George's

ART - GND

ARTGND

Watertown

Sun 4/19

11:25 am-2:18 pm

2 stops26h 53m

St. George's Point Saline Intl

Sun 4/26

3:18 pm-11:23 pm

2 stops32h 05m

$703

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Wed 4/1

4:01 pm-11:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Thu 4/2

5:00 am-3:19 pm

1 stop10h 19m

$716

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Fri 7/24

4:00 pm-11:41 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Mon 7/27

6:00 am-3:35 pm

1 stop9h 35m

$776

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 11 resultsSorted by cheapest first
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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 $139). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $288). 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.

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 25h 26m. Your travel time can differ by up to . Watertown, New York and Caribbean are separated by a distance of 1763 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 $139). Flying from Watertown, New York to Caribbean in July is currently the most expensive (average of $288). 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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