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$357+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This American Airlines deal was found by Cheapflights users on 4/28. 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 7/124:22 pm
ART
-
MBJ
2 stops22h 09m
American Airlines
Sat 7/185:14 pm
MBJ
-
ART
2 stops28h 39m
American Airlines
Deal found 4/28$357
This American Airlines deal was found by Cheapflights users on 4/27. 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 7/124:22 pm
ART
-
MBJ
2 stops22h 09m
American Airlines
Sun 7/195:14 pm
MBJ
-
ART
2 stops28h 39m
American Airlines
Deal found 4/27$362
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/1011:25 am
ART
-
SJU
2 stops17h 07m
American Airlines
Sun 5/176:00 am
SJU
-
ART
1 stop17h 23m
American Airlines
Deal found 4/23$449
This American Airlines deal was found by Cheapflights users on 4/26. 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 7/236:00 am
ART
-
SJU
2 stops16h 59m
American Airlines
Mon 7/2712:58 am
SJU
-
ART
2 stops21h 55m
American Airlines
Deal found 4/26$456
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/196:00 am
ART
-
SJU
2 stops12h 10m
American Airlines
Tue 5/267:15 pm
SJU
-
ART
2 stops20h 24m
American Airlines
Deal found 4/25$479
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/1311:25 am
ART
-
SJU
1 stop10h 40m
American Airlines
Sat 5/237:15 pm
SJU
-
ART
2 stops20h 33m
American Airlines
Deal found 4/27$529
This American Airlines deal was found by Cheapflights users on 4/26. 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 7/236:00 am
ART
-
SJU
2 stops16h 59m
American Airlines
Wed 7/297:00 am
SJU
-
ART
1 stop15h 53m
American Airlines
Deal found 4/26$541
This American Airlines deal was found by Cheapflights users on 4/26. 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 7/244:22 pm
ART
-
SJU
1 stop6h 35m
American Airlines
Wed 7/2911:54 am
SJU
-
ART
2 stops10h 59m
American Airlines
Deal found 4/26$776
This American Airlines deal was found by Cheapflights users on 4/26. 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 7/254:22 pm
ART
-
SJU
1 stop6h 59m
American Airlines
Wed 7/297:00 am
SJU
-
ART
1 stop8h 57m
American Airlines
Deal found 4/26$851

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 April 28, 2026.

Round-trip from

$357
(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 April 28, 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

Sun 7/12

4:09 pm-1:23 pm

2 stops22h 14m

Montego Bay Sangster Intl

Sat 7/18

5:17 pm-10:53 pm

2 stops28h 36m

$357

WatertownMontego Bay

ART - MBJ

ARTMBJ

Watertown

Sun 7/12

4:09 pm-1:23 pm

2 stops22h 14m

Montego Bay Sangster Intl

Sun 7/19

5:17 pm-10:53 pm

2 stops28h 36m

$362

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sun 5/10

11:25 am-4:32 am

2 stops17h 07m

San Juan Luis Munoz Marin Intl

Sun 5/17

6:00 am-11:23 pm

1 stop17h 23m

$449

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Tue 5/19

6:00 am-2:52 pm

2 stops8h 52m

San Juan Luis Munoz Marin Intl

Tue 5/26

6:20 am-10:52 pm

1 stop16h 32m

$479

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Wed 5/13

11:25 am-10:05 pm

1 stop10h 40m

San Juan Luis Munoz Marin Intl

Sat 5/23

6:20 am-10:52 pm

1 stop16h 32m

$529

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Thu 7/23

6:00 am-10:59 pm

2 stops16h 59m

San Juan Luis Munoz Marin Intl

Wed 7/29

7:00 am-10:53 pm

1 stop15h 53m

$541

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sat 7/25

6:00 am-10:33 pm

2 stops16h 33m

San Juan Luis Munoz Marin Intl

Mon 7/27

4:38 pm-3:57 pm

2 stops23h 19m

$616

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Fri 7/24

4:22 pm-10:57 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Wed 7/29

11:54 am-10:53 pm

2 stops10h 59m

$776
Quickest round-trip

WatertownSan Juan

ART - SJU

ARTSJU

Watertown

Sat 7/25

4:22 pm-11:21 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Wed 7/29

7:00 am-3:57 pm

1 stop8h 57m

$851

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Sorted by cheapest first

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
No data available for this route at this time. Please check back soon.

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 22h 09m. 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 - Varadero Juan Gualberto Gomez, Watertown - Montego Bay Sangster Intl or Watertown - San Juan Luis Munoz Marin 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.

See more FAQs

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