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Caribbean

$116+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
ART — SJU
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
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Cheap flight deals from Watertown to Caribbean

Best flights from Watertown to Caribbean
Discover carefully curated flight deals from Watertown to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 2, 2025.

This American Airlines deal was found by Cheapflights users on 11/29. 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 1/267:00 amART - SJU
1 stop8h 30mAmerican Airlines
Thu 1/298:20 amSJU - ART
2 stops14h 03mAmerican Airlines
Deal found 11/29$291
This American Airlines deal was found by Cheapflights users on 11/29. 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 1/207:00 amART - MBJ
2 stops28h 33mAmerican Airlines
Sat 1/243:12 pmMBJ - ART
2 stops30h 11mAmerican Airlines
Deal found 11/29$404
This American Airlines deal was found by Cheapflights users on 11/29. 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 1/276:50 pmART - GND
2 stops19h 10mAmerican Airlines
Sat 1/314:00 pmGND - ART
2 stops27h 14mAmerican Airlines
Deal found 11/29$707
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/56:11 pmART - FPO
2 stops18h 53mAmerican Airlines
Sun 4/126:40 pmFPO - ART
2 stops27h 49mAmerican Airlines
Deal found 12/1$707
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/46:11 pmART - FPO
2 stops18h 53mAmerican Airlines
Sun 4/126:40 pmFPO - ART
2 stops27h 49mAmerican Airlines
Deal found 12/1$767
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/56:00 amART - FPO
2 stops8h 13mAmerican Airlines
Sat 4/116:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,196
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/56:00 amART - FPO
2 stops8h 13mAmerican Airlines
Fri 4/106:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,246
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/36:00 amART - FPO
2 stops8h 13mAmerican Airlines
Sat 4/116:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,323
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/46:00 amART - FPO
2 stops11h 17mAmerican Airlines
Sat 4/116:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,323
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/36:00 amART - FPO
2 stops8h 13mAmerican Airlines
Fri 4/106:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,373
This American Airlines deal was found by Cheapflights users on 12/1. 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 4/46:00 amART - FPO
2 stops8h 13mAmerican Airlines
Fri 4/106:40 pmFPO - ART
2 stops17h 20mAmerican Airlines
Deal found 12/1$1,373
This American Airlines deal was found by Cheapflights users on 11/29. 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 2/246:19 pmART - FPO
2 stops17h 53mAmerican Airlines
Wed 2/252:54 pmFPO - ART
2 stops8h 03mAmerican Airlines
Deal found 11/29$2,803

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 December 2, 2025.

Round-trip from

$291
(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 December 2, 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

Mon 1/26

7:00 am-4:30 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

Thu 1/29

8:20 am-9:23 pm

2 stops14h 03m

$291

WatertownMontego Bay

ART - MBJ

ARTMBJ

Watertown

Tue 1/20

7:00 am-11:33 am

2 stops28h 33m

Montego Bay Sangster Intl

Sat 1/24

3:12 pm-9:23 pm

2 stops30h 11m

$404

WatertownSt. George's

ART - GND

ARTGND

Watertown

Tue 1/27

6:50 pm-3:00 pm

2 stops19h 10m

St. George's Point Saline Intl

Sat 1/31

4:00 pm-6:14 pm

2 stops27h 14m

$707

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Sun 4/5

6:11 pm-1:04 pm

2 stops18h 53m

Freeport Grand Bahama Intl

Sun 4/12

6:40 pm-10:29 pm

2 stops27h 49m

$707

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Sat 4/4

6:11 pm-1:04 pm

2 stops18h 53m

Freeport Grand Bahama Intl

Sun 4/12

6:40 pm-10:29 pm

2 stops27h 49m

$767

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Sun 4/5

6:00 am-2:13 pm

2 stops8h 13m

Freeport Grand Bahama Intl

Sat 4/11

6:40 pm-12:00 pm

2 stops17h 20m

$1,196

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Sun 4/5

6:00 am-2:13 pm

2 stops8h 13m

Freeport Grand Bahama Intl

Fri 4/10

6:40 pm-12:00 pm

2 stops17h 20m

$1,246

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Fri 4/3

6:00 am-2:13 pm

2 stops8h 13m

Freeport Grand Bahama Intl

Sat 4/11

6:40 pm-12:00 pm

2 stops17h 20m

$1,323

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Sat 4/4

6:00 am-5:17 pm

2 stops11h 17m

Freeport Grand Bahama Intl

Sat 4/11

6:40 pm-12:00 pm

2 stops17h 20m

$1,323

WatertownFreeport

ART - FPO

ARTFPO

Watertown

Fri 4/3

6:00 am-2:13 pm

2 stops8h 13m

Freeport Grand Bahama Intl

Fri 4/10

6:40 pm-12:00 pm

2 stops17h 20m

$1,373

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 17 results
1
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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, 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 $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 December 2, 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
11,041 reviews

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
American Airlines
7.2
Good
11,041 reviews
American Airlines
7.2
Good
11,041 reviews

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.

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 8h 30m. 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 - Varadero Juan Gualberto Gomez, Watertown - Freeport Grand Bahama 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.

  • 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 $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 December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$493Average$537FlexibilityNo cancel feeOn-time71%

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