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Caribbean Islands

$129+ Cheap flights from New Windsor (SWF) to Caribbean Islands

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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/309:38 am
SWF
-
SJU
1 stop13h 07m
Multiple Airlines
Thu 9/39:29 pm
SJU
-
SWF
2 stops14h 06m
Multiple Airlines
Deal found 1/27$294
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:33 pm
SWF
-
SJU
1 stop13h 14m
Multiple Airlines
Mon 2/96:00 am
SJU
-
SWF
1 stop13h 43m
Multiple Airlines
Deal found 1/28$340
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:09 am
SWF
-
PUJ
1 stop28h 27m
Multiple Airlines
Thu 2/55:47 pm
PUJ
-
SWF
1 stop17h 32m
Multiple Airlines
Deal found 1/28$396
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:33 pm
SWF
-
SJU
1 stop13h 14m
Multiple Airlines
Sun 2/89:29 pm
SJU
-
SWF
2 stops22h 14m
Multiple Airlines
Deal found 1/28$405
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:11 pm
SWF
-
SJU
2 stops33h 23m
Multiple Airlines
Sat 3/287:54 pm
SJU
-
SWF
1 stop13h 45m
Multiple Airlines
Deal found 1/27$407
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:09 am
SWF
-
STI
1 stop27h 24m
Multiple Airlines
Sun 2/84:40 pm
STI
-
SWF
1 stop18h 39m
Multiple Airlines
Deal found 1/28$422
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/307:33 pm
SWF
-
SJU
1 stop27h 26m
Multiple Airlines
Sun 3/16:00 am
SJU
-
SWF
1 stop29h 13m
Multiple Airlines
Deal found 1/27$439
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/3011:09 am
SWF
-
SXM
1 stop26h 01m
Multiple Airlines
Sun 2/13:20 pm
SXM
-
SWF
1 stop19h 59m
Multiple Airlines
Deal found 1/27$448
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:02 am
SWF
-
PUJ
1 stop8h 23m
Multiple Airlines
Sun 3/1511:35 am
PUJ
-
SWF
1 stop21h 27m
Multiple Airlines
Deal found 1/28$457
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1311:04 am
SWF
-
SJU
1 stop12h 39m
Multiple Airlines
Sat 2/143:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Deal found 1/28$473
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:40 am
SWF
-
PUJ
1 stop8h 45m
Multiple Airlines
Wed 5/204:47 pm
PUJ
-
SWF
1 stop16h 51m
Multiple Airlines
Deal found 1/28$479
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:48 am
SWF
-
SJU
1 stop10h 21m
Multiple Airlines
Wed 3/43:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Deal found 1/27$492

Find flight deals from Stewart to Caribbean Islands

Keep the following information in mind while searching for Stewart to Caribbean Islands flight deals. Data was last updated January 29, 2026.

Round-trip from

$407
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$242
From New Windsor Stewart to Caribbean Islands
Search Deals
One-way flight from New Windsor Stewart to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Caribbean Islands 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 29, 2026.
Use the filters below to find and compare flights from New Windsor to Caribbean Islands that are best for you.

Fly from

Stewart

Fly to

Caribbean Islands

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 2/6

7:33 pm-9:47 am

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:00 am-6:43 pm

1 stop13h 43m

$340

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 3/6

11:02 am-8:25 pm

1 stop8h 23m

Punta Cana

Sun 3/15

11:35 am-9:02 am

1 stop21h 27m

$457

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 5/15

11:40 am-8:25 pm

1 stop8h 45m

Punta Cana

Wed 5/20

4:47 pm-9:38 am

1 stop16h 51m

$479

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/12

11:48 am-2:53 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

Sat 2/14

3:53 am-11:08 am

1 stop8h 15m

$495

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 4/5

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Sat 4/11

2:46 am-10:55 am

1 stop8h 09m

$499

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/22

11:48 am-12:54 am

1 stop12h 06m

San Juan Luis Munoz Marin Intl

Wed 2/25

3:53 am-11:08 am

1 stop8h 15m

$504

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 2/27

11:03 am-8:25 pm

1 stop8h 22m

Punta Cana

Sun 3/1

11:35 am-10:13 am

1 stop23h 38m

$513

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Thu 4/2

10:29 am-4:10 pm

1 stop29h 41m

Oranjestad Reina Beatrix

Wed 4/8

3:41 pm-10:55 am

1 stop19h 14m

$519

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/26

11:48 am-2:01 am

1 stop14h 13m

San Juan Luis Munoz Marin Intl

Wed 4/29

3:08 am-11:08 am

1 stop8h 00m

$520

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/2

10:29 am-6:54 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 4/11

7:54 pm-10:55 am

1 stop15h 01m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
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Best time to book a flight from Stewart to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Stewart 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 New Windsor to Caribbean Islands

What is the cheapest month to book a flight from New Windsor to Caribbean Islands?

Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $79). Flying from New Windsor to Caribbean Islands in August is currently the most expensive (average of $138). 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 Stewart to Caribbean Islands. 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 New Windsor to Caribbean Islands?

    For a flight from New Windsor to Caribbean Islands, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

  • What are the most popular routes from New Windsor to Caribbean Islands?

    Most travelers choose New Windsor Stewart - San Juan Luis Munoz Marin Intl, New Windsor Stewart - Punta Cana or New Windsor Stewart - Nassau Intl when deciding on the best route from New Windsor to Caribbean Islands.

  • Can I find deals for flights from Stewart to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Stewart to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Caribbean Islands.

  • Can I find deals for business class flights from Stewart to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Stewart to Caribbean Islands 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 New Windsor to Caribbean Islands?

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $79). Flying from New Windsor to Caribbean Islands in August is currently the most expensive (average of $138). 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 Stewart to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Stewart to Caribbean Islands

Discover the top airline that operate flights from Stewart to Caribbean Islands. 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$227Average$336FlexibilityNo cancel feeOn-time62%

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