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Caribbean Islands

$117+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap 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 julio 31, 2025.

Round-trip from

$259
(Mytrip)

One-way from

$117
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$286
From New Windsor Stewart to Caribbean Islands
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One-way flight from New Windsor Stewart to Caribbean Islands
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Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 julio 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/157:37 pmSWF - SJU
2 stops21h 05mMultiple Airlines
jue. 8/212:11 amSJU - SWF
2 stops14h 35mMultiple Airlines
Deal found 7/30$259
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
vie. 8/157:37 pmSWF - PUJ
1 stop19h 23mMultiple Airlines
jue. 8/214:05 pmPUJ - SWF
1 stop24h 41mMultiple Airlines
Deal found 7/30$337
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
vie. 8/157:37 pmSWF - MBJ
1 stop16h 37mMultiple Airlines
jue. 8/2110:22 amMBJ - SWF
1 stop29h 24mMultiple Airlines
Deal found 7/30$355
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
lun. 8/117:56 pmSWF - SDQ
1 stop19h 51mMultiple Airlines
jue. 8/215:05 pmSDQ - SWF
1 stop23h 41mMultiple Airlines
Deal found 7/30$357
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/157:37 pmSWF - KIN
1 stop16h 50mMultiple Airlines
vie. 8/227:55 amKIN - SWF
1 stop7h 51mMultiple Airlines
Deal found 7/30$374
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
vie. 10/3111:31 amSWF - STI
1 stop23h 34mMultiple Airlines
dom. 11/96:18 pmSTI - SWF
1 stop17h 53mMultiple Airlines
Deal found 7/30$402
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/512:27 pmSWF - NAS
1 stop7h 48mMultiple Airlines
lun. 12/88:30 amNAS - SWF
1 stop10h 10mMultiple Airlines
Deal found 7/30$443
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/157:37 pmSWF - SXM
1 stop18h 23mMultiple Airlines
mié. 8/203:05 pmSXM - SWF
2 stops20h 18mMultiple Airlines
Deal found 7/31$462
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/177:03 pmSWF - FPO
2 stops17h 22mMultiple Airlines
vie. 8/2211:00 amFPO - SWF
1 stop5h 46mMultiple Airlines
Deal found 7/31$524
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
vie. 8/225:36 pmSWF - AUA
1 stop21h 04mMultiple Airlines
lun. 8/251:18 pmAUA - SWF
2 stops22h 38mMultiple Airlines
Deal found 7/28$569

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 julio 31, 2025.
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

vie. 8/15

7:37 pm-4:42 pm

2 stops21h 05m

San Juan Luis Munoz Marin Intl

jue. 8/21

2:11 am-4:46 pm

2 stops14h 35m

$259

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

vie. 8/15

7:37 pm-3:00 pm

1 stop19h 23m

Punta Cana

jue. 8/21

4:05 pm-4:46 pm

1 stop24h 41m

$337

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

vie. 8/15

7:37 pm-11:14 am

1 stop16h 37m

Montego Bay Sangster Intl

jue. 8/21

10:22 am-4:46 pm

1 stop29h 24m

$355

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

lun. 8/11

7:56 pm-3:47 pm

1 stop19h 51m

Santo Domingo Las Americas

jue. 8/21

5:05 pm-4:46 pm

1 stop23h 41m

$357

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

vie. 8/15

7:37 pm-11:27 am

1 stop16h 50m

Kingston Norman Manley

vie. 8/22

7:55 am-4:46 pm

1 stop7h 51m

$374

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

vie. 10/31

11:31 am-11:05 am

1 stop23h 34m

Santiago de los Caballeros

dom. 11/9

6:18 pm-11:11 am

1 stop17h 53m

$402

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

vie. 12/5

12:27 pm-8:15 pm

1 stop7h 48m

Nassau Intl

lun. 12/8

8:30 am-6:40 pm

1 stop10h 10m

$443

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

vie. 8/15

7:37 pm-2:00 pm

1 stop18h 23m

Simpson Bay Princess Juliana

mié. 8/20

3:05 pm-11:23 am

2 stops20h 18m

$462

New WindsorFreeport

SWF - FPO

SWFFPO

New Windsor Stewart

dom. 8/17

7:03 pm-12:25 pm

2 stops17h 22m

Freeport Grand Bahama Intl

vie. 8/22

11:00 am-4:46 pm

1 stop5h 46m

$524

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

vie. 8/22

5:36 pm-2:40 pm

1 stop21h 04m

Oranjestad Reina Beatrix

lun. 8/25

1:18 pm-11:56 am

2 stops22h 38m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 19 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, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from SWF to EPX?

Find hourly flight availability from Stewart to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 31, 2025.

When flying from New Windsor to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 - Nassau Intl, New Windsor Stewart - Montego Bay Sangster Intl or New Windsor Stewart - Punta Cana 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, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in June is currently the most expensive (average of $339). 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

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Top 2 airlines flying from Stewart to Caribbean Islands

Discover the top 2 airlines 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$166FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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