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Stewart

$100+ Cheap flights from Caribbean to New Windsor (SWF)

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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Caribbean to Stewart

Keep the following information in mind while searching for Caribbean to Stewart flight deals. Data was last updated June 12, 2025.

Round-trip from

$222
(Mytrip)

One-way from

$100
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$240
From Caribbean to New Windsor Stewart
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One-way flight from Caribbean to New Windsor Stewart
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Highest demand for flights based on searches. 13% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Caribbean to Stewart

Cheapest flights from Caribbean to Stewart
Explore the most affordable flight options available from Caribbean to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 7/1710:14 pmSJU - SWF
1 stop20h 52mMultiple Airlines
Mon 7/217:56 pmSWF - SJU
1 stop19h 34mMultiple Airlines
Deal found 6/10$222
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Fri 7/1110:55 amSTI - SWF
1 stop8h 11mMultiple Airlines
Mon 7/217:56 pmSWF - STI
1 stop13h 54mMultiple Airlines
Deal found 6/11$336
This eDestinos deal was found by Cheapflights users on 6/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/173:35 pmSDQ - SWF
1 stop27h 31mMultiple Airlines
Mon 8/47:56 pmSWF - SDQ
1 stop25h 49mMultiple Airlines
Deal found 6/12$351
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/257:05 amKIN - SWF
1 stop11h 01mMultiple Airlines
Fri 8/17:56 pmSWF - KIN
1 stop25h 39mMultiple Airlines
Deal found 6/10$361
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 6/263:45 pmAUA - SWF
1 stop27h 26mMultiple Airlines
Wed 7/211:50 amSWF - AUA
1 stop26h 55mMultiple Airlines
Deal found 6/10$389
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/2511:30 amNAS - SWF
1 stop7h 36mMultiple Airlines
Fri 8/17:56 pmSWF - NAS
1 stop14h 34mMultiple Airlines
Deal found 6/10$439
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/2512:10 pmMBJ - SWF
2 stops27h 48mMultiple Airlines
Fri 8/17:56 pmSWF - MBJ
1 stop16h 09mMultiple Airlines
Deal found 6/10$459
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 7/312:35 pmPUJ - SWF
2 stops30h 31mMultiple Airlines
Sun 7/66:42 pmSWF - PUJ
2 stops19h 28mMultiple Airlines
Deal found 6/10$495
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 6/267:10 amSXM - SWF
3 stops36h 01mMultiple Airlines
Mon 6/308:01 pmSWF - SXM
3 stops36h 11mMultiple Airlines
Deal found 6/10$879

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean to Stewart 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 June 12, 2025.
Use the filters below to find and compare flights from Caribbean to New Windsor that are best for you.

Fly from

Caribbean

Fly to

Stewart

Route

Depart

Return

Price

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 7/17

10:14 pm-7:06 pm

1 stop20h 52m

New Windsor Stewart

Mon 7/21

7:56 pm-3:30 pm

1 stop19h 34m

$222

Santiago de los CaballerosNew Windsor

STI - SWF

STISWF

Santiago de los Caballeros

Fri 7/11

10:55 am-7:06 pm

1 stop8h 11m

New Windsor Stewart

Mon 7/21

7:56 pm-9:50 am

1 stop13h 54m

$336

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 7/17

3:35 pm-7:06 pm

1 stop27h 31m

New Windsor Stewart

Mon 8/4

7:56 pm-9:45 pm

1 stop25h 49m

$351

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Fri 7/25

7:05 am-7:06 pm

1 stop11h 01m

New Windsor Stewart

Fri 8/1

7:56 pm-8:35 pm

1 stop25h 39m

$361

OranjestadNew Windsor

AUA - SWF

AUASWF

Oranjestad Reina Beatrix

Thu 6/26

3:45 pm-7:11 pm

1 stop27h 26m

New Windsor Stewart

Wed 7/2

11:50 am-2:45 pm

1 stop26h 55m

$389

NassauNew Windsor

NAS - SWF

NASSWF

Nassau Intl

Fri 7/25

11:30 am-7:06 pm

1 stop7h 36m

New Windsor Stewart

Fri 8/1

7:56 pm-10:30 am

1 stop14h 34m

$439

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Fri 7/25

12:10 pm-4:58 pm

2 stops27h 48m

New Windsor Stewart

Fri 8/1

7:56 pm-11:05 am

1 stop16h 09m

$459

Punta CanaNew Windsor

PUJ - SWF

PUJSWF

Punta Cana

Thu 7/3

12:35 pm-7:06 pm

2 stops30h 31m

New Windsor Stewart

Sun 7/6

6:42 pm-2:10 pm

2 stops19h 28m

$495

Simpson BayNew Windsor

SXM - SWF

SXMSWF

Simpson Bay Princess Juliana

Thu 6/26

7:10 am-7:11 pm

3 stops36h 01m

New Windsor Stewart

Mon 6/30

8:01 pm-8:12 am

3 stops36h 11m

$879

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 6/26

8:24 pm-7:11 pm

1 stop22h 47m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 18 results
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Best time to book a flight from Caribbean to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $109). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $219). 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 Caribbean to Stewart. 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 into for flights to New Windsor from Caribbean?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Caribbean.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - New Windsor Stewart, Santo Domingo Las Americas - New Windsor Stewart or Santiago de los Caballeros - New Windsor Stewart when deciding on the best route from Caribbean to New Windsor.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $109). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $219). 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

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Kingston

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