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Stewart

$161+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This eDestinos deal was found by Cheapflights users on 10/12. 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 10/309:38 amPUJ - SWF
1 stop25h 03mMultiple Airlines
Mon 11/312:01 pmSWF - PUJ
1 stop28h 32mMultiple Airlines
Deal found 10/12$381
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Tue 12/239:32 pmSJU - SWF
1 stop20h 12mMultiple Airlines
Sat 1/38:45 pmSWF - SJU
1 stop12h 48mMultiple Airlines
Deal found 10/13$421
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/249:45 pmSJU - SWF
1 stop12h 08mMultiple Airlines
Thu 11/2711:43 amSWF - SJU
1 stop14h 11mMultiple Airlines
Deal found 10/13$456
This Mytrip deal was found by Cheapflights users on 10/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:47 amSDQ - SWF
1 stop8h 20mMultiple Airlines
Mon 1/511:37 amSWF - SDQ
1 stop14h 05mMultiple Airlines
Deal found 10/12$460
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:59 amSJU - SWF
1 stop8h 04mMultiple Airlines
Sun 11/166:14 pmSWF - SJU
1 stop18h 13mMultiple Airlines
Deal found 10/12$468
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:59 amSJU - SWF
1 stop8h 38mMultiple Airlines
Sun 12/711:43 amSWF - SJU
1 stop7h 44mMultiple Airlines
Deal found 10/12$489
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:31 pmSDQ - SWF
1 stop19h 36mMultiple Airlines
Sat 1/38:45 pmSWF - SDQ
2 stops28h 05mMultiple Airlines
Deal found 10/12$495
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Wed 10/293:04 amSJU - SWF
1 stop7h 59mMultiple Airlines
Sun 11/26:16 pmSWF - SJU
1 stop18h 06mMultiple Airlines
Deal found 10/13$518
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Wed 11/1911:50 pmSDQ - SWF
2 stops35h 32mMultiple Airlines
Wed 11/2612:17 pmSWF - SDQ
1 stop26h 13mMultiple Airlines
Deal found 10/13$542
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:10 amSJU - SWF
1 stop10h 56mMultiple Airlines
Mon 12/228:25 pmSWF - SJU
1 stop17h 14mMultiple Airlines
Deal found 10/12$549
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:31 pmSDQ - SWF
1 stop19h 36mMultiple Airlines
Mon 12/2911:37 amSWF - SDQ
1 stop14h 05mMultiple Airlines
Deal found 10/12$550
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/249:45 pmSJU - SWF
1 stop12h 08mMultiple Airlines
Thu 12/411:43 amSWF - SJU
1 stop7h 44mMultiple Airlines
Deal found 10/13$592

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 October 14, 2025.

Round-trip from

$381
(eDestinos)

One-way from

$161
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$206
From Caribbean to New Windsor Stewart
Search Deals
One-way flight from Caribbean to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 14, 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

Punta CanaNew Windsor

PUJ - SWF

PUJSWF

Punta Cana

Thu 10/30

9:38 am-10:41 am

1 stop25h 03m

New Windsor Stewart

Mon 11/3

12:01 pm-5:33 pm

1 stop28h 32m

$381

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Tue 12/23

9:32 pm-4:44 pm

1 stop20h 12m

New Windsor Stewart

Sat 1/3

8:45 pm-10:33 am

1 stop12h 48m

$421

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 11/12

3:59 am-11:03 am

1 stop8h 04m

New Windsor Stewart

Sun 11/16

6:14 pm-1:27 pm

1 stop18h 13m

$468

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/4

3:59 am-11:37 am

1 stop8h 38m

New Windsor Stewart

Sun 12/7

11:43 am-8:27 pm

1 stop7h 44m

$493

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 12/25

4:31 pm-11:07 am

1 stop19h 36m

New Windsor Stewart

Sat 1/3

8:45 pm-1:50 am

2 stops28h 05m

$495

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 10/29

3:04 am-11:03 am

1 stop7h 59m

New Windsor Stewart

Sun 11/2

6:16 pm-1:22 pm

1 stop18h 06m

$518

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Wed 11/19

11:50 pm-10:22 am

2 stops35h 32m

New Windsor Stewart

Wed 11/26

12:17 pm-3:30 pm

1 stop26h 13m

$542

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 12/25

4:31 pm-11:07 am

1 stop19h 36m

New Windsor Stewart

Mon 12/29

11:37 am-2:42 am

1 stop14h 05m

$550

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Fri 12/19

8:10 am-6:06 pm

1 stop10h 56m

New Windsor Stewart

Mon 12/22

8:25 pm-12:37 am

2 stops27h 12m

$556

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Mon 11/24

9:45 pm-8:53 am

1 stop12h 08m

New Windsor Stewart

Thu 12/4

11:43 am-8:27 pm

1 stop7h 44m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 51 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, February is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $76). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $119). 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, February is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $76). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $119). 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 New Windsor?

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

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See prices for flight routes from nearby airports that may be better suited for you.
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