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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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Mytrip deal was found by Cheapflights users on 12/11. 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.
Thu 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 12/11$386
This Mytrip deal was found by Cheapflights users on 12/11. 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.
Thu 12/254:10 amSJU - SWF
1 stop7h 57mMultiple Airlines
Fri 1/211:57 amSWF - SJU
1 stop9h 08mMultiple Airlines
Deal found 12/11$414
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Sat 12/131:32 pmSJU - SWF
1 stop22h 31mMultiple Airlines
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 12/9$449
This eDestinos deal was found by Cheapflights users on 12/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amSJU - SWF
1 stop13h 06mMultiple Airlines
Mon 12/228:25 pmSWF - SJU
1 stop15h 04mMultiple Airlines
Deal found 12/10$451
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/279:58 pmSJU - SWF
1 stop14h 05mMultiple Airlines
Sat 1/38:45 pmSWF - SJU
1 stop11h 13mMultiple Airlines
Deal found 12/10$598
This Mytrip deal was found by Cheapflights users on 12/11. 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.
Thu 12/254:10 amSJU - SWF
1 stop7h 57mMultiple Airlines
Mon 12/2911:37 amSWF - SJU
1 stop9h 28mMultiple Airlines
Deal found 12/11$639
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/272:59 amSJU - SWF
1 stop9h 04mMultiple Airlines
Thu 1/111:43 amSWF - SJU
1 stop13h 29mMultiple Airlines
Deal found 12/10$679
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:55 amSJU - SWF
1 stop8h 08mMultiple Airlines
Thu 1/111:43 amSWF - SJU
1 stop7h 44mMultiple Airlines
Deal found 12/11$682

Find flight deals from Caribbean to Stewart

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

Round-trip from

$335
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$260
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. 11% potential increase in price ($27 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 December 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 December 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 1/22

4:40 pm-10:19 am

1 stop18h 39m

New Windsor Stewart

Thu 1/29

12:13 pm-11:45 am

2 stops22h 32m

$338

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/25

4:10 am-11:07 am

1 stop7h 57m

New Windsor Stewart

Fri 1/2

11:57 am-10:05 pm

1 stop9h 08m

$414

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Fri 12/19

6:00 am-6:06 pm

1 stop13h 06m

New Windsor Stewart

Mon 12/22

8:25 pm-12:29 pm

1 stop15h 04m

$451

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 2/5

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 2/8

11:48 am-11:33 pm

1 stop10h 45m

$528

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/15

9:04 pm-11:31 am

2 stops15h 27m

New Windsor Stewart

Sun 1/18

12:13 pm-3:03 am

1 stop13h 50m

$561

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 1/7

3:55 am-11:33 am

1 stop8h 38m

New Windsor Stewart

Mon 1/12

12:11 pm-2:50 am

2 stops13h 39m

$593

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/1

6:28 pm-11:07 am

1 stop17h 39m

New Windsor Stewart

Mon 1/5

11:37 am-10:05 pm

1 stop9h 28m

$593

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 1/10

9:23 pm-11:33 am

1 stop15h 10m

New Windsor Stewart

Mon 1/12

12:11 pm-11:33 pm

2 stops10h 22m

$597

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 1/7

3:55 am-11:33 am

1 stop8h 38m

New Windsor Stewart

Fri 1/9

12:11 pm-11:26 pm

2 stops10h 15m

$608

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 12/27

2:59 am-11:03 am

1 stop9h 04m

New Windsor Stewart

Thu 1/1

11:43 am-2:12 am

1 stop13h 29m

$679

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 40 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 $118). 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, Punta Cana - New Windsor Stewart or Nassau Intl - 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 $118). 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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