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$145+ Cheap flights from New Windsor (SWF) to Caribbean

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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean

Cheapest flights from Stewart to Caribbean
Explore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/111:52 am
SWF
-
SJU
2 stops36h 13m
Multiple Airlines
Sun 3/86:30 am
SJU
-
SWF
1 stop27h 42m
Multiple Airlines
Deal found 1/24$320
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 2/811:48 am
SWF
-
BQN
1 stop23h 28m
Multiple Airlines
Wed 2/113:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 1/23$337
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/2211:52 am
SWF
-
SJU
2 stops26h 10m
Multiple Airlines
Sun 3/16:00 am
SJU
-
SWF
1 stop29h 13m
Multiple Airlines
Deal found 1/25$389
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 6/2311:48 am
SWF
-
SJU
1 stop10h 57m
Multiple Airlines
Wed 7/89:29 pm
SJU
-
SWF
1 stop11h 29m
Multiple Airlines
Deal found 1/24$406
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 6/2311:48 am
SWF
-
SJU
1 stop10h 57m
Multiple Airlines
Wed 7/19:29 pm
SJU
-
SWF
1 stop11h 29m
Multiple Airlines
Deal found 1/24$412
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 5/811:40 am
SWF
-
PUJ
1 stop8h 45m
Multiple Airlines
Sun 5/2411:35 am
PUJ
-
SWF
1 stop21h 16m
Multiple Airlines
Deal found 1/24$418
This Kiwi.com deal was found by Cheapflights users on 1/26. 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
-
AUA
1 stop27h 26m
Multiple Airlines
Sun 2/14:50 pm
AUA
-
SWF
1 stop18h 29m
Multiple Airlines
Deal found 1/26$425
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/228:40 pm
SWF
-
SJU
1 stop13h 30m
Multiple Airlines
Wed 3/253:08 am
SJU
-
SWF
1 stop8h 00m
Multiple Airlines
Deal found 1/24$425
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/511:48 am
SWF
-
BQN
1 stop23h 13m
Multiple Airlines
Wed 2/113:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 1/24$444
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 6/2311:48 am
SWF
-
SJU
1 stop10h 57m
Multiple Airlines
Sat 6/279:29 pm
SJU
-
SWF
1 stop11h 29m
Multiple Airlines
Deal found 1/24$445
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/111:52 am
SWF
-
AUA
1 stop26h 43m
Multiple Airlines
Sun 3/153:41 pm
AUA
-
SWF
2 stops19h 50m
Multiple Airlines
Deal found 1/24$451
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 1/2612:11 pm
SWF
-
SJU
2 stops20h 36m
Multiple Airlines
Sat 1/318:05 pm
SJU
-
SWF
1 stop16h 28m
Multiple Airlines
Deal found 1/24$457

Find flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated January 26, 2026.

Round-trip from

$320
(Kiwi.com)

One-way from

$145
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$242
From New Windsor Stewart to Caribbean
Search Deals
One-way flight from New Windsor Stewart to Caribbean
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 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 26, 2026.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.

Fly from

Stewart

Fly to

Caribbean

Route

Depart

Return

Price

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 2/8

11:48 am-12:16 pm

1 stop23h 28m

Aguadilla Borinquen

Wed 2/11

3:58 am-11:08 am

1 stop8h 10m

$337

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 6/23

11:48 am-10:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Wed 7/1

9:29 pm-8:58 am

1 stop11h 29m

$412

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

8:40 pm-10:10 am

1 stop13h 30m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:08 am-11:08 am

1 stop8h 00m

$425

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 2/5

11:48 am-12:01 pm

1 stop23h 13m

Aguadilla Borinquen

Wed 2/11

3:58 am-11:08 am

1 stop8h 10m

$444

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Sun 3/1

11:52 am-3:35 pm

1 stop26h 43m

Oranjestad Reina Beatrix

Sun 3/15

3:41 pm-11:31 am

2 stops19h 50m

$451

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/15

8:40 pm-10:10 am

1 stop13h 30m

San Juan Luis Munoz Marin Intl

Sat 3/21

7:54 pm-9:39 am

1 stop13h 45m

$460

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 1/30

11:09 am-3:33 pm

1 stop27h 24m

Santiago de los Caballeros

Sun 2/1

4:40 pm-10:19 am

1 stop18h 39m

$466

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

$486

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 6/22

12:15 pm-10:45 pm

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Wed 7/1

9:29 pm-8:58 am

1 stop11h 29m

$490

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 2/9

12:11 pm-11:33 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:54 pm-11:08 am

1 stop16h 14m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $79). Flying from New Windsor to Caribbean 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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 26, 2026.
Peruse reviews from past customers who have flown with JetBlue from New Windsor to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,893 reviews

Boarding

7.4

Comfort

7.5

Entertainment

7.2

Crew

8.0

Overall

7.2

Food

6.6

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,893 reviews
JetBlue
7.2
Good
2,893 reviews

Boarding

7.4

Comfort

7.5

Entertainment

7.2

Crew

8.0

Overall

7.2

Food

6.6

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Caribbean. 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?

    For a flight from New Windsor to Caribbean, 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?

    The most popular route from New Windsor to Caribbean is New Windsor Stewart - San Juan Luis Munoz Marin Intl. You may also consider New Windsor Stewart - Nassau Intl or New Windsor Stewart - Punta Cana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Caribbean 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?

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $79). Flying from New Windsor to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Stewart to Caribbean

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

Discover the top airline that operate flights from Stewart to Caribbean. 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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$227Average$336FlexibilityNo cancel feeOn-time62%

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