Caribbean

$127+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Apr 11 — Apr 181
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/7. 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 6/1110:28 am
SWF
-
SJU
1 stop14h 19m
Multiple Airlines
Sat 6/135:56 pm
SJU
-
SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/7$264
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/2410:28 am
SWF
-
SJU
1 stop14h 19m
Multiple Airlines
Sat 5/305:56 pm
SJU
-
SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/7$306
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Thu 5/2110:28 am
SWF
-
SJU
1 stop29h 27m
Multiple Airlines
Wed 5/276:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 3/11$318
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Sun 4/1911:45 am
SWF
-
SJU
1 stop24h 48m
Multiple Airlines
Sun 4/268:27 pm
SJU
-
SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/10$327
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/2611:45 am
SWF
-
SJU
1 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
-
SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7$329
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/2810:28 am
SWF
-
SJU
1 stop8h 54m
Multiple Airlines
Sun 5/318:27 pm
SJU
-
SWF
1 stop12h 24m
Multiple Airlines
Deal found 3/8$332
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Sun 5/3110:28 am
SWF
-
SJU
1 stop14h 19m
Multiple Airlines
Sat 8/15:56 pm
SJU
-
SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/10$338
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/1911:45 am
SWF
-
SJU
1 stop7h 37m
Multiple Airlines
Sat 4/257:01 pm
SJU
-
SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/7$339
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/1011:45 am
SWF
-
SJU
1 stop7h 37m
Multiple Airlines
Wed 5/138:27 pm
SJU
-
SWF
1 stop12h 31m
Multiple Airlines
Deal found 3/8$352
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/1112:15 pm
SWF
-
SJU
2 stops11h 09m
Multiple Airlines
Wed 5/1312:57 pm
SJU
-
SWF
1 stop21h 58m
Multiple Airlines
Deal found 3/8$357
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/2411:40 am
SWF
-
PUJ
1 stop8h 45m
Multiple Airlines
Sun 4/2611:35 am
PUJ
-
SWF
1 stop23h 15m
Multiple Airlines
Deal found 3/7$367
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Thu 4/911:45 am
SWF
-
SDQ
1 stop13h 53m
Multiple Airlines
Wed 4/152:35 pm
SDQ
-
SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/11$399

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 March 12, 2026.

Round-trip from

$306
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$296
From New Windsor Stewart to Caribbean
One-way flight from New Windsor Stewart to Caribbean
Highest demand for flights based on searches. 6% potential increase in price ($20 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 March 12, 2026.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 5/21

10:28 am-3:55 pm

1 stop29h 27m

San Juan Luis Munoz Marin Intl

Wed 5/27

6:00 am-9:38 am

1 stop27h 38m

$318

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/26

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Fri 5/8

1:59 am-11:25 am

2 stops9h 26m

$329

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 4/24

11:40 am-8:25 pm

1 stop8h 45m

Punta Cana

Sun 4/26

11:35 am-10:50 am

1 stop23h 15m

$367

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 5/16

12:05 pm-11:59 pm

2 stops11h 54m

San Juan Luis Munoz Marin Intl

Wed 5/20

12:57 pm-9:38 am

1 stop20h 41m

$394

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 4/9

11:45 am-1:38 am

1 stop13h 53m

Santo Domingo Las Americas

Wed 4/15

2:35 pm-10:55 am

1 stop20h 20m

$399

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Sun 4/26

11:45 am-10:36 am

2 stops46h 51m

Punta Cana

Sun 5/3

11:35 am-10:50 am

1 stop23h 15m

$450

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Thu 5/28

10:28 am-10:30 am

1 stop24h 02m

Nassau Intl

Wed 6/3

4:00 pm-9:38 am

1 stop17h 38m

$451

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 6/12

9:39 am-8:25 pm

1 stop10h 46m

Punta Cana

Sun 6/14

11:35 am-8:49 am

1 stop21h 14m

$454

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Sun 5/24

10:28 am-7:15 pm

1 stop8h 47m

Nassau Intl

Wed 5/27

4:00 pm-9:38 am

1 stop17h 38m

$456

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/15

11:45 am-10:43 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Thu 5/21

6:09 pm-8:51 am

1 stop14h 42m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, May is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $93). 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 March 12, 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.

Entertainment

7.2

Comfort

7.5

Food

6.6

Overall

7.2

Crew

8.0

Boarding

7.4

Reviews

1 / 20
8.0
Excellent

Wei,Feb 2026

JFK - BOS

The JFK to BOS flight was uneventful. The delay of the inbound plane was difficult since we were near 1.5 hours in delays from the original departure time.

Entertainment

7.2

Comfort

7.5

Food

6.6

Overall

7.2

Crew

8.0

Boarding

7.4

Reviews

1 / 20
8.0
Excellent

Wei,Feb 2026

JFK - BOS

The JFK to BOS flight was uneventful. The delay of the inbound plane was difficult since we were near 1.5 hours in delays from the original departure time.

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?

  • 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, May is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $93). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Caribbean

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

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 March 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$227Average$336FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.