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$147+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$337
(Kiwi.com)

One-way from

$147
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$235
From New Windsor Stewart to Caribbean
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One-way flight from New Windsor Stewart to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/312:11 pmSWF - SDQ
1 stop26h 31mMultiple Airlines
Sun 10/53:54 pmSDQ - SWF
1 stop18h 17mMultiple Airlines
Deal found 9/9$335
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/1711:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Sun 10/263:54 pmSDQ - SWF
1 stop22h 17mMultiple Airlines
Deal found 9/11$337
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/2411:31 amSWF - PUJ
1 stop27h 18mMultiple Airlines
Thu 10/303:57 pmPUJ - SWF
1 stop18h 44mMultiple Airlines
Deal found 9/9$337
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/2411:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Sun 11/24:54 pmSDQ - SWF
1 stop19h 17mMultiple Airlines
Deal found 9/9$339
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/312:11 pmSWF - PUJ
2 stops23h 04mMultiple Airlines
Thu 10/93:57 pmPUJ - SWF
1 stop18h 54mMultiple Airlines
Deal found 9/10$341
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 11/711:31 amSWF - PUJ
1 stop23h 45mMultiple Airlines
Sun 11/161:21 pmPUJ - SWF
1 stop22h 50mMultiple Airlines
Deal found 9/9$362
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/1711:31 amSWF - MBJ
1 stop24h 29mMultiple Airlines
Thu 10/2312:09 pmMBJ - SWF
1 stop21h 32mMultiple Airlines
Deal found 9/9$374
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 11/1012:01 pmSWF - KIN
1 stop24h 12mMultiple Airlines
Sun 11/161:28 pmKIN - SWF
1 stop21h 43mMultiple Airlines
Deal found 9/9$376
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 11/1012:01 pmSWF - MBJ
1 stop24h 04mMultiple Airlines
Sat 11/155:39 pmMBJ - SWF
2 stops41h 32mMultiple Airlines
Deal found 9/10$379
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/312:11 pmSWF - KIN
1 stop23h 51mMultiple Airlines
Sun 10/512:14 pmKIN - SWF
1 stop20h 57mMultiple Airlines
Deal found 9/9$383
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/312:11 pmSWF - MBJ
1 stop23h 54mMultiple Airlines
Sun 10/1912:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/10$396
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 9/2111:43 amSWF - SDQ
2 stops28h 17mMultiple Airlines
Thu 10/25:05 pmSDQ - SWF
1 stop18h 16mMultiple Airlines
Deal found 9/9$407

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 September 11, 2025.
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 WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 10/3

12:11 pm-2:42 pm

1 stop26h 31m

Santo Domingo Las Americas

Sun 10/5

3:54 pm-10:11 am

1 stop18h 17m

$335

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 10/17

11:31 am-2:54 pm

1 stop27h 23m

Santo Domingo Las Americas

Sun 10/26

3:54 pm-2:11 pm

1 stop22h 17m

$337

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 10/24

11:31 am-2:49 pm

1 stop27h 18m

Punta Cana

Thu 10/30

3:57 pm-10:41 am

1 stop18h 44m

$337

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 10/24

11:31 am-2:54 pm

1 stop27h 23m

Santo Domingo Las Americas

Sun 11/2

4:54 pm-11:11 am

1 stop19h 17m

$339

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 10/3

12:11 pm-11:15 am

2 stops23h 04m

Punta Cana

Thu 10/9

3:57 pm-10:51 am

1 stop18h 54m

$341

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 11/7

11:31 am-12:16 pm

1 stop23h 45m

Punta Cana

Sun 11/16

1:21 pm-11:11 am

1 stop22h 50m

$362

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/17

11:31 am-11:00 am

1 stop24h 29m

Montego Bay Sangster Intl

Thu 10/23

12:09 pm-10:41 am

1 stop21h 32m

$374

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Mon 11/10

12:01 pm-12:13 pm

1 stop24h 12m

Kingston Norman Manley

Sun 11/16

1:28 pm-11:11 am

1 stop21h 43m

$376

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 11/10

12:01 pm-12:05 pm

1 stop24h 04m

Montego Bay Sangster Intl

Sat 11/15

5:39 pm-11:11 am

2 stops41h 32m

$379

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 10/3

12:11 pm-11:02 am

1 stop23h 51m

Kingston Norman Manley

Sun 10/5

12:14 pm-10:11 am

1 stop20h 57m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, September is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $254). Flying from New Windsor to Caribbean in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from SWF to CB?

Find hourly flight availability from Stewart to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Caribbean as you normally would.

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 September 11, 2025.
Peruse reviews from past customers who have flown with JetBlue and Frontier 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
2,913 reviews

Food

6.7

Boarding

7.4

Overall

7.2

Entertainment

7.3

Crew

8.0

Comfort

7.6

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
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Food

6.7

Boarding

7.4

Overall

7.2

Entertainment

7.3

Crew

8.0

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
Frontier
5.8
Fair
3,177 reviews
JetBlue
7.2
Good
2,913 reviews

Food

6.7

Boarding

7.4

Overall

7.2

Entertainment

7.3

Crew

8.0

Comfort

7.6

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 - Santo Domingo Las Americas 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, September is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $254). Flying from New Windsor to Caribbean in June is currently the most expensive (average of $339). 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

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Top 2 airlines flying from Stewart to Caribbean

Discover the top 2 airlines 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$186FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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