$195+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Jul 23 — Jul 301

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How far in advance should I book a flight from New Windsor to Caribbean?

Find a great deal and save up to 30% by booking at least 55 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Caribbean within the next two weeks, with the cheapest ticket starting at $306.

What is the cheapest month to fly from New Windsor to Caribbean?

Our data shows that September tends to be the cheapest month to fly to Caribbean from New Windsor. Users have commonly found prices around $319 for the month, but tickets can be as low as $83. Due to multiple factors, prepare for potentially higher prices in December.

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

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.

Cheap Stewart to Caribbean flights in July & August 2024

Find cheap flight options from Stewart to Caribbean specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,689,020 searches. Prices were last updated on July 18, 2024.
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 7/1810:25 amSWF - PUJ
1 stop26h 35mMultiple Airlines
Sun 7/211:54 pmPUJ - SWF
2 stops22h 12mMultiple Airlines
Deal found 7/16$929
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - NAS
1 stop7h 15mMultiple Airlines
Sun 7/214:15 pmNAS - SWF
2 stops19h 51mMultiple Airlines
Deal found 7/17$1,004
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - MBJ
2 stops26h 16mMultiple Airlines
Sat 7/203:55 pmMBJ - SWF
1 stop16h 50mMultiple Airlines
Deal found 7/17$1,047
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - NAS
1 stop10h 00mMultiple Airlines
Sun 7/214:15 pmNAS - SWF
2 stops19h 51mMultiple Airlines
Deal found 7/17$1,176
This mytrip.com deal was found by Cheapflights users on 7/18. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/167:15 pmSWF - CUR
2 stops24h 10mMultiple Airlines
Thu 8/224:35 pmCUR - SWF
2 stops25h 30mMultiple Airlines
Deal found 7/18$1,877
This mytrip.com deal was found by Cheapflights users on 7/17. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/267:15 pmSWF - CUR
2 stops23h 25mMultiple Airlines
Fri 8/305:45 pmCUR - SWF
2 stops24h 20mMultiple Airlines
Deal found 7/17$1,922
This mytrip.com deal was found by Cheapflights users on 7/17. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/187:15 pmSWF - CUR
2 stops24h 10mMultiple Airlines
Sun 7/214:10 pmCUR - SWF
3 stops25h 55mMultiple Airlines
Deal found 7/17$2,078
This mytrip.com deal was found by Cheapflights users on 7/18. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/167:15 pmSWF - CUR
2 stops24h 10mMultiple Airlines
Thu 8/223:55 pmCUR - SWF
3 stops26h 10mMultiple Airlines
Deal found 7/18$2,106

Stewart to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Stewart and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,689,020 searches. Data last updated July 18, 2024.
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 9/810:25 amSWF - NAS
1 stop6h 00mMultiple Airlines
Wed 9/114:00 pmNAS - SWF
2 stops17h 45mMultiple Airlines
Deal found 7/18$542
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 9/810:25 amSWF - NAS
1 stop6h 00mMultiple Airlines
Wed 9/114:00 pmNAS - SWF
2 stops17h 45mMultiple Airlines
Deal found 7/17$547
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 12/206:20 pmSWF - NAS
1 stop20h 25mMultiple Airlines
Mon 12/237:30 amNAS - SWF
1 stop11h 40mMultiple Airlines
Deal found 7/17$634
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 10/310:25 amSWF - NAS
1 stop6h 00mMultiple Airlines
Sat 10/54:00 pmNAS - SWF
2 stops17h 45mMultiple Airlines
Deal found 7/17$650
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/1510:25 amSWF - PUJ
1 stop26h 34mMultiple Airlines
Sun 8/251:59 pmPUJ - SWF
2 stops22h 07mMultiple Airlines
Deal found 7/18$748
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 7/1810:25 amSWF - PUJ
1 stop26h 35mMultiple Airlines
Sun 7/211:54 pmPUJ - SWF
2 stops22h 12mMultiple Airlines
Deal found 7/16$929
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - NAS
1 stop7h 15mMultiple Airlines
Sun 7/214:15 pmNAS - SWF
2 stops19h 51mMultiple Airlines
Deal found 7/17$1,004
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - MBJ
2 stops26h 16mMultiple Airlines
Sat 7/203:55 pmMBJ - SWF
1 stop16h 50mMultiple Airlines
Deal found 7/17$1,047
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 7/1810:25 amSWF - NAS
1 stop10h 00mMultiple Airlines
Sun 7/214:15 pmNAS - SWF
2 stops19h 51mMultiple Airlines
Deal found 7/17$1,176

One-way flights to Caribbean from Stewart

Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,689,020 searches. Data last updated July 18, 2024.
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/17:30 pmSWF - NAS
2 stops19h 20mMultiple Airlines
Deal found 7/17$195
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/2210:25 amSWF - SXM
2 stops27h 44mMultiple Airlines
Deal found 7/17$212
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/17:30 pmSWF - NAS
2 stops19h 20mMultiple Airlines
Deal found 7/17$215
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/87:30 pmSWF - NAS
2 stops19h 20mMultiple Airlines
Deal found 7/17$219
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/2210:25 amSWF - SXM
2 stops27h 44mMultiple Airlines
Deal found 7/17$219
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/108:24 pmSWF - PUJ
1 stop16h 38mMultiple Airlines
Deal found 7/17$222
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/17:30 pmSWF - NAS
2 stops19h 20mMultiple Airlines
Deal found 7/17$223
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/78:09 pmSWF - NAS
1 stop21h 31mMultiple Airlines
Deal found 7/17$235
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 12/206:20 pmSWF - NAS
1 stop24h 55mMultiple Airlines
Deal found 7/17$243

Find flights from Stewart to Caribbean within your budget

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 2,689,020 searches. Data last updated July 18, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$547 - $2,740

Route

Depart

Return

Price

New Windsor StewartNassau Intl

SWF - NAS

SWFNAS

New Windsor Stewart

Sun 9/8

1 stop6h 00m

Nassau Intl

Wed 9/11

2 stops17h 45m

$547

New Windsor StewartNassau Intl

SWF - NAS

SWFNAS

New Windsor Stewart

Thu 10/3

1 stop6h 00m

Nassau Intl

Sat 10/5

2 stops17h 45m

$650

New Windsor StewartPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Thu 8/15

1 stop26h 34m

Punta Cana

Sun 8/25

2 stops22h 07m

$748

New Windsor StewartWillemstad Hato Int.

SWF - CUR

SWFCUR

New Windsor Stewart

Fri 8/16

2 stops24h 10m

Willemstad Hato Int.

Thu 8/22

2 stops25h 30m

$1,877

New Windsor StewartWillemstad Hato Int.

SWF - CUR

SWFCUR

New Windsor Stewart

Mon 8/26

2 stops23h 25m

Willemstad Hato Int.

Fri 8/30

2 stops24h 20m

$1,922

New Windsor StewartWillemstad Hato Int.

SWF - CUR

SWFCUR

New Windsor Stewart

Fri 8/16

2 stops24h 10m

Willemstad Hato Int.

Thu 8/22

3 stops26h 10m

$2,106

New Windsor StewartKingston Norman Manley

SWF - KIN

SWFKIN

New Windsor Stewart

Tue 9/3

2 stops24h 55m

Kingston Norman Manley

Fri 9/6

3 stops30h 48m

$2,583

New Windsor StewartKingston Norman Manley

SWF - KIN

SWFKIN

New Windsor Stewart

Tue 9/3

2 stops24h 55m

Kingston Norman Manley

Fri 9/6

2 stops28h 35m

$2,740

Flights are sorted by cheapest first

Deals found on 7/17

No data available for this route at this time. Please check back soon.

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.

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.

  • Can I find flights from New Windsor to Caribbean for under $600 on Cheapflights?

    Yes, there are multiple flights from New Windsor to Caribbean for under $600. The cheapest flight booked recently is on Multiple Airlines for just $547, but on average you can expect to pay $1,646.

  • What are the most popular routes from New Windsor to Caribbean?

  • What does SWF to SJU mean?

    This is defined as New Windsor Stewart Airport (SWF) and San Juan Luis Munoz Marin Intl Airport (SJU). Codes like San Juan Luis Munoz Marin Intl Airport are often used to just call airports uniquely. Santo Domingo Las Americas Airport (SDQ), Punta Cana Airport (PUJ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Stewart to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Stewart to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Stewart to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Stewart to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Stewart to Caribbean that allow pets onboard?

    Many airlines flying from Stewart to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Stewart to Caribbean?

    Yes, you can often find last-minute deals on Stewart to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the New Windsor to Caribbean flight deals updated?

    The New Windsor to Caribbean flight deals you see on this page were last updated on 7/18.

  • 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 $245). Flying from New Windsor to Caribbean in March is currently the most expensive (average of $337). 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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Alternative routes for Stewart to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Stewart to Caribbean

Discover the top 3 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 2,689,020 searches. Data last updated July 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$102Average$269FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$201Average$429FlexibilityNo cancel feeOn-time62%
Linear Air TaxiCheapest$20,271Average$82,411FlexibilityNo cancel feeOn-timeN/A

Search flights from Stewart to Caribbean by cabin class

Find flights from Stewart to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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