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$128+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 29 — Nov 51
Tue 10/29
Tue 11/5
1 adult, Economy
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SWF - SJU
Oct 29 - Nov 5

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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 October 24, 2024.

This Mytrip deal was found by Cheapflights users on 10/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1810:55 amSWF - SJU
1 stop7h 54mMultiple Airlines
Sun 11/248:39 pmSJU - SWF
1 stop17h 31mMultiple Airlines
Deal found 10/23$256
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 12/912:55 pmSWF - AUA
1 stop25h 45mMultiple Airlines
Sun 12/154:40 pmAUA - SWF
1 stop20h 25mMultiple Airlines
Deal found 10/23$373
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Fri 11/2210:10 amSWF - NAS
1 stop8h 40mMultiple Airlines
Wed 11/2711:00 amNAS - SWF
1 stop6h 21mMultiple Airlines
Deal found 10/23$442
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Wed 11/276:11 pmSWF - SDQ
1 stop20h 26mMultiple Airlines
Sun 1/263:45 amSDQ - SWF
1 stop10h 35mMultiple Airlines
Deal found 10/23$527
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Tue 12/2411:40 amSWF - MBJ
1 stop26h 05mMultiple Airlines
Sun 1/121:46 pmMBJ - SWF
1 stop23h 34mMultiple Airlines
Deal found 10/23$570
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 12/306:27 pmSWF - KIN
1 stop14h 22mMultiple Airlines
Mon 1/69:54 amKIN - SWF
1 stop7h 43mMultiple Airlines
Deal found 10/23$606
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 12/306:27 pmSWF - PUJ
1 stop20h 21mMultiple Airlines
Sun 1/54:43 pmPUJ - SWF
1 stop25h 54mMultiple Airlines
Deal found 10/23$644
This Mytrip deal was found by Cheapflights users on 10/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:27 pmSWF - STI
1 stop14h 32mMultiple Airlines
Mon 1/610:54 amSTI - SWF
1 stop7h 43mMultiple Airlines
Deal found 10/23$706
This SmartFares deal was found by Cheapflights users on 10/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:30 pmSWF - SXM
2 stops19h 00mMultiple Airlines
Wed 1/13:25 pmSXM - SWF
2 stops27h 25mMultiple Airlines
Deal found 10/23$919

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 2,462,889 searches. Data last updated October 24, 2024.

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Budget

$256 - $919

Route

Depart

Return

Price

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 11/18

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Sun 11/24

1 stop17h 31m

$256

New Windsor StewartOranjestad Reina Beatrix

SWF - AUA

SWFAUA

New Windsor Stewart

Mon 12/9

1 stop25h 45m

Oranjestad Reina Beatrix

Sun 12/15

1 stop20h 25m

$373

New Windsor StewartNassau Intl

SWF - NAS

SWFNAS

New Windsor Stewart

Fri 11/22

1 stop8h 40m

Nassau Intl

Wed 11/27

1 stop6h 21m

$442

New Windsor StewartSanto Domingo Las Americas

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 1/10

1 stop11h 08m

Santo Domingo Las Americas

Sun 1/12

2 stops16h 05m

$504

New Windsor StewartMontego Bay Sangster Intl

SWF - MBJ

SWFMBJ

New Windsor Stewart

Tue 12/24

1 stop26h 05m

Montego Bay Sangster Intl

Sun 1/12

1 stop23h 34m

$570

New Windsor StewartKingston Norman Manley

SWF - KIN

SWFKIN

New Windsor Stewart

Mon 12/30

1 stop14h 22m

Kingston Norman Manley

Mon 1/6

1 stop7h 43m

$606

New Windsor StewartPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/17

2 stops27h 03m

Punta Cana

Thu 1/23

1 stop21h 35m

$629

New Windsor StewartSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/30

1 stop14h 32m

Santiago de los Caballeros

Mon 1/6

1 stop7h 43m

$706

New Windsor StewartSimpson Bay Princess Juliana

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 12/22

2 stops19h 00m

Simpson Bay Princess Juliana

Wed 1/1

2 stops27h 25m

$919

Flights are sorted by cheapest first

Deals found on 10/23

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.

Travel insights for flights from Stewart to Caribbean

Get recent, data-driven insights about flights from Stewart to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $335). 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 October 24, 2024.

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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 $300 on Cheapflights?

    Yes, there are multiple flights from New Windsor to Caribbean for under $300. The cheapest flight booked recently is on Multiple Airlines for just $256, but on average you can expect to pay $556.

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

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

  • 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. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), 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 10/23.

  • 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 March is currently the most expensive (average of $335). 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.

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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 2,462,889 searches. Data last updated October 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$367FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$227Average$429FlexibilityNo cancel feeOn-time62%
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