Cheap flights from New Windsor (SWF) to Caribbean from $168

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SWF — SJU
May 19 — May 261

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

Find a great deal and save up to 27% by booking at least 31 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 $326.

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 $324 for the month, but tickets can be as low as $85. Due to multiple factors, prepare for potentially higher prices in December.

When is the cheapest time to fly from New Windsor to Caribbean (SWF - 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 May & June 2024

Find cheap flight options from Stewart to Caribbean specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Prices were last updated on May 14, 2024.
Mon 6/310:38 amSWF - SJU
1 stop14h 25mMultiple Airlines
Tue 6/41:59 amSJU - SWF
1 stop16h 24mMultiple Airlines
Deal found 5/13$401
Mon 6/310:38 amSWF - SJU
1 stop14h 25mMultiple Airlines
Wed 6/55:10 amSJU - SWF
1 stop13h 13mMultiple Airlines
Deal found 5/13$433
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sat 5/187:57 pmSJU - SWF
2 stops13h 48mMultiple Airlines
Deal found 5/13$491
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sat 5/185:44 pmSJU - SWF
1 stop16h 01mMultiple Airlines
Deal found 5/13$503
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sun 5/194:21 pmSJU - SWF
2 stops19h 45mMultiple Airlines
Deal found 5/13$509
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sun 5/194:21 pmSJU - SWF
2 stops19h 45mMultiple Airlines
Deal found 5/13$510
Fri 5/1712:03 pmSWF - SDQ
1 stop14h 25mMultiple Airlines
Sun 5/197:17 amSDQ - SWF
2 stops28h 49mMultiple Airlines
Deal found 5/13$525
Sun 5/1910:25 amSWF - SDQ
1 stop16h 03mMultiple Airlines
Thu 5/233:46 pmSDQ - SWF
2 stops20h 20mMultiple Airlines
Deal found 5/13$531
Fri 5/1712:03 pmSWF - SDQ
1 stop14h 25mMultiple Airlines
Sun 5/197:17 amSDQ - SWF
1 stop27h 56mMultiple Airlines
Deal found 5/13$541

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 2,632,958 searches. Data last updated May 14, 2024.
Mon 6/310:38 amSWF - SJU
1 stop14h 25mMultiple Airlines
Tue 6/41:59 amSJU - SWF
1 stop16h 24mMultiple Airlines
Deal found 5/13$401
Sat 7/207:47 pmSWF - SJU
1 stop12h 11mMultiple Airlines
Sat 7/274:52 amSJU - SWF
1 stop14h 05mMultiple Airlines
Deal found 5/13$415
Mon 6/310:38 amSWF - SJU
1 stop14h 25mMultiple Airlines
Wed 6/55:10 amSJU - SWF
1 stop13h 13mMultiple Airlines
Deal found 5/13$433
Sat 7/207:47 pmSWF - SJU
1 stop12h 11mMultiple Airlines
Sat 7/274:52 amSJU - SWF
1 stop14h 05mMultiple Airlines
Deal found 5/14$447
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sat 5/187:57 pmSJU - SWF
2 stops13h 48mMultiple Airlines
Deal found 5/13$491
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sat 5/185:44 pmSJU - SWF
1 stop16h 01mMultiple Airlines
Deal found 5/13$503
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sun 5/194:21 pmSJU - SWF
2 stops19h 45mMultiple Airlines
Deal found 5/13$509
Fri 5/1712:03 pmSWF - SJU
1 stop11h 27mMultiple Airlines
Sun 5/194:21 pmSJU - SWF
2 stops19h 45mMultiple Airlines
Deal found 5/13$510
Fri 5/1712:03 pmSWF - SDQ
1 stop14h 25mMultiple Airlines
Sun 5/197:17 amSDQ - SWF
2 stops28h 49mMultiple Airlines
Deal found 5/13$525

Stewart to Caribbean flights leaving soon

Find last-minute flight options from Stewart to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Fri 5/1712:03 pmSWF - SDQ
1 stop14h 25mMultiple Airlines
Sun 5/197:17 amSDQ - SWF
2 stops28h 49mMultiple Airlines
Deal found 5/13$525
Sun 5/1910:25 amSWF - SDQ
1 stop16h 03mMultiple Airlines
Thu 5/233:46 pmSDQ - SWF
2 stops20h 20mMultiple Airlines
Deal found 5/13$531
Fri 5/1712:03 pmSWF - SDQ
1 stop14h 25mMultiple Airlines
Sun 5/197:17 amSDQ - SWF
1 stop27h 56mMultiple Airlines
Deal found 5/13$541
Thu 5/2310:25 amSWF - SJU
1 stop15h 45mMultiple Airlines
Sun 5/263:15 amSJU - SWF
1 stop16h 25mMultiple Airlines
Deal found 5/14$654
Fri 5/248:30 pmSWF - SJU
2 stops28h 00mMultiple Airlines
Sun 5/263:15 amSJU - SWF
1 stop16h 25mMultiple Airlines
Deal found 5/14$663
Fri 5/248:30 pmSWF - SJU
2 stops28h 00mMultiple Airlines
Mon 5/275:00 amSJU - SWF
1 stop14h 40mMultiple Airlines
Deal found 5/14$674
Fri 5/248:30 pmSWF - SDQ
1 stop29h 58mMultiple Airlines
Mon 5/277:17 amSDQ - SWF
1 stop12h 23mMultiple Airlines
Deal found 5/13$752
Fri 5/248:30 pmSWF - SDQ
1 stop29h 58mMultiple Airlines
Mon 5/277:17 amSDQ - SWF
1 stop12h 23mMultiple Airlines
Deal found 5/13$817
Fri 5/248:30 pmSWF - SDQ
2 stops18h 14mMultiple Airlines
Mon 5/277:17 amSDQ - SWF
1 stop12h 23mMultiple Airlines
Deal found 5/13$934

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 2,632,958 searches. Data last updated May 14, 2024.
Sun 6/910:25 amSWF - SJU
1 stop14h 57mMultiple Airlines
Deal found 5/13$168
Sun 6/910:25 amSWF - SJU
1 stop14h 57mMultiple Airlines
Deal found 5/13$169
Thu 5/3010:25 amSWF - SXM
2 stops27h 19mMultiple Airlines
Deal found 5/13$169
Mon 5/2712:46 pmSWF - SDQ
2 stops13h 42mMultiple Airlines
Deal found 5/13$194
Thu 6/610:25 amSWF - PUJ
2 stops29h 56mMultiple Airlines
Deal found 5/13$194
Mon 5/2712:09 pmSWF - SJU
3 stops29h 00mMultiple Airlines
Deal found 5/14$197
Sun 6/210:25 amSWF - SDQ
2 stops15h 51mMultiple Airlines
Deal found 5/13$198
Thu 6/610:25 amSWF - SJU
1 stop16h 08mMultiple Airlines
Deal found 5/14$200
Thu 6/610:25 amSWF - PUJ
2 stops29h 56mMultiple Airlines
Deal found 5/14$200

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 2,632,958 searches. Data last updated May 14, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$401 - $525

Route

Depart

Return

Price

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 6/3

1 stop14h 25m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop16h 24m

$401

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 7/20

1 stop12h 11m

San Juan Luis Munoz Marin Intl

Sat 7/27

1 stop14h 05m

$415

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 6/3

1 stop14h 25m

San Juan Luis Munoz Marin Intl

Wed 6/5

1 stop13h 13m

$433

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 7/27

1 stop12h 11m

San Juan Luis Munoz Marin Intl

Sat 8/3

1 stop14h 05m

$447

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/17

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sat 5/18

2 stops13h 48m

$491

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/17

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sat 5/18

1 stop16h 01m

$503

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/17

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sun 5/19

2 stops19h 45m

$509

New Windsor StewartSan Juan Luis Munoz Marin Intl

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/17

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sun 5/19

2 stops19h 45m

$510

New Windsor StewartSanto Domingo Las Americas

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 5/17

1 stop14h 25m

Santo Domingo Las Americas

Sun 5/19

2 stops28h 49m

$525

Flights are sorted by cheapest first

Deals found on 5/13

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

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 $500 on Cheapflights?

    Yes, there are multiple flights from New Windsor to Caribbean for under $500. The cheapest flight booked recently is on Multiple Airlines for just $401, but on average you can expect to pay $527.

  • Are there last-minute flights available from New Windsor to Caribbean for under $600?

    There are currently 18+ open flights from New Windsor to Caribbean within the next 7 days for less than $600.

  • 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. 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 5/14.

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 2,632,958 searches. Data last updated May 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$104Average$298FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
JetBlueCheapest$201Average$429FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
Linear Air TaxiCheapest$20,271Average$82,411FlexibilityNo cancel feeOn-timeN/A
Search Linear Air Taxi flights

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.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Stewart to Caribbean?

Cheapflights makes it easy to find Stewart to Caribbean flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Stewart to Caribbean?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Stewart to Caribbean.

Can Cheapflights find flights from Stewart to Caribbean with no change fees?

Yes, we can. To see specific flights from Stewart to Caribbean with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Stewart to Caribbean become cheaper?

Of course! You can now track prices for flights from Stewart to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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