Caribbean Islands

$125+ Cheap flights from New Windsor (SWF) to Caribbean Islands

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 26 — Dec 31
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Cheap flight deals from Stewart to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Find flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/21. 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.
Thu 12/126:30 pmSWF - SJU
1 stop7h 22mMultiple Airlines
Sun 12/159:13 pmSJU - SWF
1 stop15h 52mMultiple Airlines
Deal found 11/21$267
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/1312:55 pmSWF - AUA
1 stop25h 45mMultiple Airlines
Sun 12/154:40 pmAUA - SWF
1 stop20h 25mMultiple Airlines
Deal found 11/20$349
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 - MBJ
1 stop24h 38mMultiple Airlines
Sun 12/152:38 pmMBJ - SWF
1 stop21h 27mMultiple Airlines
Deal found 11/21$369
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/1312:55 pmSWF - KIN
1 stop20h 14mMultiple Airlines
Sun 12/151:12 pmKIN - SWF
1 stop22h 53mMultiple Airlines
Deal found 11/20$383
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/1312:55 pmSWF - NAS
1 stop6h 20mMultiple Airlines
Sun 12/154:00 pmNAS - SWF
1 stop20h 05mMultiple Airlines
Deal found 11/20$451
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Fri 12/610:57 amSWF - STI
2 stops22h 07mMultiple Airlines
Sun 12/810:54 amSTI - SWF
2 stops24h 13mMultiple Airlines
Deal found 11/20$499
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Thu 12/126:30 pmSWF - SDQ
2 stops22h 04mMultiple Airlines
Thu 12/197:58 amSDQ - SWF
1 stop10h 52mMultiple Airlines
Deal found 11/19$581
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/1312:55 pmSWF - CUR
1 stop21h 40mMultiple Airlines
Sun 12/1511:15 amCUR - SWF
2 stops25h 50mMultiple Airlines
Deal found 11/19$598
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Wed 12/411:40 amSWF - PUJ
3 stops27h 08mMultiple Airlines
Wed 12/114:23 pmPUJ - SWF
2 stops26h 27mMultiple Airlines
Deal found 11/20$660
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Tue 12/245:01 pmSWF - SXM
2 stops20h 29mMultiple Airlines
Wed 1/13:25 pmSXM - SWF
2 stops20h 04mMultiple Airlines
Deal found 11/20$735

Find flights from Stewart to Caribbean Islands within your budget

Customize your flight search to find flights from Stewart to Caribbean Islands 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 2,612,795 searches. Data last updated November 21, 2024.

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Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 1/27

7:40 pm-3:55 pm

2 stops19h 15m

San Juan Luis Munoz Marin Intl

Thu 1/30

10:09 pm-1:20 pm

1 stop16h 11m

$235

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/17

2:10 pm-3:49 pm

1 stop24h 39m

Punta Cana

Thu 1/23

4:54 pm-1:20 pm

1 stop21h 26m

$345

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Mon 1/6

6:27 pm-3:40 pm

1 stop20h 13m

Oranjestad Reina Beatrix

Thu 1/16

4:40 pm-1:20 pm

1 stop21h 40m

$346

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/9

12:55 pm-1:33 pm

1 stop24h 38m

Montego Bay Sangster Intl

Sun 12/15

2:38 pm-12:05 pm

1 stop21h 27m

$369

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 12/13

12:55 pm-9:09 am

1 stop20h 14m

Kingston Norman Manley

Sun 12/15

1:12 pm-12:05 pm

1 stop22h 53m

$383

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Mon 1/6

6:27 pm-2:45 pm

1 stop20h 18m

Nassau Intl

Fri 1/10

7:15 am-1:20 pm

1 stop6h 05m

$434

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 2/6

7:54 pm-12:55 pm

1 stop16h 01m

Santo Domingo Las Americas

Sun 2/9

6:19 pm-6:50 pm

2 stops25h 31m

$437

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/6

10:57 am-10:04 am

2 stops22h 07m

Santiago de los Caballeros

Sun 12/8

10:54 am-10:07 am

2 stops24h 13m

$499

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 2/20

7:54 pm-3:09 pm

2 stops18h 15m

Simpson Bay Princess Juliana

Mon 2/24

4:07 pm-11:49 am

2 stops20h 42m

$565

New WindsorWillemstad

SWF - CUR

SWFCUR

New Windsor Stewart

Fri 12/13

12:55 pm-11:35 am

1 stop21h 40m

Willemstad Hato Int.

Sun 12/15

11:15 am-12:05 pm

2 stops25h 50m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 20 results
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Best time to book a flight from Stewart to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

What is the cheapest month to book a flight from New Windsor to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands 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 EPX?

Find hourly flight availability from Stewart to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

When flying from New Windsor to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands. 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 Islands?

    For a flight from New Windsor to Caribbean Islands, 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 Islands?

  • Can I find deals for flights from Stewart to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Stewart to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Caribbean Islands.

  • Can I find deals for business class flights from Stewart to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Stewart to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands 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.

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Alternative routes for Stewart to Caribbean Islands

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

Top 2 airlines flying from Stewart to Caribbean Islands

Discover the top 2 airlines that operate flights from Stewart to Caribbean Islands. 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$367FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$227Average$429FlexibilityNo cancel feeOn-time62%
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