Caribbean Islands

$115+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Dec 28 — Jan 41
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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 December 23, 2024.

Round-trip from

$238
(Mytrip)

One-way from

$115
(Mytrip)
From New Windsor Stewart to Caribbean Islands
One-way flight from New Windsor Stewart to Caribbean Islands

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 December 23, 2024.

This Mytrip deal was found by Cheapflights users on 12/22. 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 12/3111:40 amSWF - SDQ
2 stops21h 17mMultiple Airlines
Sun 1/266:19 pmSDQ - SWF
2 stops18h 01mMultiple Airlines
Deal found 12/22$541
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/3111:40 amSWF - SJU
1 stop12h 45mMultiple Airlines
Thu 1/22:32 amSJU - SWF
2 stops9h 34mMultiple Airlines
Deal found 12/22$629
This Kiwi.com deal was found by Cheapflights users on 12/23. 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 12/245:01 pmSWF - STI
2 stops44h 48mMultiple Airlines
Fri 12/2710:54 amSTI - SWF
1 stop7h 43mMultiple Airlines
Deal found 12/23$757
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/236:27 pmSWF - NAS
1 stop24h 48mMultiple Airlines
Fri 12/277:15 amNAS - SWF
1 stop10h 22mMultiple Airlines
Deal found 12/22$766
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Sat 12/287:37 pmSWF - MBJ
2 stops17h 53mMultiple Airlines
Wed 1/12:38 pmMBJ - SWF
2 stops19h 51mMultiple Airlines
Deal found 12/22$840
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/276:27 pmSWF - KIN
1 stop14h 42mMultiple Airlines
Mon 1/610:14 amKIN - SWF
1 stop7h 23mMultiple Airlines
Deal found 12/22$845
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 - PUJ
2 stops22h 11mMultiple Airlines
Mon 12/306:02 pmPUJ - SWF
1 stop17h 58mMultiple Airlines
Deal found 12/22$934
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/276:27 pmSWF - AUA
1 stop20h 13mMultiple Airlines
Sun 12/294:40 pmAUA - SWF
1 stop25h 57mMultiple Airlines
Deal found 12/22$988
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 - POS
2 stops24h 38mMultiple Airlines
Sun 12/298:30 amPOS - SWF
1 stop10h 20mMultiple Airlines
Deal found 12/22$1,233
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Sun 12/226:30 pmSWF - SXM
2 stops19h 00mMultiple Airlines
Mon 12/303:25 pmSXM - SWF
2 stops20h 35mMultiple Airlines
Deal found 12/22$1,381

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 2,558,603 searches. Data last updated December 23, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 2/7

2:10 pm-3:58 pm

2 stops24h 48m

San Juan Luis Munoz Marin Intl

Sun 2/9

10:09 pm-1:20 pm

1 stop16h 11m

$238

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 1/19

6:44 pm-12:10 pm

2 stops17h 26m

Montego Bay Sangster Intl

Thu 1/23

1:16 pm-11:20 am

3 stops22h 04m

$315

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 2/7

2:10 pm-3:45 pm

1 stop24h 35m

Punta Cana

Sun 2/9

4:50 pm-1:20 pm

1 stop21h 30m

$346

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Fri 2/28

6:23 pm-3:40 pm

1 stop20h 17m

Oranjestad Reina Beatrix

Thu 3/6

6:35 pm-9:20 am

1 stop15h 45m

$381

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Mon 3/17

10:10 am-7:15 pm

1 stop9h 05m

Nassau Intl

Thu 3/20

4:00 pm-9:20 am

1 stop17h 20m

$434

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Thu 2/6

7:54 pm-1:33 pm

2 stops17h 39m

Kingston Norman Manley

Thu 2/13

1:15 pm-5:39 pm

1 stop28h 24m

$441

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Mon 2/24

12:05 pm-3:26 pm

3 stops26h 21m

Santo Domingo Las Americas

Thu 2/27

4:31 pm-11:25 am

2 stops19h 54m

$544

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 1/6

6:27 pm-9:59 am

1 stop14h 32m

Santiago de los Caballeros

Thu 1/16

1:04 pm-11:20 am

3 stops23h 16m

$567

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 1/19

7:38 pm-2:30 pm

2 stops17h 52m

Simpson Bay Princess Juliana

Sun 1/26

1:05 pm-11:20 am

3 stops23h 15m

$671

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 1/2

6:30 pm-6:25 pm

2 stops22h 55m

Port of Spain Piarco Intl

Sun 1/5

10:50 am-5:37 pm

3 stops31h 47m

$1,015

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 $380). 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 December 23, 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 $380). 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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