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$98+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
abr. 20 — abr. 271
dom. 4/20
dom. 4/27
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated abril 15, 2025.

Round-trip from

$236
(Mytrip)

One-way from

$98
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$337
From New Windsor Stewart to Caribbean
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One-way flight from New Windsor Stewart to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 15, 2025.

This Mytrip deal was found by Cheapflights users on 4/15. 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.
lun. 5/511:50 amSWF - SJU
2 stops31h 50mMultiple Airlines
jue. 5/811:50 amSJU - SWF
2 stops23h 10mMultiple Airlines
Deal found 4/15$235
This Mytrip deal was found by Cheapflights users on 4/15. 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.
vie. 5/911:50 amSWF - AUA
1 stop26h 50mMultiple Airlines
jue. 5/153:45 pmAUA - SWF
1 stop19h 20mMultiple Airlines
Deal found 4/15$330
This Mytrip deal was found by Cheapflights users on 4/15. 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.
vie. 5/211:50 amSWF - MBJ
1 stop24h 05mMultiple Airlines
dom. 5/412:00 pmMBJ - SWF
1 stop22h 00mMultiple Airlines
Deal found 4/15$341
This Mytrip deal was found by Cheapflights users on 4/14. 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.
lun. 5/511:50 amSWF - KIN
1 stop25h 41mMultiple Airlines
jue. 5/151:34 pmKIN - SWF
1 stop20h 31mMultiple Airlines
Deal found 4/14$368
This Mytrip deal was found by Cheapflights users on 4/15. 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.
lun. 4/2111:50 amSWF - PUJ
1 stop26h 52mMultiple Airlines
jue. 4/243:48 pmPUJ - SWF
1 stop19h 12mMultiple Airlines
Deal found 4/15$370
This Mytrip deal was found by Cheapflights users on 4/15. 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.
vie. 6/137:18 pmSWF - SDQ
1 stop19h 21mMultiple Airlines
dom. 6/227:15 amSDQ - SWF
2 stops35h 56mMultiple Airlines
Deal found 4/15$398
This Mytrip deal was found by Cheapflights users on 4/15. 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.
vie. 5/1611:55 amSWF - NAS
1 stop26h 50mMultiple Airlines
dom. 5/187:15 amNAS - SWF
1 stop27h 50mMultiple Airlines
Deal found 4/15$434
This Mytrip deal was found by Cheapflights users on 4/14. 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.
jue. 5/85:53 pmSWF - FPO
3 stops19h 37mMultiple Airlines
dom. 5/1111:00 amFPO - SWF
1 stop24h 00mMultiple Airlines
Deal found 4/14$596
This Mytrip deal was found by Cheapflights users on 4/15. 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.
vie. 4/1811:50 amSWF - SXM
1 stop26h 10mMultiple Airlines
lun. 4/213:05 pmSXM - SWF
2 stops20h 44mMultiple Airlines
Deal found 4/15$1,086

Cheapflights Fare Finder

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 2,558,603 searches. Data last updated abril 15, 2025.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.

Fly from

Stewart

Fly to

Caribbean

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 5/5

11:50 am-7:40 pm

2 stops31h 50m

San Juan Luis Munoz Marin Intl

jue. 5/8

11:50 am-11:00 am

2 stops23h 10m

$235

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

vie. 5/9

11:50 am-2:40 pm

1 stop26h 50m

Oranjestad Reina Beatrix

jue. 5/15

3:45 pm-11:05 am

1 stop19h 20m

$330

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

vie. 5/2

11:50 am-10:55 am

1 stop24h 05m

Montego Bay Sangster Intl

dom. 5/4

12:00 pm-11:00 am

1 stop22h 00m

$341

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

lun. 5/5

11:50 am-12:31 pm

1 stop25h 41m

Kingston Norman Manley

jue. 5/15

1:34 pm-11:05 am

1 stop20h 31m

$368

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

vie. 5/9

11:50 am-2:17 pm

1 stop26h 27m

Punta Cana

jue. 5/15

3:22 pm-11:05 am

1 stop19h 43m

$372

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

vie. 6/13

7:18 pm-2:39 pm

1 stop19h 21m

Santo Domingo Las Americas

dom. 6/22

7:15 am-7:11 pm

2 stops35h 56m

$398

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

vie. 5/16

11:55 am-2:45 pm

1 stop26h 50m

Nassau Intl

dom. 5/18

7:15 am-11:05 am

1 stop27h 50m

$434

New WindsorFreeport

SWF - FPO

SWFFPO

New Windsor Stewart

jue. 5/8

5:53 pm-1:30 pm

3 stops19h 37m

Freeport Grand Bahama Intl

dom. 5/11

11:00 am-11:00 am

1 stop24h 00m

$596

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

jue. 5/29

12:06 pm-2:00 pm

2 stops25h 54m

Simpson Bay Princess Juliana

jue. 6/5

2:10 pm-6:05 pm

3 stops27h 55m

$1,329

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 5/5

11:50 am-7:40 pm

2 stops31h 50m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 17 results
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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.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Caribbean

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 December is currently the most expensive (average of $336). 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 abril 15, 2025.

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.

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

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

  • 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.

  • 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 December is currently the most expensive (average of $336). 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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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 2,558,603 searches. Data last updated abril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$186FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$175Average$336FlexibilityNo cancel feeOn-time62%

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