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$103+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
mar. 23 — mar. 301
dom. 3/23
dom. 3/30
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 marzo 18, 2025.

Round-trip from

$213
(Mytrip)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$217
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. 7% potential increase in price ($21 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 March 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 marzo 18, 2025.

This Mytrip deal was found by Cheapflights users on 3/17. 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. 5/1211:50 amSWF - SJU
2 stops23h 39mMultiple Airlines
jue. 5/159:27 pmSJU - SWF
1 stop13h 38mMultiple Airlines
Deal found 3/17$213
This Mytrip deal was found by Cheapflights users on 3/17. 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 - PUJ
1 stop26h 52mMultiple Airlines
jue. 5/83:22 pmPUJ - SWF
1 stop19h 38mMultiple Airlines
Deal found 3/17$325
This Mytrip deal was found by Cheapflights users on 3/17. 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. 4/710:10 amSWF - AUA
1 stop28h 35mMultiple Airlines
dom. 4/133:45 pmAUA - SWF
1 stop19h 15mMultiple Airlines
Deal found 3/17$336
This Mytrip deal was found by Cheapflights users on 3/16. 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. 4/2811:50 amSWF - MBJ
1 stop24h 05mMultiple Airlines
jue. 5/112:00 pmMBJ - SWF
1 stop22h 00mMultiple Airlines
Deal found 3/16$336
This Mytrip deal was found by Cheapflights users on 3/17. 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. 4/410:10 amSWF - KIN
1 stop27h 18mMultiple Airlines
dom. 4/61:36 pmKIN - SWF
1 stop18h 44mMultiple Airlines
Deal found 3/17$372
This Mytrip deal was found by Cheapflights users on 3/17. 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. 4/410:10 amSWF - NAS
1 stop9h 05mMultiple Airlines
dom. 4/67:15 amNAS - SWF
1 stop26h 05mMultiple Airlines
Deal found 3/17$433
This Mytrip deal was found by Cheapflights users on 3/17. 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 - FPO
1 stop26h 05mMultiple Airlines
jue. 5/1510:45 amFPO - SWF
1 stop24h 20mMultiple Airlines
Deal found 3/17$440
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
lun. 3/3110:10 amSWF - SDQ
2 stops15h 32mMultiple Airlines
jue. 4/32:54 pmSDQ - SWF
1 stop27h 52mMultiple Airlines
Deal found 3/17$509
This Mytrip deal was found by Cheapflights users on 3/16. 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.
mié. 7/211:50 amSWF - CUR
1 stop23h 45mMultiple Airlines
lun. 7/75:10 pmCUR - SWF
2 stops18h 46mMultiple Airlines
Deal found 3/16$739

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 2,558,603 searches. Data last updated marzo 18, 2025.

Fly from

Stewart

Fly to

Caribbean

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 5/12

11:50 am-11:29 am

2 stops23h 39m

San Juan Luis Munoz Marin Intl

jue. 5/15

9:27 pm-11:05 am

1 stop13h 38m

$213

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

lun. 5/5

11:50 am-2:42 pm

1 stop26h 52m

Punta Cana

jue. 5/8

3:22 pm-11:00 am

1 stop19h 38m

$325

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

lun. 4/7

10:10 am-2:45 pm

1 stop28h 35m

Oranjestad Reina Beatrix

dom. 4/13

3:45 pm-11:00 am

1 stop19h 15m

$336

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

lun. 4/28

11:50 am-10:55 am

1 stop24h 05m

Montego Bay Sangster Intl

jue. 5/1

12:00 pm-11:00 am

1 stop22h 00m

$336

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

vie. 4/4

10:10 am-12:28 pm

1 stop27h 18m

Kingston Norman Manley

dom. 4/6

1:36 pm-9:20 am

1 stop18h 44m

$372

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

vie. 4/4

10:10 am-7:15 pm

1 stop9h 05m

Nassau Intl

dom. 4/6

7:15 am-9:20 am

1 stop26h 05m

$433

New WindsorFreeport

SWF - FPO

SWFFPO

New Windsor Stewart

vie. 5/9

11:50 am-1:55 pm

1 stop26h 05m

Freeport Grand Bahama Intl

jue. 5/15

10:45 am-11:05 am

1 stop24h 20m

$440

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

lun. 3/31

10:10 am-1:42 am

2 stops15h 32m

Santo Domingo Las Americas

jue. 4/3

2:54 pm-6:46 pm

1 stop27h 52m

$509

New WindsorWillemstad

SWF - CUR

SWFCUR

New Windsor Stewart

lun. 4/14

11:50 am-11:35 am

1 stop23h 45m

Willemstad Hato Int.

sáb. 4/19

5:10 pm-5:03 pm

2 stops23h 53m

$865

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 4/4

10:10 am-7:11 pm

2 stops33h 01m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

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.

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 $346). 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 marzo 18, 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 - Nassau Intl. You may also consider New Windsor Stewart - San Juan Luis Munoz Marin Intl or New Windsor Stewart - Montego Bay Sangster 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 March is currently the most expensive (average of $346). 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 airline flying from Stewart to Caribbean

Discover the top airline 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 marzo 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$186FlexibilityNo cancel feeOn-time62%
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