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$125+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Caribbean (0CB). 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 20, 2024.

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 November 20, 2024.

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.
Thu 12/126:30 pmSWF - SJU
1 stop7h 22mMultiple Airlines
Sun 12/159:13 pmSJU - SWF
1 stop15h 52mMultiple Airlines
Deal found 11/20$270
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 11/19. 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.
Mon 12/912:55 pmSWF - MBJ
1 stop24h 38mMultiple Airlines
Sun 12/152:38 pmMBJ - SWF
1 stop21h 27mMultiple Airlines
Deal found 11/19$369
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 - KIN
1 stop20h 14mMultiple Airlines
Thu 12/121:12 pmKIN - SWF
1 stop22h 53mMultiple Airlines
Deal found 11/18$373
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.
Mon 12/912:55 pmSWF - NAS
1 stop5h 55mMultiple Airlines
Thu 12/124:00 pmNAS - SWF
1 stop20h 05mMultiple Airlines
Deal found 11/19$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.
Sat 12/287:37 pmSWF - PUJ
2 stops19h 18mMultiple Airlines
Mon 12/304:50 pmPUJ - SWF
2 stops19h 10mMultiple Airlines
Deal found 11/20$712
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 12/187:30 pmSWF - SXM
3 stops42h 00mMultiple Airlines
Sat 12/283:25 pmSXM - SWF
2 stops20h 04mMultiple Airlines
Deal found 11/20$752

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 2,629,791 searches. Data last updated November 20, 2024.

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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 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 WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/10

2:10 pm-3:49 pm

1 stop24h 39m

Punta Cana

Sun 1/12

4:54 pm-1:20 pm

1 stop21h 26m

$363

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

Mon 12/9

12:55 pm-9:09 am

1 stop20h 14m

Kingston Norman Manley

Thu 12/12

1:12 pm-12:05 pm

1 stop22h 53m

$373

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 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 WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Sun 1/26

6:44 pm-12:55 pm

1 stop17h 11m

Santo Domingo Las Americas

Thu 2/6

6:19 pm-11:25 am

2 stops18h 06m

$500

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

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 1/3

11:46 am-2:30 pm

3 stops25h 44m

Simpson Bay Princess Juliana

Fri 1/10

3:25 pm-5:19 pm

3 stops26h 54m

$633

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

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 $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 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 November 20, 2024.

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 - San Juan Luis Munoz Marin Intl. You may also consider New Windsor Stewart - Nassau Intl or New Windsor Stewart - Santo Domingo Las Americas.

  • 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 $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.

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.
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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$367FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$227Average$429FlexibilityNo cancel feeOn-time62%
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