Caribbean

$117+ 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
Dec 24 — Dec 311
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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 December 19, 2024.

Round-trip from

$241
(Mytrip)

One-way from

$117
(Mytrip)
From New Windsor Stewart to Caribbean
One-way flight from New Windsor Stewart to Caribbean

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 December 19, 2024.

This Mytrip deal was found by Cheapflights users on 12/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:27 pmSWF - KIN
1 stop14h 42mMultiple Airlines
Sat 1/116:10 pmKIN - SWF
2 stops23h 54mMultiple Airlines
Deal found 12/18$589
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/306:27 pmSWF - NAS
1 stop20h 18mMultiple Airlines
Mon 1/611:00 amNAS - SWF
1 stop6h 37mMultiple Airlines
Deal found 12/18$612
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Sun 12/296:30 pmSWF - SDQ
1 stop17h 35mMultiple Airlines
Thu 1/96:19 pmSDQ - SWF
1 stop20h 01mMultiple Airlines
Deal found 12/18$631
This Mytrip deal was found by Cheapflights users on 12/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/236:27 pmSWF - SJU
2 stops27h 03mMultiple Airlines
Sun 1/1210:09 pmSJU - SWF
1 stop16h 11mMultiple Airlines
Deal found 12/18$667
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Mon 12/236:27 pmSWF - PUJ
1 stop20h 28mMultiple Airlines
Fri 12/276:02 pmPUJ - SWF
1 stop25h 45mMultiple Airlines
Deal found 12/17$715
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/306:27 pmSWF - MBJ
1 stop19h 03mMultiple Airlines
Wed 1/12:45 pmMBJ - SWF
1 stop27h 05mMultiple Airlines
Deal found 12/18$718
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Fri 12/276:27 pmSWF - STI
1 stop14h 32mMultiple Airlines
Sun 2/91:04 pmSTI - SWF
1 stop25h 16mMultiple Airlines
Deal found 12/18$786
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Fri 12/276:27 pmSWF - AUA
1 stop20h 13mMultiple Airlines
Thu 1/94:45 pmAUA - SWF
1 stop21h 35mMultiple Airlines
Deal found 12/18$814
This Mytrip deal was found by Cheapflights users on 12/17. 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.
Fri 12/276:27 pmSWF - CUR
1 stop16h 08mMultiple Airlines
Mon 12/305:10 pmCUR - SWF
2 stops18h 50mMultiple Airlines
Deal found 12/17$1,000
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Fri 12/208:00 pmSWF - POS
2 stops41h 09mMultiple Airlines
Sun 12/298:30 amPOS - SWF
1 stop10h 20mMultiple Airlines
Deal found 12/18$1,253

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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 2/3

7:40 pm-9:50 pm

2 stops25h 10m

San Juan Luis Munoz Marin Intl

Thu 2/6

10:09 pm-1:20 pm

1 stop16h 11m

$241

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/10

2:10 pm-3:45 pm

1 stop24h 35m

Punta Cana

Thu 1/16

4:50 pm-1:20 pm

1 stop21h 30m

$328

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 1/30

6:44 pm-12:10 pm

2 stops17h 26m

Montego Bay Sangster Intl

Sun 2/2

1:16 pm-11:20 am

3 stops22h 04m

$389

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 2/7

2:10 pm-5:14 pm

1 stop26h 04m

Santo Domingo Las Americas

Thu 2/13

4:31 pm-5:39 pm

1 stop26h 08m

$399

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

$430

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Mon 1/6

6:27 pm-9:09 am

1 stop14h 42m

Kingston Norman Manley

Sun 1/12

2:38 pm-11:20 am

2 stops20h 42m

$441

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Thu 1/9

6:44 pm-3:40 pm

3 stops43h 56m

Oranjestad Reina Beatrix

Thu 1/16

4:45 pm-11:20 am

2 stops19h 35m

$512

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 1/3

6:27 pm-9:59 am

1 stop14h 32m

Santiago de los Caballeros

Thu 1/9

1:04 pm-1:20 pm

1 stop25h 16m

$640

New WindsorPort of Spain

SWF - POS

SWFPOS

New Windsor Stewart

Thu 1/30

6:44 pm-8:00 pm

2 stops24h 16m

Port of Spain Piarco Intl

Mon 2/3

8:30 am-6:50 pm

1 stop11h 20m

$649

New WindsorWillemstad

SWF - CUR

SWFCUR

New Windsor Stewart

Mon 1/20

2:10 pm-11:35 am

1 stop20h 25m

Willemstad Hato Int.

Thu 1/23

9:55 am-1:35 pm

2 stops28h 40m

$676

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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 $334). 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 December 19, 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?

  • 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 $334). 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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