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Stewart

$109+ Cheap flights from Caribbean to New Windsor (SWF)

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
ene. 21 — ene. 281
mar. 1/21
mar. 1/28
1 adult, Economy
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Cheap flight deals from Caribbean to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Stewart (SWF). 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 enero 16, 2025.

Round-trip from

$250
(Mytrip)

One-way from

$109
(Mytrip)
From Caribbean to New Windsor Stewart
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One-way flight from Caribbean to New Windsor Stewart
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Find flight deals from Caribbean to Stewart

Cheapest flights from Caribbean to Stewart
Explore the most affordable flight options available from Caribbean to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 16, 2025.

This Mytrip deal was found by Cheapflights users on 1/16. 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.
jue. 1/2310:09 pmSJU - SWF
1 stop16h 26mMultiple Airlines
dom. 1/266:44 pmSWF - SJU
1 stop15h 34mMultiple Airlines
Deal found 1/16$250
This Mytrip deal was found by Cheapflights users on 1/14. 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. 2/132:48 pmMBJ - SWF
2 stops20h 37mMultiple Airlines
jue. 2/207:54 pmSWF - MBJ
2 stops17h 49mMultiple Airlines
Deal found 1/14$402
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/272:15 pmNAS - SWF
1 stop20h 45mMultiple Airlines
vie. 5/211:50 amSWF - NAS
1 stop8h 00mMultiple Airlines
Deal found 1/16$458
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/232:38 pmKIN - SWF
1 stop22h 57mMultiple Airlines
dom. 1/266:44 pmSWF - KIN
2 stops18h 49mMultiple Airlines
Deal found 1/15$478
This Mytrip deal was found by Cheapflights users on 1/16. 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.
jue. 1/3011:00 amSDQ - SWF
2 stops27h 20mMultiple Airlines
dom. 2/27:38 pmSWF - SDQ
2 stops15h 18mMultiple Airlines
Deal found 1/16$478

Find flights from Caribbean to Stewart within your budget

Customize your flight search to find flights from Caribbean to Stewart 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 enero 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

mié. 4/30

8:30 pm-10:56 am

1 stop14h 26m

New Windsor Stewart

lun. 5/5

8:39 pm-9:56 am

1 stop13h 17m

$313

NassauNew Windsor

NAS - SWF

NASSWF

Nassau Intl

dom. 4/27

2:15 pm-11:00 am

1 stop20h 45m

New Windsor Stewart

vie. 5/2

11:50 am-7:50 pm

1 stop8h 00m

$458

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

jue. 1/30

11:00 am-1:20 pm

2 stops27h 20m

New Windsor Stewart

dom. 2/2

7:38 pm-11:56 am

2 stops15h 18m

$478

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

jue. 1/30

10:09 pm-1:20 pm

1 stop16h 11m

$109

Punta CanaNew Windsor

PUJ - SWF

PUJSWF

Punta Cana

jue. 2/13

4:48 pm-5:39 pm

1 stop25h 51m

$179

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

jue. 2/6

1:16 pm-1:20 pm

1 stop24h 04m

$202

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

mié. 2/5

1:55 pm-7:14 pm

1 stop30h 19m

$212

OranjestadNew Windsor

AUA - SWF

AUASWF

Oranjestad Reina Beatrix

dom. 2/9

4:45 pm-1:20 pm

1 stop21h 35m

$213

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

jue. 1/23

2:38 pm-1:35 pm

1 stop22h 57m

$243

NassauNew Windsor

NAS - SWF

NASSWF

Nassau Intl

vie. 1/31

7:15 am-1:20 pm

1 stop6h 05m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 12 results
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Best time to book a flight from Caribbean to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Caribbean 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 Caribbean to Stewart

Get recent, data-driven insights about flights from Caribbean to Stewart including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Caribbean to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $109). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $225). 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.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Stewart. 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 into for flights to New Windsor from Caribbean?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Caribbean.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - New Windsor Stewart, Montego Bay Sangster Intl - New Windsor Stewart or Nassau Intl - New Windsor Stewart when deciding on the best route from Caribbean to New Windsor.

  • Can I find deals for flights from Caribbean to Stewart that include hotel bookings?

    Yes. In addition to deals on Caribbean to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Stewart.

  • Can I find deals for business class flights from Caribbean to Stewart?

    Yes. Cheapflights offers flight deals from Caribbean to Stewart 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 Caribbean to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $109). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $225). 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

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Kingston

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