HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$132+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 3/117:05 pm
SJU
-
SWF
1 stop16h 03m
Multiple Airlines
Mon 3/1612:11 pm
SWF
-
SJU
2 stops9h 52m
Multiple Airlines
Deal found 1/24$347
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 3/113:08 am
SJU
-
SWF
1 stop8h 00m
Multiple Airlines
Mon 3/1612:11 pm
SWF
-
SJU
2 stops20h 42m
Multiple Airlines
Deal found 1/24$358
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 6/107:05 pm
SJU
-
SWF
1 stop13h 53m
Multiple Airlines
Sun 6/149:38 am
SWF
-
SJU
1 stop23h 09m
Multiple Airlines
Deal found 1/26$463
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Sat 8/19:49 pm
SJU
-
SWF
1 stop11h 49m
Multiple Airlines
Wed 8/512:05 pm
SWF
-
SJU
2 stops10h 40m
Multiple Airlines
Deal found 1/24$465
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 2/113:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Thu 2/1911:48 am
SWF
-
SJU
1 stop11h 05m
Multiple Airlines
Deal found 1/25$505
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Wed 3/43:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Mon 3/912:11 pm
SWF
-
SJU
2 stops13h 47m
Multiple Airlines
Deal found 1/23$506
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sat 5/23:08 am
SJU
-
SWF
1 stop8h 00m
Multiple Airlines
Mon 5/412:11 pm
SWF
-
SJU
2 stops20h 36m
Multiple Airlines
Deal found 1/26$508
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 2/258:05 pm
SJU
-
SWF
1 stop16h 03m
Multiple Airlines
Sun 3/111:48 am
SWF
-
SJU
1 stop12h 06m
Multiple Airlines
Deal found 1/26$510
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/96:00 am
SJU
-
SWF
1 stop13h 43m
Multiple Airlines
Thu 2/1211:48 am
SWF
-
SJU
1 stop10h 21m
Multiple Airlines
Deal found 1/24$514
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 5/147:05 pm
SJU
-
SWF
2 stops16h 30m
Multiple Airlines
Sun 5/179:38 am
SWF
-
SJU
1 stop13h 10m
Multiple Airlines
Deal found 1/26$526
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Thu 1/293:32 pm
SDQ
-
SWF
1 stop19h 47m
Multiple Airlines
Thu 2/1211:42 am
SWF
-
SDQ
1 stop25h 38m
Multiple Airlines
Deal found 1/24$537
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 3/181:45 am
SJU
-
SWF
1 stop9h 23m
Multiple Airlines
Sun 3/2211:48 am
SWF
-
SJU
1 stop14h 25m
Multiple Airlines
Deal found 1/26$556

Find flight deals from Caribbean to Stewart

Keep the following information in mind while searching for Caribbean to Stewart flight deals. Data was last updated January 26, 2026.

Round-trip from

$347
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$202
From Caribbean to New Windsor Stewart
Search Deals
One-way flight from Caribbean to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
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 January 26, 2026.
Use the filters below to find and compare flights from Caribbean to New Windsor that are best for you.

Fly from

Caribbean

Fly to

Stewart

Route

Depart

Return

Price

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/11

7:05 pm-11:08 am

1 stop16h 03m

New Windsor Stewart

Mon 3/16

12:11 pm-10:03 pm

2 stops9h 52m

$347

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/11

3:08 am-11:08 am

1 stop8h 00m

New Windsor Stewart

Mon 3/16

12:11 pm-8:53 am

2 stops20h 42m

$358

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 2/11

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Thu 2/19

11:48 am-11:53 pm

1 stop11h 05m

$505

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/4

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Mon 3/9

12:11 pm-1:58 am

2 stops13h 47m

$506

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 2/25

8:05 pm-11:08 am

1 stop16h 03m

New Windsor Stewart

Sun 3/1

11:48 am-12:54 am

1 stop12h 06m

$510

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Mon 2/9

6:00 am-6:43 pm

1 stop13h 43m

New Windsor Stewart

Thu 2/12

11:48 am-11:09 pm

1 stop10h 21m

$514

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 1/29

3:32 pm-10:19 am

1 stop19h 47m

New Windsor Stewart

Thu 2/12

11:42 am-2:20 pm

1 stop25h 38m

$537

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 2/7

8:05 pm-11:08 am

1 stop16h 03m

New Windsor Stewart

Mon 2/9

12:11 pm-11:33 pm

2 stops10h 22m

$558

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/18

1:45 am-11:08 am

1 stop9h 23m

New Windsor Stewart

Sun 3/22

11:48 am-10:45 pm

1 stop10h 57m

$561

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/18

1:45 am-11:08 am

1 stop9h 23m

New Windsor Stewart

Mon 3/23

12:11 pm-10:03 pm

2 stops9h 52m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 46 results
1
2
3
...
5

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.

Cheapflights Insights

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $74). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $120). 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, Providenciales - New Windsor Stewart or Castries Hewanorra - 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, January is the cheapest month in which you can book a flight from Caribbean to New Windsor (average of $74). Flying from Caribbean to New Windsor in August is currently the most expensive (average of $120). 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 New Windsor?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Atlanta to John F Kennedy Intl flights
Charles de Gaulle to John F Kennedy Intl flights
Charles de Gaulle to Newark flights
Miami to John F Kennedy Intl flights
Atlanta to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
Los Angeles to Newark flights
Dallas/Fort Worth to Newark flights
San Francisco to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Los Angeles to LaGuardia flights
Miami to LaGuardia flights
Fort Lauderdale to Newark flights
Frankfurt to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
O'Hare Intl to LaGuardia flights
Orlando to John F Kennedy Intl flights
Hobby to John F Kennedy Intl flights
Heathrow to Newark flights
Atlanta to Newark flights
Heathrow to John F Kennedy Intl flights
Hobby to LaGuardia flights
Denver to Newark flights
Orly to Newark flights
Denver to John F Kennedy Intl flights
Frankfurt to John F Kennedy Intl flights
Tampa to LaGuardia flights
O'Hare Intl to Newark flights
Seattle to John F Kennedy Intl flights
Orlando to LaGuardia flights
Tel Aviv to John F Kennedy Intl flights
Denver to LaGuardia flights
Orlando to Newark flights
Charles de Gaulle to LaGuardia flights
Tampa to John F Kennedy Intl flights
Orly to John F Kennedy Intl flights
Tampa to Newark flights
Luis Munoz Marin Intl to John F Kennedy Intl flights
Raleigh to Newark flights
San Francisco to LaGuardia flights
Hobby to Newark flights
Austin to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
Charlotte to John F Kennedy Intl flights
Raleigh to John F Kennedy Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.