Caribbean

$134+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
jul. 10 — jul. 171
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Cheap 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 junio 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/6. 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. 8/277:31 pm
SWF
-
SJU
1 stop20h 27m
Multiple Airlines
jue. 9/36:00 am
SJU
-
SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/6$271
This Kiwi.com deal was found by Cheapflights users on 6/8. 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. 10/810:18 am
SWF
-
SJU
1 stop13h 20m
Multiple Airlines
mié. 10/145:12 pm
SJU
-
SWF
1 stop16h 16m
Multiple Airlines
Deal found 6/8$279
This Kiwi.com deal was found by Cheapflights users on 6/10. 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. 9/37:30 pm
SWF
-
SJU
1 stop20h 28m
Multiple Airlines
dom. 9/66:00 am
SJU
-
SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/10$289
This Kiwi.com deal was found by Cheapflights users on 6/6. 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. 8/277:31 pm
SWF
-
SJU
1 stop20h 27m
Multiple Airlines
dom. 8/306:00 am
SJU
-
SWF
1 stop12h 41m
Multiple Airlines
Deal found 6/6$294
This Kiwi.com deal was found by Cheapflights users on 6/8. 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. 10/1111:53 am
SWF
-
SJU
1 stop11h 45m
Multiple Airlines
mié. 10/145:12 pm
SJU
-
SWF
1 stop16h 16m
Multiple Airlines
Deal found 6/8$298
This Kiwi.com deal was found by Cheapflights users on 6/8. 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. 8/201:00 pm
SWF
-
SJU
1 stop26h 58m
Multiple Airlines
jue. 8/276:00 am
SJU
-
SWF
1 stop12h 41m
Multiple Airlines
Deal found 6/8$299
This Kiwi.com deal was found by Cheapflights users on 6/8. 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. 10/810:18 am
SWF
-
SJU
1 stop13h 20m
Multiple Airlines
sáb. 10/105:12 pm
SJU
-
SWF
1 stop17h 51m
Multiple Airlines
Deal found 6/8$300
This Kiwi.com deal was found by Cheapflights users on 6/7. 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. 8/1310:28 am
SWF
-
SJU
1 stop29h 43m
Multiple Airlines
mié. 8/196:00 am
SJU
-
SWF
1 stop30h 10m
Multiple Airlines
Deal found 6/7$307
This Kiwi.com deal was found by Cheapflights users on 6/7. 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. 8/611:45 am
SWF
-
SJU
1 stop12h 56m
Multiple Airlines
mié. 8/126:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/7$309
This Kiwi.com deal was found by Cheapflights users on 6/9. 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. 10/1111:53 am
SWF
-
NAS
1 stop7h 22m
Multiple Airlines
mié. 10/144:00 pm
NAS
-
SWF
1 stop17h 28m
Multiple Airlines
Deal found 6/9$438
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
vie. 8/2810:56 am
SWF
-
PUJ
1 stop9h 29m
Multiple Airlines
sáb. 9/56:25 pm
PUJ
-
SWF
2 stops24h 15m
Multiple Airlines
Deal found 6/9$482
This Kiwi.com deal was found by Cheapflights users on 6/7. 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. 8/307:31 pm
SWF
-
NAS
1 stop14h 59m
Multiple Airlines
dom. 9/611:30 am
NAS
-
SWF
1 stop7h 10m
Multiple Airlines
Deal found 6/7$498

Find flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated junio 10, 2026.

Round-trip from

$271
(Kiwi.com)

One-way from

$134
(Kiwi.com)

Popular in

May

Cheapest in

October

Average price

$347
From New Windsor Stewart to Caribbean
One-way flight from New Windsor Stewart to Caribbean
Highest demand for flights based on searches. 12% potential increase in price ($45 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in June 2026

Cheapflights Fare Finder

 
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 junio 10, 2026.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

jue. 8/27

7:31 pm-3:58 pm

1 stop20h 27m

San Juan Luis Munoz Marin Intl

dom. 8/30

6:00 am-6:41 pm

1 stop12h 41m

$295

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 8/2

10:28 am-4:05 pm

1 stop29h 37m

San Juan Luis Munoz Marin Intl

mié. 8/5

6:00 am-9:38 am

1 stop27h 38m

$325

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 8/16

10:28 am-4:11 pm

1 stop29h 43m

San Juan Luis Munoz Marin Intl

sáb. 8/22

6:00 am-12:10 pm

1 stop30h 10m

$339

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

jue. 7/30

10:28 am-4:05 pm

1 stop29h 37m

San Juan Luis Munoz Marin Intl

mié. 8/5

6:00 am-9:38 am

1 stop27h 38m

$357

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

sáb. 7/4

12:05 pm-12:37 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

mié. 7/8

6:00 am-9:38 am

1 stop27h 38m

$410

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

dom. 10/11

11:53 am-7:15 pm

1 stop7h 22m

Nassau Intl

mié. 10/14

4:00 pm-9:28 am

1 stop17h 28m

$438

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

mié. 10/14

12:39 pm-9:25 am

2 stops20h 46m

Nassau Intl

mié. 10/21

4:00 pm-9:48 am

1 stop17h 48m

$500

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

sáb. 10/10

12:39 pm-9:25 am

2 stops20h 46m

Nassau Intl

sáb. 10/17

4:00 pm-11:03 am

1 stop19h 03m

$502

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

dom. 11/15

12:00 pm-7:15 pm

1 stop7h 15m

Nassau Intl

jue. 11/19

11:30 am-5:58 pm

1 stop6h 28m

$504

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

sáb. 9/19

12:39 pm-6:50 pm

2 stops30h 11m

Punta Cana

dom. 9/27

11:35 am-10:31 am

1 stop22h 56m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 56 resultsSorted by cheapest first
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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.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Caribbean
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated junio 10, 2026.
Peruse reviews from past customers who have flown with JetBlue from New Windsor to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.1

Food

6.6

Boarding

7.3

Comfort

7.5

Entertainment

7.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Wei,Feb 2026

JFK - BOS

The JFK to BOS flight was uneventful. The delay of the inbound plane was difficult since we were near 1.5 hours in delays from the original departure time.

Overall

7.1

Food

6.6

Boarding

7.3

Comfort

7.5

Entertainment

7.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Wei,Feb 2026

JFK - BOS

The JFK to BOS flight was uneventful. The delay of the inbound plane was difficult since we were near 1.5 hours in delays from the original departure time.

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.

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.

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 junio 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$227Average$345FlexibilityNo cancel feeOn-time62%

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