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$109+ Cheap flights from Newburgh, NY 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap flight deals from Newburgh to Caribbean

Cheapest flights from Newburgh to Caribbean
Explore the most affordable flight options available from Newburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/11. 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 4/3011:45 am
SWF
-
SJU
1 stop8h 59m
Multiple Airlines
Mon 5/43:19 pm
SJU
-
SWF
2 stops44h 06m
Multiple Airlines
Deal found 2/11$320
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sun 2/2211:52 am
SWF
-
SJU
1 stop26h 39m
Multiple Airlines
Thu 2/268:05 pm
SJU
-
SWF
2 stops16h 26m
Multiple Airlines
Deal found 2/8$327
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 5/711:45 am
SWF
-
SJU
1 stop8h 59m
Multiple Airlines
Sat 5/97:05 pm
SJU
-
SWF
1 stop13h 53m
Multiple Airlines
Deal found 2/9$329
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 4/58:12 pm
SWF
-
SJU
1 stop13h 58m
Multiple Airlines
Wed 4/87:54 pm
SJU
-
SWF
1 stop15h 01m
Multiple Airlines
Deal found 2/9$332
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/711:45 am
SWF
-
SJU
1 stop9h 04m
Multiple Airlines
Wed 5/137:05 pm
SJU
-
SWF
1 stop13h 53m
Multiple Airlines
Deal found 2/11$344
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sun 3/2210:29 am
SWF
-
SJU
1 stop8h 26m
Multiple Airlines
Wed 3/253:08 am
SJU
-
SWF
1 stop8h 00m
Multiple Airlines
Deal found 2/10$348
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 2/2611:48 am
SWF
-
BQN
1 stop14h 09m
Multiple Airlines
Wed 3/43:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 2/9$349
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/1910:29 am
SWF
-
STI
1 stop15h 20m
Multiple Airlines
Wed 3/253:43 pm
STI
-
SWF
1 stop17h 56m
Multiple Airlines
Deal found 2/11$359
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 5/711:45 am
SWF
-
SJU
1 stop8h 59m
Multiple Airlines
Sun 5/107:15 am
SJU
-
SWF
1 stop11h 42m
Multiple Airlines
Deal found 2/10$361
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sun 3/111:48 am
SWF
-
BQN
1 stop14h 09m
Multiple Airlines
Wed 3/43:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 2/8$383
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/3110:28 am
SWF
-
SJU
1 stop10h 16m
Multiple Airlines
Sat 6/65:56 pm
SJU
-
SWF
1 stop15h 42m
Multiple Airlines
Deal found 2/11$384
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sat 2/211:29 pm
SWF
-
BQN
1 stop12h 28m
Multiple Airlines
Wed 2/253:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 2/9$387

Find flight deals from Newburgh to Caribbean

Keep the following information in mind while searching for Newburgh to Caribbean flight deals. Data was last updated February 11, 2026.

Round-trip from

$320
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$299
From Newburgh to Caribbean
Search Deals
One-way flight from Newburgh to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newburgh 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 February 11, 2026.
Use the filters below to find and compare flights from Newburgh to Caribbean that are best for you.

Fly from

Newburgh

Fly to

Caribbean

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 5/7

11:45 am-8:44 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sat 5/9

7:05 pm-8:58 am

1 stop13h 53m

$329

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/5

8:12 pm-10:10 am

1 stop13h 58m

San Juan Luis Munoz Marin Intl

Wed 4/8

7:54 pm-10:55 am

1 stop15h 01m

$333

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

10:29 am-6:55 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:08 am-11:08 am

1 stop8h 00m

$348

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 2/26

11:48 am-2:57 am

1 stop14h 09m

Aguadilla Borinquen

Wed 3/4

3:58 am-11:08 am

1 stop8h 10m

$349

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 3/19

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Wed 3/25

3:43 pm-9:39 am

1 stop17h 56m

$359

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 3/1

11:48 am-2:57 am

1 stop14h 09m

Aguadilla Borinquen

Wed 3/4

3:58 am-11:08 am

1 stop8h 10m

$383

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sat 2/21

1:29 pm-2:57 am

1 stop12h 28m

Aguadilla Borinquen

Wed 2/25

3:58 am-11:08 am

1 stop8h 10m

$387

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/30

11:45 am-8:44 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sun 5/3

7:05 pm-11:31 am

2 stops16h 26m

$391

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Mon 3/16

12:11 pm-1:57 am

2 stops13h 46m

Aguadilla Borinquen

Wed 3/25

2:42 am-8:57 am

1 stop30h 15m

$407

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Sun 4/5

10:29 am-1:30 pm

1 stop27h 01m

Simpson Bay Princess Juliana

Wed 4/8

2:35 pm-10:55 am

1 stop20h 20m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 60 results
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2
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6

Best time to book a flight from Newburgh to Caribbean

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

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

Currently, March is the cheapest month in which you can book a flight from Newburgh to Caribbean (average of $79). Flying from Newburgh to Caribbean in August is currently the most expensive (average of $138). 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 N3W to CB?

Find hourly flight availability from Newburgh 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 February 11, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 28% on flights from Newburgh to Caribbean by exploring options for tickets in the evening.

What is the cheapest day to fly from Newburgh to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Newburgh to Caribbean. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Newburgh to Caribbean flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Newburgh to Caribbean

Explore weekly flight availability from Newburgh to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 11, 2026.

The most flights from N3W to 0CB are scheduled on a Wednesday (34 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (8 on average).

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 February 11, 2026.
Read through reviews of airlines operating flights from Newburgh to Caribbean, such as JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,895 reviews

Entertainment

7.2

Overall

7.2

Crew

8.0

Comfort

7.5

Boarding

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,895 reviews
JetBlue
7.2
Good
2,895 reviews

Entertainment

7.2

Overall

7.2

Crew

8.0

Comfort

7.5

Boarding

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

Related info for your journey

Find useful and relevant information for your journey from Newburgh to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from Newburgh to Caribbean?

    The most popular route from Newburgh to Caribbean is New Windsor Stewart - San Juan Luis Munoz Marin Intl. You may also consider New Windsor Stewart - Punta Cana or New Windsor Stewart - Nassau Intl.

  • What are the most reliable airlines from Newburgh to Caribbean?

    Before booking your flight to Caribbean from Newburgh, check out the most reliable airlines to get you to your destination on time: LATAM Airlines (75%), TAP AIR PORTUGAL (74%), LOT( 74%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $70. On average you can expect to pay $722. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $329.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Newburgh 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 Newburgh to Caribbean?

    Currently, March is the cheapest month in which you can book a flight from Newburgh to Caribbean (average of $79). Flying from Newburgh to Caribbean in August is currently the most expensive (average of $138). 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 Newburgh to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Newburgh to Caribbean

Discover the top 10 airlines that operate flights from Newburgh 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$331FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$432FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$101Average$472FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$128Average$377FlexibilityNo cancel feeOn-time65%
ArajetCheapest$128Average$369FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$157Average$377FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$161Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$163Average$482FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$198Average$512FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$229Average$470FlexibilityNo cancel feeOn-timeN/A

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