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$150+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Oct 13 — Oct 201
Mon 10/13
Mon 10/20
1 adult, Economy
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Cheap flight deals from Newburgh to Caribbean

Keep the following information in mind while searching for Newburgh to Caribbean flight deals. Data was last updated September 13, 2025.

Round-trip from

$337
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$235
From Newburgh to Caribbean
Search Deals
One-way flight from Newburgh to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/1711:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Sun 10/263:54 pmSDQ - SWF
1 stop22h 17mMultiple Airlines
Deal found 9/11$337
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/3112:24 pmSWF - BQN
2 stops13h 53mMultiple Airlines
Wed 11/53:59 amBQN - SWF
1 stop8h 04mMultiple Airlines
Deal found 9/12$338
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/312:11 pmSWF - PUJ
2 stops23h 30mMultiple Airlines
Thu 10/93:57 pmPUJ - SWF
1 stop18h 54mMultiple Airlines
Deal found 9/12$346
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/312:11 pmSWF - MBJ
1 stop23h 54mMultiple Airlines
Sun 10/1912:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/10$396
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/1011:41 amSWF - MBJ
1 stop26h 39mMultiple Airlines
Thu 10/1612:09 pmMBJ - SWF
1 stop21h 32mMultiple Airlines
Deal found 9/11$424
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/1711:31 amSWF - KIN
1 stop9h 34mMultiple Airlines
Sun 11/21:14 pmKIN - SWF
1 stop21h 57mMultiple Airlines
Deal found 9/11$439
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/312:11 pmSWF - MBJ
2 stops23h 06mMultiple Airlines
Sun 10/52:50 pmMBJ - SWF
1 stop18h 21mMultiple Airlines
Deal found 9/12$445
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/312:11 pmSWF - NAS
1 stop7h 04mMultiple Airlines
Sun 10/54:00 pmNAS - SWF
1 stop18h 11mMultiple Airlines
Deal found 9/12$456
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/265:45 pmSWF - SDQ
2 stops22h 22mMultiple Airlines
Sun 11/24:54 pmSDQ - SWF
1 stop19h 17mMultiple Airlines
Deal found 9/11$463
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 12/512:27 pmSWF - NAS
1 stop6h 48mMultiple Airlines
Sun 12/74:00 pmNAS - SWF
1 stop19h 37mMultiple Airlines
Deal found 9/11$466
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/265:45 pmSWF - PUJ
2 stops21h 15mMultiple Airlines
Sun 11/24:57 pmPUJ - SWF
1 stop19h 14mMultiple Airlines
Deal found 9/10$466
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 12/1512:27 pmSWF - NAS
1 stop6h 48mMultiple Airlines
Mon 12/2211:30 amNAS - SWF
1 stop8h 05mMultiple Airlines
Deal found 9/11$469

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 September 13, 2025.
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 WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 10/17

11:31 am-2:54 pm

1 stop27h 23m

Santo Domingo Las Americas

Sun 10/26

3:54 pm-2:11 pm

1 stop22h 17m

$337

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Fri 10/31

12:24 pm-2:17 am

2 stops13h 53m

Aguadilla Borinquen

Wed 11/5

3:59 am-11:03 am

1 stop8h 04m

$338

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 10/3

12:11 pm-11:41 am

2 stops23h 30m

Punta Cana

Thu 10/9

3:57 pm-10:51 am

1 stop18h 54m

$346

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 2/9

7:33 pm-4:40 pm

1 stop20h 07m

Punta Cana

Fri 2/13

1:10 pm-12:39 pm

1 stop24h 29m

$378

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/3

12:11 pm-11:05 am

1 stop23h 54m

Montego Bay Sangster Intl

Sun 10/19

12:09 pm-10:11 am

1 stop21h 02m

$396

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/10

11:41 am-1:20 pm

1 stop26h 39m

Montego Bay Sangster Intl

Thu 10/16

12:09 pm-10:41 am

1 stop21h 32m

$424

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 10/17

11:31 am-8:05 pm

1 stop9h 34m

Kingston Norman Manley

Sun 11/2

1:14 pm-11:11 am

1 stop21h 57m

$439

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 10/17

11:31 am-8:05 pm

1 stop9h 34m

Kingston Norman Manley

Thu 10/23

12:14 pm-10:41 am

1 stop21h 27m

$439

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/3

12:11 pm-10:17 am

2 stops23h 06m

Montego Bay Sangster Intl

Sun 10/5

2:50 pm-10:11 am

1 stop18h 21m

$446

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Fri 10/3

12:11 pm-7:15 pm

1 stop7h 04m

Nassau Intl

Sun 10/5

4:00 pm-10:11 am

1 stop18h 11m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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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, September is the cheapest month in which you can book a flight from Newburgh to Caribbean (average of $254). Flying from Newburgh to Caribbean in June is currently the most expensive (average of $339). 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 September 13, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Newburgh to Caribbean as you normally would.

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 September 13, 2025.

The most flights from N3W to 0CB are scheduled on a Friday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 September 13, 2025.
Read through reviews of airlines operating flights from Newburgh to Caribbean, such as JetBlue and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,913 reviews

Entertainment

7.3

Crew

8.0

Comfort

7.6

Overall

7.2

Food

6.7

Boarding

7.4

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
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Entertainment

7.3

Crew

8.0

Comfort

7.6

Overall

7.2

Food

6.7

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
Frontier
5.8
Fair
3,176 reviews
JetBlue
7.2
Good
2,913 reviews

Entertainment

7.3

Crew

8.0

Comfort

7.6

Overall

7.2

Food

6.7

Boarding

7.4

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 - Montego Bay Sangster 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 (82%), Delta (80%), Virgin Atlantic( 80%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $89. On average you can expect to pay $612. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $511.

  • 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, September is the cheapest month in which you can book a flight from Newburgh to Caribbean (average of $254). Flying from Newburgh to Caribbean in June is currently the most expensive (average of $339). 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 9 airlines flying from Newburgh to Caribbean

Discover the top 9 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 September 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$88Average$333FlexibilityNo cancel feeOn-time62%
DeltaCheapest$119Average$452FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$509FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$388FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$155Average$561FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$157Average$491FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$179Average$562FlexibilityNo cancel feeOn-time69%
ArajetCheapest$199Average$427FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$274Average$448FlexibilityNo cancel feeOn-time71%

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