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$151+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$365
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$328
From Newburgh to Caribbean
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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 ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
jue. 9/1111:43 amSWF - BQN
1 stop14h 44mMultiple Airlines
sáb. 9/133:32 amBQN - SWF
1 stop7h 31mMultiple Airlines
Deal found 8/11$365
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
lun. 8/187:37 pmSWF - SDQ
1 stop20h 23mMultiple Airlines
dom. 8/245:05 pmSDQ - SWF
1 stop23h 41mMultiple Airlines
Deal found 8/11$379
This Kiwi.com deal was found by Cheapflights users on 8/13. 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. 10/312:11 pmSWF - KIN
1 stop8h 54mMultiple Airlines
dom. 10/512:08 pmKIN - SWF
1 stop21h 03mMultiple Airlines
Deal found 8/13$421
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
vie. 8/157:37 pmSWF - SDQ
1 stop20h 23mMultiple Airlines
jue. 8/215:05 pmSDQ - SWF
1 stop23h 41mMultiple Airlines
Deal found 8/12$432
This Kiwi.com deal was found by Cheapflights users on 8/13. 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. 8/225:36 pmSWF - SDQ
1 stop22h 24mMultiple Airlines
dom. 8/245:05 pmSDQ - SWF
1 stop23h 41mMultiple Airlines
Deal found 8/13$436
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
jue. 8/217:52 pmSWF - BQN
1 stop30h 52mMultiple Airlines
lun. 8/253:43 amBQN - SWF
1 stop8h 13mMultiple Airlines
Deal found 8/11$438
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
vie. 10/2411:31 amSWF - AUA
1 stop27h 07mMultiple Airlines
jue. 11/64:50 pmAUA - SWF
1 stop18h 51mMultiple Airlines
Deal found 8/12$439
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
vie. 8/225:36 pmSWF - KIN
1 stop18h 51mMultiple Airlines
lun. 8/257:55 amKIN - SWF
1 stop7h 51mMultiple Airlines
Deal found 8/12$445
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
lun. 8/187:37 pmSWF - SDQ
1 stop20h 23mMultiple Airlines
jue. 8/215:05 pmSDQ - SWF
1 stop23h 41mMultiple Airlines
Deal found 8/13$448
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/225:36 pmSWF - MBJ
2 stops20h 25mMultiple Airlines
dom. 8/2410:22 amMBJ - SWF
1 stop29h 24mMultiple Airlines
Deal found 8/14$451
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
lun. 10/611:01 amSWF - NAS
1 stop8h 14mMultiple Airlines
jue. 10/1611:30 amNAS - SWF
1 stop23h 11mMultiple Airlines
Deal found 8/11$455
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
vie. 10/312:11 pmSWF - NAS
1 stop7h 04mMultiple Airlines
dom. 10/52:15 pmNAS - SWF
1 stop19h 56mMultiple Airlines
Deal found 8/11$456

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 agosto 14, 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 WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

jue. 9/11

11:43 am-2:27 am

1 stop14h 44m

Aguadilla Borinquen

sáb. 9/13

3:32 am-11:03 am

1 stop7h 31m

$365

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

vie. 10/3

12:11 pm-8:05 pm

1 stop8h 54m

Kingston Norman Manley

dom. 10/5

12:08 pm-10:11 am

1 stop21h 03m

$421

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

vie. 10/31

11:31 am-2:32 pm

1 stop27h 01m

Oranjestad Reina Beatrix

jue. 11/13

4:50 pm-10:11 am

1 stop18h 21m

$439

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

vie. 10/24

11:31 am-2:38 pm

1 stop27h 07m

Oranjestad Reina Beatrix

jue. 11/6

4:50 pm-10:41 am

1 stop18h 51m

$439

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

lun. 11/10

12:01 pm-3:45 pm

1 stop26h 44m

Oranjestad Reina Beatrix

jue. 11/13

4:50 pm-10:11 am

1 stop18h 21m

$439

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

vie. 8/22

5:36 pm-11:27 am

1 stop18h 51m

Kingston Norman Manley

lun. 8/25

7:55 am-4:46 pm

1 stop7h 51m

$445

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

vie. 8/22

5:36 pm-1:01 pm

2 stops20h 25m

Montego Bay Sangster Intl

dom. 8/31

10:22 am-10:12 am

2 stops22h 50m

$449

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

lun. 10/6

11:01 am-7:15 pm

1 stop8h 14m

Nassau Intl

jue. 10/16

11:30 am-10:41 am

1 stop23h 11m

$455

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

lun. 8/25

5:36 pm-11:14 am

1 stop18h 38m

Montego Bay Sangster Intl

dom. 8/31

12:19 pm-1:05 pm

1 stop23h 46m

$455

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

vie. 8/22

5:36 pm-1:01 pm

2 stops20h 25m

Montego Bay Sangster Intl

dom. 8/24

10:22 am-4:46 pm

1 stop29h 24m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

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 agosto 14, 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 agosto 14, 2025.

The most flights from N3W to 0CB are scheduled on a Thursday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 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 agosto 14, 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

Crew

8.0

Comfort

7.6

Overall

7.2

Entertainment

7.3

Boarding

7.4

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
JetBlue
7.2
Good
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Crew

8.0

Comfort

7.6

Overall

7.2

Entertainment

7.3

Boarding

7.4

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
Frontier
5.8
Fair
3,217 reviews
JetBlue
7.2
Good
2,913 reviews

Crew

8.0

Comfort

7.6

Overall

7.2

Entertainment

7.3

Boarding

7.4

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.

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 - Freeport Grand Bahama Intl 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 (89%), KLM (82%), Delta( 82%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $88. On average you can expect to pay $490. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $419.

  • 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

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 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$88Average$330FlexibilityNo cancel feeOn-time62%
DeltaCheapest$125Average$463FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$505FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$390FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$157Average$508FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$179Average$563FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$188Average$577FlexibilityNo cancel feeOn-time71%
ArajetCheapest$203Average$458FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$274Average$458FlexibilityNo cancel feeOn-time71%

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