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$152+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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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 October 14, 2025.

This Mytrip deal was found by Cheapflights users on 10/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Sun 12/73:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 10/13$328
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/1111:43 amSWF - SJU
1 stop14h 07mMultiple Airlines
Fri 12/198:10 amSJU - SWF
1 stop10h 56mMultiple Airlines
Deal found 10/11$338
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/253:43 amSTI - SWF
1 stop8h 24mMultiple Airlines
Deal found 10/14$365
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/1212:27 pmSWF - SJU
2 stops30h 22mMultiple Airlines
Fri 12/198:10 amSJU - SWF
1 stop10h 56mMultiple Airlines
Deal found 10/11$371
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Mon 12/812:27 pmSWF - MBJ
1 stop23h 43mMultiple Airlines
Thu 12/111:05 pmMBJ - SWF
1 stop22h 32mMultiple Airlines
Deal found 10/14$374
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Mon 11/312:01 pmSWF - PUJ
2 stops23h 44mMultiple Airlines
Sun 11/94:25 pmPUJ - SWF
1 stop19h 46mMultiple Airlines
Deal found 10/13$379
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/1711:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Sun 10/193:54 pmSDQ - SWF
1 stop18h 17mMultiple Airlines
Deal found 10/12$396
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Thu 11/1311:43 amSWF - BQN
1 stop14h 21mMultiple Airlines
Sat 11/153:59 amBQN - SWF
1 stop8h 04mMultiple Airlines
Deal found 10/12$426
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/1111:43 amSWF - SJU
1 stop14h 07mMultiple Airlines
Sun 12/216:59 pmSJU - SWF
1 stop25h 36mMultiple Airlines
Deal found 10/11$430
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Sun 11/308:41 pmSWF - SJU
1 stop29h 13mMultiple Airlines
Thu 12/49:32 pmSJU - SWF
1 stop22h 08mMultiple Airlines
Deal found 10/13$435
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/1212:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Sun 12/143:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 10/12$444
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Fri 11/711:31 amSWF - PUJ
2 stops13h 40mMultiple Airlines
Sun 11/94:25 pmPUJ - SWF
1 stop19h 46mMultiple Airlines
Deal found 10/13$449

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 October 14, 2025.

Round-trip from

$328
(Mytrip)

One-way from

$154
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$220
From Newburgh to Caribbean
Search Deals
One-way flight from Newburgh to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 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 WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/5

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/7

3:43 am-11:37 am

1 stop8h 54m

$328

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/8

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Thu 12/25

3:43 am-11:07 am

1 stop8h 24m

$365

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/8

12:27 pm-12:10 pm

1 stop23h 43m

Montego Bay Sangster Intl

Thu 12/11

1:05 pm-11:37 am

1 stop22h 32m

$374

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 11/3

12:01 pm-12:45 pm

2 stops23h 44m

Punta Cana

Sun 11/9

4:25 pm-11:11 am

1 stop19h 46m

$379

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 1/12

11:09 am-12:05 pm

1 stop24h 56m

Montego Bay Sangster Intl

Thu 1/22

1:12 pm-10:19 am

1 stop21h 07m

$391

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 1/5

11:37 am-12:05 pm

1 stop24h 28m

Montego Bay Sangster Intl

Wed 1/7

3:05 pm-11:08 am

1 stop20h 03m

$428

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/12

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/14

3:43 am-11:37 am

1 stop8h 54m

$444

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 11/7

11:31 am-2:11 am

2 stops13h 40m

Punta Cana

Sun 11/9

4:25 pm-11:11 am

1 stop19h 46m

$449

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 11/21

11:12 am-8:27 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Tue 11/25

11:54 am-11:27 am

2 stops24h 33m

$455

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/12

12:27 pm-7:49 pm

2 stops30h 22m

San Juan Luis Munoz Marin Intl

Sun 12/21

6:59 pm-7:35 pm

1 stop25h 36m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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, 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 October 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 7% on flights from Newburgh to Caribbean by exploring options for tickets at noon.

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 October 12, 2025.

Travelers seeking maximum savings on their Newburgh to Caribbean flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday mornings 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 October 14, 2025.

The most flights from N3W to 0CB are scheduled on a Monday (41 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (18 on average).

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 - Santo Domingo Las Americas or New Windsor Stewart - Punta Cana.

  • 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: WestJet (79%), Delta (78%), Virgin Atlantic( 78%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $68. On average you can expect to pay $643. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $368.

  • 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$348FlexibilityNo cancel feeOn-time62%
DeltaCheapest$119Average$444FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$512FlexibilityNo cancel feeOn-time62%
ArajetCheapest$139Average$381FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$143Average$414FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$152Average$461FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$155Average$549FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$509FlexibilityNo cancel feeOn-time69%
Caribbean AirlinesCheapest$214Average$806FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$274Average$450FlexibilityNo cancel feeOn-time71%

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