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Caribbean

$122+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/4. 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 - SJU
1 stop11h 18mMultiple Airlines
Sun 12/74:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/4$326
This Mytrip deal was found by Cheapflights users on 11/5. 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 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$330
This Mytrip deal was found by Cheapflights users on 11/5. 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
Thu 12/113:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 11/5$333
This Mytrip deal was found by Cheapflights users on 11/5. 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 - SJU
1 stop11h 18mMultiple Airlines
Thu 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$335
This Mytrip deal was found by Cheapflights users on 11/5. 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 - SJU
1 stop11h 18mMultiple Airlines
Thu 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$338
This Mytrip deal was found by Cheapflights users on 11/3. 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 11/1712:01 pmSWF - PUJ
2 stops23h 44mMultiple Airlines
Thu 11/203:11 pmPUJ - SWF
2 stops20h 11mMultiple Airlines
Deal found 11/3$346
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/711:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Thu 12/113:55 amBQN - SWF
2 stops8h 49mMultiple Airlines
Deal found 11/5$354
This Mytrip deal was found by Cheapflights users on 11/5. 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 11/1712:01 pmSWF - PUJ
2 stops23h 44mMultiple Airlines
Sun 11/233:11 pmPUJ - SWF
2 stops19h 56mMultiple Airlines
Deal found 11/5$371
This Mytrip deal was found by Cheapflights users on 11/4. 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 11/2111:12 amSWF - PUJ
2 stops27h 13mMultiple Airlines
Sun 11/233:11 pmPUJ - SWF
2 stops19h 56mMultiple Airlines
Deal found 11/4$374
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/711:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Sat 12/133:55 amBQN - SWF
2 stops32h 42mMultiple Airlines
Deal found 11/6$375
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/2011:06 amSWF - SJU
1 stop11h 03mMultiple Airlines
Tue 11/255:19 pmSJU - SWF
1 stop19h 08mMultiple Airlines
Deal found 11/4$376
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 - STI
1 stop13h 15mMultiple Airlines
Thu 1/294:40 pmSTI - SWF
1 stop18h 39mMultiple Airlines
Deal found 11/4$388

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 November 6, 2025.

Round-trip from

$326
(Mytrip)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$266
From Newburgh to Caribbean
Search Deals
One-way flight from Newburgh to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 6, 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 WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/5

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Sun 12/7

4:10 am-11:37 am

1 stop8h 27m

$333

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

Thu 12/11

3:43 am-11:37 am

1 stop8h 54m

$333

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/12

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Sun 12/14

4:10 am-11:37 am

1 stop8h 27m

$334

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

4:10 am-11:37 am

1 stop8h 27m

$338

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 11/17

12:01 pm-12:45 pm

2 stops23h 44m

Punta Cana

Thu 11/20

3:11 pm-10:22 am

2 stops20h 11m

$346

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/22

7:28 pm-11:37 pm

1 stop27h 09m

San Juan Luis Munoz Marin Intl

Thu 2/26

9:37 pm-10:13 am

1 stop13h 36m

$349

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 12/7

11:43 am-2:58 am

1 stop14h 15m

Aguadilla Borinquen

Thu 12/11

3:55 am-6:40 pm

1 stop15h 45m

$358

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 11/17

12:01 pm-12:45 pm

2 stops23h 44m

Punta Cana

Sun 11/23

3:11 pm-10:07 am

2 stops19h 56m

$371

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 11/21

11:12 am-3:25 pm

2 stops27h 13m

Punta Cana

Sun 11/23

3:11 pm-10:07 am

2 stops19h 56m

$374

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 12/7

11:43 am-2:58 am

1 stop14h 15m

Aguadilla Borinquen

Sat 12/13

3:55 am-11:03 am

1 stop8h 08m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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 November 6, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 9% 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 November 2, 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 November 6, 2025.

The most flights from N3W to 0CB are scheduled on a Thursday (44 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 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 - Montego Bay Sangster Intl 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: Delta (78%), LATAM Airlines (77%), Virgin Atlantic( 77%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $73. On average you can expect to pay $455. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $328.

  • 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

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 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$351FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$448FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$123Average$428FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$133Average$505FlexibilityNo cancel feeOn-time62%
ArajetCheapest$139Average$387FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$152Average$455FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$161Average$545FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$521FlexibilityNo cancel feeOn-time69%
Caribbean AirlinesCheapest$214Average$808FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$274Average$450FlexibilityNo cancel feeOn-time71%

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