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Caribbean

$127+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 26, 2025.

This Mytrip deal was found by Cheapflights users on 11/26. 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 11/26$226
This Mytrip deal was found by Cheapflights users on 11/26. 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
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 11/26$249
This Mytrip deal was found by Cheapflights users on 11/26. 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 12/116:00 amSJU - SWF
2 stops30h 37mMultiple Airlines
Deal found 11/26$258
This Mytrip deal was found by Cheapflights users on 11/26. 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 12/1411:38 amSJU - SWF
2 stops24h 59mMultiple Airlines
Deal found 11/26$280
This Mytrip deal was found by Cheapflights users on 11/24. 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 11/24$281
This Mytrip deal was found by Cheapflights users on 11/26. 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
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/26$282
This Mytrip deal was found by Cheapflights users on 11/25. 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 12/711:38 amSJU - SWF
2 stops24h 59mMultiple Airlines
Deal found 11/25$299
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/57:30 pmSWF - BQN
1 stop30h 28mMultiple Airlines
Sun 12/73:55 amBQN - SWF
1 stop15h 45mMultiple Airlines
Deal found 11/24$386
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/228:25 pmSWF - AUA
1 stop18h 10mMultiple Airlines
Thu 12/254:40 pmAUA - SWF
1 stop19h 27mMultiple Airlines
Deal found 11/25$439
This Mytrip deal was found by Cheapflights users on 11/26. 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 - NAS
1 stop6h 48mMultiple Airlines
Fri 12/1911:30 amNAS - SWF
1 stop6h 36mMultiple Airlines
Deal found 11/26$465
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/228:25 pmSWF - MBJ
2 stops18h 04mMultiple Airlines
Thu 1/812:57 pmMBJ - SWF
1 stop21h 22mMultiple Airlines
Deal found 11/25$466
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/196:56 pmSWF - AUA
1 stop19h 39mMultiple Airlines
Sun 1/114:41 pmAUA - SWF
1 stop18h 38mMultiple Airlines
Deal found 11/25$488

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 26, 2025.

Round-trip from

$226
(Mytrip)

One-way from

$127
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$284
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 ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 26, 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 12/12

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Sun 12/14

11:38 am-11:37 am

2 stops24h 59m

$284

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

$285

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

5:00 pm-11:37 am

2 stops19h 37m

$285

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 12/11

11:43 am-12:16 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Sun 12/14

4:10 am-11:37 am

1 stop8h 27m

$307

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

$315

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

Thu 12/11

1:27 pm-11:37 am

2 stops23h 10m

$324

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/9

11:09 am-1:37 am

2 stops13h 28m

San Juan Luis Munoz Marin Intl

Sat 1/17

2:59 am-10:19 am

2 stops32h 20m

$326

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 12/14

5:00 pm-11:37 am

2 stops19h 37m

$347

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/16

11:09 am-4:36 pm

1 stop28h 27m

Punta Cana

Thu 1/22

5:47 pm-10:19 am

1 stop17h 32m

$391

New WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Thu 1/8

6:49 pm-2:14 pm

2 stops42h 25m

Simpson Bay Princess Juliana

Thu 1/15

3:09 pm-10:19 am

1 stop20h 10m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

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 26, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 11% 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 25, 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 26, 2025.

The most flights from N3W to 0CB are scheduled on a Tuesday (52 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (19 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 - 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: Delta (79%), LATAM Airlines (77%), Virgin Atlantic( 77%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $74. On average you can expect to pay $414. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $285.

  • 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

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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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$351FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$454FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$506FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$143Average$416FlexibilityNo cancel feeOn-time65%
ArajetCheapest$146Average$387FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$152Average$473FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$161Average$563FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$536FlexibilityNo cancel feeOn-time69%
AviancaCheapest$274Average$441FlexibilityNo cancel feeOn-time71%
Hahn AirCheapest$318Average$475FlexibilityNo cancel feeOn-timeN/A

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