HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$101+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — SJU
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Newburgh to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/23. 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 12/2912:52 pmSWF - BQN
1 stop13h 18mMultiple Airlines
Sat 1/103:43 amBQN - SWF
1 stop8h 50mMultiple Airlines
Deal found 12/23$480
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/2912:52 pmSWF - BQN
1 stop13h 18mMultiple Airlines
Wed 12/316:42 pmBQN - SWF
1 stop17h 21mMultiple Airlines
Deal found 12/22$620
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/2912:52 pmSWF - BQN
1 stop13h 18mMultiple Airlines
Tue 12/306:42 pmBQN - SWF
1 stop23h 02mMultiple Airlines
Deal found 12/22$628
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Tue 12/3011:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Wed 12/316:42 pmBQN - SWF
1 stop17h 21mMultiple Airlines
Deal found 12/22$670
This Mytrip deal was found by Cheapflights users on 12/24. 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.
Mon 12/2911:37 amSWF - STI
1 stop14h 05mMultiple Airlines
Wed 1/144:40 pmSTI - SWF
2 stops18h 18mMultiple Airlines
Deal found 12/24$682
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Wed 12/315:34 pmSWF - SJU
1 stop14h 49mMultiple Airlines
Sun 1/47:35 amSJU - SWF
2 stops29h 09mMultiple Airlines
Deal found 12/25$686
This Kiwi.com deal was found by Cheapflights users on 12/23. 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.
Tue 12/3011:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Sat 1/103:43 amBQN - SWF
1 stop8h 50mMultiple Airlines
Deal found 12/23$690
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Wed 12/315:34 pmSWF - NAS
1 stop24h 06mMultiple Airlines
Sun 1/44:25 pmNAS - SWF
1 stop19h 37mMultiple Airlines
Deal found 12/24$715
This Kiwi.com deal was found by Cheapflights users on 12/23. 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.
Sat 12/278:45 pmSWF - BQN
1 stop29h 25mMultiple Airlines
Mon 12/296:42 pmBQN - SWF
1 stop17h 21mMultiple Airlines
Deal found 12/23$736
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sat 12/278:45 pmSWF - PUJ
1 stop16h 24mMultiple Airlines
Tue 12/303:08 pmPUJ - SWF
1 stop26h 36mMultiple Airlines
Deal found 12/25$744
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/2912:52 pmSWF - BQN
1 stop13h 18mMultiple Airlines
Wed 12/313:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/22$749
This Kiwi.com deal was found by Cheapflights users on 12/23. 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.
Sat 12/278:45 pmSWF - BQN
1 stop29h 25mMultiple Airlines
Mon 12/293:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/23$753

Find flight deals from Newburgh to Caribbean

Keep the following information in mind while searching for Newburgh to Caribbean flight deals. Data was last updated December 26, 2025.

Round-trip from

$325
(Mytrip)

One-way from

$101
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$363
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 ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 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 WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 1/12

11:09 am-3:33 pm

1 stop27h 24m

Santiago de los Caballeros

Sun 1/18

4:40 pm-10:19 am

1 stop18h 39m

$396

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Mon 1/12

12:11 pm-2:58 am

2 stops13h 47m

Aguadilla Borinquen

Sun 1/18

3:48 am-6:43 pm

1 stop15h 55m

$443

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Sat 1/3

8:45 pm-2:09 pm

1 stop16h 24m

Punta Cana

Sat 1/10

6:49 pm-9:58 am

2 stops16h 09m

$447

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Mon 1/5

11:37 am-7:15 pm

1 stop7h 38m

Nassau Intl

Thu 1/8

11:30 am-10:19 am

1 stop22h 49m

$482

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 2/9

7:33 pm-6:00 pm

1 stop21h 27m

Punta Cana

Sat 2/14

9:27 pm-11:08 am

2 stops14h 41m

$498

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/1

11:48 am-11:09 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:05 pm-11:08 am

1 stop16h 03m

$515

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 2/6

12:11 pm-11:33 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:05 pm-11:08 am

1 stop16h 03m

$521

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/5

11:48 am-11:33 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:05 pm-11:08 am

1 stop16h 03m

$526

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/2

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Sat 4/4

3:40 pm-9:39 am

1 stop17h 59m

$531

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 3/22

10:29 am-2:27 pm

1 stop27h 58m

Santiago de los Caballeros

Sat 4/4

3:40 pm-9:39 am

1 stop17h 59m

$531

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 60 results
1
2
3
...
6

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 December 26, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 12% 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 December 20, 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. Thursday 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 December 26, 2025.

The most flights from N3W to 0CB are scheduled on a Thursday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 December 26, 2025.
Read through reviews of airlines operating flights from Newburgh to Caribbean, such as JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,900 reviews

Entertainment

7.2

Overall

7.2

Food

6.7

Comfort

7.5

Boarding

7.4

Crew

8.0

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
2,900 reviews
JetBlue
7.2
Good
2,900 reviews

Entertainment

7.2

Overall

7.2

Food

6.7

Comfort

7.5

Boarding

7.4

Crew

8.0

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 - Aguadilla Borinquen 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: Virgin Atlantic (78%), LATAM Airlines (78%), Delta( 76%).

  • What are the cheapest flights from Newburgh to Caribbean?

    The cheapest flight price from Newburgh to Caribbean is $83. On average you can expect to pay $911. The most popular route, (New Windsor Stewart - San Juan Luis Munoz Marin Intl), can usually be booked for $434.

  • 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.
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Fort Lauderdale flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to Miami flights
John F Kennedy Intl to Cancún flights
Newark to Cancún flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to West Palm Beach flights
Newark to West Palm Beach flights
Newark to Las Vegas flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Orlando flights
Newark to Orlando flights
John F Kennedy Intl to Mexico City flights
John F Kennedy Intl to Heathrow flights
John F Kennedy Intl to Dallas/Fort Worth flights
LaGuardia to Orlando flights
Newark to Mexico City flights
Newark to Luis Munoz Marin Intl flights
Newark to Heathrow flights
LaGuardia to Cancún flights
John F Kennedy Intl to Haneda flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Charles de Gaulle flights
Newark to Tampa flights
Newark to Los Angeles flights
LaGuardia to Tampa flights
LaGuardia to West Palm Beach flights
John F Kennedy Intl to San Francisco flights
Newark to Haneda flights
John F Kennedy Intl to Sky Harbor Intl flights
Newark to Narita flights
Newark to Charles de Gaulle flights
Newark to Dallas/Fort Worth flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Hobby flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Tel Aviv flights
John F Kennedy Intl to Tampa flights
Newark to Sky Harbor Intl flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Las Vegas flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Newark to Punta Cana flights
LaGuardia to Los Angeles flights
LaGuardia to Hobby flights
John F Kennedy Intl to O'Hare Intl flights

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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$117Average$455FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$144Average$486FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$146Average$404FlexibilityNo cancel feeOn-time65%
ArajetCheapest$146Average$395FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$157Average$469FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$161Average$555FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$532FlexibilityNo cancel feeOn-time69%
AviancaCheapest$274Average$496FlexibilityNo cancel feeOn-time71%
Hahn AirCheapest$318Average$477FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.