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Puerto Rico

$99+ Cheap flights from Westchester County to Puerto Rico

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Westchester County to Puerto Rico

Keep the following information in mind while searching for Westchester County to Puerto Rico flight deals. Data was last updated September 16, 2025.

Round-trip from

$216
(JetBlue)

One-way from

$99
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$246
From Westchester County to Puerto Rico
Search Deals
One-way flight from Westchester County to Puerto Rico
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Highest demand for flights based on searches. 6% potential increase in price ($20 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 September 2025
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Find flight deals from Westchester County to Puerto Rico

Cheapest flights from Westchester County to Puerto Rico
Explore the most affordable flight options available from Westchester County to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:00 amHPN - SJU
Nonstop3h 45mJetBlue
Mon 9/295:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 9/14$216
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/15:29 pmHPN - SJU
2 stops17h 42mAmerican Airlines
Sat 10/44:45 pmSJU - HPN
1 stop16h 44mAmerican Airlines
Deal found 9/15$220
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:29 pmHPN - SJU
2 stops17h 42mAmerican Airlines
Tue 9/301:37 pmSJU - HPN
2 stops19h 45mAmerican Airlines
Deal found 9/15$225
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:00 amHPN - SJU
Nonstop3h 45mJetBlue
Tue 10/284:05 amSJU - HPN
1 stop10h 01mJetBlue
Deal found 9/15$227
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:00 amHPN - SJU
Nonstop3h 51mJetBlue
Wed 11/56:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/14$230
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/278:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sat 9/275:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 9/14$231
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:00 amHPN - SJU
Nonstop3h 45mJetBlue
Fri 10/316:21 pmSJU - HPN
1 stop27h 16mJetBlue
Deal found 9/15$234
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sat 9/275:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 9/14$236
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:00 pmHPN - SJU
1 stop8h 23mJetBlue
Tue 12/1611:34 amSJU - HPN
1 stop8h 56mJetBlue
Deal found 9/15$237
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:00 pmHPN - SJU
1 stop8h 23mJetBlue
Wed 12/175:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/15$241
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:00 amHPN - SJU
Nonstop3h 51mJetBlue
Sat 12/135:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/15$244
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:30 amHPN - BQN
1 stop8h 48mJetBlue
Sat 11/84:00 amBQN - HPN
1 stop10h 32mJetBlue
Deal found 9/15$340

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Puerto Rico 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 September 16, 2025.
Use the filters below to find and compare flights from Westchester County to Puerto Rico that are best for you.

Fly from

Westchester County

Fly to

Puerto Rico

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Thu 9/25

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 9/29

5:01 pm-9:03 pm

Nonstop4h 02m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 9/29

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 10/6

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/8

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/1

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 10/14

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 9/29

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Fri 10/3

5:01 pm-9:03 pm

Nonstop4h 02m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 9/27

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 9/29

5:01 pm-9:03 pm

Nonstop4h 02m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sun 9/28

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sun 10/5

5:01 pm-9:00 pm

Nonstop3h 59m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 9/27

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sat 10/4

5:01 pm-9:00 pm

Nonstop3h 59m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/29

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Wed 11/5

12:30 pm-9:37 pm

1 stop10h 07m

$227

White PlainsAguadilla

HPN - BQN

HPNBQN

White Plains Westchester County

Thu 10/30

8:30 am-5:18 pm

1 stop8h 48m

Aguadilla Borinquen

Sat 11/8

4:00 am-1:32 pm

1 stop10h 32m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 43 results
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Best time to book a flight from Westchester County to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Westchester County 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 Westchester County to Puerto Rico

What is the cheapest month to book a flight from Westchester County to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Westchester County to Puerto Rico (average of $254). Flying from Westchester County to Puerto Rico 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 REU to PR?

Find hourly flight availability from Westchester County to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Westchester County to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Westchester County to Puerto Rico

Explore weekly flight availability from Westchester County to Puerto Rico. 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 September 16, 2025.

The most flights from zzREU to PR0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Westchester County to Puerto Rico, such as American Airlines, JetBlue, and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
JetBlue
7.2
Good
2,914 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
Frontier
5.8
Fair
3,174 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Boarding

7.5

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Puerto Rico?

    A quick flight from Westchester County to Puerto Rico can take about 3h 45m. JetBlue provides one of the quickest options available for as low as $216. There are 1627 mi between Westchester County and Puerto Rico. Generally, flights for this route are nonstop.

  • Can I find deals for flights from Westchester County to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Westchester County to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Puerto Rico.

  • Can I find deals for business class flights from Westchester County to Puerto Rico?

    Yes. Cheapflights offers flight deals from Westchester County to Puerto Rico 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 Westchester County to Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Westchester County to Puerto Rico (average of $254). Flying from Westchester County to Puerto Rico 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 Westchester County to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Westchester County to Puerto Rico

Discover the top 3 airlines that operate flights from Westchester County to Puerto Rico. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$376FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$524FlexibilityNo cancel feeOn-time71%

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