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Puerto Rico

$89+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This JetBlue deal was found by Cheapflights users on 12/27. 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 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Sat 1/34:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/27$281
This American Airlines deal was found by Cheapflights users on 12/28. 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 12/316:30 amHPN - SJU
2 stops13h 41mAmerican Airlines
Thu 1/86:00 amSJU - HPN
1 stop17h 59mAmerican Airlines
Deal found 12/28$398
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Fri 1/95:45 pmSJU - HPN
Nonstop4h 22mJetBlue
Deal found 12/25$411
This JetBlue deal was found by Cheapflights users on 12/27. 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 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Tue 12/304:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/27$415
This JetBlue deal was found by Cheapflights users on 12/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 amHPN - SJU
1 stop7h 14mJetBlue
Sat 1/34:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/26$456
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:04 amHPN - SJU
2 stops11h 55mAmerican Airlines
Fri 1/98:20 amSJU - HPN
2 stops12h 48mAmerican Airlines
Deal found 12/25$457
This CheapOair deal was found by Cheapflights users on 12/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:23 amHPN - SJU
2 stops13h 33mMultiple Airlines
Fri 1/24:12 pmSJU - HPN
Nonstop4h 17mMultiple Airlines
Deal found 12/26$481
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amHPN - SJU
Nonstop3h 52mJetBlue
Thu 1/88:30 pmSJU - HPN
1 stop16h 25mJetBlue
Deal found 12/25$496
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:04 amHPN - SJU
2 stops11h 55mAmerican Airlines
Tue 1/66:00 amSJU - HPN
1 stop17h 59mAmerican Airlines
Deal found 12/26$507
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:30 amHPN - SJU
2 stops8h 47mAmerican Airlines
Thu 1/86:07 amSJU - HPN
2 stops15h 01mAmerican Airlines
Deal found 12/26$511

Find 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 December 28, 2025.

Round-trip from

$206
(JetBlue)

One-way from

$89
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$365
From Westchester County to Puerto Rico
Search Deals
One-way flight from Westchester County to Puerto Rico
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 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 December 2025
Search Deals

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 December 28, 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

Mon 2/2

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 2/5

5:45 pm-9:00 pm

Nonstop4h 15m

$206

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/31

10:00 am-11:56 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:00 am-5:00 pm

1 stop12h 00m

$215

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/28

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:45 pm-9:07 pm

Nonstop4h 22m

$241

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/28

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:45 pm-9:07 pm

Nonstop4h 22m

$241

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/10

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sun 1/11

5:45 pm-9:07 pm

Nonstop4h 22m

$246

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 2/3

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:15 pm-9:30 pm

Nonstop4h 15m

$256

White PlainsPonce

HPN - PSE

HPNPSE

White Plains Westchester County

Tue 1/13

7:30 am-3:13 pm

1 stop6h 43m

Ponce Mercedita

Sat 1/17

4:10 pm-11:01 pm

1 stop7h 51m

$279

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sun 2/15

6:55 pm-11:41 am

1 stop15h 46m

San Juan Luis Munoz Marin Intl

Thu 2/19

6:15 pm-9:29 am

1 stop16h 14m

$291

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/31

7:30 am-6:50 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Wed 2/4

10:45 am-5:42 pm

1 stop7h 57m

$297

White PlainsAguadilla

HPN - BQN

HPNBQN

White Plains Westchester County

Mon 2/9

7:30 pm-3:30 am

1 stop7h 00m

Aguadilla Borinquen

Wed 2/11

5:01 am-2:02 pm

1 stop10h 01m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 39 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, October is the cheapest month in which you can book a flight from Westchester County to Puerto Rico (average of $175). Flying from Westchester County to Puerto Rico in August is currently the most expensive (average of $327). 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 December 28, 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.

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 December 28, 2025.
Read through reviews of airlines operating flights from Westchester County to Puerto Rico, such as Delta, 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.
Delta
7.9
Good
8,017 reviews

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
7.9
Good
8,017 reviews
Delta
7.9
Good
8,017 reviews

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.2
Good
2,901 reviews
Delta
7.9
Good
8,017 reviews

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Frontier
5.8
Fair
3,064 reviews
Delta
7.9
Good
8,017 reviews

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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 $206. There are 1627 mi between Westchester County and Puerto Rico. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, October is the cheapest month in which you can book a flight from Westchester County to Puerto Rico (average of $175). Flying from Westchester County to Puerto Rico in August is currently the most expensive (average of $327). 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$224FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$206Average$374FlexibilityNo cancel feeOn-time62%

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