$117 Find Cheap Flights from New Windsor to Puerto Rico

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Puerto Rico departing on 8/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Flights Deals

Book Cheap New Windsor to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Puerto Rico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Puerto Rico

Fri, Aug 15 - Thu, Aug 21
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7:37 pm - 4:42 pmSWF-SJU
21h 05m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Fri, Aug 22 - Thu, Aug 28
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5:36 pm - 3:10 pmSWF-SJU
21h 34m2 stops
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2:11 am - 1:05 pmSJU-SWF
10h 54m2 stops
Mon, Aug 18 - Thu, Aug 21
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7:37 pm - 3:10 pmSWF-SJU
19h 33m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Mon, Aug 11 - Thu, Aug 14
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7:56 pm - 2:45 pmSWF-SJU
18h 49m2 stops
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2:11 am - 6:47 pmSJU-SWF
16h 36m2 stops
Mon, Aug 25 - Thu, Aug 28
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5:36 pm - 4:42 pmSWF-SJU
23h 06m2 stops
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8:00 am - 1:05 pmSJU-SWF
29h 05m2 stops
Mon, Aug 25 - Thu, Aug 28
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5:36 pm - 1:49 pmSWF-SJU
20h 13m2 stops
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2:11 am - 1:05 pmSJU-SWF
10h 54m2 stops
Mon, Aug 25 - Thu, Aug 28
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5:36 pm - 4:42 pmSWF-SJU
23h 06m2 stops
 Logo
2:11 am - 1:05 pmSJU-SWF
10h 54m2 stops
Mon, Aug 18 - Thu, Aug 21
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7:37 pm - 3:10 pmSWF-SJU
19h 33m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Fri, Aug 22 - Thu, Aug 28
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5:36 pm - 3:10 pmSWF-SJU
21h 34m2 stops
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8:00 am - 1:05 pmSJU-SWF
29h 05m2 stops
Fri, Aug 15 - Thu, Aug 21
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7:37 pm - 4:42 pmSWF-SJU
21h 05m2 stops
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4:12 pm - 4:46 pmSJU-SWF
24h 34m2 stops
Booking Insights

KAYAK's insights & trends for New Windsor to Puerto Rico flights

Get data-powered insights and trends into flights from New Windsor to Puerto Rico to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from New Windsor to Puerto Rico take?

The duration of a flight to Puerto Rico depends on your arrival airport. The shortest routes to Puerto Rico from New Windsor are to Aguadilla, which takes 7h 15m, and San Juan, which takes 8h 48m.


Good to know

Low seasonOctober
Cheapest flight$117
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly and prices are also 35% lower on average.
Flight from Stewart Intl. to San Juan

FAQs - booking Puerto Rico flights

  • How does KAYAK find such low prices on flights from Stewart Intl. to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stewart Intl. to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stewart Intl. to Puerto Rico is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stewart Intl. to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Stewart Intl. to Puerto Rico with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Stewart Intl. to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally in the evening, when round-trip flights cost $298 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally at night, which is peak travel time and where the average cost of a ticket is $357.

Reviews of the top airlines flying from New Windsor to Puerto Rico

 
Need help choosing which airline to fly with from New Windsor to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
JetBlueOverall score based on 2913 reviews
8.0Crew
6.7Food
7.4Boarding
7.6Comfort
7.3Entertainment
Airline reviews

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

2.0 MediocreAnthony, Jul 2025JFK - SAV
Read more JetBlue reviews

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

Everything you need to know for your flight from New Windsor to Puerto Rico

Information on your arrival and departure airports

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