$169 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 10/17. 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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Cheap Flights from New Windsor to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla1 stop$447
Aguadilla
Aguadilla1 stop$447

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

Thu, Oct 16 - Sat, Oct 18
Multiple Airlines Logo
11:43 am - 2:04 amSWF-BQN
14h 21m1 stop
Multiple Airlines Logo
2:59 am - 11:03 amBQN-SWF
8h 04m1 stop
$447Multiple Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
Multiple Airlines Logo
11:06 am - 11:09 pmSWF-SJU
11h 03m1 stop
Multiple Airlines Logo
5:05 pm - 10:07 amSJU-SWF
18h 02m1 stop
$517Multiple Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27
Multiple Airlines Logo
11:43 am - 8:02 amSWF-SJU
20h 19m1 stop
Multiple Airlines Logo
3:39 am - 11:03 amSJU-SWF
7h 24m1 stop
$523Multiple Airlines
Find Deal
Thu, Oct 30 - Sat, Nov 1
Multiple Airlines Logo
11:43 am - 1:44 amSWF-SJU
14h 01m1 stop
Multiple Airlines Logo
2:48 am - 11:03 amSJU-SWF
9h 15m1 stop
$560Multiple Airlines
Find Deal
Thu, Oct 9 - Sat, Oct 11
Multiple Airlines Logo
11:43 am - 1:44 amSWF-SJU
14h 01m1 stop
Multiple Airlines Logo
2:49 am - 11:03 amSJU-SWF
8h 14m1 stop
$571Multiple Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
Multiple Airlines Logo
11:43 am - 8:02 amSWF-SJU
20h 19m1 stop
Multiple Airlines Logo
6:44 am - 11:44 amSJU-SWF
29h 00m2 stops
$576Multiple Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 11
Multiple Airlines Logo
12:24 pm - 2:34 amSWF-SJU
14h 10m2 stops
Multiple Airlines Logo
2:49 am - 11:03 amSJU-SWF
8h 14m1 stop
$586Multiple Airlines
Find Deal
Thu, Sep 25 - Sat, Sep 27
Multiple Airlines Logo
11:43 am - 11:04 amSWF-SJU
23h 21m2 stops
Multiple Airlines Logo
3:39 am - 11:03 amSJU-SWF
7h 24m1 stop
$589Multiple Airlines
Find Deal
Thu, Oct 23 - Sat, Oct 25
Multiple Airlines Logo
11:43 am - 1:44 amSWF-SJU
14h 01m1 stop
Multiple Airlines Logo
2:49 am - 11:03 amSJU-SWF
8h 14m1 stop
$591Multiple Airlines
Find Deal
Thu, Oct 23 - Sat, Oct 25
Multiple Airlines Logo
11:43 am - 1:44 amSWF-SJU
14h 01m1 stop
Multiple Airlines Logo
2:49 am - 11:03 amSJU-SWF
8h 14m1 stop
$592Multiple Airlines
Find Deal
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 17m, and San Juan, which takes 7h 44m.

Good to know

Cheapest flight$169
Flight from Stewart Intl. to Aguadilla

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 airline 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 2914 reviews
8.0Crew
6.7Food
7.4Boarding
7.6Comfort
7.2Entertainment
Airline reviews

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

10.0 ExcellentEmily, Sep 2025JFK - RSW
Read more JetBlue reviews

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

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.

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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