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Cheap flights from New Windsor to Puerto Rico from $111

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Puerto Rico departing on 5/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from New Windsor to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:52 am - 3:31 pm
SWF
-
SJU
26h 39m
1 stop
Multiple Airlines Logo
8:05 pm - 11:31 am
SJU
-
SWF
16h 26m
2 stops
$327Multiple Airlines
Sun, Feb 22 - Thu, Feb 26
Multiple Airlines Logo
11:45 am - 8:44 pm
SWF
-
SJU
8h 59m
1 stop
Multiple Airlines Logo
7:05 pm - 8:58 am
SJU
-
SWF
13h 53m
1 stop
$329Multiple Airlines
Thu, May 7 - Sat, May 9
Multiple Airlines Logo
8:12 pm - 10:10 am
SWF
-
SJU
13h 58m
1 stop
Multiple Airlines Logo
7:54 pm - 10:55 am
SJU
-
SWF
15h 01m
1 stop
$332Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
Multiple Airlines Logo
8:12 pm - 10:10 am
SWF
-
SJU
13h 58m
1 stop
Multiple Airlines Logo
7:54 pm - 10:55 am
SJU
-
SWF
15h 01m
1 stop
$333Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
Multiple Airlines Logo
10:29 am - 6:55 pm
SWF
-
SJU
8h 26m
1 stop
Multiple Airlines Logo
3:08 am - 11:08 am
SJU
-
SWF
8h 00m
1 stop
$348Multiple Airlines
Sun, Mar 22 - Wed, Mar 25
Multiple Airlines Logo
10:29 am - 6:55 pm
SWF
-
SJU
8h 26m
1 stop
Multiple Airlines Logo
3:08 am - 11:08 am
SJU
-
SWF
8h 00m
1 stop
$349Multiple Airlines
Sun, Mar 22 - Wed, Mar 25
Multiple Airlines Logo
11:48 am - 2:57 am
SWF
-
BQN
14h 09m
1 stop
Multiple Airlines Logo
3:58 am - 11:08 am
BQN
-
SWF
8h 10m
1 stop
$349Multiple Airlines
Thu, Feb 26 - Wed, Mar 4
Multiple Airlines Logo
10:29 am - 6:55 pm
SWF
-
SJU
8h 26m
1 stop
Multiple Airlines Logo
12:04 pm - 11:31 am
SJU
-
SWF
23h 27m
2 stops
$361Multiple Airlines
Sun, Mar 22 - Thu, Mar 26
Multiple Airlines Logo
11:52 am - 3:31 pm
SWF
-
SJU
26h 39m
1 stop
Multiple Airlines Logo
3:53 am - 11:08 am
SJU
-
SWF
8h 15m
1 stop
$363Multiple Airlines
Sun, Feb 22 - Wed, Feb 25
Multiple Airlines Logo
10:29 am - 6:55 pm
SWF
-
SJU
8h 26m
1 stop
Multiple Airlines Logo
3:08 am - 11:08 am
SJU
-
SWF
8h 00m
1 stop
$380Multiple Airlines
Sun, Mar 22 - Wed, Mar 25

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor 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, momondo users made 832,500 searches. Data last updated February 11, 2026.
Use the filters below to find and compare flights from New Windsor to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/22

11:52 am-3:31 pm

1 stop26h 39m

San Juan Luis Munoz Marin Intl

Thu 2/26

8:05 pm-11:31 am

2 stops16h 26m

$327

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 5/7

11:45 am-8:44 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sat 5/9

7:05 pm-8:58 am

1 stop13h 53m

$329

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/5

8:12 pm-10:10 am

1 stop13h 58m

San Juan Luis Munoz Marin Intl

Wed 4/8

7:54 pm-10:55 am

1 stop15h 01m

$332

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/5

8:12 pm-10:10 am

1 stop13h 58m

San Juan Luis Munoz Marin Intl

Wed 4/8

7:54 pm-10:55 am

1 stop15h 01m

$333

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

10:29 am-6:55 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:08 am-11:08 am

1 stop8h 00m

$348

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

10:29 am-6:55 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:08 am-11:08 am

1 stop8h 00m

$349

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 2/26

11:48 am-2:57 am

1 stop14h 09m

Aguadilla Borinquen

Wed 3/4

3:58 am-11:08 am

1 stop8h 10m

$349

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

10:29 am-6:55 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Thu 3/26

12:04 pm-11:31 am

2 stops23h 27m

$361

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/22

11:52 am-3:31 pm

1 stop26h 39m

San Juan Luis Munoz Marin Intl

Wed 2/25

3:53 am-11:08 am

1 stop8h 15m

$363

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

10:29 am-6:55 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:08 am-11:08 am

1 stop8h 00m

$380

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Puerto Rico from

How to get the cheapest flight ticket from New Windsor to Puerto Rico

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to Puerto Rico?

JetBlue, Frontier and United Airlines are the top three most popular airlines that fly to Puerto Rico from New Windsor according to our data. JetBlue is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 6 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.

Cheap New Windsor to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Puerto Rico

Fastest flight time

7h 54m

Direct flights

None
The fastest flight from New Windsor to Puerto Rico takes 7h 54m
There are no direct flights from New Windsor to Puerto Rico. There are no popular flight routes from New Windsor to Puerto Rico.
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  • When did momondo last update prices for flights from New Windsor Stewart Airport to Puerto Rico?

    Prices for flights from New Windsor Stewart Airport to Puerto Rico were last updated today.

  • How many operators does momondo search for flights from New Windsor Stewart Airport to Puerto Rico?

  • How old do you have to be to fly from New Windsor Stewart Airport to Puerto Rico?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from New Windsor Stewart Airport to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The travel and health documents you'll need for your trip to Puerto Rico may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Puerto Rico. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from New Windsor to Puerto Rico

Compare and see reviews for airlines that fly from New Windsor to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $227Free CancellationRating
7.2
2,894 reviews
Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from New Windsor to Puerto Rico?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Rico from New Windsor.

Can I find flights from New Windsor to Puerto Rico with flexible booking policies on momondo?

All flight searches from New Windsor to Puerto Rico on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from New Windsor to Puerto Rico?

momondo helps you find the best flight between New Windsor and Puerto Rico by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from New Windsor to Puerto Rico right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from New Windsor and alert you when they change.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Puerto Rico

Popular cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo
Flights to San Juanfrom $92
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