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Cheap flights from New Windsor to Puerto Rico from $101

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 1/9. 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
11:09 am - 1:41 am
SWF
-
SJU
13h 32m2 stops
Multiple Airlines Logo
2:59 am - 10:19 am
SJU
-
SWF
32h 20m2 stops
$325Multiple Airlines
Fri, Jan 30 - Sat, Jan 31
Multiple Airlines Logo
12:11 pm - 2:31 pm
SWF
-
SJU
26h 20m2 stops
Multiple Airlines Logo
9:49 pm - 10:55 am
SJU
-
SWF
13h 06m1 stop
$434Multiple Airlines
Mon, Apr 27 - Wed, May 6
Multiple Airlines Logo
12:11 pm - 2:58 am
SWF
-
BQN
13h 47m2 stops
Multiple Airlines Logo
3:48 am - 6:43 pm
BQN
-
SWF
15h 55m1 stop
$443Multiple Airlines
Mon, Jan 12 - Sun, Jan 18
Multiple Airlines Logo
11:45 am - 2:31 pm
SWF
-
SJU
26h 46m1 stop
Multiple Airlines Logo
7:05 pm - 10:50 am
SJU
-
SWF
15h 45m1 stop
$457Multiple Airlines
Sun, Apr 19 - Sun, Apr 26
Multiple Airlines Logo
12:52 pm - 3:10 am
SWF
-
BQN
13h 18m1 stop
Multiple Airlines Logo
3:43 am - 11:33 am
BQN
-
SWF
8h 50m1 stop
$480Multiple Airlines
Mon, Dec 29 - Sat, Jan 10
Multiple Airlines Logo
11:45 am - 6:48 pm
SWF
-
SJU
31h 03m2 stops
Multiple Airlines Logo
7:05 pm - 10:50 am
SJU
-
SWF
15h 45m1 stop
$498Multiple Airlines
Sun, Apr 19 - Sun, Apr 26
Multiple Airlines Logo
11:48 am - 8:11 pm
SWF
-
SJU
8h 23m1 stop
Multiple Airlines Logo
10:00 pm - 10:50 am
SJU
-
SWF
12h 50m1 stop
$506Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
11:48 am - 11:33 pm
SWF
-
SJU
10h 45m1 stop
Multiple Airlines Logo
8:05 pm - 11:08 am
SJU
-
SWF
16h 03m1 stop
$515Multiple Airlines
Sun, Feb 8 - Wed, Feb 11
Multiple Airlines Logo
12:13 pm - 11:33 pm
SWF
-
SJU
10h 20m1 stop
Multiple Airlines Logo
8:05 pm - 11:31 am
SJU
-
SWF
16h 26m2 stops
$521Multiple Airlines
Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
11:48 am - 11:33 pm
SWF
-
SJU
10h 45m1 stop
Multiple Airlines Logo
8:05 pm - 11:08 am
SJU
-
SWF
16h 03m1 stop
$526Multiple Airlines
Thu, Feb 5 - Sat, Feb 7

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 December 25, 2025.
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

Fri 1/30

11:09 am-1:41 am

2 stops13h 32m

San Juan Luis Munoz Marin Intl

Sat 1/31

2:59 am-10:19 am

2 stops32h 20m

$325

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 4/27

12:11 pm-2:31 pm

2 stops26h 20m

San Juan Luis Munoz Marin Intl

Wed 5/6

9:49 pm-10:55 am

1 stop13h 06m

$434

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Mon 1/12

12:11 pm-2:58 am

2 stops13h 47m

Aguadilla Borinquen

Sun 1/18

3:48 am-6:43 pm

1 stop15h 55m

$443

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/19

11:45 am-2:31 pm

1 stop26h 46m

San Juan Luis Munoz Marin Intl

Sun 4/26

7:05 pm-10:50 am

1 stop15h 45m

$457

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Mon 12/29

12:52 pm-3:10 am

1 stop13h 18m

Aguadilla Borinquen

Sat 1/10

3:43 am-11:33 am

1 stop8h 50m

$480

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/19

11:45 am-6:48 pm

2 stops31h 03m

San Juan Luis Munoz Marin Intl

Sun 4/26

7:05 pm-10:50 am

1 stop15h 45m

$498

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/9

11:48 am-8:11 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Sun 4/12

10:00 pm-10:50 am

1 stop12h 50m

$506

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/8

11:48 am-11:33 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Wed 2/11

8:05 pm-11:08 am

1 stop16h 03m

$515

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 1/22

12:13 pm-11:33 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Thu 1/29

8:05 pm-11:31 am

2 stops16h 26m

$521

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/5

11:48 am-11:33 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:05 pm-11:08 am

1 stop16h 03m

$526

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from New Windsor is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $170. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $449.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the afternoon. Flights from New Windsor to Puerto Rico during this time can be as low as $298. In contrast, the most expensive time of day to depart to Puerto Rico is in the evening when prices are around $357.

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

6h 57m

Direct flights

None
The fastest flight from New Windsor to Puerto Rico takes 6h 57m
There are no direct flights from New Windsor to Puerto Rico. There are no popular flight routes from New Windsor to Puerto Rico.
Search flight deals

  • 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 $244Free CancellationRating
7.2
2,897 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.

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Find better results for your trip to Puerto Rico

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