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Cheap flights from New Windsor to Puerto Rico from $169

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 10/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from New Windsor to Puerto Rico

Cheap round-trip flights

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, Oct 16 - Sat, Oct 18
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, Nov 20 - Sun, Nov 23
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, Sep 25 - Sat, Sep 27
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 30 - Sat, Nov 1
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, Oct 9 - Sat, Oct 11
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
Thu, Sep 25 - Sun, Sep 28
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
Fri, Oct 3 - Sat, Oct 11
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, Sep 25 - Sat, Sep 27
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
Thu, Oct 23 - Sat, Oct 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 September 17, 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 WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 10/16

11:43 am-2:04 am

1 stop14h 21m

Aguadilla Borinquen

Sat 10/18

2:59 am-11:03 am

1 stop8h 04m

$447

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/20

11:06 am-11:09 pm

1 stop11h 03m

San Juan Luis Munoz Marin Intl

Sun 11/23

5:05 pm-10:07 am

1 stop18h 02m

$517

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 9/25

11:43 am-8:02 am

1 stop20h 19m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:39 am-11:03 am

1 stop7h 24m

$523

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/30

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Sat 11/1

2:48 am-11:03 am

1 stop9h 15m

$560

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/9

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Sat 10/11

2:49 am-11:03 am

1 stop8h 14m

$571

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 9/25

11:43 am-8:02 am

1 stop20h 19m

San Juan Luis Munoz Marin Intl

Sun 9/28

6:44 am-11:44 am

2 stops29h 00m

$576

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 10/3

12:24 pm-2:34 am

2 stops14h 10m

San Juan Luis Munoz Marin Intl

Sat 10/11

2:49 am-11:03 am

1 stop8h 14m

$586

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 9/25

11:43 am-11:04 am

2 stops23h 21m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:39 am-11:03 am

1 stop7h 24m

$589

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/23

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Sat 10/25

2:49 am-11:03 am

1 stop8h 14m

$591

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/23

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Sat 10/25

2:49 am-11:03 am

1 stop8h 14m

$592

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

Direct flights

None
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 $244Free CancellationRating
7.2
2,914 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

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Fri 10/17
Fri 10/24
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Find better results for your trip to Puerto Rico

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Popular flights according to clicks in the last 7 days on momondo
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