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Cheap flights from New Windsor to Puerto Rico from $99

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 11/12. 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
1 adult, Economy, 0 bags

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
10:18 am - 11:38 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
13h 20m1 stop Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 9:48 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
16h 36m1 stop Fort Lauderdale
$184Multiple Airlines
Thu, Oct 15 - Wed, Oct 28
Multiple Airlines Logo
10:18 am - 11:38 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
13h 20m1 stop Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 11:08 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
17h 56m1 stop Fort Lauderdale
$190Multiple Airlines
Thu, Oct 15 - Sat, Oct 24
Multiple Airlines Logo
11:48 am - 1:34 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
25h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 9:28 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
16h 16m1 stop Fort Lauderdale
$193Multiple Airlines
Sun, Oct 4 - Wed, Oct 14
Multiple Airlines Logo
10:38 am - 11:38 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
13h 00m1 stop Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 12:08 pmSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
18h 56m1 stop Fort Lauderdale
$201Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Multiple Airlines Logo
10:38 am - 11:38 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
13h 00m1 stop Fort Lauderdale
Multiple Airlines Logo
6:12 pm - 10:10 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
16h 58m1 stop Fort Lauderdale
$202Multiple Airlines
Thu, Oct 29 - Wed, Nov 4
Multiple Airlines Logo
10:18 am - 1:31 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
27h 13m1 stop Fort Lauderdale
Multiple Airlines Logo
8:45 am - 9:48 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
25h 03m1 stop Fort Lauderdale
$215Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
11:53 am - 1:31 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
25h 38m1 stop Fort Lauderdale
Multiple Airlines Logo
8:45 am - 9:48 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
25h 03m1 stop Fort Lauderdale
$221Multiple Airlines
Sun, Oct 18 - Wed, Oct 21
Multiple Airlines Logo
10:18 am - 1:31 pmSWF  New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl
27h 13m1 stop Fort Lauderdale
Multiple Airlines Logo
8:45 am - 9:48 amSJU  San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart
25h 03m1 stop Fort Lauderdale
$223Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
12:16 pm - 10:14 amSWF  New Windsor Stewart-BQN Aguadilla Borinquen
21h 58m2 stops Charleston Orlando
Multiple Airlines Logo
11:08 am - 10:16 amBQN  Aguadilla Borinquen-SWF New Windsor Stewart
23h 08m1 stop Orlando
$352Multiple Airlines
Fri, Sep 11 - Thu, Sep 17
Multiple Airlines Logo
11:06 am - 10:14 amSWF  New Windsor Stewart-BQN Aguadilla Borinquen
23h 08m1 stop Orlando Sanford Intl
Multiple Airlines Logo
11:08 am - 10:16 amBQN  Aguadilla Borinquen-SWF New Windsor Stewart
23h 08m1 stop Orlando
$355Multiple Airlines
Fri, Sep 11 - Thu, Sep 17

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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 August 16, 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

Cheapest round-trip
Quickest round-trip

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-11:38 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Wed 10/28

5:12 pm-9:48 am

1 stop16h 36m

$184

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-11:38 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Sat 10/24

5:12 pm-11:08 am

1 stop17h 56m

$190

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Sun 10/4

11:48 am-1:34 pm

1 stop25h 46m

San Juan Luis Munoz Marin Intl

Wed 10/14

5:12 pm-9:28 am

1 stop16h 16m

$193

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/29

10:38 am-11:38 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Sat 10/31

5:12 pm-12:08 pm

1 stop18h 56m

$201

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/29

10:38 am-11:38 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Wed 11/4

6:12 pm-10:10 am

1 stop16h 58m

$202

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-1:31 pm

1 stop27h 13m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$215

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Sun 10/18

11:53 am-1:31 pm

1 stop25h 38m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$221

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-1:31 pm

1 stop27h 13m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$223

New WindsorAguadilla

SWF New Windsor Stewart - BQN Aguadilla Borinquen

SWFBQN

New Windsor Stewart

Fri 9/11

12:16 pm-10:14 am

2 stops21h 58m

Aguadilla Borinquen

Thu 9/17

11:08 am-10:16 am

1 stop23h 08m

$352

New WindsorAguadilla

SWF New Windsor Stewart - BQN Aguadilla Borinquen

SWFBQN

New Windsor Stewart

Fri 9/11

11:06 am-10:14 am

1 stop23h 08m

Aguadilla Borinquen

Thu 9/17

11:08 am-10:16 am

1 stop23h 08m

$355

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 airlines fly to Puerto Rico?

JetBlue, United Airlines and Frontier 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 49% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 5 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 50m

Direct flights

None
The fastest flight from New Windsor to Puerto Rico takes 7h 50m
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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Frequently asked questions about flying from New Windsor to Puerto Rico

  • 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 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.

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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