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Cheap flights from Pennsylvania to New York 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 Pennsylvania to New York departing on 10/19. 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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Cheap round-trip flights

Multiple Airlines Logo
6:51 pm - 10:41 amPIT-SWF
15h 50m1 stop
Multiple Airlines Logo
3:01 pm - 11:16 pmSWF-PIT
8h 15m1 stop
$201Multiple Airlines
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Thu, Oct 23 - Mon, Oct 27
Multiple Airlines Logo
9:06 pm - 10:26 amPIT-SWF
13h 20m1 stop
Multiple Airlines Logo
3:01 pm - 11:16 pmSWF-PIT
8h 15m1 stop
$243Multiple Airlines
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Mon, Oct 20 - Mon, Oct 27
Multiple Airlines Logo
6:19 am - 4:55 pmPHL-SWF
10h 36m2 stops
Multiple Airlines Logo
3:01 pm - 11:59 pmSWF-PHL
8h 58m1 stop
$253Multiple Airlines
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Thu, Oct 23 - Mon, Oct 27
Multiple Airlines Logo
12:36 pm - 5:49 pmPIT-SWF
5h 13m1 stop
Multiple Airlines Logo
3:01 pm - 11:16 pmSWF-PIT
8h 15m1 stop
$256Multiple Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
Multiple Airlines Logo
5:33 am - 10:11 amPHL-SWF
28h 38m1 stop
Multiple Airlines Logo
5:45 pm - 9:32 amSWF-PHL
15h 47m2 stops
$257Multiple Airlines
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Sun, Oct 19 - Sun, Oct 26
Multiple Airlines Logo
6:51 pm - 10:41 amPIT-SWF
15h 50m1 stop
Multiple Airlines Logo
3:01 pm - 10:21 amSWF-PIT
19h 20m2 stops
$268Multiple Airlines
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Thu, Oct 23 - Mon, Oct 27
Multiple Airlines Logo
10:09 am - 7:31 pmIAD-SWF
9h 22m1 stop
Multiple Airlines Logo
12:24 pm - 9:13 pmSWF-IAD
8h 49m2 stops
$272Multiple Airlines
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Mon, Oct 20 - Fri, Oct 24
Multiple Airlines Logo
5:44 pm - 10:41 amPIT-SWF
16h 57m1 stop
Multiple Airlines Logo
12:01 pm - 10:37 pmSWF-PIT
10h 36m1 stop
$272Multiple Airlines
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Thu, Nov 6 - Mon, Nov 10
Allegiant Air Logo
12:36 pm - 5:49 pmPIT-SWF
5h 13m1 stop
Allegiant Air Logo
7:11 pm - 8:16 pmSWF-PIT
25h 05m1 stop
$307Allegiant Air
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Fri, Oct 3 - Sun, Oct 5
Allegiant Air Logo
9:06 pm - 10:26 amPIT-SWF
13h 20m1 stop
Allegiant Air Logo
8:21 pm - 2:43 pmSWF-PIT
18h 22m1 stop
$311Allegiant Air
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Mon, Oct 6 - Fri, Oct 10

Allegiant Air flights from Pennsylvania to New Windsor

Our best Allegiant Air deals on Pennsylvania to New Windsor flight tickets
Allegiant Air
Oct 3
PIT12:36 pmPittsburgh
5h 13m
1 stop
SWF5:49 pmNew Windsor Stewart
Oct 5
SWF7:11 pmNew Windsor Stewart
25h 05m
1 stop
PIT8:16 pmPittsburgh
$307
Find similar
Allegiant Air
Oct 6
PIT9:06 pmPittsburgh
13h 20m
1 stop
SWF10:26 amNew Windsor Stewart
Oct 10
SWF8:21 pmNew Windsor Stewart
18h 22m
1 stop
PIT2:43 pmPittsburgh
$311
Find similar
Allegiant Air
Nov 21
IAD9:10 amWashington, D.C. Dulles Intl
9h 28m
1 stop
SWF6:38 pmNew Windsor Stewart
Nov 24
SWF10:57 amNew Windsor Stewart
23h 53m
2 stops
IAD10:50 amWashington, D.C. Dulles Intl
$334
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Pennsylvania to New Windsor 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 23, 2025.
Use the filters below to find and compare flights from Pennsylvania to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/23

6:51 pm-10:41 am

1 stop15h 50m

New Windsor Stewart

Mon 10/27

3:01 pm-11:16 pm

1 stop8h 15m

$201

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 10/20

9:06 pm-10:26 am

1 stop13h 20m

New Windsor Stewart

Mon 10/27

3:01 pm-11:16 pm

1 stop8h 15m

$243

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 10/23

6:19 am-4:55 pm

2 stops10h 36m

New Windsor Stewart

Mon 10/27

3:01 pm-11:59 pm

1 stop8h 58m

$253

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/24

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Mon 10/27

3:01 pm-11:16 pm

1 stop8h 15m

$256

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 10/19

5:33 am-10:11 am

1 stop28h 38m

New Windsor Stewart

Sun 10/26

5:45 pm-9:32 am

2 stops15h 47m

$257

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/23

6:51 pm-10:41 am

1 stop15h 50m

New Windsor Stewart

Mon 10/27

3:01 pm-10:21 am

2 stops19h 20m

$268

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Mon 10/20

10:09 am-7:31 pm

1 stop9h 22m

New Windsor Stewart

Fri 10/24

12:24 pm-9:13 pm

2 stops8h 49m

$272

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 11/6

5:44 pm-10:41 am

1 stop16h 57m

New Windsor Stewart

Mon 11/10

12:01 pm-10:37 pm

1 stop10h 36m

$272

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/3

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Sun 10/5

7:11 pm-8:16 pm

1 stop25h 05m

$307

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 10/6

9:06 pm-10:26 am

1 stop13h 20m

New Windsor Stewart

Fri 10/10

8:21 pm-2:43 pm

1 stop18h 22m

$311

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Pennsylvania to New Windsor

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 airline that flies from Pennsylvania to New Windsor Stewart?

Allegiant Air is the most popular carrier operating from Pennsylvania to New Windsor Stewart

What airlines fly to New Windsor?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to New Windsor from Pennsylvania according to our data. American Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 5 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

Cheap Pennsylvania to New Windsor flight deals and tips

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

Direct flights

None
There are no direct flights from Pennsylvania to New Windsor. There are no popular flight routes from Pennsylvania to New Windsor.
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  • When did momondo last update prices for flights from Pennsylvania to New Windsor Stewart Airport?

    Prices for flights from Pennsylvania to New Windsor Stewart Airport refresh daily.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pennsylvania to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The required travel and health documents for your New Windsor Stewart Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at New Windsor Stewart Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Pennsylvania to New Windsor. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Pennsylvania to New Windsor with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo provides multiple filters to help you find the best flight to New Windsor from Pennsylvania. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

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

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