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Cheap flights from Portland, Maine to New York from $181

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to New York departing on 9/25. 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 Portland, Maine to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
11:08 am - 10:16 am
PWM
-
SWF
23h 08m
1 stop
Breeze Airways Logo
12:39 pm - 9:21 am
SWF
-
PWM
20h 42m
2 stops
$354Breeze Airways
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
6:38 pm - 10:55 am
PWM
-
SWF
16h 17m
1 stop
Multiple Airlines Logo
6:19 pm - 5:58 pm
SWF
-
PWM
23h 39m
1 stop
$644Multiple Airlines
Sat, Jul 18 - Tue, Jul 21
Breeze Airways Logo
9:52 am - 11:08 am
PWM
-
SWF
25h 16m
1 stop
Breeze Airways Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$688Breeze Airways
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
7:00 am - 5:40 pm
PWM
-
SWF
10h 40m
2 stops
Multiple Airlines Logo
11:48 am - 10:27 am
SWF
-
PWM
22h 39m
1 stop
$692Multiple Airlines
Sun, Jul 5 - Tue, Jul 7
Multiple Airlines Logo
7:00 am - 5:40 pm
PWM
-
SWF
10h 40m
2 stops
Multiple Airlines Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$701Multiple Airlines
Thu, Jul 2 - Fri, Jul 10
Multiple Airlines Logo
6:38 pm - 10:55 am
PWM
-
SWF
16h 17m
1 stop
Multiple Airlines Logo
6:19 pm - 4:16 pm
SWF
-
PWM
21h 57m
2 stops
$712Multiple Airlines
Sat, Jul 18 - Tue, Jul 21
Breeze Airways Logo
3:51 pm - 11:25 am
PWM
-
SWF
19h 34m
2 stops
Breeze Airways Logo
10:33 am - 9:12 am
SWF
-
PWM
22h 39m
1 stop
$714Breeze Airways
Fri, Sep 4 - Sun, Sep 6
Breeze Airways Logo
3:51 pm - 11:25 am
PWM
-
SWF
19h 34m
2 stops
Breeze Airways Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$724Breeze Airways
Fri, Jul 24 - Mon, Jul 27
Breeze Airways Logo
3:16 pm - 11:25 am
PWM
-
SWF
20h 09m
2 stops
Breeze Airways Logo
10:33 am - 9:12 am
SWF
-
PWM
22h 39m
1 stop
$734Breeze Airways
Tue, Jul 21 - Thu, Jul 23
Breeze Airways Logo
11:07 am - 9:53 am
PWM
-
SWF
22h 46m
1 stop
Breeze Airways Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$748Breeze Airways
Wed, Jul 15 - Fri, Jul 17

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Breeze Airways flights from Portland, Maine to New Windsor

Our best Breeze Airways deals on Portland, Maine to New Windsor flight tickets
Breeze Airways
Sep 16
PWM11:08 amPortland
23h 08m
1 stop
SWF10:16 amNew Windsor Stewart
Sep 23
SWF12:39 pmNew Windsor Stewart
20h 42m
2 stops
PWM9:21 amPortland
$354
Breeze Airways
Sep 22
PWM5:09 pmPortland
18h 30m
1 stop
SWF11:39 amNew Windsor Stewart
Sep 25
SWF10:48 amNew Windsor Stewart
6h 02m
1 stop
PWM4:50 pmPortland
$380
Breeze Airways
Aug 10
PWM9:52 amPortland
25h 16m
1 stop
SWF11:08 amNew Windsor Stewart
Aug 17
SWF12:17 pmNew Windsor Stewart
5h 32m
1 stop
PWM5:49 pmPortland
$688

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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 June 18, 2026.
Use the filters below to find and compare flights from Portland, Maine to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/16

11:08 am-10:16 am

1 stop23h 08m

New Windsor Stewart

Wed 9/23

12:39 pm-9:21 am

2 stops20h 42m

$354

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 7/18

6:38 pm-10:55 am

1 stop16h 17m

New Windsor Stewart

Tue 7/21

6:19 pm-5:58 pm

1 stop23h 39m

$644

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 8/10

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Mon 8/17

12:17 pm-5:49 pm

1 stop5h 32m

$688

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sun 7/5

7:00 am-5:40 pm

2 stops10h 40m

New Windsor Stewart

Tue 7/7

11:48 am-10:27 am

1 stop22h 39m

$692
Quickest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 7/2

7:00 am-5:40 pm

2 stops10h 40m

New Windsor Stewart

Fri 7/10

12:17 pm-5:49 pm

1 stop5h 32m

$701

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 7/18

6:38 pm-10:55 am

1 stop16h 17m

New Windsor Stewart

Tue 7/21

6:19 pm-4:16 pm

2 stops21h 57m

$712

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 9/4

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Sun 9/6

10:33 am-9:12 am

1 stop22h 39m

$714

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 7/24

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Mon 7/27

12:17 pm-5:49 pm

1 stop5h 32m

$724

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Tue 7/21

3:16 pm-11:25 am

2 stops20h 09m

New Windsor Stewart

Thu 7/23

10:33 am-9:12 am

1 stop22h 39m

$734

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 7/15

11:07 am-9:53 am

1 stop22h 46m

New Windsor Stewart

Fri 7/17

12:17 pm-5:49 pm

1 stop5h 32m

$748

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 New York from

How to get the cheapest flight ticket from Portland, Maine 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 Portland to New Windsor Stewart?

Breeze Airways is the most popular carrier operating from Portland to New Windsor Stewart

What airlines fly to New Windsor?

United Airlines, Delta and American Airlines are the top three most popular airlines that fly to New Windsor from Portland, Maine according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 4 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

When to book flights from Portland, Maine to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to New Windsor according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland, Maine to New Windsor (PWM to SWF) flight deals and tips

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

Fastest flight time

18h 09m

Direct flights

None
The fastest flight from Portland, Maine to New Windsor takes 18h 09m
There are no direct flights from Portland, Maine to New Windsor. There are no popular flight routes from Portland, Maine to New Windsor.
Search flight deals

Frequently asked questions about flying from Portland, Maine to New Windsor

  • How far is Portland to New Windsor Stewart by plane?

    A flight from Portland to New Windsor Stewart will travel around 243.8 mi. 18h 09m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Portland Airport to New Windsor Stewart Airport?

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

  • How old do you have to be to fly from Portland Airport 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 Portland Airport to New Windsor Stewart Airport.

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

    The travel and health documents you'll need for your trip to New Windsor Stewart Airport 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 New Windsor Stewart Airport. It is always advisable to seek advice from your airline or a trusted 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 Portland to New Windsor?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to New Windsor for you.

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

Flights from Portland 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 Portland to New Windsor?

Once all potential Portland to New Windsor flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland 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 Portland and alert you when they change.

An easier way to manage your New Windsor 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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