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Cheap flights from Portland, Maine to New York from $155

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 10/31. 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.
Multiple Airlines Logo
6:31 pm - 9:38 amPWM  Portland-SWF New Windsor Stewart
15h 07m2 stops Tampa Fort Lauderdale
Multiple Airlines Logo
8:48 pm - 9:08 amSWF  New Windsor Stewart-PWM Portland
12h 20m1 stop Orlando Sanford Intl
$378Multiple Airlines
Wed, Sep 30 - Fri, Oct 2
Breeze Airways Logo
3:11 pm - 11:37 amPWM  Portland-SWF New Windsor Stewart
20h 26m2 stops Pittsburgh Charleston
Breeze Airways Logo
11:10 am - 5:49 pmSWF  New Windsor Stewart-PWM Portland
6h 39m1 stop Charleston
$394Breeze Airways
Thu, Aug 27 - Mon, Aug 31
Breeze Airways Logo
3:16 pm - 11:25 amPWM  Portland-SWF New Windsor Stewart
20h 09m2 stops Pittsburgh Raleigh-Durham
Breeze Airways Logo
10:33 am - 9:12 amSWF  New Windsor Stewart-PWM Portland
22h 39m1 stop Orlando
$449Breeze Airways
Tue, Sep 1 - Sun, Sep 6
Multiple Airlines Logo
7:00 am - 5:15 pmPWM  Portland-SWF New Windsor Stewart
10h 15m2 stops Akron/Canton Myrtle Beach Intl
Multiple Airlines Logo
10:56 am - 9:08 amSWF  New Windsor Stewart-PWM Portland
22h 12m1 stop Orlando
$474Multiple Airlines
Sun, Sep 6 - Sun, Sep 13
Multiple Airlines Logo
7:00 am - 5:31 pmPWM  Portland-SWF New Windsor Stewart
10h 31m2 stops Akron/Canton Myrtle Beach Intl
Multiple Airlines Logo
10:56 am - 9:08 amSWF  New Windsor Stewart-PWM Portland
22h 12m1 stop Orlando
$515Multiple Airlines
Sun, Sep 20 - Sun, Sep 27
Multiple Airlines Logo
6:38 pm - 10:27 amPWM  Portland-SWF New Windsor Stewart
15h 49m1 stop Tampa
Multiple Airlines Logo
11:48 am - 5:45 pmSWF  New Windsor Stewart-PWM Portland
29h 57m2 stops Orlando Charleston
$545Multiple Airlines
Sat, Aug 22 - Tue, Aug 25
Multiple Airlines Logo
6:38 pm - 10:27 amPWM  Portland-SWF New Windsor Stewart
15h 49m1 stop Tampa
Multiple Airlines Logo
11:48 am - 10:27 amSWF  New Windsor Stewart-PWM Portland
22h 39m1 stop Orlando
$608Multiple Airlines
Sat, Aug 22 - Tue, Aug 25
Breeze Airways Logo
11:08 am - 10:16 amPWM  Portland-SWF New Windsor Stewart
23h 08m1 stop Orlando
Breeze Airways Logo
12:39 pm - 9:19 pmSWF  New Windsor Stewart-PWM Portland
8h 40m2 stops Raleigh-Durham Columbus
$624Breeze Airways
Wed, Sep 16 - Wed, Sep 23
Breeze Airways Logo
5:09 pm - 11:39 amPWM  Portland-SWF New Windsor Stewart
18h 30m1 stop Raleigh-Durham
Breeze Airways Logo
10:56 am - 9:08 amSWF  New Windsor Stewart-PWM Portland
22h 12m1 stop Orlando
$628Breeze Airways
Tue, Sep 29 - Thu, Oct 1
Breeze Airways Logo
5:09 pm - 11:39 amPWM  Portland-SWF New Windsor Stewart
18h 30m1 stop Raleigh-Durham
Breeze Airways Logo
10:56 am - 9:08 amSWF  New Windsor Stewart-PWM Portland
22h 12m1 stop Orlando
$638Breeze Airways
Tue, Nov 10 - Thu, Nov 12

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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
Aug 27
PWM3:11 pmPortland
20h 26m
2 stops
SWF11:37 amNew Windsor Stewart
Aug 31
SWF11:10 amNew Windsor Stewart
6h 39m
1 stop
PWM5:49 pmPortland
$394
Breeze Airways
Sep 1
PWM3:16 pmPortland
20h 09m
2 stops
SWF11:25 amNew Windsor Stewart
Sep 6
SWF10:33 amNew Windsor Stewart
22h 39m
1 stop
PWM9:12 amPortland
$449
Breeze Airways
Sep 16
PWM11:08 amPortland
23h 08m
1 stop
SWF10:16 amNew Windsor Stewart
Sep 23
SWF12:39 pmNew Windsor Stewart
8h 40m
2 stops
PWM9:19 pmPortland
$624

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 August 6, 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 Portland - SWF New Windsor Stewart

PWMSWF

Portland

Wed 9/30

6:31 pm-9:38 am

2 stops15h 07m

New Windsor Stewart

Fri 10/2

8:48 pm-9:08 am

1 stop12h 20m

$378
Quickest round-trip

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Thu 8/27

3:11 pm-11:37 am

2 stops20h 26m

New Windsor Stewart

Mon 8/31

11:10 am-5:49 pm

1 stop6h 39m

$394

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Tue 9/1

3:16 pm-11:25 am

2 stops20h 09m

New Windsor Stewart

Sun 9/6

10:33 am-9:12 am

1 stop22h 39m

$449

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Sun 9/6

7:00 am-5:15 pm

2 stops10h 15m

New Windsor Stewart

Sun 9/13

10:56 am-9:08 am

1 stop22h 12m

$474

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Sun 9/20

7:00 am-5:31 pm

2 stops10h 31m

New Windsor Stewart

Sun 9/27

10:56 am-9:08 am

1 stop22h 12m

$515

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Sat 8/22

6:38 pm-10:27 am

1 stop15h 49m

New Windsor Stewart

Tue 8/25

11:48 am-5:45 pm

2 stops29h 57m

$545

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Sat 8/22

6:38 pm-10:27 am

1 stop15h 49m

New Windsor Stewart

Tue 8/25

11:48 am-10:27 am

1 stop22h 39m

$608

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Wed 9/16

11:08 am-10:16 am

1 stop23h 08m

New Windsor Stewart

Wed 9/23

12:39 pm-9:19 pm

2 stops8h 40m

$624

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Tue 9/29

5:09 pm-11:39 am

1 stop18h 30m

New Windsor Stewart

Thu 10/1

10:56 am-9:08 am

1 stop22h 12m

$628

PortlandNew Windsor

PWM Portland - SWF New Windsor Stewart

PWMSWF

Portland

Tue 11/10

5:09 pm-11:39 am

1 stop18h 30m

New Windsor Stewart

Thu 11/12

10:56 am-9:08 am

1 stop22h 12m

$638

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 40% 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

17h 14m

Direct flights

None
The fastest flight from Portland, Maine to New Windsor takes 17h 14m
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. 17h 14m 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.

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