Cheap flights from Portland, Maine to New York from $288

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 9/17. 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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Cheap round-trip flights

Breeze Airways Logo
3:21 pm - 11:03 amPWM-SWF
19h 42m1 stop
Breeze Airways Logo
12:24 pm - 2:26 pmSWF-PWM
26h 02m2 stops
$628Breeze Airways
Find Deal
Wed, Sep 10 - Fri, Sep 12
Breeze Airways Logo
3:21 pm - 11:03 amPWM-SWF
19h 42m1 stop
Breeze Airways Logo
12:24 pm - 2:26 pmSWF-PWM
26h 02m2 stops
$655Breeze Airways
Find Deal
Wed, Sep 24 - Fri, Sep 26
Breeze Airways Logo
5:40 pm - 11:44 amPWM-SWF
18h 04m2 stops
Breeze Airways Logo
11:43 am - 9:06 amSWF-PWM
21h 23m1 stop
$664Breeze Airways
Find Deal
Thu, Sep 11 - Thu, Sep 18
Breeze Airways Logo
11:26 am - 11:03 amPWM-SWF
23h 37m1 stop
Breeze Airways Logo
12:24 pm - 10:36 amSWF-PWM
22h 12m2 stops
$673Breeze Airways
Find Deal
Wed, Oct 1 - Fri, Oct 3
Breeze Airways Logo
5:40 pm - 11:44 amPWM-SWF
18h 04m2 stops
Breeze Airways Logo
11:43 am - 9:06 amSWF-PWM
21h 23m1 stop
$692Breeze Airways
Find Deal
Thu, Sep 11 - Sun, Sep 14
Breeze Airways Logo
3:21 pm - 11:03 amPWM-SWF
19h 42m1 stop
Breeze Airways Logo
12:24 pm - 1:41 pmSWF-PWM
25h 17m3 stops
$695Breeze Airways
Find Deal
Wed, Sep 10 - Fri, Sep 12
Breeze Airways Logo
5:40 pm - 11:44 amPWM-SWF
18h 04m2 stops
Breeze Airways Logo
11:43 am - 9:06 amSWF-PWM
21h 23m1 stop
$698Breeze Airways
Find Deal
Thu, Sep 25 - Sun, Sep 28
Breeze Airways Logo
5:40 pm - 11:44 amPWM-SWF
18h 04m2 stops
Breeze Airways Logo
11:43 am - 9:06 amSWF-PWM
21h 23m1 stop
$723Breeze Airways
Find Deal
Thu, Nov 20 - Sun, Nov 23
Breeze Airways Logo
5:40 pm - 11:44 amPWM-SWF
18h 04m2 stops
Breeze Airways Logo
11:43 am - 9:06 amSWF-PWM
21h 23m1 stop
$726Breeze Airways
Find Deal
Thu, Sep 18 - Sun, Sep 21
Breeze Airways Logo
3:21 pm - 11:03 amPWM-SWF
19h 42m1 stop
Breeze Airways Logo
12:24 pm - 1:41 pmSWF-PWM
25h 17m3 stops
$745Breeze Airways
Find Deal
Wed, Sep 24 - Fri, Sep 26

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 10
PWM3:21 pmPortland
19h 42m
1 stop
SWF11:03 amNew Windsor Stewart
Sep 12
SWF12:24 pmNew Windsor Stewart
26h 02m
2 stops
PWM2:26 pmPortland
Breeze Airways
Sep 24
PWM3:21 pmPortland
19h 42m
1 stop
SWF11:03 amNew Windsor Stewart
Sep 26
SWF12:24 pmNew Windsor Stewart
26h 02m
2 stops
PWM2:26 pmPortland
Breeze Airways
Sep 11
PWM5:40 pmPortland
18h 04m
2 stops
SWF11:44 amNew Windsor Stewart
Sep 18
SWF11:43 amNew Windsor Stewart
21h 23m
1 stop
PWM9:06 amPortland

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 28, 2025.
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

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/10

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Fri 9/12

12:24 pm-2:26 pm

2 stops26h 02m

$628

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Fri 9/26

12:24 pm-2:26 pm

2 stops26h 02m

$655

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 9/11

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Thu 9/18

11:43 am-9:06 am

1 stop21h 23m

$664

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 10/1

11:26 am-11:03 am

1 stop23h 37m

New Windsor Stewart

Fri 10/3

12:24 pm-10:36 am

2 stops22h 12m

$673

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 9/11

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 9/14

11:43 am-9:06 am

1 stop21h 23m

$692

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/10

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Fri 9/12

12:24 pm-1:41 pm

3 stops25h 17m

$695

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 9/25

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 9/28

11:43 am-9:06 am

1 stop21h 23m

$698

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 11/20

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 11/23

11:43 am-9:06 am

1 stop21h 23m

$723

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 9/18

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 9/21

11:43 am-9:06 am

1 stop21h 23m

$726

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Fri 9/26

12:24 pm-1:41 pm

3 stops25h 17m

$745

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 JetBlue 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 35% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 6 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

Direct flights

None
There are no direct flights from Portland, Maine to New Windsor. There are no popular flight routes 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 04m 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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1 adult
Tue 9/2
Tue 9/9

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