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Cheap flights from Portland, Maine to New York from $157

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 6/2. 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
0 bags

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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
9:52 am - 8:58 am
PWM
-
SWF
23h 06m
1 stop
Multiple Airlines Logo
6:50 pm - 10:39 pm
SWF
-
PWM
27h 49m
2 stops
$537Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Multiple Airlines Logo
11:07 am - 8:58 am
PWM
-
SWF
21h 51m
1 stop
Multiple Airlines Logo
5:49 pm - 2:31 pm
SWF
-
PWM
20h 42m
2 stops
$543Multiple Airlines
Wed, Jul 29 - Mon, Aug 3
Multiple Airlines Logo
11:07 am - 8:58 am
PWM
-
SWF
21h 51m
1 stop
Multiple Airlines Logo
9:41 am - 9:12 am
SWF
-
PWM
23h 31m
1 stop
$570Multiple Airlines
Wed, May 27 - Fri, May 29
Multiple Airlines Logo
11:07 am - 8:58 am
PWM
-
SWF
21h 51m
1 stop
Multiple Airlines Logo
9:41 am - 9:12 am
SWF
-
PWM
23h 31m
1 stop
$572Multiple Airlines
Wed, May 27 - Fri, May 29
Breeze Airways Logo
11:07 am - 8:58 am
PWM
-
SWF
21h 51m
1 stop
Breeze Airways Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$574Breeze Airways
Wed, Jul 29 - Mon, Aug 3
Multiple Airlines Logo
9:52 am - 8:58 am
PWM
-
SWF
23h 06m
1 stop
Multiple Airlines Logo
4:40 pm - 2:26 pm
SWF
-
PWM
21h 46m
2 stops
$584Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Multiple Airlines Logo
9:52 am - 8:58 am
PWM
-
SWF
23h 06m
1 stop
Multiple Airlines Logo
4:40 pm - 2:26 pm
SWF
-
PWM
21h 46m
2 stops
$595Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Multiple Airlines Logo
4:44 pm - 6:56 pm
PWM
-
SWF
26h 12m
2 stops
Multiple Airlines Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$620Multiple Airlines
Tue, Jul 28 - Mon, Aug 3
Breeze Airways Logo
3:11 pm - 11:37 am
PWM
-
SWF
20h 26m
2 stops
Breeze Airways Logo
12:17 pm - 5:49 pm
SWF
-
PWM
5h 32m
1 stop
$698Breeze Airways
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
9:52 am - 11:08 am
PWM
-
SWF
25h 16m
1 stop
Multiple Airlines Logo
10:28 am - 10:39 pm
SWF
-
PWM
12h 11m
2 stops
$703Multiple Airlines
Mon, Jul 6 - Thu, Jul 16

Breeze Airways flights from Portland, Maine to New Windsor

Our best Breeze Airways deals on Portland, Maine to New Windsor flight tickets
Breeze Airways
Jul 29
PWM11:07 amPortland
21h 51m
1 stop
SWF8:58 amNew Windsor Stewart
Aug 3
SWF12:17 pmNew Windsor Stewart
5h 32m
1 stop
PWM5:49 pmPortland
$574
Breeze Airways
Jul 30
PWM3:11 pmPortland
20h 26m
2 stops
SWF11:37 amNew Windsor Stewart
Aug 3
SWF12:17 pmNew Windsor Stewart
5h 32m
1 stop
PWM5:49 pmPortland
$698
Breeze Airways
May 29
PWM3:51 pmPortland
19h 34m
2 stops
SWF11:25 amNew Windsor Stewart
May 31
SWF9:38 amNew Windsor Stewart
23h 34m
1 stop
PWM9:12 amPortland
$722

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 April 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 - SWF

PWMSWF

Portland

Sat 8/8

9:52 am-8:58 am

1 stop23h 06m

New Windsor Stewart

Sat 8/15

6:50 pm-10:39 pm

2 stops27h 49m

$537

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 7/29

11:07 am-8:58 am

1 stop21h 51m

New Windsor Stewart

Mon 8/3

5:49 pm-2:31 pm

2 stops20h 42m

$543

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 5/27

11:07 am-8:58 am

1 stop21h 51m

New Windsor Stewart

Fri 5/29

9:41 am-9:12 am

1 stop23h 31m

$570

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 5/27

11:07 am-8:58 am

1 stop21h 51m

New Windsor Stewart

Fri 5/29

9:41 am-9:12 am

1 stop23h 31m

$572

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 7/29

11:07 am-8:58 am

1 stop21h 51m

New Windsor Stewart

Mon 8/3

12:17 pm-5:49 pm

1 stop5h 32m

$574

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 8/8

9:52 am-8:58 am

1 stop23h 06m

New Windsor Stewart

Sat 8/15

4:40 pm-2:26 pm

2 stops21h 46m

$584

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 8/8

9:52 am-8:58 am

1 stop23h 06m

New Windsor Stewart

Sat 8/15

4:40 pm-2:26 pm

2 stops21h 46m

$595

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Tue 7/28

4:44 pm-6:56 pm

2 stops26h 12m

New Windsor Stewart

Mon 8/3

12:17 pm-5:49 pm

1 stop5h 32m

$620
Quickest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 7/30

3:11 pm-11:37 am

2 stops20h 26m

New Windsor Stewart

Mon 8/3

12:17 pm-5:49 pm

1 stop5h 32m

$698

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 7/6

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Thu 7/16

10:28 am-10:39 pm

2 stops12h 11m

$703

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 35% 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.

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

9h 19m

Direct flights

None
The fastest flight from Portland, Maine to New Windsor takes 9h 19m
There are no direct flights from Portland, Maine to New Windsor. There are no popular flight routes from Portland, Maine to New Windsor.
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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. 9h 19m 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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