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Cheap flights from Portland, Maine to New York from $168

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 10/20. 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 - 11:08 am
PWM
-
SWF
25h 16m
1 stop
Multiple Airlines Logo
5:39 pm - 9:19 pm
SWF
-
PWM
27h 40m
2 stops
$416Multiple Airlines
Mon, Aug 10 - Mon, Aug 24
Breeze Airways Logo
11:07 am - 8:58 am
PWM
-
SWF
21h 51m
1 stop
Breeze Airways Logo
9:38 am - 9:12 am
SWF
-
PWM
23h 34m
1 stop
$430Breeze Airways
Wed, Jun 10 - Sun, Jun 14
Multiple Airlines Logo
9:52 am - 11:25 am
PWM
-
SWF
25h 33m
2 stops
Multiple Airlines Logo
9:39 am - 9:12 am
SWF
-
PWM
23h 33m
1 stop
$438Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
9:52 am - 8:58 am
PWM
-
SWF
23h 06m
1 stop
Multiple Airlines Logo
10:28 am - 10:39 pm
SWF
-
PWM
12h 11m
2 stops
$492Multiple Airlines
Sat, Aug 8 - Thu, Aug 13
Multiple Airlines Logo
9:52 am - 11:08 am
PWM
-
SWF
25h 16m
1 stop
Multiple Airlines Logo
4:13 pm - 2:26 pm
SWF
-
PWM
22h 13m
2 stops
$533Multiple Airlines
Mon, Jun 29 - Sat, Jul 4
Multiple Airlines Logo
3:11 pm - 8:49 am
PWM
-
SWF
17h 38m
2 stops
Multiple Airlines Logo
9:38 am - 9:12 am
SWF
-
PWM
23h 34m
1 stop
$536Multiple Airlines
Thu, Jun 11 - Sun, Jun 14
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
$538Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Breeze Airways Logo
9:52 am - 11:08 am
PWM
-
SWF
25h 16m
1 stop
Breeze Airways Logo
12:17 pm - 9:12 am
SWF
-
PWM
20h 55m
2 stops
$544Breeze Airways
Mon, Jun 29 - Fri, Jul 3
Breeze Airways Logo
9:52 am - 8:58 am
PWM
-
SWF
23h 06m
1 stop
Breeze Airways Logo
12:05 pm - 10:39 pm
SWF
-
PWM
34h 34m
2 stops
$550Breeze Airways
Sat, Aug 8 - Sat, Aug 15
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
$554Multiple Airlines
Mon, Jun 29 - Thu, Jul 9

Breeze Airways flights from Portland, Maine to New Windsor

Our best Breeze Airways deals on Portland, Maine to New Windsor flight tickets
Breeze Airways
Jun 10
PWM11:07 amPortland
21h 51m
1 stop
SWF8:58 amNew Windsor Stewart
Jun 14
SWF9:38 amNew Windsor Stewart
23h 34m
1 stop
PWM9:12 amPortland
$430
Breeze Airways
Jun 29
PWM9:52 amPortland
25h 16m
1 stop
SWF11:08 amNew Windsor Stewart
Jul 3
SWF12:17 pmNew Windsor Stewart
20h 55m
2 stops
PWM9:12 amPortland
$544
Breeze Airways
Aug 8
PWM9:52 amPortland
23h 06m
1 stop
SWF8:58 amNew Windsor Stewart
Aug 15
SWF12:05 pmNew Windsor Stewart
34h 34m
2 stops
PWM10:39 pmPortland
$550

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 May 13, 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

Mon 8/10

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Mon 8/24

5:39 pm-9:19 pm

2 stops27h 40m

$416

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 6/10

11:07 am-8:58 am

1 stop21h 51m

New Windsor Stewart

Sun 6/14

9:38 am-9:12 am

1 stop23h 34m

$430

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 6/5

9:52 am-11:25 am

2 stops25h 33m

New Windsor Stewart

Fri 6/12

9:39 am-9:12 am

1 stop23h 33m

$438
Quickest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 8/8

9:52 am-8:58 am

1 stop23h 06m

New Windsor Stewart

Thu 8/13

10:28 am-10:39 pm

2 stops12h 11m

$492

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 6/29

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Sat 7/4

4:13 pm-2:26 pm

2 stops22h 13m

$533

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 6/11

3:11 pm-8:49 am

2 stops17h 38m

New Windsor Stewart

Sun 6/14

9:38 am-9:12 am

1 stop23h 34m

$536

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

$538

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 6/29

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Fri 7/3

12:17 pm-9:12 am

2 stops20h 55m

$544

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 8/8

9:52 am-8:58 am

1 stop23h 06m

New Windsor Stewart

Sat 8/15

12:05 pm-10:39 pm

2 stops34h 34m

$550

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 6/29

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Thu 7/9

10:28 am-10:39 pm

2 stops12h 11m

$554

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 36% 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

10h 40m

Direct flights

None
The fastest flight from Portland, Maine to New Windsor takes 10h 40m
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. 10h 40m 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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