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Cheap flights from Massachusetts to New York from $85

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to New York departing on 1/9. 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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0 bags

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Find the cheapest flights from Massachusetts to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:27 pm - 10:19 amBOS-SWF
16h 52m1 stop
Multiple Airlines Logo
7:33 pm - 2:38 pmSWF-BOS
19h 05m1 stop
$189Multiple Airlines
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Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
5:27 pm - 10:19 amBOS-SWF
16h 52m1 stop
Multiple Airlines Logo
7:33 pm - 2:38 pmSWF-BOS
19h 05m1 stop
$195Multiple Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
5:27 pm - 10:19 amBOS-SWF
16h 52m1 stop
Multiple Airlines Logo
7:33 pm - 2:38 pmSWF-BOS
19h 05m1 stop
$200Multiple Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
5:27 pm - 10:19 amBOS-SWF
16h 52m1 stop
Multiple Airlines Logo
7:33 pm - 2:38 pmSWF-BOS
19h 05m1 stop
$201Multiple Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
6:22 pm - 11:02 amBOS-SWF
16h 40m1 stop
Multiple Airlines Logo
5:57 pm - 9:08 amSWF-BOS
15h 11m1 stop
$271Multiple Airlines
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Sat, Feb 28 - Sun, Mar 1
Multiple Airlines Logo
8:11 pm - 11:03 amBOS-SWF
14h 52m1 stop
Multiple Airlines Logo
12:27 pm - 11:56 pmSWF-BOS
11h 29m1 stop
$275Multiple Airlines
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Sat, Dec 13 - Mon, Dec 15
Multiple Airlines Logo
8:11 pm - 11:03 amBOS-SWF
14h 52m1 stop
Multiple Airlines Logo
7:30 pm - 10:01 amSWF-BOS
14h 31m1 stop
$277Multiple Airlines
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Sat, Dec 13 - Mon, Dec 15
Multiple Airlines Logo
5:45 am - 11:37 amBOS-SWF
29h 52m1 stop
Multiple Airlines Logo
8:11 pm - 10:01 amSWF-BOS
13h 50m1 stop
$297Multiple Airlines
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Sun, Dec 14 - Fri, Dec 19
Multiple Airlines Logo
8:11 pm - 11:44 amBOS-SWF
15h 33m2 stops
Multiple Airlines Logo
8:11 pm - 10:01 amSWF-BOS
13h 50m1 stop
$320Multiple Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
Allegiant Air Logo
11:42 am - 9:30 amALB-SWF
21h 48m1 stop
Allegiant Air Logo
6:28 pm - 8:56 pmSWF-ALB
26h 28m1 stop
$747Allegiant Air
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Sun, Dec 28 - Sun, Jan 4

Allegiant Air flights from Massachusetts to New Windsor

Our best Allegiant Air deals on Massachusetts to New Windsor flight tickets
Allegiant Air
Feb 15
BOS9:29 amBoston Logan Intl
24h 45m
2 stops
SWF10:14 amNew Windsor Stewart
Feb 19
SWF12:22 pmNew Windsor Stewart
20h 19m
2 stops
BOS8:41 amBoston Logan Intl
$512
Find similar
Allegiant Air
Dec 28
ALB11:42 amAlbany Intl
21h 48m
1 stop
SWF9:30 amNew Windsor Stewart
Jan 4
SWF6:28 pmNew Windsor Stewart
26h 28m
1 stop
ALB8:56 pmAlbany Intl
$747
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 December 3, 2025.
Use the filters below to find and compare flights from Massachusetts to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/12

7:33 pm-2:38 pm

1 stop19h 05m

$189

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/12

7:33 pm-2:38 pm

1 stop19h 05m

$195

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/12

7:33 pm-2:38 pm

1 stop19h 05m

$200

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/12

7:33 pm-2:38 pm

1 stop19h 05m

$201

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 2/28

6:22 pm-11:02 am

1 stop16h 40m

New Windsor Stewart

Sun 3/1

5:57 pm-9:08 am

1 stop15h 11m

$271

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 12/13

8:11 pm-11:03 am

1 stop14h 52m

New Windsor Stewart

Mon 12/15

12:27 pm-11:56 pm

1 stop11h 29m

$275

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 12/13

8:11 pm-11:03 am

1 stop14h 52m

New Windsor Stewart

Mon 12/15

7:30 pm-10:01 am

1 stop14h 31m

$277

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 12/14

5:45 am-11:37 am

1 stop29h 52m

New Windsor Stewart

Fri 12/19

8:11 pm-10:01 am

1 stop13h 50m

$297

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 12/14

8:11 pm-11:44 am

2 stops15h 33m

New Windsor Stewart

Fri 12/19

8:11 pm-10:01 am

1 stop13h 50m

$320

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Sun 12/28

11:42 am-9:30 am

1 stop21h 48m

New Windsor Stewart

Sun 1/4

6:28 pm-8:56 pm

1 stop26h 28m

$747

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Massachusetts 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 Massachusetts to New Windsor Stewart?

Allegiant Air is the most popular carrier operating from Massachusetts to New Windsor Stewart

What airlines fly to New Windsor?

Delta, United Airlines and JetBlue are the top three most popular airlines that fly to New Windsor from Massachusetts according to our data. Delta is the first choice among our users, with 32% 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.

Cheap Massachusetts to New Windsor flight deals and tips

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

Fastest flight time

14h 52m

Direct flights

None
The fastest flight from Massachusetts to New Windsor takes 14h 52m
There are no direct flights from Massachusetts to New Windsor. There are no popular flight routes from Massachusetts to New Windsor.
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  • When did momondo last update prices for flights from Massachusetts to New Windsor Stewart Airport?

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

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

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

    The necessary travel and health documents for your New Windsor Stewart Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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 Massachusetts to New Windsor?

It is quick and easy to find Massachusetts to New Windsor flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to New Windsor that suits you.

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

Yes. momondo allows you to filter the results for Massachusetts to New Windsor flights to just show those with flexible booking policies.

How can momondo help me find flights from Massachusetts to New Windsor?

Once all potential Massachusetts 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 Massachusetts to New Windsor right now. Can momondo alert me if prices change?

Price alerts on flights to New Windsor from Massachusetts are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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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