HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$88+ Cheap flights from Massachusetts to New Windsor (SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Massachusetts to Stewart

Cheapest flights from Massachusetts to Stewart
Explore the most affordable flight options available from Massachusetts to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:56 amBOS - SWF
2 stops10h 25mMultiple Airlines
Mon 12/228:25 pmSWF - BOS
1 stop27h 32mMultiple Airlines
Deal found 12/16$687
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:56 amBOS - SWF
2 stops10h 25mMultiple Airlines
Sun 12/2111:43 amSWF - BOS
1 stop22h 18mMultiple Airlines
Deal found 12/17$802
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:30 pmBDL - SWF
1 stop17h 14mMultiple Airlines
Sun 12/286:28 pmSWF - BDL
1 stop18h 17mMultiple Airlines
Deal found 12/16$885
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Wed 12/2410:40 amSWF - BOS
2 stops25h 15mMultiple Airlines
Deal found 12/16$1,117
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:05 amBDL - SWF
1 stop9h 51mMultiple Airlines
Sun 12/2811:43 amSWF - BDL
2 stops10h 40mMultiple Airlines
Deal found 12/17$1,237

Find flight deals from Massachusetts to Stewart

Keep the following information in mind while searching for Massachusetts to Stewart flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$173
(Mytrip)

One-way from

$88
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$192
Provider with most accurate pricing for Boston Logan Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-New York (NYC) flights.
Search Deals
From Massachusetts to New Windsor Stewart
Search Deals
One-way flight from Massachusetts to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Stewart 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, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Massachusetts to New Windsor that are best for you.

Fly from

Massachusetts

Fly to

Stewart

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

11:09 am-11:57 pm

1 stop12h 48m

$173

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Sun 1/11

12:13 pm-11:19 pm

1 stop11h 06m

$293

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 3/4

6:10 pm-9:19 am

1 stop15h 09m

New Windsor Stewart

Sun 3/8

5:56 pm-9:08 am

1 stop15h 12m

$320

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 3/11

6:10 pm-9:19 am

1 stop15h 09m

New Windsor Stewart

Sun 3/15

12:29 pm-12:07 am

1 stop11h 38m

$401

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 1/4

12:22 pm-11:44 am

2 stops23h 22m

New Windsor Stewart

Sun 1/18

12:13 pm-11:19 pm

1 stop11h 06m

$442

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/29

5:27 pm-10:19 am

1 stop16h 52m

$102

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 1/11

5:27 pm-10:19 am

1 stop16h 52m

$108

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 1/14

3:43 pm-11:33 am

1 stop19h 50m

$125

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 5/20

5:40 am-9:38 am

1 stop27h 58m

$126

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 1/31

6:39 pm-5:59 pm

1 stop23h 20m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 20 results
1
2

Best time to book a flight from Massachusetts to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to New Windsor

What is the cheapest month to book a flight from Massachusetts to New Windsor?

Currently, December is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $86). Flying from Massachusetts to New Windsor in February is currently the most expensive (average of $135). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Massachusetts?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Massachusetts.

  • What are the most popular routes from Massachusetts to New Windsor?

    Most travelers choose Boston Logan Intl - New Windsor Stewart, Albany Intl - New Windsor Stewart or Hartford Bradley Intl - New Windsor Stewart when deciding on the best route from Massachusetts to New Windsor.

  • Can I find deals for flights from Massachusetts to Stewart that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Stewart.

  • Can I find deals for business class flights from Massachusetts to Stewart?

    Yes. Cheapflights offers flight deals from Massachusetts to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to New Windsor?

    Currently, December is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $86). Flying from Massachusetts to New Windsor in February is currently the most expensive (average of $135). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
Los Angeles to Newark flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Newark flights
O'Hare Intl to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Hobby to LaGuardia flights
Atlanta to LaGuardia flights
Atlanta to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Los Angeles to LaGuardia flights
Hobby to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
San Francisco to Newark flights
Fort Lauderdale to LaGuardia flights
Hobby to Newark flights
Miami to LaGuardia flights
Miami to Newark flights
Tampa to John F Kennedy Intl flights
Orlando to Newark flights
Seattle to John F Kennedy Intl flights
Charlotte to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
West Palm Beach to Newark flights
O'Hare Intl to LaGuardia flights
Atlanta to Newark flights
George Bush Intcntl to Newark flights
O'Hare Intl to Newark flights
Austin to John F Kennedy Intl flights
Tampa to LaGuardia flights
Orlando to LaGuardia flights
San Francisco to LaGuardia flights
George Bush Intcntl to LaGuardia flights
Seattle to Newark flights
Raleigh to LaGuardia flights
Raleigh to John F Kennedy Intl flights
Charlotte to Newark flights
Tampa to Newark flights
Sky Harbor Intl to John F Kennedy Intl flights
Detroit to John F Kennedy Intl flights
San Diego to John F Kennedy Intl flights
Denver to LaGuardia flights
Love Field to LaGuardia flights
West Palm Beach to John F Kennedy Intl flights
Burbank to LaGuardia flights
Ontario to John F Kennedy Intl flights
Austin to Newark flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.