HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$85+ Cheap flights from Boston to New Windsor (BOS - 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston 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 Boston to Stewart

Cheapest flights from Boston to Stewart
Explore the most affordable flight options available from Boston to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 3, 2025.

This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:08 amBOS - SWF
2 stops24h 29mMultiple Airlines
Mon 12/1512:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Deal found 11/30$230
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Sat 12/138:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Mon 12/1512:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Deal found 12/2$275
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Thu 12/118:11 pmBOS - SWF
2 stops15h 33mMultiple Airlines
Fri 12/127:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Deal found 12/1$276
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/145:45 amBOS - SWF
1 stop29h 52mMultiple Airlines
Fri 12/198:11 pmSWF - BOS
1 stop13h 50mMultiple Airlines
Deal found 12/2$297
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/78:11 pmBOS - SWF
1 stop22h 29mMultiple Airlines
Wed 12/245:34 pmSWF - BOS
1 stop16h 18mMultiple Airlines
Deal found 12/2$339
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/195:45 amBOS - SWF
1 stop12h 21mMultiple Airlines
Fri 12/198:11 pmSWF - BOS
1 stop13h 50mMultiple Airlines
Deal found 12/2$398
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/1710:56 amBOS - SWF
1 stop24h 07mMultiple Airlines
Sun 12/2111:43 amSWF - BOS
1 stop22h 18mMultiple Airlines
Deal found 12/1$434
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Sat 12/138:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Thu 12/1811:43 amSWF - BOS
2 stops12h 14mMultiple Airlines
Deal found 12/2$440

Find flight deals from Boston to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$85
(Mytrip)

Popular in

February

Cheapest in

December

Average price

$167
Provider with most accurate pricing for Boston Logan Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-New Windsor Stewart flights.
Search Deals
From Boston Logan Intl to New Windsor Stewart
Search Deals
One-way flight from Boston Logan Intl to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 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 Boston 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 3, 2025.
Use the filters below to find and compare flights from Boston to New Windsor that are best for you.

Fly from

Boston

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

7:33 pm-2:38 pm

1 stop19h 05m

$189

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

Fri 1/16

7:00 am-6:43 pm

1 stop11h 43m

New Windsor Stewart

Mon 1/19

11:09 am-11:57 pm

1 stop12h 48m

$388

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 12/14

11:08 am-11:37 am

2 stops24h 29m

New Windsor Stewart

Fri 12/19

6:56 pm-11:34 am

2 stops16h 38m

$392

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 12/19

5:45 am-6:06 pm

1 stop12h 21m

New Windsor Stewart

Fri 12/19

8:11 pm-10:01 am

1 stop13h 50m

$398

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 12/17

10:56 am-11:03 am

1 stop24h 07m

New Windsor Stewart

Sun 12/21

11:43 am-10:01 am

1 stop22h 18m

$434

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 12/13

8:11 pm-11:03 am

1 stop14h 52m

New Windsor Stewart

Thu 12/18

11:43 am-11:57 pm

2 stops12h 14m

$440

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 1/28

6:39 pm-5:59 pm

1 stop23h 20m

$99

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/29

3:43 pm-11:31 am

2 stops19h 48m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 15 results
1
2

Compare providers for flights from Boston to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Stewart in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Boston-New Windsor flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Boston-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-New Windsor flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Boston 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 Boston to New Windsor

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

Currently, August is the cheapest month in which you can book a flight from Boston to New Windsor (average of $57). Flying from Boston 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 Boston to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston 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 Boston to New Windsor?

    Currently, August is the cheapest month in which you can book a flight from Boston to New Windsor (average of $57). Flying from Boston 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 Boston to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Boston to LaGuardia flights
Boston to Newark flights
Boston to John F Kennedy Intl flights
Boston to Islip flights
Boston to Buffalo flights
Boston to Rochester flights
Boston to Syracuse flights
Hartford to Buffalo flights
Hartford to John F Kennedy Intl flights
Albany to John F Kennedy Intl flights
Hartford to Newark flights
Worcester to John F Kennedy Intl flights
Boston to White Plains flights
Albany to LaGuardia flights
Hyannis to John F Kennedy Intl flights
Boston to Ithaca flights
Hartford to LaGuardia flights
Boston to Albany flights
West Tisbury to John F Kennedy Intl flights
Hartford to Syracuse flights
Albany to Newark flights
Worcester to Newark flights
Hartford to Rochester flights
Albany to Stewart flights
Albany to Buffalo flights
Boston to Saranac Lake flights
Hartford to White Plains flights
Nantucket to John F Kennedy Intl flights
Boston to Binghamton flights
Boston to Rutland flights
Albany to Rochester flights
Boston to Niagara Falls flights
Boston to Massena flights
Albany to White Plains flights
Worcester to Buffalo flights
Hartford to Stewart flights
Boston to Elmira flights
Hartford to Elmira flights
Albany to Islip flights
Nantucket to LaGuardia flights
Hyannis to LaGuardia flights
Provincetown to Newark flights
Provincetown to LaGuardia flights
Hyannis to Newark flights
Nantucket to White Plains flights
New Bedford to Rochester flights
New Bedford to Buffalo flights
Nantucket 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.