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Stewart

$104+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/46:10 pm
BOS
-
SWF
1 stop15h 09m
Multiple Airlines
Fri 3/2012:11 pm
SWF
-
BOS
2 stops9h 22m
Multiple Airlines
Deal found 1/26$301
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 1/315:27 pm
BOS
-
SWF
2 stops18h 06m
Multiple Airlines
Sun 2/16:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/24$383
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/199:57 am
BOS
-
SWF
1 stop7h 15m
Multiple Airlines
Sat 2/218:24 pm
SWF
-
BOS
2 stops15h 11m
Multiple Airlines
Deal found 1/26$497
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/129:57 am
BOS
-
SWF
1 stop7h 15m
Multiple Airlines
Fri 2/1311:04 am
SWF
-
BOS
1 stop10h 57m
Multiple Airlines
Deal found 1/25$527

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(Kiwi.com)

One-way from

$104
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$237
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. 6% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 26, 2026.
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

Wed 3/4

6:10 pm-9:19 am

1 stop15h 09m

New Windsor Stewart

Fri 3/20

12:11 pm-9:33 pm

2 stops9h 22m

$301

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/19

9:57 am-5:12 pm

1 stop7h 15m

New Windsor Stewart

Sat 2/21

8:24 pm-11:35 am

2 stops15h 11m

$497

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/12

9:57 am-5:12 pm

1 stop7h 15m

New Windsor Stewart

Fri 2/13

11:04 am-10:01 pm

1 stop10h 57m

$527

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 2/11

6:00 am-10:52 am

2 stops28h 52m

$122

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/5

6:00 am-10:19 am

2 stops28h 19m

$135

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 2/8

5:34 am-10:19 am

1 stop28h 45m

$142

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 2/1

5:23 pm-10:19 am

1 stop16h 56m

$142

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/19

9:57 am-5:12 pm

1 stop7h 15m

$150

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 2/7

6:39 pm-5:59 pm

1 stop23h 20m

$159

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 3/29

4:23 pm-8:57 am

1 stop16h 34m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-New Windsor flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 April is currently the most expensive (average of $109). 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 April is currently the most expensive (average of $109). 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

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