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Stewart

$97+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$206
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$138
From Boston Logan Intl to New Windsor Stewart
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One-way flight from Boston Logan Intl to New Windsor Stewart
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Highest demand for flights based on searches. 11% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/168:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Mon 10/2011:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Deal found 9/9$206
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/128:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Mon 10/2011:01 amSWF - BOS
1 stop12h 58mMultiple Airlines
Deal found 9/9$250
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Mon 10/611:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Deal found 9/9$275
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/308:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Sun 11/21:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
Deal found 9/11$288
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/169:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Fri 10/1711:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
Deal found 9/9$291
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Mon 11/39:55 amBOS - SWF
1 stop7h 54mMultiple Airlines
Mon 11/1012:01 pmSWF - BOS
1 stop12h 39mMultiple Airlines
Deal found 9/8$327
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/210:00 amBOS - SWF
1 stop6h 55mMultiple Airlines
Fri 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Deal found 9/11$328
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/91:31 pmBOS - SWF
2 stops21h 20mMultiple Airlines
Mon 10/1311:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Deal found 9/10$332

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 September 11, 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 10/16

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Mon 10/20

11:01 am-11:26 am

1 stop24h 25m

$206

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 10/12

8:24 pm-10:11 am

1 stop13h 47m

New Windsor Stewart

Mon 10/20

11:01 am-11:59 pm

1 stop12h 58m

$250

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/30

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Sun 11/2

1:35 pm-8:53 pm

1 stop7h 18m

$288

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/16

9:55 am-4:55 pm

1 stop7h 00m

New Windsor Stewart

Fri 10/17

11:31 am-11:59 pm

1 stop12h 28m

$291

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Mon 11/3

9:55 am-5:49 pm

1 stop7h 54m

New Windsor Stewart

Mon 11/10

12:01 pm-12:40 am

1 stop12h 39m

$327

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/2

10:00 am-4:55 pm

1 stop6h 55m

New Windsor Stewart

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

$328

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/9

1:31 pm-10:51 am

2 stops21h 20m

New Windsor Stewart

Mon 10/13

11:01 am-11:26 am

1 stop24h 25m

$332

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 10/26

9:55 am-4:55 pm

1 stop7h 00m

New Windsor Stewart

Sun 11/2

1:35 pm-8:53 pm

1 stop7h 18m

$362

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/16

8:24 pm-10:41 am

1 stop14h 17m

$112

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 10/12

6:16 am-10:11 am

1 stop27h 55m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 17 results
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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, October is the cheapest month in which you can book a flight from Boston to New Windsor (average of $109). Flying from Boston to New Windsor in December is currently the most expensive (average of $202). 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, October is the cheapest month in which you can book a flight from Boston to New Windsor (average of $109). Flying from Boston to New Windsor in December is currently the most expensive (average of $202). 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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