HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$155+ Cheap flights from New Windsor to Boston (SWF - BOS)

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Boston 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 Stewart to Boston

Cheapest flights from Stewart to Boston
Explore the most affordable flight options available from Stewart to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/3. 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 9/410:36 am
SWF
-
BOS
2 stops25h 09m
Multiple Airlines
Thu 9/1711:05 am
BOS
-
SWF
1 stop23h 11m
Multiple Airlines
Deal found 5/3$425
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 8/910:28 am
SWF
-
BOS
2 stops14h 55m
Multiple Airlines
Wed 8/1211:05 am
BOS
-
SWF
1 stop21h 53m
Multiple Airlines
Deal found 5/5$455
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 8/210:28 am
SWF
-
BOS
2 stops14h 55m
Multiple Airlines
Wed 8/511:05 am
BOS
-
SWF
1 stop21h 53m
Multiple Airlines
Deal found 5/3$458
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/109:38 am
SWF
-
BOS
2 stops23h 31m
Multiple Airlines
Sun 5/1710:07 am
BOS
-
SWF
1 stop24h 48m
Multiple Airlines
Deal found 5/3$606
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/311:45 am
SWF
-
BOS
2 stops21h 24m
Multiple Airlines
Wed 5/610:07 am
BOS
-
SWF
1 stop22h 51m
Multiple Airlines
Deal found 5/2$908
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/612:05 pm
SWF
-
BOS
2 stops21h 07m
Multiple Airlines
Wed 5/1310:07 am
BOS
-
SWF
1 stop22h 51m
Multiple Airlines
Deal found 5/5$1,215

Find flight deals from Stewart to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Boston (BOS). 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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$425
(Kiwi.com)

One-way from

$155
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$221
Provider with most accurate pricing for New Windsor Stewart-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Boston Logan Intl flights.
Search Deals
From New Windsor Stewart to Boston Logan Intl
Search Deals
One-way flight from New Windsor Stewart to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Boston 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 May 7, 2026.
Use the filters below to find and compare flights from New Windsor to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 9/4

10:36 am-11:45 am

2 stops25h 09m

Boston Logan Intl

Thu 9/17

11:05 am-10:16 am

1 stop23h 11m

$425
Quickest round-trip

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 8/9

10:28 am-1:23 am

2 stops14h 55m

Boston Logan Intl

Wed 8/12

11:05 am-8:58 am

1 stop21h 53m

$455

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 8/2

10:28 am-1:23 am

2 stops14h 55m

Boston Logan Intl

Wed 8/5

11:05 am-8:58 am

1 stop21h 53m

$458
Cheapest one-way

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Wed 5/27

12:05 pm-7:49 am

2 stops43h 44m

$166

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 6/1

9:41 am-7:49 am

2 stops46h 08m

$177

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 7/30

11:45 am-9:05 am

2 stops45h 20m

$232

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 6/12

12:17 pm-1:27 am

3 stops37h 10m

$234
Quickest one-way

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 7/26

10:28 am-1:23 am

2 stops14h 55m

$235

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 7/13

5:49 pm-1:23 am

3 stops31h 34m

$240

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 6/15

5:55 pm-7:52 am

3 stops37h 57m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Compare providers for flights from Stewart to Boston

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 Stewart to Boston in May.
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 New Windsor-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Boston 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 New Windsor-Boston 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 Stewart to Boston

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

Related info for your journey

Find useful and relevant information for your journey from Stewart to Boston. 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 Stewart to Boston that include hotel bookings?

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

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

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

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

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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

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.

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.
Site
©2026 Cheapflights