$178+ Cheap flights from New Windsor to Boston (SWF - BOS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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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
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Cheapest flights from Stewart to BostonExplore 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 September 8, 2026.
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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/3012:39 pm -
2 stops21h 43m
Sat 10/310:19 am -
1 stop24h 39m
Deal found 9/7![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/312:39 pm -
2 stops22h 19m
Sat 10/1010:19 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1912:39 pm -
2 stops22h 19m
Sat 10/1710:19 am -
1 stop24h 44m
Deal found 9/7![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/810:56 am -
1 stop24h 06m
Thu 10/1511:47 am -
2 stops47h 52m
Deal found 9/6![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/1612:39 pm -
2 stops21h 43m
Sat 9/1911:36 am -
1 stop22h 40m
Deal found 9/3![Multiple Airlines logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/2010:56 am -
1 stop23h 55m
Thu 9/2411:17 am -
2 stops48h 22m
Deal found 9/5![Multiple Airlines logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Sat 9/1212:54 pm -
2 stops21h 29m
Deal found 9/3![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Fri 9/1112:54 pm -
2 stops22h 45m
Deal found 9/3![Multiple Airlines logo]()
$590
Best flights from Stewart to BostonDiscover carefully curated flight deals from Stewart to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 8, 2026.
Discover carefully curated flight deals from Stewart to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/3012:39 pm -
2 stops21h 43m
Sat 10/310:19 am -
1 stop24h 39m
Deal found 9/7![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/312:39 pm -
2 stops22h 19m
Sat 10/1010:19 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1912:39 pm -
2 stops22h 19m
Sat 10/1710:19 am -
1 stop24h 44m
Deal found 9/7![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/810:56 am -
1 stop24h 06m
Thu 10/1511:47 am -
2 stops47h 52m
Deal found 9/6![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/2010:56 am -
1 stop23h 55m
Thu 9/2411:17 am -
2 stops48h 22m
Deal found 9/5![Multiple Airlines logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Sat 9/1212:54 pm -
2 stops21h 29m
Deal found 9/3![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Fri 9/1112:54 pm -
2 stops22h 45m
Deal found 9/3![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/1111:06 am -
1 stop23h 45m
Sun 9/1311:53 am -
2 stops23h 43m
Deal found 9/3![Multiple Airlines logo]()
$640
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/1310:56 am -
1 stop23h 55m
Wed 9/1612:54 pm -
2 stops21h 22m
Deal found 9/4![Multiple Airlines logo]()
$653
Last-minute flights from Stewart to BostonDiscover last-minute flight deals from Stewart to Boston. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Boston. Data last updated September 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Sat 9/1212:54 pm -
2 stops21h 29m
Deal found 9/3![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/1010:56 am -
1 stop23h 55m
Fri 9/1112:54 pm -
2 stops22h 45m
Deal found 9/3![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/1612:39 pm -
2 stops21h 43m
Sat 9/1911:36 am -
1 stop22h 40m
Deal found 9/3![Multiple Airlines logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1912:39 pm -
2 stops22h 19m
Sat 10/1710:19 am -
1 stop24h 44m
Deal found 9/7![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/2010:56 am -
1 stop23h 55m
Thu 9/2411:17 am -
2 stops48h 22m
Deal found 9/5![Multiple Airlines logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/3012:39 pm -
2 stops21h 43m
Sat 10/310:19 am -
1 stop24h 39m
Deal found 9/7![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/312:39 pm -
2 stops22h 19m
Sat 10/1010:19 am -
1 stop24h 44m
Deal found 9/5![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/810:56 am -
1 stop24h 06m
Thu 10/1511:47 am -
2 stops47h 52m
Deal found 9/6![Multiple Airlines logo]()
$529
One-way flights from Stewart to BostonSearch for one-way flight options from Stewart to Boston. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
Search for one-way flight options from Stewart to Boston. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/3012:39 pm -
2 stops21h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/28:48 pm -
1 stop13h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 11/812:00 pm -
2 stops21h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Allegiant Air logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/267:01 pm -
2 stops40h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/2312:39 pm -
2 stops21h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Thu 10/1510:18 am -
3 stops48h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 10/312:39 pm -
2 stops22h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$204
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $322 (Kiwi.com) |
One-way from | $178 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $262 |
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 7,457,451 searches. Data last updated September 8, 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
Cheapest round-trip
Quickest round-trip
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sun 11/8
12:00 pm-9:41 am
2 stops21h 41m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sun 10/18
11:53 am-11:52 am
2 stops47h 59m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Thu 10/1
7:36 pm-9:29 am
2 stops37h 53m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Fri 9/11
11:06 am-10:51 am
1 stop23h 45m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$242
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sun 10/4
10:56 am-10:51 am
1 stop23h 55m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$253
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sat 9/26
12:39 pm-10:58 am
2 stops22h 19m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Thu 9/24
10:56 am-10:51 am
1 stop23h 55m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Mon 9/28
12:16 pm-12:09 pm
3 stops47h 53m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Thu 10/8
10:56 am-11:02 am
1 stop24h 06m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$301
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Wed 9/30
12:39 pm-10:22 am
2 stops21h 43m
Boston Logan Intl
Sat 10/3
10:19 am-10:58 am
1 stop24h 39m
$322
Showing 1-10 of 18 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
SWF-BOS
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Seekonk
Dedham
Cranston
Warwick
Pawtucket
Peabody
Auburn
Revere
York Beach
Londonderry
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
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