$151+ Cheap flights from Boston to New Windsor (BOS - SWF)
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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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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
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Cheapest flights from Boston to StewartExplore 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 8, 2026.
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 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.
Sat 10/310:19 am -
1 stop24h 39m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$319
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 10/310:19 am -
1 stop24h 39m
Sat 10/1012:39 pm -
2 stops22h 23m
Deal found 9/5![Multiple Airlines logo]()
$344
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 10/310:19 am -
1 stop24h 39m
Mon 11/2311:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$361
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 10/310:19 am -
1 stop24h 39m
Fri 11/2011:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$363
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 10/212:54 pm -
2 stops22h 45m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$397
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.
Sat 10/1010:19 am -
1 stop24h 44m
Wed 10/1412:39 pm -
2 stops22h 23m
Deal found 9/6![Multiple Airlines logo]()
$405
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.
Sat 10/1010:19 am -
1 stop24h 44m
Thu 10/1510:56 am -
1 stop24h 06m
Deal found 9/4![Multiple Airlines logo]()
$410
Best flights from Boston to StewartDiscover carefully curated flight deals from Boston to Stewart 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 Boston to Stewart 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.
Sat 10/310:19 am -
1 stop24h 39m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$319
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 10/310:19 am -
1 stop24h 39m
Sat 10/1012:39 pm -
2 stops22h 23m
Deal found 9/5![Multiple Airlines logo]()
$344
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 10/310:19 am -
1 stop24h 39m
Mon 11/2311:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$361
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 10/310:19 am -
1 stop24h 39m
Fri 11/2011:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$363
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 10/212:54 pm -
2 stops22h 45m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$397
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.
Sat 10/1010:19 am -
1 stop24h 44m
Wed 10/1412:39 pm -
2 stops22h 23m
Deal found 9/6![Multiple Airlines logo]()
$405
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.
Sat 10/1010:19 am -
1 stop24h 44m
Thu 10/1510:56 am -
1 stop24h 06m
Deal found 9/4![Multiple Airlines logo]()
$410
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 9/1911:36 am -
1 stop22h 40m
Wed 9/2312:39 pm -
2 stops21h 43m
Deal found 9/3![Multiple Airlines logo]()
$502
Last-minute flights from Boston to StewartDiscover last-minute flight deals from Boston to Stewart. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Stewart. Data last updated September 8, 2026 and is based on user searches.
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 10/212:54 pm -
2 stops22h 45m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$397
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 10/310:19 am -
1 stop24h 39m
Sat 11/2112:39 pm -
1 stop19h 51m
Deal found 9/7![Multiple Airlines logo]()
$319
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 10/310:19 am -
1 stop24h 39m
Sat 10/1012:39 pm -
2 stops22h 23m
Deal found 9/5![Multiple Airlines logo]()
$344
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 10/310:19 am -
1 stop24h 39m
Mon 11/2311:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$361
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 10/310:19 am -
1 stop24h 39m
Fri 11/2011:29 am -
1 stop22h 42m
Deal found 9/7![Multiple Airlines logo]()
$363
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.
Sat 10/1010:19 am -
1 stop24h 44m
Wed 10/1412:39 pm -
2 stops22h 23m
Deal found 9/6![Multiple Airlines logo]()
$405
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.
Sat 10/1010:19 am -
1 stop24h 44m
Thu 10/1510:56 am -
1 stop24h 06m
Deal found 9/4![Multiple Airlines logo]()
$410
One-way flights from Boston to StewartSearch for one-way flight options from Boston to Stewart. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
Search for one-way flight options from Boston to Stewart. 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 9/4. 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 11/412:39 pm -
2 stops21h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$151
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 10/1710:19 am -
1 stop24h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Allegiant Air logo]()
$156
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 10/2112:57 pm -
2 stops20h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$167
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 10/2410:19 am -
1 stop24h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Allegiant Air logo]()
$171
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.
Tue 11/1012:15 pm -
3 stops23h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$178
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 10/1010:19 am -
1 stop24h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Allegiant Air logo]()
$187
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 10/212:54 pm -
3 stops46h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$190
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 9/3012:54 pm -
2 stops20h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$196
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.
Tue 10/2012:57 pm -
2 stops44h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$198
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.
Tue 10/2711:12 am -
3 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$205
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (Kiwi.com) |
One-way from | $151 (Kiwi.com) |
Popular in | August |
Cheapest in | November |
Average price | $274 |
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 7,457,451 searches. Data last updated September 8, 2026.
Use the filters below to find and compare flights from Boston to New Windsor that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Fri 10/2
12:54 pm-10:58 am
3 stops46h 04m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Quickest round-trip
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Wed 10/21
12:57 pm-10:16 am
2 stops21h 19m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$233
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Wed 9/23
12:54 pm-10:16 am
2 stops21h 22m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$236
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Thu 10/29
12:34 pm-11:39 am
3 stops47h 05m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$242
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Thu 9/24
11:17 am-10:08 am
2 stops22h 51m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$247
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Fri 12/11
11:57 am-11:39 am
2 stops23h 42m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$255
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Sat 9/19
12:54 pm-10:23 am
2 stops21h 29m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Fri 10/16
11:47 am-11:39 am
2 stops23h 52m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$275
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Tue 11/24
11:06 am-10:26 am
1 stop23h 20m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
BostonNew Windsor
BOS Boston Logan Intl - SWF New Windsor Stewart
BOSSWF
Boston Logan Intl
Sun 12/13
9:35 am-11:36 am
3 stops26h 01m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$299
Showing 1-10 of 18 resultsSorted by cheapest first
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 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 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.
BOS-SWF
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 Boston to Stewart. 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 New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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