$142+ Cheap flights from Westchester County to Boston (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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Apr 6 — Apr 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Westchester County 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 Westchester County to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Westchester County to BostonExplore the most affordable flight options available from Westchester County to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 7, 2026.
Explore the most affordable flight options available from Westchester County to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 6/612:00 pm
HPN
- BOS
1 stop22h 47m
Multiple Airlines
Tue 6/910:12 am
BOS
- HPN
1 stop25h 05m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:30 am
HPN
- BOS
1 stop3h 45m
American Airlines
Sat 4/2512:01 pm
BOS
- HPN
2 stops22h 29m
American Airlines
Deal found 3/5![American Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Mon 3/309:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 3/3112:36 pm
BOS
- HPN
2 stops24h 11m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$304
This Gotogate deal was found by Cheapflights users on 3/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Wed 3/48:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/2![Cape Air logo]()
$305
This Expedia deal was found by Cheapflights users on 3/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$324
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Thu 3/55:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/2![Cape Air logo]()
$330
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:23 am
HPN
- BOS
1 stop22h 47m
Cape Air
Tue 3/108:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/2![Cape Air logo]()
$335
This Booking.com deal was found by Cheapflights users on 3/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:16 pm
HPN
- BOS
1 stop22h 02m
Cape Air
Thu 3/125:40 pm
BOS
- HPN
1 stop15h 12m
Cape Air
Deal found 3/5![Cape Air logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/135:16 pm
HPN
- BOS
1 stop14h 54m
Cape Air
Sun 3/155:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/3![Cape Air logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Fri 4/249:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Mon 4/2710:08 am
BOS
- HPN
2 stops25h 20m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/219:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Wed 3/259:45 am
BOS
- HPN
2 stops25h 43m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$345
Best flights from Westchester County to BostonDiscover carefully curated flight deals from Westchester County to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 7, 2026.
Discover carefully curated flight deals from Westchester County to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 7, 2026.
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Sat 3/2112:39 pm
BOS
- HPN
1 stop20h 13m
Cape Air
Deal found 3/2![Cape Air logo]()
$335
This Priceline deal was found by Cheapflights users on 3/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Mon 4/273:00 pm
BOS
- HPN
1 stop7h 36m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$361
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Mon 3/308:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/2![Cape Air logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Fri 3/209:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Sun 3/225:49 pm
BOS
- HPN
2 stops41h 39m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$388
This Cape Air deal was found by Cheapflights users on 3/4. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:16 pm
HPN
- BOS
1 stop23h 54m
Cape Air
Fri 3/278:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/4![Cape Air logo]()
$355
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Mon 4/612:39 pm
BOS
- HPN
1 stop4h 07m
Cape Air
Deal found 3/2![Cape Air logo]()
$365
This Cape Air deal was found by Cheapflights users on 3/6. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:16 pm
HPN
- BOS
1 stop18h 42m
Cape Air
Sun 3/228:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/6![Cape Air logo]()
$365
This Cape Air deal was found by Cheapflights users on 3/3. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Sun 3/222:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/3![Cape Air logo]()
$375
This Cape Air deal was found by Cheapflights users on 3/4. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:23 am
HPN
- BOS
1 stop22h 47m
Cape Air
Wed 4/12:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/4![Cape Air logo]()
$385
This Cape Air deal was found by Cheapflights users on 3/5. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Sat 4/255:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/5![Cape Air logo]()
$390
This Cape Air deal was found by Cheapflights users on 3/6. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Wed 4/82:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/6![Cape Air logo]()
$390
This Cape Air deal was found by Cheapflights users on 3/6. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Sun 4/262:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/6![Cape Air logo]()
$395
Last-minute flights from Westchester County to BostonDiscover last-minute flight deals from Westchester County to Boston. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Boston. Data last updated March 7, 2026 and is based on user searches.
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Thu 3/55:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/2![Cape Air logo]()
$330
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:23 am
HPN
- BOS
1 stop5h 55m
Cape Air
Sun 3/85:40 pm
BOS
- HPN
1 stop15h 12m
Cape Air
Deal found 3/2![Cape Air logo]()
$335
This Cape Air deal was found by Cheapflights users on 3/3. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Mon 3/92:24 pm
BOS
- HPN
1 stop18h 28m
Cape Air
Deal found 3/3![Cape Air logo]()
$355
This Booking.com deal was found by Cheapflights users on 3/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:16 pm
HPN
- BOS
1 stop22h 02m
Cape Air
Thu 3/125:40 pm
BOS
- HPN
1 stop15h 12m
Cape Air
Deal found 3/5![Cape Air logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/135:16 pm
HPN
- BOS
1 stop14h 54m
Cape Air
Sun 3/155:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/3![Cape Air logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/199:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Mon 3/239:45 am
BOS
- HPN
2 stops25h 43m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/219:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Wed 3/259:45 am
BOS
- HPN
2 stops25h 43m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$345
This Cape Air deal was found by Cheapflights users on 3/3. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Fri 3/272:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/3![Cape Air logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Mon 3/309:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 3/3112:36 pm
BOS
- HPN
2 stops24h 11m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Fri 4/249:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Mon 4/2710:08 am
BOS
- HPN
2 stops25h 20m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 3/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:30 am
HPN
- BOS
1 stop3h 45m
American Airlines
Sat 4/2512:01 pm
BOS
- HPN
2 stops22h 29m
American Airlines
Deal found 3/5![American Airlines logo]()
$222
This Expedia deal was found by Cheapflights users on 3/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$324
One-way flights from Westchester County to BostonSearch for one-way flight options from Westchester County to Boston. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
Search for one-way flight options from Westchester County to Boston. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Priceline deal was found by Cheapflights users on 3/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2110:48 am
HPN
- BOS
1 stop11h 58m
JetBlue
Deal found 3/3![JetBlue logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Tue 7/211:29 pm
HPN
- BOS
1 stop21h 18m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/181:27 pm
HPN
- BOS
1 stop22h 13m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$159
This Gotogate deal was found by Cheapflights users on 3/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/6![Cape Air logo]()
$169
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/155:16 pm
HPN
- BOS
1 stop23h 54m
Cape Air
Deal found 3/2![Cape Air logo]()
$170
This Cape Air deal was found by Cheapflights users on 3/2. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:16 pm
HPN
- BOS
1 stop23h 54m
Cape Air
Deal found 3/2![Cape Air logo]()
$180
This Booking.com deal was found by Cheapflights users on 3/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/2![Cape Air logo]()
$181
This JetBlue deal was found by Cheapflights users on 3/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:29 am
HPN
- BOS
1 stop6h 41m
JetBlue
Deal found 3/5![JetBlue logo]()
$182
This Cape Air deal was found by Cheapflights users on 3/4. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Deal found 3/4![Cape Air logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/2112:08 pm
HPN
- BOS
3 stops13h 23m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$199
This Cape Air deal was found by Cheapflights users on 3/4. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:23 am
HPN
- BOS
1 stop26h 35m
Cape Air
Deal found 3/4![Cape Air logo]()
$200
Find flight deals from Westchester County to Boston
Keep the following information in mind while searching for Westchester County to Boston flight deals. Data was last updated March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $208 (Kiwi.com) |
One-way from | $142 (Priceline) |
Popular in | February |
Cheapest in | November |
Average price | $254 |
Cheapflights Fare Finder
Customize your flight search to find flights from Westchester County 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 March 7, 2026.
Use the filters below to find and compare flights from Westchester County to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Tue 3/17
9:23 am-11:58 am
1 stop26h 35m
Boston Logan Intl
Sat 3/21
12:39 pm-8:52 am
1 stop20h 13m
$335
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Fri 3/27
9:23 am-11:58 am
1 stop26h 35m
Boston Logan Intl
Mon 3/30
8:48 am-4:46 pm
1 stop7h 58m
$355
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Wed 3/25
5:16 pm-5:10 pm
1 stop23h 54m
Boston Logan Intl
Fri 3/27
8:48 am-4:46 pm
1 stop7h 58m
$355
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Fri 4/24
9:23 am-5:10 pm
1 stop7h 47m
Boston Logan Intl
Mon 4/27
3:00 pm-10:36 pm
1 stop7h 36m
$361
Quickest round-trip
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Mon 3/30
9:23 am-5:10 pm
1 stop7h 47m
Boston Logan Intl
Mon 4/6
12:39 pm-4:46 pm
1 stop4h 07m
$365
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Fri 3/20
5:16 pm-11:58 am
1 stop18h 42m
Boston Logan Intl
Sun 3/22
8:48 am-4:46 pm
1 stop7h 58m
$365
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Wed 3/18
9:23 am-3:18 pm
1 stop5h 55m
Boston Logan Intl
Sun 3/22
2:24 pm-4:46 pm
1 stop26h 22m
$375
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Fri 3/27
9:23 am-8:10 am
1 stop22h 47m
Boston Logan Intl
Wed 4/1
2:24 pm-4:46 pm
1 stop26h 22m
$385
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Fri 3/20
9:23 am-3:18 pm
1 stop5h 55m
Boston Logan Intl
Sun 3/22
5:49 pm-11:28 am
2 stops41h 39m
$388
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sat 4/25
9:23 am-3:18 pm
1 stop5h 55m
Boston Logan Intl
Sat 4/25
5:40 pm-4:46 pm
1 stop23h 06m
$390
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Westchester County to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Westchester County with our price prediction graph.
HPN-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.
Cheapflights Insights
Everything you need to know about your flight from Westchester County to Boston
zzREU-BOS
HPN-BOS
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Westchester County 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 locationsMedford
Cambridge
Concord
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Lincoln
Smithfield
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Lowell
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.
Alternative routes
Boston flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights