$96+ Cheap flights from Westchester County to Maryland
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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BWI
Mar 6 — Mar 131
1 adult, Economy
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Cheapest flights from Westchester County to MarylandExplore the most affordable flight options available from Westchester County to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Westchester County to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/181:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Sun 2/225:51 pm
PHL
- HPN
2 stops41h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$259
This Priceline deal was found by Cheapflights users on 2/3. 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 4/1410:48 am
HPN
- DCA
1 stop8h 12m
JetBlue
Wed 4/152:45 pm
DCA
- HPN
1 stop7h 51m
JetBlue
Deal found 2/3![JetBlue logo]()
$274
This JetBlue deal was found by Cheapflights users on 2/1. 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 3/103:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Wed 3/113:59 pm
DCA
- HPN
1 stop6h 46m
JetBlue
Deal found 2/1![JetBlue logo]()
$329
This Priceline deal was found by Cheapflights users on 2/3. 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.
Fri 5/292:29 pm
HPN
- DCA
1 stop6h 31m
JetBlue
Mon 6/17:59 am
DCA
- HPN
1 stop6h 58m
JetBlue
Deal found 2/3![JetBlue logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/251:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Fri 2/278:15 am
PHL
- HPN
2 stops12h 44m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/58:00 am
HPN
- IAD
1 stop28h 42m
Multiple Airlines
Thu 3/126:30 am
IAD
- HPN
2 stops14h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$338
This JetBlue deal was found by Cheapflights users on 2/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:00 pm
HPN
- DCA
1 stop9h 31m
JetBlue
Mon 2/93:55 pm
DCA
- HPN
1 stop6h 35m
JetBlue
Deal found 2/2![JetBlue logo]()
$355
This Expedia deal was found by Cheapflights users on 2/3. 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.
Sat 2/283:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Thu 3/59:00 am
DCA
- HPN
1 stop12h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$366
This Expedia deal was found by Cheapflights users on 2/3. 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.
Mon 3/238:35 pm
HPN
- DCA
2 stops19h 43m
JetBlue
Wed 3/257:00 am
DCA
- HPN
1 stop7h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$368
This JetBlue deal was found by Cheapflights users on 2/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1710:48 am
HPN
- DCA
1 stop8h 12m
JetBlue
Tue 4/2111:00 am
DCA
- HPN
1 stop8h 25m
JetBlue
Deal found 2/2![JetBlue logo]()
$374
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2111:29 am
HPN
- DCA
Nonstop1h 20m
American Airlines
Sun 3/229:40 am
DCA
- HPN
Nonstop1h 19m
American Airlines
Deal found 2/3![American Airlines logo]()
$380
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Mon 3/93:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Tue 3/1012:15 pm
DCA
- HPN
1 stop9h 15m
JetBlue
Deal found 2/1![JetBlue logo]()
$381
Best flights from Westchester County to MarylandDiscover carefully curated flight deals from Westchester County to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Westchester County to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/181:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Sun 2/225:51 pm
PHL
- HPN
2 stops41h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$259
This Priceline deal was found by Cheapflights users on 2/3. 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 4/1410:48 am
HPN
- DCA
1 stop8h 12m
JetBlue
Wed 4/152:45 pm
DCA
- HPN
1 stop7h 51m
JetBlue
Deal found 2/3![JetBlue logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:47 am
HPN
- DCA
1 stop25h 32m
American Airlines
Sun 3/151:05 pm
DCA
- HPN
Nonstop1h 25m
American Airlines
Deal found 2/3![American Airlines logo]()
$385
This JetBlue deal was found by Cheapflights users on 2/1. 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 3/103:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Wed 3/113:59 pm
DCA
- HPN
1 stop6h 46m
JetBlue
Deal found 2/1![JetBlue logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/251:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Fri 2/278:15 am
PHL
- HPN
2 stops12h 44m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$334
This Priceline deal was found by Cheapflights users on 2/3. 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.
Fri 5/292:29 pm
HPN
- DCA
1 stop6h 31m
JetBlue
Mon 6/17:59 am
DCA
- HPN
1 stop6h 58m
JetBlue
Deal found 2/3![JetBlue logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/58:00 am
HPN
- IAD
1 stop28h 42m
Multiple Airlines
Thu 3/126:30 am
IAD
- HPN
2 stops14h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2110:05 am
HPN
- DCA
1 stop23h 14m
American Airlines
Sun 3/221:05 pm
DCA
- HPN
Nonstop1h 25m
American Airlines
Deal found 2/2![American Airlines logo]()
$385
This KAYAK deal was found by Cheapflights users on 2/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:56 pm
HPN
- BWI
1 stop9h 06m
Delta
Mon 2/164:45 pm
BWI
- HPN
1 stop19h 21m
Delta
Deal found 2/3![Delta logo]()
$805
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:16 pm
HPN
- DCA
Nonstop1h 28m
American Airlines
Tue 4/2110:00 am
DCA
- HPN
1 stop6h 46m
American Airlines
Deal found 2/2![American Airlines logo]()
$390
This Expedia deal was found by Cheapflights users on 2/3. 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.
Mon 3/238:35 pm
HPN
- DCA
2 stops17h 23m
JetBlue
Wed 3/257:00 am
DCA
- HPN
1 stop7h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 3/198:00 am
HPN
- PHL
1 stop16h 53m
Multiple Airlines
Thu 3/265:05 am
PHL
- HPN
2 stops15h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/211:37 pm
HPN
- IAD
1 stop6h 53m
American Airlines
Sun 3/225:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$400
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Mon 3/93:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Tue 3/1012:15 pm
DCA
- HPN
1 stop9h 15m
JetBlue
Deal found 2/1![JetBlue logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/198:00 am
HPN
- PHL
1 stop11h 04m
Multiple Airlines
Fri 2/208:06 am
PHL
- HPN
2 stops12h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/201:37 pm
HPN
- IAD
1 stop6h 53m
American Airlines
Sat 3/219:19 am
IAD
- HPN
1 stop7h 41m
American Airlines
Deal found 2/2![American Airlines logo]()
$400
This JetBlue deal was found by Cheapflights users on 2/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:58 pm
HPN
- DCA
1 stop7h 33m
JetBlue
Thu 3/1212:20 pm
DCA
- HPN
1 stop9h 42m
JetBlue
Deal found 2/3![JetBlue logo]()
$386
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:37 pm
HPN
- IAD
1 stop6h 53m
American Airlines
Sun 3/155:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$400
This JetBlue deal was found by Cheapflights users on 2/1. 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 3/103:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Thu 3/127:00 am
DCA
- HPN
1 stop7h 30m
JetBlue
Deal found 2/1![JetBlue logo]()
$389
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:59 pm
HPN
- IAD
1 stop5h 00m
American Airlines
Tue 4/2110:32 am
IAD
- HPN
1 stop6h 14m
American Airlines
Deal found 2/2![American Airlines logo]()
$400
This Expedia deal was found by Cheapflights users on 2/3. 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.
Fri 3/69:23 am
HPN
- PHL
2 stops13h 13m
Multiple Airlines
Sun 3/86:00 am
PHL
- HPN
2 stops10h 46m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$473
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:37 pm
HPN
- IAD
1 stop6h 53m
American Airlines
Sun 3/225:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$429
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Thu 2/263:05 pm
HPN
- PHL
1 stop8h 39m
JetBlue
Mon 3/212:44 pm
PHL
- HPN
1 stop10h 01m
JetBlue
Deal found 2/1![JetBlue logo]()
$430
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:47 am
HPN
- IAD
1 stop5h 45m
American Airlines
Thu 3/125:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:47 am
HPN
- IAD
1 stop5h 45m
American Airlines
Sun 3/85:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$429
This KAYAK deal was found by Cheapflights users on 2/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:12 pm
HPN
- BWI
1 stop5h 53m
Delta
Tue 2/1011:45 am
BWI
- HPN
1 stop4h 04m
Delta
Deal found 2/3![Delta logo]()
$1,063
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:05 am
HPN
- IAD
1 stop4h 34m
American Airlines
Sun 2/225:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/3![American Airlines logo]()
$484
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:37 pm
HPN
- IAD
1 stop6h 53m
American Airlines
Sun 2/225:00 am
IAD
- HPN
1 stop4h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$485
This KAYAK deal was found by Cheapflights users on 2/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/810:29 am
HPN
- BWI
1 stop5h 09m
Delta
Tue 2/101:02 pm
BWI
- HPN
1 stop4h 58m
Delta
Deal found 2/4![Delta logo]()
$1,243
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:12 pm
HPN
- BWI
1 stop5h 41m
Delta
Sun 3/85:40 am
BWI
- HPN
1 stop6h 13m
Delta
Deal found 2/2![Delta logo]()
$1,363
Last-minute flights from Westchester County to MarylandDiscover last-minute flight deals from Westchester County to Maryland. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Maryland. Data last updated February 4, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 2/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:00 pm
HPN
- DCA
1 stop9h 31m
JetBlue
Mon 2/93:55 pm
DCA
- HPN
1 stop6h 35m
JetBlue
Deal found 2/2![JetBlue logo]()
$355
This JetBlue deal was found by Cheapflights users on 2/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:00 pm
HPN
- DCA
1 stop9h 31m
JetBlue
Sun 2/83:55 pm
DCA
- HPN
1 stop6h 35m
JetBlue
Deal found 2/2![JetBlue logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/181:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Sun 2/225:51 pm
PHL
- HPN
2 stops41h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/251:27 pm
HPN
- PHL
1 stop8h 18m
Multiple Airlines
Fri 2/278:15 am
PHL
- HPN
2 stops12h 44m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$334
This Expedia deal was found by Cheapflights users on 2/3. 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.
Sat 2/283:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Thu 3/59:00 am
DCA
- HPN
1 stop12h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/58:00 am
HPN
- IAD
1 stop28h 42m
Multiple Airlines
Thu 3/126:30 am
IAD
- HPN
2 stops14h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$338
This JetBlue deal was found by Cheapflights users on 2/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:58 pm
HPN
- DCA
1 stop7h 33m
JetBlue
Thu 3/1212:20 pm
DCA
- HPN
1 stop9h 42m
JetBlue
Deal found 2/3![JetBlue logo]()
$386
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Mon 3/93:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Tue 3/1012:15 pm
DCA
- HPN
1 stop9h 15m
JetBlue
Deal found 2/1![JetBlue logo]()
$381
This JetBlue deal was found by Cheapflights users on 2/1. 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 3/103:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Wed 3/113:59 pm
DCA
- HPN
1 stop6h 46m
JetBlue
Deal found 2/1![JetBlue logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 3/198:00 am
HPN
- PHL
1 stop16h 53m
Multiple Airlines
Thu 3/265:05 am
PHL
- HPN
2 stops15h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2111:29 am
HPN
- DCA
Nonstop1h 20m
American Airlines
Sun 3/229:40 am
DCA
- HPN
Nonstop1h 19m
American Airlines
Deal found 2/3![American Airlines logo]()
$380
This Expedia deal was found by Cheapflights users on 2/3. 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.
Mon 3/238:35 pm
HPN
- DCA
2 stops19h 43m
JetBlue
Wed 3/257:00 am
DCA
- HPN
1 stop7h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$368
One-way flights from Westchester County to MarylandSearch for one-way flight options from Westchester County to Maryland. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Westchester County to Maryland. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This JetBlue deal was found by Cheapflights users on 2/1. 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 3/33:05 pm
HPN
- DCA
1 stop7h 26m
JetBlue
Deal found 2/1![JetBlue logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/312:08 pm
HPN
- BWI
2 stops31h 22m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/912:08 pm
HPN
- BWI
3 stops36h 33m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/912:08 pm
HPN
- IAD
3 stops36h 23m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$133
This JetBlue deal was found by Cheapflights users on 2/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:45 am
HPN
- DCA
1 stop9h 59m
JetBlue
Deal found 2/3![JetBlue logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/912:08 pm
HPN
- DCA
3 stops33h 51m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/912:08 pm
HPN
- BWI
3 stops36h 23m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$161
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/213:29 pm
HPN
- DCA
1 stop7h 30m
JetBlue
Deal found 2/2![JetBlue logo]()
$161
This Expedia deal was found by Cheapflights users on 2/3. 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.
Mon 3/27:30 pm
HPN
- DCA
2 stops17h 29m
JetBlue
Deal found 2/3![JetBlue logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/212:08 pm
HPN
- DCA
3 stops33h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$171
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:00 pm
HPN
- DCA
2 stops16h 33m
JetBlue
Deal found 2/2![JetBlue logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/312:08 pm
HPN
- IAD
3 stops44h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$180
Find flight deals from Westchester County to Maryland
Keep the following information in mind while searching for Westchester County to Maryland flight deals. Data was last updated February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Kiwi.com) |
One-way from | $96 (JetBlue) |
Popular in | January |
Cheapest in | April |
Average price | $233 |
Cheapflights Fare Finder
Customize your flight search to find flights from Westchester County to Maryland 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 February 4, 2026.
Use the filters below to find and compare flights from Westchester County to Maryland that are best for you.
Fly from
Westchester County
Fly to
Maryland
Route
Depart
Return
Price
White PlainsPhiladelphia
HPN - PHL
HPNPHL
White Plains Westchester County
Wed 2/18
1:27 pm-9:45 pm
1 stop8h 18m
Philadelphia
Sun 2/22
5:51 pm-11:28 am
2 stops41h 37m
$259
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Tue 4/14
10:48 am-7:00 pm
1 stop8h 12m
Washington, D.C. Reagan-National
Wed 4/15
2:45 pm-10:36 pm
1 stop7h 51m
$274
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Tue 3/10
3:05 pm-10:31 pm
1 stop7h 26m
Washington, D.C. Reagan-National
Wed 3/11
3:59 pm-10:45 pm
1 stop6h 46m
$329
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Fri 5/29
2:29 pm-9:00 pm
1 stop6h 31m
Washington, D.C. Reagan-National
Mon 6/1
7:59 am-2:57 pm
1 stop6h 58m
$333
White PlainsPhiladelphia
HPN - PHL
HPNPHL
White Plains Westchester County
Wed 2/25
1:27 pm-9:45 pm
1 stop8h 18m
Philadelphia
Fri 2/27
8:15 am-8:59 pm
2 stops12h 44m
$334
White PlainsWashington, D.C.
HPN - IAD
HPNIAD
White Plains Westchester County
Thu 3/5
8:00 am-12:42 pm
1 stop28h 42m
Washington, D.C. Dulles Intl
Thu 3/12
6:30 am-8:30 pm
2 stops14h 00m
$338
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Mon 3/23
8:35 pm-1:58 pm
2 stops17h 23m
Washington, D.C. Reagan-National
Wed 3/25
7:00 am-2:30 pm
1 stop7h 30m
$368
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Mon 3/9
3:05 pm-10:31 pm
1 stop7h 26m
Washington, D.C. Reagan-National
Tue 3/10
12:15 pm-9:30 pm
1 stop9h 15m
$381
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Sat 3/14
7:47 am-9:19 am
1 stop25h 32m
Washington, D.C. Reagan-National
Sun 3/15
1:05 pm-2:30 pm
Nonstop1h 25m
$385
White PlainsWashington, D.C.
HPN - DCA
HPNDCA
White Plains Westchester County
Sat 3/21
10:05 am-9:19 am
1 stop23h 14m
Washington, D.C. Reagan-National
Sun 3/22
1:05 pm-2:30 pm
Nonstop1h 25m
$385
Showing 1-10 of 60 results
Best time to book a flight from Westchester County to Maryland
Have a flexible travel schedule? Discover the best time to fly to Maryland from Westchester County with our price prediction graph.
HPN-DCA
HPN-BWI
HPN-IAD
HPN-PHL
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 Maryland
zzREU-USMD
HPN-DCA
HPN-BWI
HPN-IAD
HPN-PHL
No data available for this route at this time. Please check back soon.
Related info for your journey
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