Maryland

$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
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Cheap flight deals from Westchester County to Maryland

Cheapest flights from Westchester County to Maryland
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$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$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$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$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$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$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$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$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$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$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$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$381

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
Provider with most accurate pricing for New York (NYC)-Washington, D.C. (WAS) flight deals.
Provider most trusted by Cheapflights users for New York (NYC)-Washington, D.C. (WAS) flights.
From Westchester County to Maryland
One-way flight from Westchester County to Maryland
Highest demand for flights based on searches. 16% potential increase in price ($38 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 60 results
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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.
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
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 Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Westchester County to Maryland?

    JetBlue and American Airlines can get you from Westchester County to Maryland in just under 6h 53m. Your travel time can differ by up to 1h 19m. The distance from Westchester County to Maryland is about 246 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Westchester County to Maryland that include hotel bookings?

    Yes. In addition to deals on Westchester County to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Maryland?

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

  • Can I find deals for business class flights from Westchester County to Maryland?

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

See more FAQs

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