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$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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BWI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/303:00 pmHPN - DCA
Nonstop1h 20mAmerican Airlines
Tue 1/68:02 amDCA - HPN
Nonstop1h 27mAmerican Airlines
Deal found 12/16$383
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/246:30 amHPN - DCA
Nonstop1h 20mAmerican Airlines
Fri 12/265:01 pmDCA - HPN
Nonstop1h 23mAmerican Airlines
Deal found 12/17$418
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/315:16 pmHPN - DCA
Nonstop1h 20mAmerican Airlines
Fri 1/25:30 pmDCA - HPN
1 stop5h 30mAmerican Airlines
Deal found 12/17$428
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/308:00 amHPN - PHL
2 stops39h 38mMultiple Airlines
Fri 1/26:00 amPHL - HPN
1 stop5h 28mMultiple Airlines
Deal found 12/17$436
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/303:00 pmHPN - DCA
Nonstop1h 20mAmerican Airlines
Thu 1/17:05 pmDCA - HPN
Nonstop1h 22mAmerican Airlines
Deal found 12/16$444
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/185:16 pmHPN - DCA
Nonstop1h 20mAmerican Airlines
Mon 12/227:05 pmDCA - HPN
Nonstop1h 22mAmerican Airlines
Deal found 12/16$445
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/186:56 pmHPN - IAD
1 stop5h 08mAmerican Airlines
Mon 12/224:29 pmIAD - HPN
1 stop6h 31mAmerican Airlines
Deal found 12/16$465
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/187:52 amHPN - IAD
1 stop5h 43mAmerican Airlines
Sat 12/206:35 amIAD - HPN
1 stop6h 30mAmerican Airlines
Deal found 12/16$471
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/186:56 pmHPN - DCA
1 stop4h 49mAmerican Airlines
Sat 12/205:00 amDCA - HPN
1 stop4h 29mAmerican Airlines
Deal found 12/16$492
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/307:52 amHPN - IAD
1 stop5h 35mAmerican Airlines
Tue 1/611:34 amIAD - HPN
1 stop5h 11mAmerican Airlines
Deal found 12/16$556
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/306:56 pmHPN - IAD
1 stop5h 08mAmerican Airlines
Thu 1/16:35 amIAD - HPN
1 stop6h 30mAmerican Airlines
Deal found 12/17$557
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 12/296:56 pmHPN - IAD
1 stop5h 08mAmerican Airlines
Wed 12/319:12 amIAD - HPN
1 stop7h 34mAmerican Airlines
Deal found 12/16$570

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$274
(Expedia)

One-way from

$96
(Priceline)

Popular in

January

Cheapest in

April

Average price

$256
Provider with most accurate pricing for New York (NYC)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Washington, D.C. (WAS) flights.
Search Deals
From Westchester County to Maryland
Search Deals
One-way flight from Westchester County to Maryland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 2025.
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 PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Sun 1/11

8:55 pm-9:15 am

1 stop12h 20m

Washington, D.C. Reagan-National

Tue 1/13

10:45 am-5:42 pm

1 stop6h 57m

$274

White PlainsPhiladelphia

HPN - PHL

HPNPHL

White Plains Westchester County

Tue 1/13

1:00 pm-11:09 pm

1 stop10h 09m

Philadelphia

Tue 1/20

7:00 am-5:42 pm

1 stop10h 42m

$291

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Sat 2/7

2:00 pm-10:31 pm

1 stop8h 31m

Washington, D.C. Reagan-National

Wed 2/11

7:10 am-4:28 pm

1 stop9h 18m

$295

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Tue 1/20

1:00 pm-10:31 pm

1 stop9h 31m

Washington, D.C. Reagan-National

Fri 1/23

7:30 am-5:42 pm

1 stop10h 12m

$295

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Wed 2/25

3:05 pm-10:31 pm

1 stop7h 26m

Washington, D.C. Reagan-National

Fri 2/27

12:15 pm-9:30 pm

1 stop9h 15m

$316

White PlainsWashington, D.C.

HPN - IAD

HPNIAD

White Plains Westchester County

Wed 1/7

7:40 pm-8:06 pm

1 stop24h 26m

Washington, D.C. Dulles Intl

Tue 1/13

6:00 am-12:37 pm

2 stops30h 37m

$317

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Thu 1/8

8:55 pm-9:15 am

1 stop12h 20m

Washington, D.C. Reagan-National

Sat 1/10

3:55 pm-10:30 pm

1 stop6h 35m

$328

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Tue 1/13

1:00 pm-10:31 pm

1 stop9h 31m

Washington, D.C. Reagan-National

Tue 1/20

3:55 pm-10:30 pm

1 stop6h 35m

$329

White PlainsBaltimore

HPN - BWI

HPNBWI

White Plains Westchester County

Thu 1/29

8:55 pm-7:03 pm

1 stop22h 08m

Baltimore/Washington

Thu 2/5

9:26 am-10:30 pm

1 stop13h 04m

$330

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Sat 1/10

1:00 pm-10:31 pm

1 stop9h 31m

Washington, D.C. Reagan-National

Mon 1/12

3:55 pm-10:30 pm

1 stop6h 35m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 59 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 5h 04m. Your travel time can differ by up to 7h 16m. 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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Alternative routes for Westchester County to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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