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$111+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BWI
oct. 16 — oct. 231
jeu. 10/16
jeu. 10/23
1 adult, Economy
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Cheap 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 septembre 16, 2025.

Round-trip from

$203
(CheapOair)

One-way from

$111
(JetBlue)

Popular in

December

Cheapest in

April

Average price

$232
From Westchester County to Maryland
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One-way flight from Westchester County to Maryland
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Highest demand for flights based on searches. 19% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septembre 16, 2025.

This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/148:55 pmHPN - DCA
1 stop18h 07mJetBlue
mar. 10/215:30 pmDCA - HPN
1 stop16h 36mJetBlue
Deal found 9/15$203
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/298:55 pmHPN - DCA
1 stop15h 30mJetBlue
lun. 10/68:30 pmDCA - HPN
1 stop13h 36mJetBlue
Deal found 9/13$218
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/298:55 pmHPN - DCA
1 stop23h 59mJetBlue
ven. 10/38:00 pmDCA - HPN
1 stop14h 06mJetBlue
Deal found 9/15$228
This JetBlue deal was found by Cheapflights users on 9/14. 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.
sam. 12/131:00 pmHPN - DCA
1 stop9h 29mJetBlue
mar. 12/1611:00 amDCA - HPN
1 stop8h 30mJetBlue
Deal found 9/14$232
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/68:55 pmHPN - DCA
1 stop13h 32mJetBlue
mar. 10/78:30 pmDCA - HPN
1 stop13h 36mJetBlue
Deal found 9/15$233
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/307:59 pmHPN - DCA
1 stop17h 45mJetBlue
sam. 10/410:41 amDCA - HPN
1 stop12h 05mJetBlue
Deal found 9/15$238
This KAYAK deal was found by Cheapflights users on 9/15. 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.
mar. 9/303:23 pmHPN - DCA
Nonstop1h 17mAmerican Airlines
mar. 9/308:07 pmDCA - HPN
2 stops14h 38mAmerican Airlines
Deal found 9/15$239
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/137:59 pmHPN - DCA
1 stop22h 40mJetBlue
lun. 10/208:30 pmDCA - HPN
1 stop13h 36mJetBlue
Deal found 9/15$243
This JetBlue deal was found by Cheapflights users on 9/14. 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.
lun. 10/271:00 pmHPN - DCA
1 stop9h 29mJetBlue
mar. 10/286:45 amDCA - HPN
1 stop7h 21mJetBlue
Deal found 9/14$247
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/317:00 pmHPN - DCA
1 stop27h 15mJetBlue
dim. 11/25:45 amDCA - HPN
1 stop16h 37mJetBlue
Deal found 9/14$249
This JetBlue deal was found by Cheapflights users on 9/15. 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.
ven. 10/249:39 amHPN - PHL
1 stop9h 25mJetBlue
ven. 10/3112:00 pmPHL - HPN
1 stop9h 37mJetBlue
Deal found 9/15$253
This Expedia deal was found by Cheapflights users on 9/13. 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.
ven. 9/268:55 pmHPN - DCA
1 stop12h 20mJetBlue
sam. 9/2711:00 amDCA - HPN
1 stop11h 48mJetBlue
Deal found 9/13$253

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 septembre 16, 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

lun. 9/29

8:55 pm-12:25 pm

1 stop15h 30m

Washington, D.C. Reagan-National

lun. 10/6

5:30 pm-10:06 am

1 stop16h 36m

$218

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

lun. 9/29

8:55 pm-8:54 pm

1 stop23h 59m

Washington, D.C. Reagan-National

ven. 10/3

8:00 pm-10:06 am

1 stop14h 06m

$228

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

sam. 12/13

1:00 pm-10:29 pm

1 stop9h 29m

Washington, D.C. Reagan-National

mar. 12/16

11:00 am-7:30 pm

1 stop8h 30m

$232

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

lun. 10/6

8:55 pm-10:27 am

1 stop13h 32m

Washington, D.C. Reagan-National

mar. 10/7

8:30 pm-10:06 am

1 stop13h 36m

$233

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

mar. 10/7

8:55 pm-10:27 am

1 stop13h 32m

Washington, D.C. Reagan-National

mer. 10/8

8:30 pm-10:06 am

1 stop13h 36m

$238

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

mar. 9/30

7:59 pm-1:44 pm

1 stop17h 45m

Washington, D.C. Reagan-National

sam. 10/4

10:41 am-10:46 pm

1 stop12h 05m

$238

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

lun. 10/13

7:59 pm-6:39 pm

1 stop22h 40m

Washington, D.C. Reagan-National

lun. 10/20

8:30 pm-10:06 am

1 stop13h 36m

$243

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

lun. 10/27

1:00 pm-10:29 pm

1 stop9h 29m

Washington, D.C. Reagan-National

mar. 10/28

6:45 am-2:06 pm

1 stop7h 21m

$247

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

ven. 9/26

8:55 pm-9:15 am

1 stop12h 20m

Washington, D.C. Reagan-National

sam. 9/27

11:00 am-10:48 pm

1 stop11h 48m

$253

White PlainsPhiladelphia

HPN - PHL

HPNPHL

White Plains Westchester County

lun. 9/29

8:25 am-11:59 pm

2 stops15h 34m

Philadelphia

ven. 10/3

6:15 am-11:28 am

1 stop5h 13m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, American Airlines, and Delta can get you from Westchester County to Maryland in just under 5h 24m. Your travel time can differ by up to 10h 06m. 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.

  • What is the cheapest month to book a flight from Westchester County to Maryland?

    Currently, August is the cheapest month in which you can book a flight from Westchester County to Maryland (average of $241). Flying from Westchester County to Maryland in March is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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