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$125+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BWI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$251
(JetBlue)

One-way from

$125
(JetBlue)

Popular in

December

Cheapest in

April

Average price

$229
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. 17% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This JetBlue deal was found by Cheapflights users on 7/29. 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.
Wed 8/278:30 amHPN - DCA
1 stop10h 02mJetBlue
Wed 9/310:05 amDCA - HPN
1 stop8h 59mJetBlue
Deal found 7/29$251
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/1811:04 amHPN - DCA
Nonstop1h 11mAmerican Airlines
Tue 10/281:35 pmDCA - HPN
Nonstop1h 16mAmerican Airlines
Deal found 7/30$323
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/186:59 pmHPN - IAD
1 stop4h 51mAmerican Airlines
Tue 10/288:09 amIAD - HPN
1 stop4h 51mAmerican Airlines
Deal found 7/30$343
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 12/134:19 pmHPN - IAD
1 stop16h 52mDelta
Tue 12/165:25 pmIAD - HPN
2 stops18h 21mDelta
Deal found 7/30$420
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/128:25 amHPN - BWI
2 stops16h 33mMultiple Airlines
Sun 9/148:52 pmBWI - HPN
2 stops14h 36mMultiple Airlines
Deal found 7/29$428
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/312:00 pmHPN - PHL
3 stops21h 46mMultiple Airlines
Thu 9/45:15 pmPHL - HPN
2 stops18h 13mMultiple Airlines
Deal found 7/30$480
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/307:59 amHPN - BWI
1 stop13h 06mAmerican Airlines
Mon 9/17:45 pmBWI - HPN
1 stop21h 14mAmerican Airlines
Deal found 7/29$534
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/156:30 amHPN - PHL
2 stops8h 12mAmerican Airlines
Tue 8/191:55 pmPHL - HPN
2 stops9h 30mAmerican Airlines
Deal found 7/30$547
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/207:40 pmHPN - IAD
1 stop18h 19mMultiple Airlines
Thu 8/214:56 pmIAD - HPN
3 stops18h 25mMultiple Airlines
Deal found 7/31$566
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/67:40 pmHPN - IAD
1 stop18h 19mBreeze Airways
Sun 8/108:25 amIAD - HPN
1 stop10h 35mBreeze Airways
Deal found 7/31$662

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 July 31, 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

Wed 8/27

8:30 am-6:32 pm

1 stop10h 02m

Washington, D.C. Reagan-National

Wed 9/3

10:05 am-7:04 pm

1 stop8h 59m

$251

White PlainsWashington, D.C.

HPN - DCA

HPNDCA

White Plains Westchester County

Sat 10/18

11:04 am-12:15 pm

Nonstop1h 11m

Washington, D.C. Reagan-National

Tue 10/28

1:35 pm-2:51 pm

Nonstop1h 16m

$323

White PlainsWashington, D.C.

HPN - IAD

HPNIAD

White Plains Westchester County

Sat 10/18

6:59 pm-11:50 pm

1 stop4h 51m

Washington, D.C. Dulles Intl

Tue 10/28

8:09 am-1:00 pm

1 stop4h 51m

$343

White PlainsWashington, D.C.

HPN - IAD

HPNIAD

White Plains Westchester County

Sat 12/13

4:19 pm-9:11 am

1 stop16h 52m

Washington, D.C. Dulles Intl

Tue 12/16

5:25 pm-11:46 am

2 stops18h 21m

$420

White PlainsBaltimore

HPN - BWI

HPNBWI

White Plains Westchester County

Fri 9/12

8:25 am-12:58 am

2 stops16h 33m

Baltimore/Washington

Sun 9/14

8:52 pm-11:28 am

2 stops14h 36m

$428

White PlainsPhiladelphia

HPN - PHL

HPNPHL

White Plains Westchester County

Wed 9/3

12:00 pm-9:46 am

3 stops21h 46m

Philadelphia

Thu 9/4

5:15 pm-11:28 am

2 stops18h 13m

$480

White PlainsBaltimore

HPN - BWI

HPNBWI

White Plains Westchester County

Sat 8/30

7:59 am-9:05 pm

1 stop13h 06m

Baltimore/Washington

Mon 9/1

7:45 pm-4:59 pm

1 stop21h 14m

$534

White PlainsPhiladelphia

HPN - PHL

HPNPHL

White Plains Westchester County

Fri 8/15

6:30 am-2:42 pm

2 stops8h 12m

Philadelphia

Tue 8/19

1:55 pm-11:25 pm

2 stops9h 30m

$547

White PlainsWashington, D.C.

HPN - IAD

HPNIAD

White Plains Westchester County

Wed 8/20

7:40 pm-1:59 pm

1 stop18h 19m

Washington, D.C. Dulles Intl

Thu 8/21

4:56 pm-11:21 am

3 stops18h 25m

$566

White PlainsBaltimore

HPN - BWI

HPNBWI

White Plains Westchester County

Sat 9/20

5:20 pm-11:37 pm

1 stop6h 17m

Baltimore/Washington

Mon 9/22

9:46 am-3:49 pm

1 stop6h 03m

$1,125

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 23 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.

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Delta, Breeze Airways, and Qatar Airways from Westchester County to Maryland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Breeze Airways
8.0
Very good
191 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Qatar Airways
7.4
Good
3,609 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.3
Good
2,914 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • What are the cheapest airlines to fly from Westchester County to Maryland one-way?

    $125 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $166 and $253, respectively.

  • 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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