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Westchester County

$187+ Cheap flights from Chesapeake, VA to Westchester County

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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HPN
Mar 1 — Mar 81
Sat 3/1
Sat 3/8
1 adult, Economy
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Cheap flight deals from Chesapeake to Westchester County

Keep the following information in mind while searching for Chesapeake to Westchester County flight deals. Data was last updated February 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(American Airlines)

One-way from

$187
(eDestinos)

Popular in

July

Cheapest in

September

Average price

$247
Provider with most accurate pricing for Norfolk-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-New York (NYC) flights.
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From Chesapeake to Westchester County
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One-way flight from Chesapeake to Westchester County
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Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chesapeake to Westchester County

Cheapest flights from Chesapeake to Westchester County
Explore the most affordable flight options available from Chesapeake to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 24, 2025.

This American Airlines deal was found by Cheapflights users on 2/24. 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 3/216:32 amORF - HPN
1 stop4h 16mAmerican Airlines
Sun 3/236:35 pmHPN - ORF
1 stop5h 18mAmerican Airlines
Deal found 2/24$214
This Mytrip deal was found by Cheapflights users on 2/24. 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 3/217:00 amORF - HPN
2 stops29h 45mMultiple Airlines
Sun 3/238:20 amHPN - ORF
2 stops25h 20mMultiple Airlines
Deal found 2/24$498
This Breeze Airways deal was found by Cheapflights users on 2/24. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1012:51 pmORF - HPN
1 stop22h 24mBreeze Airways
Wed 4/168:00 amHPN - ORF
1 stop24h 18mBreeze Airways
Deal found 2/24$920

Find flights from Chesapeake to Westchester County within your budget

Customize your flight search to find flights from Chesapeake to Westchester County 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 24, 2025.

Fly from

Chesapeake

Fly to

Westchester County

Route

Depart

Return

Price

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Fri 3/21

6:32 am-10:48 am

1 stop4h 16m

White Plains Westchester County

Sun 3/23

6:35 pm-11:53 pm

1 stop5h 18m

$214

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Fri 3/21

7:00 am-12:45 pm

2 stops29h 45m

White Plains Westchester County

Sun 3/23

8:20 am-9:40 am

2 stops25h 20m

$498

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Thu 4/10

12:51 pm-11:15 am

1 stop22h 24m

White Plains Westchester County

Wed 4/16

8:00 am-8:18 am

1 stop24h 18m

$920

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Wed 5/21

2:14 pm-12:30 pm

2 stops22h 16m

$187

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 3/4

7:00 am-12:45 pm

3 stops29h 45m

$206

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 3/4

5:04 am-9:29 am

1 stop4h 25m

$282

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sat 6/28

12:35 pm-6:14 pm

1 stop5h 39m

$567

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Best time to book a flight from Chesapeake to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Chesapeake 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.

Travel insights for flights from Chesapeake to Westchester County

Get recent, data-driven insights about flights from Chesapeake to Westchester County including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Westchester County (average of $276). Flying from Chesapeake to Westchester County in March is currently the most expensive (average of $341). 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.

What is the cheapest time of day to fly from C6E to REU?

Find hourly flight availability from Chesapeake to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 24, 2025.

When flying from Chesapeake to Westchester County, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Westchester County

Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated February 24, 2025.
Breeze Airways
8.1
Very good
150 reviews

Food

6.7

Overall

8.1

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Reviews

1 / 11

10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Breeze Airways
8.1
Very good
150 reviews
Breeze Airways
8.1
Very good
150 reviews

Food

6.7

Overall

8.1

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Reviews

1 / 11

10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Delta
8.0
Very good
8,174 reviews
Breeze Airways
8.1
Very good
150 reviews

Food

6.7

Overall

8.1

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Reviews

1 / 11

10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
150 reviews

Food

6.7

Overall

8.1

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Reviews

1 / 11

10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Westchester County. 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 Chesapeake to Westchester County one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $187. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Chesapeake to Westchester County for a low price.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to Westchester County 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 Chesapeake to Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Westchester County (average of $276). Flying from Chesapeake to Westchester County in March is currently the most expensive (average of $341). 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.

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Alternative routes for Chesapeake to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chesapeake to Westchester County

Discover the top airline that operate flights from Chesapeake to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$445FlexibilityNo cancel feeOn-time71%
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