HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Westchester County

$191+ Cheap flights from Chesapeake, VA to Westchester County

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HPN
may. 17 — may. 241
sáb. 5/17
sáb. 5/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Westchester County with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 mayo 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Flightnetwork
3 stars

Round-trip from

$191
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$228
Provider with most accurate pricing for Norfolk-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-New York (NYC) flights.
Search Deals
From Chesapeake to Westchester County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 mayo 12, 2025.

This American Airlines deal was found by Cheapflights users on 5/10. 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.
jue. 5/293:16 pmORF - HPN
1 stop5h 00mAmerican Airlines
sáb. 6/76:59 pmHPN - ORF
1 stop5h 00mAmerican Airlines
Deal found 5/10$191
This Priceline deal was found by Cheapflights users on 5/11. 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.
mar. 8/123:58 pmORF - HPN
1 stop4h 32mBreeze Airways
jue. 8/1412:05 pmHPN - ORF
1 stop5h 00mBreeze Airways
Deal found 5/11$323
This Mytrip deal was found by Cheapflights users on 5/10. 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.
jue. 5/2912:13 pmORF - HPN
2 stops23h 08mMultiple Airlines
sáb. 6/78:10 amHPN - ORF
2 stops26h 19mMultiple Airlines
Deal found 5/10$478
This Delta deal was found by Cheapflights users on 5/11. 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.
mar. 7/15:23 amORF - HPN
1 stop12h 41mDelta
mar. 7/810:26 amHPN - ORF
1 stop8h 27mDelta
Deal found 5/11$505

Cheapflights Fare Finder

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 mayo 12, 2025.
Use the filters below to find and compare flights from Chesapeake to Westchester County that are best for you.

Fly from

Chesapeake

Fly to

Westchester County

Route

Depart

Return

Price

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

jue. 5/29

3:16 pm-8:16 pm

1 stop5h 00m

White Plains Westchester County

sáb. 6/7

6:59 pm-11:59 pm

1 stop5h 00m

$191

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

mar. 8/12

3:58 pm-8:30 pm

1 stop4h 32m

White Plains Westchester County

jue. 8/14

12:05 pm-5:05 pm

1 stop5h 00m

$323

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

jue. 5/29

12:13 pm-11:21 am

2 stops23h 08m

White Plains Westchester County

sáb. 6/7

8:10 am-10:29 am

2 stops26h 19m

$478

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

mar. 7/1

5:23 am-6:04 pm

1 stop12h 41m

White Plains Westchester County

mar. 7/8

10:26 am-6:53 pm

1 stop8h 27m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Westchester County

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 $339). 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 mayo 12, 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 mayo 12, 2025.
Breeze Airways
8.1
Very good
161 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Overall

8.1

Comfort

8.2

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
161 reviews
Breeze Airways
8.1
Very good
161 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Overall

8.1

Comfort

8.2

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
7,950 reviews
Breeze Airways
8.1
Very good
161 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Overall

8.1

Comfort

8.2

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
161 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Overall

8.1

Comfort

8.2

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.

  • 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 $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
Raleigh to John F Kennedy Intl flights
Raleigh to LaGuardia flights
Raleigh to Newark flights
Dulles Intl to LaGuardia flights
Dulles Intl to John F Kennedy Intl flights
Reagan-National to John F Kennedy Intl flights
Dulles Intl to Newark flights
Richmond to John F Kennedy Intl flights
Reagan-National to LaGuardia flights
Richmond to Newark flights
Reagan-National to Newark flights
Norfolk to John F Kennedy Intl flights
Raleigh to White Plains flights
Richmond to LaGuardia flights
Greensboro to John F Kennedy Intl flights
Greensboro to LaGuardia flights
Greensboro to Newark flights
Dulles Intl to Albany flights
Norfolk to Newark flights
Reagan-National to Albany flights
Norfolk to LaGuardia flights
Dulles Intl to Buffalo flights
Dulles Intl to Syracuse flights
Reagan-National to Buffalo flights
Raleigh to Buffalo flights
Reagan-National to Syracuse flights
Raleigh to Islip flights
Raleigh to Syracuse flights
Charlottesville to LaGuardia flights
Raleigh to Stewart flights
Reagan-National to Rochester flights
Dulles Intl to Rochester flights
Charlottesville to John F Kennedy Intl flights
Raleigh to Albany flights
Greensboro to Syracuse flights
Greensboro to Buffalo flights
Greensboro to Rochester flights
Charlottesville to Newark flights
Reagan-National to White Plains flights
Richmond to Buffalo flights
Roanoke to Newark flights
Roanoke to John F Kennedy Intl flights
Greensboro to Albany flights
Raleigh to Rochester flights
Norfolk to Buffalo flights
Roanoke to Albany flights
Roanoke to LaGuardia flights
Dulles Intl to White Plains flights
Reagan-National to Ithaca flights
Dulles Intl to Ithaca flights

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 mayo 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$346FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.