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Westchester County

$183+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HPN
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$198
(Priceline)

Popular in

June

Cheapest in

September

Average price

$249
From Chesapeake to Westchester County
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 30, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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 7/410:47 amORF - HPN
1 stop6h 12mAmerican Airlines
Sat 7/56:30 amHPN - ORF
1 stop2h 44mAmerican Airlines
Deal found 6/30$183
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/263:58 pmORF - HPN
1 stop4h 32mBreeze Airways
Thu 8/2812:05 pmHPN - ORF
1 stop5h 00mBreeze Airways
Deal found 6/30$198
This Mytrip deal was found by Cheapflights users on 6/28. 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.
Sun 7/139:05 amORF - HPN
3 stops26h 16mMultiple Airlines
Thu 7/179:18 amHPN - ORF
2 stops29h 12mMultiple Airlines
Deal found 6/28$599

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 June 30, 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

Tue 8/26

3:58 pm-8:30 pm

1 stop4h 32m

White Plains Westchester County

Thu 8/28

12:05 pm-5:05 pm

1 stop5h 00m

$198

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Fri 8/15

7:51 pm-11:25 pm

1 stop3h 34m

White Plains Westchester County

Mon 8/18

5:29 pm-10:57 pm

1 stop5h 28m

$199

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sun 7/13

9:05 am-11:21 am

3 stops26h 16m

White Plains Westchester County

Thu 7/17

9:18 am-2:30 pm

2 stops29h 12m

$599

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sat 8/9

6:29 am-10:30 am

1 stop4h 01m

$206

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sat 8/9

5:20 pm-8:59 pm

2 stops27h 39m

$262

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sun 11/2

2:59 pm-12:40 pm

3 stops21h 41m

$304

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sat 8/16

8:05 am-2:29 pm

1 stop6h 24m

$671

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 30, 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 June 30, 2025.
Get a feel of what it's like to fly with Breeze Airways, Delta, and American Airlines from Chesapeake to Westchester County by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Crew

8.8

Boarding

8.4

Overall

8.1

Comfort

8.2

Food

6.8

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
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Crew

8.8

Boarding

8.4

Overall

8.1

Comfort

8.2

Food

6.8

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
7,969 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Crew

8.8

Boarding

8.4

Overall

8.1

Comfort

8.2

Food

6.8

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
182 reviews

Entertainment

6.6

Crew

8.8

Boarding

8.4

Overall

8.1

Comfort

8.2

Food

6.8

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 American Airlines, with whom users have recently found tickets for as low as $206. However, be on the lookout for offers from Breeze Airways 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 $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

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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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$226FlexibilityNo cancel feeOn-time71%

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