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Westchester County

$90+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HPN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:40 pmORF - HPN
2 stops16h 54mMultiple Airlines
Sat 1/31:29 pmHPN - ORF
1 stop18h 34mMultiple Airlines
Deal found 12/15$547
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:00 amORF - HPN
1 stop4h 29mAmerican Airlines
Sat 1/35:16 pmHPN - ORF
1 stop5h 42mAmerican Airlines
Deal found 12/15$630
This Gotogate deal was found by Cheapflights users on 12/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:00 amORF - HPN
3 stops28h 34mBreeze Airways
Sat 1/31:29 pmHPN - ORF
1 stop18h 34mBreeze Airways
Deal found 12/15$752
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:10 amORF - HPN
1 stop4h 44mDelta
Fri 12/265:16 pmHPN - ORF
1 stop6h 12mDelta
Deal found 12/15$1,563
This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/216:23 amORF - HPN
1 stop5h 37mDelta
Tue 12/236:55 pmHPN - ORF
1 stop5h 23mDelta
Deal found 12/16$1,773

Find 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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$219
(American Airlines)

One-way from

$90
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$260
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
Search Deals
One-way flight from Chesapeake to Westchester County
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 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

Fri 1/9

3:06 pm-8:08 pm

1 stop5h 02m

White Plains Westchester County

Mon 1/12

6:30 am-10:37 am

1 stop4h 07m

$219

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 1/6

3:06 pm-8:08 pm

1 stop5h 02m

White Plains Westchester County

Tue 1/13

1:30 pm-6:41 pm

1 stop5h 11m

$219

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Thu 1/1

6:00 am-10:34 am

1 stop4h 34m

White Plains Westchester County

Mon 1/5

5:16 pm-11:01 pm

1 stop5h 45m

$370

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Thu 1/1

7:15 am-8:30 pm

1 stop13h 15m

White Plains Westchester County

Mon 1/5

12:10 pm-6:45 pm

2 stops30h 35m

$450

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 12/30

7:40 pm-12:34 pm

2 stops16h 54m

White Plains Westchester County

Sat 1/3

1:29 pm-8:03 am

1 stop18h 34m

$547

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 12/30

5:00 am-9:29 am

1 stop4h 29m

White Plains Westchester County

Sat 1/3

5:16 pm-10:58 pm

1 stop5h 42m

$630

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Mon 1/5

12:35 pm-10:00 pm

1 stop9h 25m

White Plains Westchester County

Thu 1/8

8:15 am-4:35 pm

1 stop8h 20m

$663

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Tue 12/30

8:00 am-12:34 pm

3 stops28h 34m

White Plains Westchester County

Sat 1/3

1:29 pm-8:03 am

1 stop18h 34m

$752

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sat 1/10

10:31 pm-8:30 pm

2 stops21h 59m

$90

NorfolkWhite Plains

ORF - HPN

ORFHPN

Norfolk

Sun 1/11

7:33 pm-9:27 am

1 stop13h 54m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 16 results
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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 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 December 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Chesapeake to Westchester County at noon. If you’re flexible enough to do this you can expect to save up to 50% on your trip compared to booking a flight in the morning.

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 December 18, 2025.
Get a feel of what it's like to fly with 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.
American Airlines
7.2
Good
11,055 reviews

Entertainment

6.9

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Entertainment

6.9

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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.

  • How long is the flight from Chesapeake to Westchester County?

    American Airlines can get you from Chesapeake to Westchester County in just under 5h 02m. Your travel time can differ by up to . Airlines will cover a distance of 318 mi.

  • 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.

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$224FlexibilityNo cancel feeOn-time71%

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