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Chesapeake

$99+ Cheap flights from White Plains (HPN) to Chesapeake, VA

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from White Plains to Chesapeake

Cheapest flights from White Plains to Chesapeake
Explore the most affordable flight options available from White Plains to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/295:16 pmHPN - ORF
1 stop5h 45mAmerican Airlines
Sat 1/36:01 amORF - HPN
1 stop4h 33mAmerican Airlines
Deal found 12/14$321
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.
Mon 12/295:16 pmHPN - ORF
1 stop5h 45mAmerican Airlines
Thu 1/16:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 12/15$345
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.
Thu 12/258:00 amHPN - ORF
1 stop8h 03mMultiple Airlines
Thu 1/17:40 pmORF - HPN
2 stops15h 48mMultiple Airlines
Deal found 12/15$425
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:30 amHPN - ORF
1 stop2h 58mAmerican Airlines
Wed 12/174:40 pmORF - HPN
1 stop5h 50mAmerican Airlines
Deal found 12/15$463
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:19 pmHPN - ORF
1 stop4h 51mAmerican Airlines
Thu 12/186:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 12/15$487
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.
Thu 12/258:00 amHPN - ORF
1 stop8h 03mBreeze Airways
Thu 1/17:15 amORF - HPN
1 stop13h 15mBreeze Airways
Deal found 12/15$537
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 12/305:16 pmHPN - ORF
1 stop5h 45mAmerican Airlines
Sat 1/36:01 amORF - HPN
1 stop4h 33mAmerican Airlines
Deal found 12/15$574
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.
Sat 12/275:16 pmHPN - ORF
1 stop5h 42mAmerican Airlines
Sat 1/36:01 amORF - HPN
1 stop4h 33mAmerican Airlines
Deal found 12/15$590
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/247:52 amHPN - ORF
1 stop6h 22mAmerican Airlines
Fri 12/266:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 12/14$599

Find flight deals from White Plains to Chesapeake

Keep the following information in mind while searching for White Plains to Chesapeake flight deals. Data was last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Breeze Airways)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$542
Provider with most accurate pricing for New York (NYC)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Norfolk flights.
Search Deals
From White Plains Westchester County to Chesapeake
Search Deals
One-way flight from White Plains Westchester County to Chesapeake
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains to Chesapeake 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 16, 2025.
Use the filters below to find and compare flights from White Plains to Chesapeake that are best for you.

Fly from

White Plains

Fly to

Chesapeake

Route

Depart

Return

Price

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 1/8

12:08 pm-4:50 pm

1 stop4h 42m

Norfolk

Sun 1/11

1:09 pm-8:30 pm

1 stop7h 21m

$193

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sun 2/15

5:16 pm-11:04 pm

1 stop5h 48m

Norfolk

Sat 2/21

6:00 am-10:30 am

1 stop4h 30m

$198

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 1/8

12:08 pm-4:50 pm

1 stop4h 42m

Norfolk

Sun 1/11

6:45 am-11:28 am

2 stops28h 43m

$200

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 1/9

8:00 am-8:00 am

2 stops24h 00m

Norfolk

Sun 1/11

1:09 pm-8:30 pm

1 stop7h 21m

$213

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 12/29

5:16 pm-11:01 pm

1 stop5h 45m

Norfolk

Sat 1/3

6:01 am-10:34 am

1 stop4h 33m

$321

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sat 1/3

5:16 pm-10:58 pm

1 stop5h 42m

Norfolk

Mon 1/5

5:00 am-9:29 am

1 stop4h 29m

$328

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 6/4

6:35 am-9:26 am

1 stop2h 51m

Norfolk

Sun 6/7

8:28 pm-11:18 pm

1 stop2h 50m

$342

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 6/4

12:07 pm-5:11 pm

1 stop5h 04m

Norfolk

Sun 6/7

5:48 pm-11:27 am

2 stops17h 39m

$368

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sat 1/3

1:29 pm-8:03 am

1 stop18h 34m

Norfolk

Mon 1/5

7:40 pm-11:29 am

2 stops15h 49m

$393

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Tue 1/13

8:00 am-8:00 am

2 stops24h 00m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 15 results
1
2

Best time to book a flight from White Plains to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from White Plains 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 White Plains to Chesapeake

What is the cheapest month to book a flight from White Plains to Chesapeake?

Currently, May is the cheapest month in which you can book a flight from White Plains to Chesapeake (average of $96). Flying from White Plains to Chesapeake in September is currently the most expensive (average of $179). 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 HPN to C6E?

Find hourly flight availability from White Plains to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.

One of the essential ways to save on airfare from White Plains to Chesapeake is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 42% on airfare.

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated December 16, 2025.
See what other customers who have flown with American Airlines from White Plains to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,049 reviews

Entertainment

6.9

Comfort

7.2

Food

6.5

Overall

7.2

Boarding

7.5

Crew

8.0

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
11,049 reviews
American Airlines
7.2
Good
11,049 reviews

Entertainment

6.9

Comfort

7.2

Food

6.5

Overall

7.2

Boarding

7.5

Crew

8.0

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 White Plains to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from White Plains to Chesapeake?

    White Plains Westchester County (HPN), located 3.7 mi from the city center, is the airport you fly out of when you book flights from White Plains to Chesapeake. 1 airline have flights from Westchester County to Chesapeake on a regular basis. Booking flights from White Plains Westchester County to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from White Plains to Chesapeake?

    Airlines like Breeze Airways and American Airlines fly from White Plains to Chesapeake in about 4h 42m. The time it takes to get you to your destination can typically vary by up to 1h 06m. There are 318 mi between White Plains and Chesapeake. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from White Plains to Chesapeake that include hotel bookings?

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

  • How can I find direct flights from White Plains to Chesapeake?

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

  • Can I find deals for business class flights from White Plains to Chesapeake?

    Yes. Cheapflights offers flight deals from White Plains to Chesapeake 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 White Plains to Chesapeake?

    Currently, May is the cheapest month in which you can book a flight from White Plains to Chesapeake (average of $96). Flying from White Plains to Chesapeake in September is currently the most expensive (average of $179). 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 White Plains to Chesapeake

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Top airline flying from White Plains to Chesapeake

Discover the top airline that operate flights from White Plains to Chesapeake. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$455FlexibilityNo cancel feeOn-time71%

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