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Chesapeake

$87+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$183
(American Airlines)

One-way from

$87
(CheapOair)

Popular in

May

Cheapest in

April

Average price

$213
From White Plains Westchester County to Chesapeake
Search Deals
One-way flight from White Plains Westchester County to Chesapeake
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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. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/296:30 amHPN - ORF
1 stop3h 16mAmerican Airlines
Wed 11/56:00 amORF - HPN
1 stop7h 00mAmerican Airlines
Deal found 9/10$183
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 9/136:30 amHPN - ORF
1 stop2h 56mAmerican Airlines
Tue 9/162:52 pmORF - HPN
1 stop5h 08mAmerican Airlines
Deal found 9/10$223
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/36:30 amHPN - ORF
1 stop2h 56mAmerican Airlines
Sun 10/55:30 amORF - HPN
1 stop5h 06mAmerican Airlines
Deal found 9/9$229
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:29 pmHPN - ORF
1 stop5h 31mAmerican Airlines
Mon 10/61:03 pmORF - HPN
1 stop7h 26mAmerican Airlines
Deal found 9/11$234
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 9/266:50 pmHPN - ORF
1 stop4h 25mAmerican Airlines
Mon 9/292:52 pmORF - HPN
1 stop5h 08mAmerican Airlines
Deal found 9/10$239
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:29 pmHPN - ORF
1 stop5h 31mAmerican Airlines
Sat 10/256:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 9/11$240
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/105:29 pmHPN - ORF
1 stop5h 31mAmerican Airlines
Sun 9/145:30 amORF - HPN
1 stop5h 06mAmerican Airlines
Deal found 9/9$248
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/176:59 pmHPN - ORF
1 stop4h 55mAmerican Airlines
Sun 10/195:00 amORF - HPN
1 stop4h 29mAmerican Airlines
Deal found 9/10$255
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/125:29 pmHPN - ORF
1 stop5h 31mAmerican Airlines
Sun 9/217:04 pmORF - HPN
1 stop4h 22mAmerican Airlines
Deal found 9/9$266
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:00 amHPN - ORF
1 stop8h 25mMultiple Airlines
Sun 9/285:47 pmORF - HPN
2 stops17h 41mMultiple Airlines
Deal found 9/10$271
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 9/1110:05 amHPN - ORF
1 stop4h 39mAmerican Airlines
Sun 9/145:30 amORF - HPN
1 stop5h 06mAmerican Airlines
Deal found 9/9$273
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/235:29 pmHPN - ORF
1 stop5h 31mAmerican Airlines
Sun 10/267:35 pmORF - HPN
1 stop3h 54mAmerican Airlines
Deal found 9/10$285

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 September 11, 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

Wed 10/29

6:30 am-9:46 am

1 stop3h 16m

Norfolk

Wed 11/5

6:00 am-1:00 pm

1 stop7h 00m

$183

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Wed 11/5

6:30 am-9:20 am

1 stop2h 50m

Norfolk

Wed 11/12

6:00 am-1:00 pm

1 stop7h 00m

$183

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 10/3

6:30 am-9:26 am

1 stop2h 56m

Norfolk

Sun 10/5

5:30 am-10:36 am

1 stop5h 06m

$229

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 9/29

5:29 pm-11:00 pm

1 stop5h 31m

Norfolk

Mon 10/6

1:03 pm-8:29 pm

1 stop7h 26m

$234

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 9/26

6:50 pm-11:15 pm

1 stop4h 25m

Norfolk

Mon 9/29

2:52 pm-8:00 pm

1 stop5h 08m

$239

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 9/25

3:23 pm-6:34 pm

1 stop3h 11m

Norfolk

Mon 9/29

11:14 am-4:59 pm

1 stop5h 45m

$239

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 10/20

5:29 pm-11:00 pm

1 stop5h 31m

Norfolk

Sat 10/25

6:00 am-10:34 am

1 stop4h 34m

$240

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sat 2/28

5:09 pm-10:54 pm

1 stop5h 45m

Norfolk

Tue 3/3

6:35 am-10:44 am

1 stop4h 09m

$243

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 10/2

8:00 am-3:53 pm

1 stop7h 53m

$87

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 10/9

8:00 am-3:53 pm

1 stop7h 53m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 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, January is the cheapest month in which you can book a flight from White Plains to Chesapeake (average of $281). Flying from White Plains to Chesapeake in March is currently the most expensive (average of $351). 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 September 11, 2025.

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

How much does it cost to fly round-trip from White Plains to Chesapeake?

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 September 11, 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
10,000 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 American Airlines fly from White Plains to Chesapeake in about 3h 16m. The time it takes to get you to your destination can typically vary by up to . There are 318 mi between White Plains and Chesapeake.

  • 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, January is the cheapest month in which you can book a flight from White Plains to Chesapeake (average of $281). Flying from White Plains to Chesapeake in March is currently the most expensive (average of $351). 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 White Plains to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$158Average$376FlexibilityNo cancel feeOn-time71%

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