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Chesapeake

$105+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
jul. 23 — jul. 301
mié. 7/23
mié. 7/30
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 julio 18, 2025.

Round-trip from

$183
(American Airlines)

One-way from

$105
(CheapOair)

Popular in

May

Cheapest in

January

Average price

$277
From White Plains Westchester County to Chesapeake
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One-way flight from White Plains Westchester County to Chesapeake
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Highest demand for flights based on searches. 6% potential increase in price ($18 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 July 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 julio 18, 2025.

This American Airlines deal was found by Cheapflights users on 7/17. 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.
sáb. 9/136:50 pmHPN - ORF
1 stop4h 14mAmerican Airlines
mar. 9/166:00 amORF - HPN
1 stop4h 45mAmerican Airlines
Deal found 7/17$183
This Priceline deal was found by Cheapflights users on 7/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/312:05 pmHPN - ORF
1 stop5h 00mBreeze Airways
mar. 8/53:58 pmORF - HPN
1 stop4h 32mBreeze Airways
Deal found 7/16$383
This Mytrip deal was found by Cheapflights users on 7/17. 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.
dom. 8/3112:05 pmHPN - ORF
1 stop5h 00mMultiple Airlines
dom. 9/75:38 pmORF - HPN
2 stops17h 50mMultiple Airlines
Deal found 7/17$526

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 julio 18, 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

sáb. 9/13

6:50 pm-11:04 pm

1 stop4h 14m

Norfolk

mar. 9/16

6:00 am-10:45 am

1 stop4h 45m

$183

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 8/3

12:05 pm-5:05 pm

1 stop5h 00m

Norfolk

mar. 8/5

3:58 pm-8:30 pm

1 stop4h 32m

$383

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 8/31

12:05 pm-5:05 pm

1 stop5h 00m

Norfolk

dom. 9/7

5:38 pm-11:28 am

2 stops17h 50m

$526

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 9/14

8:00 am-4:25 pm

1 stop8h 25m

$105

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

lun. 8/11

9:00 pm-5:02 pm

2 stops20h 02m

$216

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

lun. 8/11

1:31 pm-6:29 pm

1 stop4h 58m

$219

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

jue. 7/24

9:18 am-5:35 pm

3 stops32h 17m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

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 julio 18, 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.

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 julio 18, 2025.
See what other customers who have flown with Delta, Breeze Airways, and JetBlue 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.
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,958 reviews
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Breeze Airways
8.0
Very good
187 reviews
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.3
Good
2,910 reviews
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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. 2 airlines 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.

  • What are the cheapest airlines to fly from White Plains to Chesapeake one-way?

    $105 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on JetBlue and American Airlines, with prices starting from $216 and $219, respectively.

  • 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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Top 2 airlines flying from White Plains to Chesapeake

Discover the top 2 airlines 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 julio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$118Average$278FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$399FlexibilityNo cancel feeOn-time71%

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