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Chesapeake

$183+ Cheap flights from White Plains (HPN) to Chesapeake, VA

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$254
Provider with most accurate pricing for New York (NYC)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Norfolk flights.
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From White Plains Westchester County to Chesapeake
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 9/135:25 pmHPN - ORF
1 stop5h 45mAmerican Airlines
Tue 9/166:49 pmORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 4/29$183
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Wed 5/148:10 amHPN - ORF
2 stops26h 19mMultiple Airlines
Sun 5/1812:13 pmORF - HPN
2 stops23h 08mMultiple Airlines
Deal found 4/29$527
This Priceline deal was found by Cheapflights users on 4/27. 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.
Thu 5/2212:05 pmHPN - ORF
1 stop5h 00mBreeze Airways
Tue 5/273:58 pmORF - HPN
1 stop4h 32mBreeze Airways
Deal found 4/27$560

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 April 29, 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

Sat 9/13

5:25 pm-11:10 pm

1 stop5h 45m

Norfolk

Tue 9/16

6:49 pm-11:23 pm

1 stop4h 34m

$183

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Wed 5/14

8:10 am-10:29 am

2 stops26h 19m

Norfolk

Sun 5/18

12:13 pm-11:21 am

2 stops23h 08m

$527

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 5/22

12:05 pm-5:05 pm

1 stop5h 00m

Norfolk

Tue 5/27

3:58 pm-8:30 pm

1 stop4h 32m

$560

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 7/28

8:00 am-11:19 am

1 stop27h 19m

$215

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 5/15

1:45 pm-7:37 pm

1 stop5h 52m

$229

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 5/16

12:06 pm-10:29 am

2 stops22h 23m

$245

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sat 5/31

12:59 pm-6:35 pm

1 stop5h 36m

$682

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 June is currently the most expensive (average of $367). 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 April 29, 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.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 April 29, 2025.
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

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
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

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
7,929 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

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
160 reviews

Crew

8.8

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

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 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. 3 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?

    $215 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 American Airlines and Delta, with prices starting from $229 and $682, 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 June is currently the most expensive (average of $367). 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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Top 3 airlines flying from White Plains to Chesapeake

Discover the top 3 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$118Average$158FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$159Average$199FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$193Average$382FlexibilityNo cancel feeOn-time71%

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