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

$85 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 JetBlue, with prices starting from $211 and $316, respectively.

What is the cheapest day to fly from White Plains to Chesapeake?

Travelers seeking maximum savings on their White Plains to Chesapeake flight should consider departing on Friday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

How far in advance should I book a flight from White Plains to Chesapeake?

To save up to 44% on this flight, we recommend booking at least 59 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from White Plains to Chesapeake from $209 1-2 weeks out and tickets from $283 for flights departing within the next 72 hours.

What is the cheapest month to fly from White Plains to Chesapeake?

The best pricing can be found in the month of September. Prices to Chesapeake from White Plains average $240. You can even find prices in September for less than $240, as users have found deals to Chesapeake from as low as $164. The month of December appears to be one of the more expensive times to travel to Chesapeake from White Plains. Flying in the targeted month can save you up to 24%.

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.

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.

$85+ Flights from White Plains to Chesapeake

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Cheap flight deals from White Plains to Chesapeake

Round-trip from	$183 (American Airlines)
One-way from	$85 (Priceline)
Popular in	May
Cheapest in	January
Average price	$302

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. 5% potential increase in price ($14 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 29, 2025.

sáb. 9/136:30 amHPN - ORF

1 stop2h 56mAmerican Airlines

mar. 9/167:04 pmORF - HPN

1 stop4h 22mAmerican Airlines

Deal found 7/29

$183

jue. 8/2812:05 pmHPN - ORF

1 stop5h 00mBreeze Airways

mar. 9/23:58 pmORF - HPN

1 stop4h 32mBreeze Airways

Deal found 7/28

$343

jue. 9/181:19 pmHPN - ORF

3 stops23h 51mMultiple Airlines

jue. 9/255:38 pmORF - HPN

2 stops17h 50mMultiple Airlines

Deal found 7/28

$458

Best flights from White Plains to Chesapeake
Discover carefully curated flight deals from White Plains to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated julio 29, 2025.

sáb. 9/136:30 amHPN - ORF

1 stop2h 56mAmerican Airlines

mar. 9/167:04 pmORF - HPN

1 stop4h 22mAmerican Airlines

Deal found 7/29

$183

jue. 8/2812:05 pmHPN - ORF

1 stop5h 00mBreeze Airways

mar. 9/23:58 pmORF - HPN

1 stop4h 32mBreeze Airways

Deal found 7/28

$343

jue. 9/181:19 pmHPN - ORF

3 stops23h 51mMultiple Airlines

jue. 9/255:38 pmORF - HPN

2 stops17h 50mMultiple Airlines

Deal found 7/28

$458

Last-minute flights from White Plains to Chesapeake
Discover last-minute flight deals from White Plains to Chesapeake. Data last updated julio 29, 2025 and is based on user searches.

dom. 8/36:51 pmHPN - ORF

1 stop4h 50mAmerican Airlines

mié. 8/139:50 amORF - HPN

1 stop4h 49mAmerican Airlines

Deal found 7/28

$246

dom. 8/38:10 amHPN - ORF

3 stops24h 27mMultiple Airlines

mié. 8/135:20 pmORF - HPN

2 stops18h 05mMultiple Airlines

Deal found 7/28

$772

vie. 8/81:23 pmHPN - ORF

2 stops27h 58mBreeze Airways

dom. 8/109:40 pmORF - HPN

1 stop15h 11mBreeze Airways

Deal found 7/28

$723

mié. 8/138:10 amHPN - ORF

2 stops13h 39mMultiple Airlines

dom. 8/175:34 pmORF - HPN

2 stops17h 47mMultiple Airlines

Deal found 7/29

$500

sáb. 8/236:59 pmHPN - ORF

1 stop4h 59mAmerican Airlines

mié. 8/276:10 amORF - HPN

1 stop6h 50mAmerican Airlines

Deal found 7/27

$212

jue. 8/2812:05 pmHPN - ORF

1 stop5h 00mBreeze Airways

mar. 9/23:58 pmORF - HPN

1 stop4h 32mBreeze Airways

Deal found 7/28

$343

One-way flights from White Plains to Chesapeake
Search for one-way flight options from White Plains to Chesapeake. Find affordable one-way fares based on user searches. Data last updated julio 29, 2025.

dom. 9/78:00 amHPN - ORF

1 stop8h 25mBreeze Airways

Deal found 7/28

$85

mié. 8/277:47 amHPN - ORF

1 stop6h 11mAmerican Airlines

Deal found 7/27

$211

jue. 8/288:10 amHPN - ORF

3 stops28h 34mMultiple Airlines

Deal found 7/27

$278

mié. 8/278:50 pmHPN - ORF

2 stops21h 00mJetBlue

Deal found 7/27

$316

sáb. 8/25:00 pmHPN - ORF

2 stops18h 33mDelta

Deal found 7/29

$533

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

sáb. 9/13

6:30 am-9:26 am

1 stop2h 56m

Norfolk

mar. 9/16

7:04 pm-11:26 pm

1 stop4h 22m

$183

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

jue. 8/28

12:05 pm-5:05 pm

1 stop5h 00m

Norfolk

mar. 9/2

3:58 pm-8:30 pm

1 stop4h 32m

$343

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

jue. 9/18

1:19 pm-1:10 pm

3 stops23h 51m

Norfolk

jue. 9/25

5:38 pm-11:28 am

2 stops17h 50m

$458

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 9/7

8:00 am-4:25 pm

1 stop8h 25m

$85

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

mié. 8/27

7:47 am-1:58 pm

1 stop6h 11m

$211

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

jue. 8/28

8:10 am-12:44 pm

3 stops28h 34m

$278

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

mié. 8/27

8:50 pm-5:50 pm

2 stops21h 00m

$316

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

sáb. 8/2

5:00 pm-11:33 am

2 stops18h 33m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 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?

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

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

7,979 reviews

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

7,979 reviews

Delta

8.0

Very good

7,979 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Breeze Airways

8.0

Very good

190 reviews

Delta

8.0

Very good

7,979 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

JetBlue

7.3

Good

2,913 reviews

Delta

8.0

Very good

7,979 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,979 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Related info for your journey

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?
$85 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 JetBlue, with prices starting from $211 and $316, 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

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Chesapeake car rentals

Richmond Byrd Intl Airport car rentals

Norfolk Airport car rentals

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Top 2 airlines flying from White Plains to Chesapeake

Airline	Cheapest	Average	Flexibility	On-time
Breeze Airways	Cheapest$118	Average$278	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$158	Average$368	FlexibilityNo cancel fee	On-time71%

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$85+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from White Plains to Chesapeake with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

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 29, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from White Plains to Chesapeake

Cheapest flights from White Plains to ChesapeakeExplore 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 29, 2025.

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 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from White Plains to Chesapeake that are best for you.

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.

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?

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 29, 2025.

Reviews of airlines servicing Chesapeake

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.

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?

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

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for White Plains to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from White Plains to Chesapeake

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Book with Flexibility

Travel Smart

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 29, 2025.