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Chesapeake

$183+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:08 pm
HPN
-
ORF
1 stop4h 42m
Multiple Airlines
Mon 3/28:49 am
ORF
-
HPN
2 stops26h 39m
Multiple Airlines
Deal found 2/11$240
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Thu 2/266:54 pm
HPN
-
ORF
1 stop5h 05m
American Airlines
Mon 3/26:28 pm
ORF
-
HPN
1 stop4h 31m
American Airlines
Deal found 2/11$259
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/245:16 pm
HPN
-
ORF
1 stop4h 50m
American Airlines
Tue 4/282:06 pm
ORF
-
HPN
1 stop6h 21m
American Airlines
Deal found 2/10$268
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/251:27 pm
HPN
-
ORF
2 stops21h 24m
Multiple Airlines
Sun 3/19:30 pm
ORF
-
HPN
1 stop23h 29m
Multiple Airlines
Deal found 2/10$273
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/236:30 am
HPN
-
ORF
1 stop3h 43m
American Airlines
Mon 4/272:08 pm
ORF
-
HPN
1 stop6h 19m
American Airlines
Deal found 2/10$276
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/115:15 pm
HPN
-
ORF
1 stop5h 50m
American Airlines
Wed 2/187:06 am
ORF
-
HPN
1 stop6h 01m
American Airlines
Deal found 2/10$283
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Thu 3/56:30 am
HPN
-
ORF
1 stop3h 34m
American Airlines
Wed 3/112:33 pm
ORF
-
HPN
1 stop3h 51m
American Airlines
Deal found 2/11$290
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/256:30 am
HPN
-
ORF
1 stop3h 34m
American Airlines
Sun 3/16:28 pm
ORF
-
HPN
1 stop4h 31m
American Airlines
Deal found 2/10$291
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Sun 3/18:00 am
HPN
-
ORF
1 stop14h 04m
Multiple Airlines
Thu 3/56:45 am
ORF
-
HPN
2 stops28h 43m
Multiple Airlines
Deal found 2/13$307
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 4/238:00 am
HPN
-
ORF
1 stop14h 04m
Multiple Airlines
Mon 4/276:43 pm
ORF
-
HPN
2 stops16h 45m
Multiple Airlines
Deal found 2/10$326
This American Airlines deal was found by Cheapflights users on 2/12. 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 4/245:16 pm
HPN
-
ORF
1 stop4h 50m
American Airlines
Sun 4/266:00 am
ORF
-
HPN
1 stop4h 30m
American Airlines
Deal found 2/12$333
This American Airlines deal was found by Cheapflights users on 2/13. 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 4/306:30 am
HPN
-
ORF
1 stop3h 43m
American Airlines
Sun 5/32:08 pm
ORF
-
HPN
1 stop6h 19m
American Airlines
Deal found 2/13$353

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 February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(Kiwi.com)

One-way from

$183
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$219
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. 35% potential increase in price ($182 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease ($49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 14, 2026.
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 2/26

6:54 pm-11:59 pm

1 stop5h 05m

Norfolk

Mon 3/2

6:28 pm-10:59 pm

1 stop4h 31m

$259

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 4/24

5:16 pm-10:06 pm

1 stop4h 50m

Norfolk

Tue 4/28

2:06 pm-8:27 pm

1 stop6h 21m

$268

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Wed 2/25

1:27 pm-10:51 am

2 stops21h 24m

Norfolk

Sun 3/1

9:30 pm-8:59 pm

1 stop23h 29m

$273

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 3/5

6:30 am-10:04 am

1 stop3h 34m

Norfolk

Wed 3/11

2:33 pm-6:24 pm

1 stop3h 51m

$290

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Wed 2/25

6:30 am-10:04 am

1 stop3h 34m

Norfolk

Sun 3/1

6:28 pm-10:59 pm

1 stop4h 31m

$291

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sun 3/1

8:00 am-10:04 pm

1 stop14h 04m

Norfolk

Thu 3/5

6:45 am-11:28 am

2 stops28h 43m

$307

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 4/24

5:16 pm-10:06 pm

1 stop4h 50m

Norfolk

Sun 4/26

6:00 am-10:30 am

1 stop4h 30m

$333

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 4/30

6:30 am-10:13 am

1 stop3h 43m

Norfolk

Sun 5/3

2:08 pm-8:27 pm

1 stop6h 19m

$353

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sun 3/1

12:08 pm-4:50 pm

1 stop4h 42m

Norfolk

Thu 3/5

1:09 pm-8:30 pm

1 stop7h 21m

$357

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 4/20

12:08 pm-10:58 pm

2 stops10h 50m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 16 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 $97). Flying from White Plains to Chesapeake in March 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.

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 February 14, 2026.
See what other customers who have flown with Delta and 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.
Delta
7.9
Good
8,203 reviews

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

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
7.9
Good
8,203 reviews
Delta
7.9
Good
8,203 reviews

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

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
11,288 reviews
Delta
7.9
Good
8,203 reviews

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

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.

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

    Airlines like American Airlines fly from White Plains to Chesapeake in about 5h 05m. 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, May is the cheapest month in which you can book a flight from White Plains to Chesapeake (average of $97). Flying from White Plains to Chesapeake in March 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.

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 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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$459FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$237FlexibilityNo cancel feeOn-timeN/A

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