$92 Find Cheap Flights from White Plains to Chesapeake

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from White Plains to Chesapeake departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals from White Plains to Chesapeake (HPN-ORF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from White Plains to Chesapeake that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from White Plains to Chesapeake

KAYAK's recommended round-trip deals from the most popular airlines that fly from White Plains to Chesapeake.
Discover the best prices for you by selecting your travel dates on KAYAK.
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American Airlines Logo
7:53 pm - 11:40 pmHPN-ORF
3h 47m1 stop
American Airlines Logo
10:13 am - 3:02 pmORF-HPN
4h 49m1 stop
$183American Airlines
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Sat, Sep 13 - Tue, Sep 16
American Airlines Logo
5:07 pm - 11:15 pmHPN-ORF
6h 08m1 stop
American Airlines Logo
5:00 am - 9:29 amORF-HPN
4h 29m1 stop
$297American Airlines
Find Deal
Thu, May 8 - Sun, May 11
American Airlines Logo
6:30 am - 11:06 amHPN-ORF
4h 36m1 stop
American Airlines Logo
5:49 am - 10:42 amORF-HPN
4h 53m1 stop
$298American Airlines
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Sat, Apr 19 - Mon, Apr 28
American Airlines Logo
6:30 am - 9:26 amHPN-ORF
2h 56m1 stop
American Airlines Logo
6:00 am - 4:59 pmORF-HPN
10h 59m2 stops
$395American Airlines
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Wed, Jul 2 - Sat, Jul 5
American Airlines Logo
11:29 am - 5:25 pmHPN-ORF
5h 56m2 stops
American Airlines Logo
5:15 am - 9:22 amORF-HPN
4h 07m1 stop
$571American Airlines
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Sat, Sep 13 - Tue, Sep 16
 Logo
8:10 am - 10:29 amHPN-ORF
26h 19m2 stops
 Logo
12:13 pm - 11:21 amORF-HPN
23h 08m2 stops
Thu, May 8 - Sun, May 11
 Logo
8:10 am - 10:29 amHPN-ORF
26h 19m2 stops
 Logo
3:11 pm - 11:21 amORF-HPN
20h 10m3 stops
Thu, May 8 - Sun, May 11
Breeze Airways Logo
1:23 pm - 5:21 pmHPN-ORF
27h 58m2 stops
Breeze Airways Logo
9:40 pm - 12:51 pmORF-HPN
15h 11m1 stop
$825Breeze Airways
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Fri, Jun 20 - Sun, Jun 22
Breeze Airways Logo
1:23 pm - 5:21 pmHPN-ORF
27h 58m2 stops
Breeze Airways Logo
9:40 pm - 8:59 pmORF-HPN
23h 19m3 stops
$937Breeze Airways
Find Deal
Fri, Jun 20 - Sun, Jun 22
Breeze Airways Logo
1:23 pm - 5:21 pmHPN-ORF
27h 58m2 stops
Breeze Airways Logo
1:51 pm - 8:59 pmORF-HPN
31h 08m2 stops
$940Breeze Airways
Find Deal
Fri, Jun 20 - Sun, Jun 22

Good to know

Low season

May

High season

August

Cheapest flight

$92
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from White Plains to Norfolk

When to book flights from White Plains to Chesapeake

Are your dates flexible? Find out the best times to travel from White Plains to Chesapeake based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from White Plains to Chesapeake

  • Which airports will I be using when flying from White Plains to Chesapeake?

    When flying out of White Plains you’ll be using White Plains Westchester County. Chesapeake does not have its own airport so you’ll be flying into nearby Norfolk airport, which is 10.1 mi away.

  • How long does a flight from White Plains to Chesapeake take?

    There are no direct flights covering the 318 miles separating White Plains and Chesapeake but indirect flights take around 2h 56m.

  • What’s the cheapest day of the week to fly between White Plains and Chesapeake?

    Consider leaving on a Saturday and avoid Wednesdays if you are looking for the best rates. For your return to White Plains, you’ll find the best rates on Wednesdays and the most expensive ones on Tuesdays.

  • How does KAYAK find such low prices on flights from White Plains to Chesapeake?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from White Plains to Chesapeake.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from White Plains to Chesapeake?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chesapeake from White Plains is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from White Plains to Chesapeake?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chesapeake with an airline and back to White Plains with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from White Plains to Chesapeake?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chesapeake from White Plains up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from White Plains to Chesapeake?

    In the last 72 hours, the cheapest one-way ticket between White Plains and Chesapeake found on KAYAK was with Breeze Airways for $92. American Airlines offered a round-trip connection from $183 and Breeze Airways from $825.

See more FAQs

Top tips for finding cheap flights from White Plains to Chesapeake

  • There is no airport in Chesapeake. Instead, you’ll be flying into Norfolk Airport when flying between White Plains and Chesapeake.
  • High season is considered to be March, April and May. The cheapest month to fly is September.

Top airlines flying from White Plains to Chesapeake

Need help choosing which airline to fly with from White Plains to Chesapeake? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Breeze AirwaysOverall score based on 157 reviews
8.3Boarding
6.7Food
8.8Crew
6.6Entertainment
8.2Comfort
Airline reviews

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

2.0 MediocreAnonymous, Mar 2025TPA - PVD
Read more Breeze Airways reviews

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

I was surprised at how wonderful it was. The aircraft was clean. The crew was warm and welcoming and as a result the passengers were friendly. One warning the only free thing was water. I kind of liked picking wet hat I was willing to pay for and what I was willing to skip.

The flight wasn’t big on frills, which is fine with me. I flew into Islip MacArthur Airport, which saved me from having to go through LaGuardia to visit friends on Long Island. It was inexpensive and super convenient!

Great experience! This was my first time flying with them and I could not have been happier.

Airplane was newer and very clean, lots of space. Crew was great. There was no food and entertainment but that was expected so not an issue.

I like that the price is right! The airplane is clean and the staff is friendly. We landed safely, so that is always a gold star in my book! Great job!

Purposely delayed the flight by 2 hours and 58 minutes so that they would not have to give me the FAA mandated refund for a delay of 3 hours. Offered flight credit instead. All that is offered on board is water and coffee, everything else costs money. They charge you for carry on and checked bags. Would not fly again.

nice flight. no frills but a 3 hour flight I caught up on my sleep. Stan O

First time flying Breeze, was very impressed. I will use Breeze again.

The flight was rescheduled and canceled. I had to go with another airline last minute to honor my school commitment. The reimbursement is a joke -$150 for a one way plane ticket.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

I got bumped due to weight restrictions even tho there were empty seats on my flight. I got put on an other flight with a stopover. My flight that originally was going to take 5-6 hours ever up being 14+ hours and my luggage arrived to my destination without me because I was made to check in my luggage on my original flight when I was deemed ok to board only to be asked to deplane. Worst flight experience.

I was pleasantly surprised with an upgrade at boarding. I finally had a mostly gluten free food options and a very attentive attendant.

It was good. It’s been a long time since my wife and I fly any where and things have changed. Our trip was to see our new grandson. We fly economy and that was not good for my bad back. It was a quick flight but uncomfortable.

Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.

AA had a nationwide tech glitch today and after two connections snd hours of delay, I arrived 7 hours late to my destination

The plane was very warm and the crew turned on the lights for the entire snack service.

Due to an issue with the plane. We waited almost 2 hours to take off. The service reps were great. We had a longer layover but was able to run for it and catch our flight. This also happened on our way out. Maybe the planes need a good look over. The people who work front desk and flight attendants are the best

Everything you need to know for your flight from White Plains to Chesapeake

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