$154 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 5/25. 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from White Plains to Chesapeake.
Discover the best prices and deals for you by selecting your travel dates.
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5:03 pm - 11:04 pmHPN-ORF
6h 01m1 stop
3:16 pm - 8:16 pmORF-HPN
5h 00m1 stop
$313American Airlines
Find Deal
Thu, Mar 20 - Mon, Mar 24
8:00 am - 8:39 amHPN-ORF
24h 39m2 stops
3:00 pm - 11:15 amORF-HPN
20h 15m2 stops
$368Breeze Airways
Find Deal
Wed, Feb 19 - Sun, Feb 23
1:29 pm - 8:37 amHPN-ORF
19h 08m2 stops
9:40 pm - 12:51 pmORF-HPN
15h 11m1 stop
$393Breeze Airways
Find Deal
Tue, Apr 29 - Thu, May 1
1:29 pm - 8:37 amHPN-ORF
19h 08m2 stops
8:59 pm - 12:51 pmORF-HPN
15h 52m2 stops
Tue, Apr 29 - Thu, May 1
5:09 pm - 10:54 pmHPN-ORF
5h 45m1 stop
5:04 am - 9:29 amORF-HPN
4h 25m1 stop
$423American Airlines
Find Deal
Wed, Feb 19 - Sun, Feb 23
1:29 pm - 8:37 amHPN-ORF
19h 08m2 stops
3:11 pm - 12:51 pmORF-HPN
21h 40m3 stops
$425Breeze Airways
Find Deal
Tue, Apr 29 - Thu, May 1
6:35 pm - 11:53 pmHPN-ORF
5h 18m1 stop
6:32 am - 10:48 amORF-HPN
4h 16m1 stop
$427American Airlines
Find Deal
Fri, Mar 14 - Mon, Mar 17
6:36 am - 9:34 amHPN-ORF
2h 58m1 stop
7:03 pm - 11:22 pmORF-HPN
4h 19m1 stop
$457American Airlines
Find Deal
Fri, Jun 27 - Sun, Jun 29
6:00 am - 12:11 pmHPN-ORF
6h 11m1 stop
4:19 pm - 10:13 pmORF-HPN
5h 54m1 stop
$1,401Delta
Find Deal
Wed, Mar 5 - Wed, Mar 5
6:00 am - 12:11 pmHPN-ORF
6h 11m1 stop
4:19 pm - 10:13 pmORF-HPN
5h 54m1 stop
$1,461Delta
Find Deal
Thu, Mar 6 - Thu, Mar 6

Good to know

Low season

June

High season

August

Cheapest flight

$154
Best time to beat the crowds but there is an average 11% increase 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 58m.

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

    Consider leaving on a Thursday 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 Fridays.

  • 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 $154. American Airlines offered a round-trip connection from $313 and Breeze Airways from $368.

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 146 reviews
6.5Entertainment
6.7Food
8.8Crew
8.3Boarding
8.2Comfort
Airline reviews

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.

10.0 ExcellentMike, Feb 2025MHT - MCO
Read more Breeze Airways reviews

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.

The flight itself was A+ but boarding sucked. They boarded all passengers at once, and as a result I did not get to put my carryon in an overhead bin near me so I had to wait till near the end to deplane.

Really appreciate the great crew and pilot for keeping us informed about everything going on, updates, etc. It's so reassuring just to know (for example) why there might be a delay, etc. I'm very satisfied with the excellent service.

This was my first time flying Breeze. The plane was one of the nicer planes I have been on. The flight attendants were friendly and helpful. I will fly them again.

Well, Kayak should have communicated with Breeze that when I purchased the ticket, Kayak should have relayed that I had one carry on as part of my ticket purchase. So, KAYAK, tell the airlines!

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

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The boarding process was incredibly slow, as was deplaning. They started beverage service and there was an extremely small amount of turbulence, so they discontinued it. They said they’d resume if possible, but even thought the rest of the flight was perfectly smooth, they didn’t bother. Getting our checked bags took longer than I’ve ever waited and they couldn’t even tell us which carousel they were coming out on, so everyone was running back and forth for 30 minutes.

It was really good. The boarding was good and smooth. They even checked our carry ons if you wanted to without any charge.

Flight was delayed , waited in the tarmac for 3 hours and then came back and was cancelled

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

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