$153+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
May 2 — May 91
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from White Plains to Chesapeake with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from White Plains to Chesapeake
Cheapest
Best
Last-minute
One-way
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 April 2, 2026.
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 2, 2026.
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Wed 4/226:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Wed 4/296:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/29![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Mon 4/206:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Mon 4/275:00 am
ORF
- HPN
1 stop4h 29m
American Airlines
Deal found 3/28![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/28. 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 5/273:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sat 5/305:17 am
ORF
- HPN
1 stop5h 13m
American Airlines
Deal found 3/28![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/176:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Mon 4/205:00 am
ORF
- HPN
1 stop4h 29m
American Airlines
Deal found 3/30![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 8/173:29 pm
HPN
- ORF
1 stop3h 28m
American Airlines
Sat 8/227:28 pm
ORF
- HPN
1 stop3h 56m
American Airlines
Deal found 3/30![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/147:30 am
HPN
- ORF
1 stop4h 18m
American Airlines
Sat 4/186:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/30![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/87:49 am
HPN
- ORF
1 stop6h 28m
American Airlines
Tue 4/142:06 pm
ORF
- HPN
1 stop6h 21m
American Airlines
Deal found 4/1![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 3/28. 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 7/83:23 pm
HPN
- ORF
1 stop6h 29m
American Airlines
Sun 7/126:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/28![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Tue 5/127:30 am
HPN
- ORF
1 stop4h 18m
American Airlines
Mon 5/182:08 pm
ORF
- HPN
1 stop6h 19m
American Airlines
Deal found 3/28![American Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/188:00 am
HPN
- ORF
2 stops27h 26m
Multiple Airlines
Thu 6/259:52 pm
ORF
- HPN
1 stop22h 57m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/17:47 am
HPN
- ORF
1 stop6h 29m
American Airlines
Sat 4/46:15 pm
ORF
- HPN
1 stop4h 44m
American Airlines
Deal found 3/30![American Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/156:30 am
HPN
- ORF
1 stop3h 46m
American Airlines
Sun 5/176:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 4/1![American Airlines logo]()
$373
Best flights from White Plains to ChesapeakeDiscover 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 April 2, 2026.
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 April 2, 2026.
This American Airlines deal was found by Cheapflights users on 3/30. 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 46m
American Airlines
Tue 4/285:13 pm
ORF
- HPN
1 stop5h 47m
American Airlines
Deal found 3/30![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Tue 4/218:00 am
HPN
- ORF
2 stops24h 00m
Breeze Airways
Thu 4/231:09 pm
ORF
- HPN
1 stop7h 21m
Breeze Airways
Deal found 3/31![Breeze Airways logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/168:00 am
HPN
- ORF
1 stop14h 04m
Multiple Airlines
Sun 4/1912:32 pm
ORF
- HPN
2 stops22h 56m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 4/217:30 am
HPN
- ORF
1 stop4h 18m
American Airlines
Sat 4/256:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/31![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 8/173:29 pm
HPN
- ORF
1 stop3h 28m
American Airlines
Sat 8/227:28 pm
ORF
- HPN
1 stop3h 56m
American Airlines
Deal found 3/30![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/29. 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 7/186:30 am
HPN
- ORF
1 stop4h 29m
American Airlines
Sat 7/255:42 am
ORF
- HPN
1 stop4h 48m
American Airlines
Deal found 3/29![American Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Sun 6/286:30 am
HPN
- ORF
1 stop4h 20m
American Airlines
Fri 7/105:42 am
ORF
- HPN
1 stop4h 48m
American Airlines
Deal found 4/1![American Airlines logo]()
$454
This KAYAK deal was found by Cheapflights users on 3/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:00 am
HPN
- ORF
1 stop25h 20m
Breeze Airways
Sat 8/2210:31 pm
ORF
- HPN
2 stops22h 28m
Breeze Airways
Deal found 3/30![Breeze Airways logo]()
$654
This American Airlines deal was found by Cheapflights users on 3/28. 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 5/275:29 pm
HPN
- ORF
1 stop4h 24m
American Airlines
Sat 5/307:06 am
ORF
- HPN
2 stops11h 22m
American Airlines
Deal found 3/28![American Airlines logo]()
$480
This Booking.com deal was found by Cheapflights users on 3/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:00 am
HPN
- ORF
2 stops24h 26m
Breeze Airways
Mon 5/185:24 pm
ORF
- HPN
2 stops18h 03m
Breeze Airways
Deal found 3/28![Breeze Airways logo]()
$667
Last-minute flights from White Plains to ChesapeakeDiscover last-minute flight deals from White Plains to Chesapeake. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chesapeake. Data last updated April 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/17:47 am
HPN
- ORF
1 stop6h 29m
American Airlines
Sat 4/46:15 pm
ORF
- HPN
1 stop4h 44m
American Airlines
Deal found 3/30![American Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Wed 4/15:30 pm
HPN
- ORF
1 stop5h 32m
American Airlines
Sun 4/56:14 am
ORF
- HPN
1 stop4h 45m
American Airlines
Deal found 3/29![American Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/26:00 am
HPN
- ORF
1 stop4h 06m
American Airlines
Sat 4/410:51 am
ORF
- HPN
1 stop4h 08m
American Airlines
Deal found 3/30![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/87:49 am
HPN
- ORF
1 stop6h 28m
American Airlines
Tue 4/142:06 pm
ORF
- HPN
1 stop6h 21m
American Airlines
Deal found 4/1![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/147:30 am
HPN
- ORF
1 stop4h 18m
American Airlines
Sat 4/186:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/30![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/176:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Mon 4/205:00 am
ORF
- HPN
1 stop4h 29m
American Airlines
Deal found 3/30![American Airlines logo]()
$294
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:59 pm
HPN
- ORF
1 stop12h 13m
JetBlue
Fri 4/2410:10 am
ORF
- HPN
1 stop12h 26m
JetBlue
Deal found 3/29![JetBlue logo]()
$415
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Mon 4/206:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Mon 4/275:00 am
ORF
- HPN
1 stop4h 29m
American Airlines
Deal found 3/28![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Wed 4/226:59 pm
HPN
- ORF
1 stop5h 00m
American Airlines
Wed 4/296:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 3/29![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Tue 5/127:30 am
HPN
- ORF
1 stop4h 18m
American Airlines
Mon 5/182:08 pm
ORF
- HPN
1 stop6h 19m
American Airlines
Deal found 3/28![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/156:30 am
HPN
- ORF
1 stop3h 46m
American Airlines
Sun 5/176:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 4/1![American Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 3/28. 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 5/273:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sat 5/305:17 am
ORF
- HPN
1 stop5h 13m
American Airlines
Deal found 3/28![American Airlines logo]()
$292
One-way flights from White Plains to ChesapeakeSearch for one-way flight options from White Plains to Chesapeake. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
Search for one-way flight options from White Plains to Chesapeake. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:27 pm
HPN
- ORF
2 stops8h 34m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sun 6/286:30 am
HPN
- ORF
1 stop4h 20m
American Airlines
Deal found 3/31![American Airlines logo]()
$251
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:48 am
HPN
- ORF
1 stop6h 25m
JetBlue
Deal found 4/1![JetBlue logo]()
$254
This Orbitz deal was found by Cheapflights users on 3/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:59 pm
HPN
- ORF
1 stop12h 13m
JetBlue
Deal found 3/30![JetBlue logo]()
$264
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Tue 6/166:59 pm
HPN
- ORF
1 stop4h 42m
American Airlines
Deal found 3/29![American Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/87:49 am
HPN
- ORF
1 stop4h 53m
American Airlines
Deal found 4/1![American Airlines logo]()
$351
This Gotogate deal was found by Cheapflights users on 4/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:00 am
HPN
- ORF
2 stops24h 53m
Breeze Airways
Deal found 4/1![Breeze Airways logo]()
$419
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:00 pm
HPN
- ORF
2 stops9h 45m
Breeze Airways
Deal found 4/1![Breeze Airways logo]()
$424
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:00 am
HPN
- ORF
2 stops29h 29m
Breeze Airways
Deal found 4/1![Breeze Airways logo]()
$440
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:00 am
HPN
- ORF
1 stop14h 04m
Breeze Airways
Deal found 3/31![Breeze Airways logo]()
$470
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 April 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $256 (American Airlines) |
One-way from | $153 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $199 |
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 2, 2026.
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
Cheapest round-trip
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 4/23
6:30 am-10:16 am
1 stop3h 46m
Norfolk
Tue 4/28
5:13 pm-11:00 pm
1 stop5h 47m
$269
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Tue 4/21
7:30 am-11:48 am
1 stop4h 18m
Norfolk
Sat 4/25
6:00 am-10:30 am
1 stop4h 30m
$269
Quickest round-trip
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Mon 8/17
3:29 pm-6:57 pm
1 stop3h 28m
Norfolk
Sat 8/22
7:28 pm-11:24 pm
1 stop3h 56m
$308
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Sat 7/18
6:30 am-10:59 am
1 stop4h 29m
Norfolk
Sat 7/25
5:42 am-10:30 am
1 stop4h 48m
$391
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Tue 4/21
8:00 am-8:00 am
2 stops24h 00m
Norfolk
Thu 4/23
1:09 pm-8:30 pm
1 stop7h 21m
$429
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Sun 6/28
6:30 am-10:50 am
1 stop4h 20m
Norfolk
Fri 7/10
5:42 am-10:30 am
1 stop4h 48m
$454
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Wed 5/27
5:29 pm-9:53 pm
1 stop4h 24m
Norfolk
Sat 5/30
7:06 am-6:28 pm
2 stops11h 22m
$480
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 4/16
8:00 am-10:04 pm
1 stop14h 04m
Norfolk
Sun 4/19
12:32 pm-11:28 am
2 stops22h 56m
$486
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Mon 8/17
8:00 am-9:20 am
1 stop25h 20m
Norfolk
Sat 8/22
10:31 pm-8:59 pm
2 stops22h 28m
$654
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Tue 5/12
8:00 am-8:26 am
2 stops24h 26m
Norfolk
Mon 5/18
5:24 pm-11:27 am
2 stops18h 03m
$667
Showing 1-10 of 20 resultsSorted by cheapest first
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.
HPN-ORF
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
HPN-C6E
HPN-ORF
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 February 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 April 2, 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.
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
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.
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
Complete your trip
Flights by cabin class
Other flight options
Other flights from White Plains
Popular flights
Top destinations
Alternative routes for White Plains to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from White Plains to Chesapeake by cabin class
Find flights from White Plains to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
White Plains and Chesapeake flights
Browse other White Plains and Chesapeake flight options. Last updated on April 2, 2026.
Other flights from White Plains
Browse through other flights departing from White Plains. Flights are based on user searches made on Cheapflights and were last updated on April 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
White Plains to Chesapeake flights
Consider these flights traveling from White Plains to Chesapeake.
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 April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$237 | FlexibilityNo cancel fee | On-timeN/A |