$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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Jun 17 — Jun 241
Round-trip
1 adult, Economy
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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
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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 May 18, 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 May 18, 2026.
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/283:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sun 5/315:04 am
ORF
- HPN
1 stop4h 24m
American Airlines
Deal found 5/14![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/2010:05 am
HPN
- ORF
1 stop4h 30m
American Airlines
Tue 6/165:05 am
ORF
- HPN
1 stop4h 23m
American Airlines
Deal found 5/14![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 5/17. 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 10/217:50 pm
HPN
- ORF
1 stop3h 49m
American Airlines
Sun 10/255:54 am
ORF
- HPN
1 stop4h 40m
American Airlines
Deal found 5/17![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 5/17. 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 7/46:30 am
HPN
- ORF
1 stop5h 27m
American Airlines
Sun 7/56:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/17![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 5/13. 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 6/43:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sun 6/75:05 am
ORF
- HPN
1 stop4h 23m
American Airlines
Deal found 5/13![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/235:59 pm
HPN
- ORF
1 stop6h 03m
American Airlines
Mon 5/256:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/14![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 7/315:26 pm
HPN
- ORF
1 stop3h 45m
American Airlines
Sun 8/26:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/13![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/186:30 am
HPN
- ORF
1 stop4h 19m
American Airlines
Sat 6/205:42 am
ORF
- HPN
1 stop4h 48m
American Airlines
Deal found 5/14![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/305:59 pm
HPN
- ORF
1 stop6h 03m
American Airlines
Wed 6/35:41 pm
ORF
- HPN
1 stop5h 45m
American Airlines
Deal found 5/15![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 5/14. 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 10/147:50 pm
HPN
- ORF
1 stop3h 49m
American Airlines
Sun 10/185:54 am
ORF
- HPN
1 stop4h 40m
American Airlines
Deal found 5/14![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/2211:00 am
HPN
- ORF
1 stop6h 09m
American Airlines
Sun 5/246:00 am
ORF
- HPN
1 stop4h 45m
American Airlines
Deal found 5/15![American Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Thu 7/98:00 am
HPN
- ORF
2 stops12h 39m
Multiple Airlines
Sun 7/129:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$397
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 May 18, 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 May 18, 2026.
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 7/155:26 pm
HPN
- ORF
1 stop3h 45m
American Airlines
Sun 7/196:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/13![American Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Thu 6/118:00 am
HPN
- ORF
2 stops27h 26m
Multiple Airlines
Thu 6/189:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Fri 6/56:09 pm
HPN
- ORF
2 stops14h 57m
Breeze Airways
Sun 6/79:52 pm
ORF
- HPN
1 stop23h 08m
Breeze Airways
Deal found 5/15![Breeze Airways logo]()
$489
This Orbitz deal was found by Cheapflights users on 5/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:55 am
HPN
- ORF
2 stops10h 07m
JetBlue
Sun 7/196:00 am
ORF
- HPN
2 stops14h 38m
JetBlue
Deal found 5/13![JetBlue logo]()
$619
This American Airlines deal was found by Cheapflights users on 5/17. 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 7/46:30 am
HPN
- ORF
1 stop5h 27m
American Airlines
Sun 7/56:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/17![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 5/14. 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 7/211:00 am
HPN
- ORF
1 stop6h 12m
American Airlines
Sun 7/56:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/14![American Airlines logo]()
$393
This Orbitz deal was found by Cheapflights users on 5/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:30 am
HPN
- ORF
1 stop12h 32m
JetBlue
Sun 8/26:00 am
ORF
- HPN
2 stops14h 38m
JetBlue
Deal found 5/13![JetBlue logo]()
$631
This KAYAK deal was found by Cheapflights users on 5/14. 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 6/107:55 am
HPN
- ORF
1 stop4h 39m
American Airlines
Wed 6/105:41 pm
ORF
- HPN
1 stop5h 45m
American Airlines
Deal found 5/14![American Airlines logo]()
$539
This Orbitz deal was found by Cheapflights users on 5/17. 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 7/1710:55 am
HPN
- ORF
2 stops10h 07m
JetBlue
Sun 7/196:00 am
ORF
- HPN
2 stops14h 38m
JetBlue
Deal found 5/17![JetBlue logo]()
$644
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/186:30 am
HPN
- ORF
1 stop4h 19m
American Airlines
Sat 6/205:42 am
ORF
- HPN
2 stops11h 17m
American Airlines
Deal found 5/14![American Airlines logo]()
$651
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/3011:00 am
HPN
- ORF
1 stop10h 36m
American Airlines
Wed 6/311:52 am
ORF
- HPN
2 stops11h 34m
American Airlines
Deal found 5/15![American Airlines logo]()
$706
Last-minute flights from White Plains to ChesapeakeDiscover last-minute flight deals from White Plains to Chesapeake. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chesapeake. Data last updated May 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/1711:16 am
ORF
- HPN
1 stop3h 15m
American Airlines
Deal found 5/14![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/2010:05 am
HPN
- ORF
1 stop4h 30m
American Airlines
Tue 6/165:05 am
ORF
- HPN
1 stop4h 23m
American Airlines
Deal found 5/14![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/2211:00 am
HPN
- ORF
1 stop6h 09m
American Airlines
Sun 5/246:00 am
ORF
- HPN
1 stop4h 45m
American Airlines
Deal found 5/15![American Airlines logo]()
$393
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/235:59 pm
HPN
- ORF
1 stop6h 03m
American Airlines
Mon 5/256:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 5/14![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/283:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sun 5/315:04 am
ORF
- HPN
1 stop4h 24m
American Airlines
Deal found 5/14![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/305:59 pm
HPN
- ORF
1 stop6h 03m
American Airlines
Wed 6/35:41 pm
ORF
- HPN
1 stop5h 45m
American Airlines
Deal found 5/15![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 5/13. 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 6/43:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sun 6/75:05 am
ORF
- HPN
1 stop4h 23m
American Airlines
Deal found 5/13![American Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Thu 6/412:07 pm
HPN
- ORF
2 stops8h 10m
Multiple Airlines
Sun 6/79:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Fri 6/56:09 pm
HPN
- ORF
2 stops14h 57m
Breeze Airways
Sun 6/79:52 pm
ORF
- HPN
1 stop23h 08m
Breeze Airways
Deal found 5/15![Breeze Airways logo]()
$489
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Mon 6/156:59 pm
HPN
- ORF
1 stop4h 44m
American Airlines
Wed 6/175:41 pm
ORF
- HPN
1 stop5h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/186:30 am
HPN
- ORF
1 stop4h 19m
American Airlines
Sat 6/205:42 am
ORF
- HPN
1 stop4h 48m
American Airlines
Deal found 5/14![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 5/17. 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 6/276:59 pm
HPN
- ORF
1 stop5h 07m
American Airlines
Sat 7/45:26 am
ORF
- HPN
1 stop5h 09m
American Airlines
Deal found 5/17![American Airlines logo]()
$410
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 May 18, 2026.
Search for one-way flight options from White Plains to Chesapeake. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Sat 6/612:00 pm
HPN
- ORF
2 stops23h 11m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Fri 6/56:09 pm
HPN
- ORF
2 stops26h 08m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$162
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/66:59 pm
HPN
- ORF
1 stop5h 07m
American Airlines
Deal found 5/14![American Airlines logo]()
$254
This Justfly.com deal was found by Cheapflights users on 5/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:45 pm
HPN
- ORF
1 stop16h 28m
JetBlue
Deal found 5/17![JetBlue logo]()
$255
This Justfly.com deal was found by Cheapflights users on 5/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:29 pm
HPN
- ORF
1 stop15h 14m
JetBlue
Deal found 5/17![JetBlue logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 5/2612:27 pm
HPN
- ORF
2 stops45h 31m
Breeze Airways
Deal found 5/15![Breeze Airways logo]()
$277
This American Airlines deal was found by Cheapflights users on 5/15. 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 5/265:59 pm
HPN
- ORF
1 stop5h 42m
American Airlines
Deal found 5/15![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Sun 6/285:29 pm
HPN
- ORF
1 stop4h 24m
American Airlines
Deal found 5/13![American Airlines logo]()
$462
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 May 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (American Airlines) |
One-way from | $153 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $383 |
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 May 18, 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
Quickest round-trip
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Wed 7/15
5:26 pm-9:11 pm
1 stop3h 45m
Norfolk
Sun 7/19
6:00 am-10:30 am
1 stop4h 30m
$318
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Sat 7/4
6:30 am-11:57 am
1 stop5h 27m
Norfolk
Sun 7/5
6:00 am-10:30 am
1 stop4h 30m
$318
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 6/11
8:00 am-11:26 am
2 stops27h 26m
Norfolk
Thu 6/18
9:52 pm-9:00 pm
1 stop23h 08m
$393
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 7/2
11:00 am-5:12 pm
1 stop6h 12m
Norfolk
Sun 7/5
6:00 am-10:30 am
1 stop4h 30m
$393
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 6/5
6:09 pm-9:06 am
2 stops14h 57m
Norfolk
Sun 6/7
9:52 pm-9:00 pm
1 stop23h 08m
$489
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Wed 6/10
7:55 am-12:34 pm
1 stop4h 39m
Norfolk
Wed 6/10
5:41 pm-11:26 pm
1 stop5h 45m
$539
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Wed 7/15
10:55 am-9:02 pm
2 stops10h 07m
Norfolk
Sun 7/19
6:00 am-8:38 pm
2 stops14h 38m
$619
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 7/31
8:30 am-9:02 pm
1 stop12h 32m
Norfolk
Sun 8/2
6:00 am-8:38 pm
2 stops14h 38m
$631
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 7/17
10:55 am-9:02 pm
2 stops10h 07m
Norfolk
Sun 7/19
6:00 am-8:38 pm
2 stops14h 38m
$644
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 6/18
6:30 am-10:49 am
1 stop4h 19m
Norfolk
Sat 6/20
5:42 am-4:59 pm
2 stops11h 17m
$651
Showing 1-10 of 19 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
How much does it cost to fly round-trip from White Plains to Chesapeake?
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 May 18, 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.
Overall
7.9
Crew
8.5
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Overall
7.9
Crew
8.5
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Overall
7.9
Crew
8.5
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Reviews
1 / 20
2.0
MediocreBarney,May 2026
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.
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Alternative routes for White Plains to Chesapeake
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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
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White Plains and Chesapeake flights
Browse other White Plains and Chesapeake flight options. Last updated on May 18, 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 May 18, 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 May 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$447 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$239 | FlexibilityNo cancel fee | On-timeN/A |