$146+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Aug 2 — Aug 91
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
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
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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 July 3, 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 July 3, 2026.
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 7/215:26 pm
HPN
- ORF
1 stop4h 31m
American Airlines
Tue 8/1811:40 am
ORF
- HPN
1 stop3h 11m
American Airlines
Deal found 7/1![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/76:51 pm
HPN
- ORF
1 stop4h 17m
American Airlines
Mon 8/105:42 pm
ORF
- HPN
1 stop5h 47m
American Airlines
Deal found 7/3![American Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 6/29. 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 8/86:51 pm
HPN
- ORF
1 stop4h 17m
American Airlines
Fri 8/146:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 6/29![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/2710:00 am
HPN
- ORF
1 stop5h 08m
American Airlines
Sun 8/305:03 am
ORF
- HPN
1 stop4h 26m
American Airlines
Deal found 6/30![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/1411:00 am
HPN
- ORF
1 stop6h 12m
American Airlines
Sat 7/186:00 am
ORF
- HPN
1 stop4h 56m
American Airlines
Deal found 6/29![American Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 am
HPN
- ORF
2 stops15h 53m
Multiple Airlines
Sun 8/309:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Sun 9/612:07 pm
HPN
- ORF
1 stop5h 06m
Multiple Airlines
Sun 9/1312:57 pm
ORF
- HPN
2 stops32h 03m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/146:30 am
HPN
- ORF
1 stop4h 40m
American Airlines
Fri 8/216:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/1![American Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:00 am
HPN
- ORF
1 stop25h 20m
Multiple Airlines
Fri 8/712:10 pm
ORF
- HPN
2 stops23h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/308:00 am
HPN
- ORF
2 stops28h 25m
Multiple Airlines
Thu 9/39:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/13:22 pm
HPN
- ORF
1 stop6h 31m
American Airlines
Sun 7/56:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 6/29![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/206:59 pm
HPN
- ORF
1 stop4h 46m
American Airlines
Sat 7/256:00 am
ORF
- HPN
1 stop4h 56m
American Airlines
Deal found 6/30![American Airlines logo]()
$367
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 July 3, 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 July 3, 2026.
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 7/2811:00 am
HPN
- ORF
1 stop6h 12m
American Airlines
Tue 8/1811:40 am
ORF
- HPN
1 stop3h 11m
American Airlines
Deal found 7/1![American Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/2812:27 pm
HPN
- ORF
2 stops8h 12m
Multiple Airlines
Thu 7/309:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/16:59 pm
HPN
- ORF
1 stop5h 19m
American Airlines
Sat 8/86:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/2![American Airlines logo]()
$283
This Gotogate deal was found by Cheapflights users on 7/3. 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.
Fri 8/288:00 am
HPN
- ORF
2 stops24h 26m
Breeze Airways
Mon 8/3112:04 pm
ORF
- HPN
2 stops23h 23m
Breeze Airways
Deal found 7/3![Breeze Airways logo]()
$589
This Expedia deal was found by Cheapflights users on 6/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:30 am
HPN
- ORF
1 stop12h 39m
JetBlue
Mon 9/73:35 pm
ORF
- HPN
2 stops20h 22m
JetBlue
Deal found 6/28![JetBlue logo]()
$593
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:29 am
HPN
- ORF
1 stop9h 21m
Delta
Mon 7/2012:33 pm
ORF
- HPN
1 stop9h 52m
Delta
Deal found 6/28![Delta logo]()
$635
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/146:30 am
HPN
- ORF
1 stop4h 40m
American Airlines
Fri 8/216:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/1![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 9/47:55 am
HPN
- ORF
1 stop7h 13m
American Airlines
Mon 9/711:40 am
ORF
- HPN
1 stop3h 11m
American Airlines
Deal found 6/28![American Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:00 am
HPN
- ORF
1 stop25h 20m
Multiple Airlines
Thu 7/1612:10 pm
ORF
- HPN
2 stops29h 19m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$464
This Booking.com deal was found by Cheapflights users on 6/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:08 pm
HPN
- ORF
2 stops7h 58m
Breeze Airways
Mon 9/286:00 am
ORF
- HPN
2 stops29h 27m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$614
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/163:22 pm
HPN
- ORF
1 stop6h 26m
American Airlines
Fri 8/216:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/1![American Airlines logo]()
$487
Last-minute flights from White Plains to ChesapeakeDiscover last-minute flight deals from White Plains to Chesapeake. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chesapeake. Data last updated July 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Fri 7/31:43 pm
HPN
- ORF
1 stop4h 11m
American Airlines
Sun 7/56:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 6/29![American Airlines logo]()
$393
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/1411:00 am
HPN
- ORF
1 stop6h 12m
American Airlines
Sat 7/186:00 am
ORF
- HPN
1 stop4h 56m
American Airlines
Deal found 6/29![American Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 7/2. 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 7/176:59 pm
HPN
- ORF
1 stop4h 46m
American Airlines
Tue 7/216:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/2![American Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/206:59 pm
HPN
- ORF
1 stop4h 46m
American Airlines
Sat 7/256:00 am
ORF
- HPN
1 stop4h 56m
American Airlines
Deal found 6/30![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 7/215:26 pm
HPN
- ORF
1 stop4h 31m
American Airlines
Tue 8/1811:40 am
ORF
- HPN
1 stop3h 11m
American Airlines
Deal found 7/1![American Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:00 am
HPN
- ORF
1 stop25h 20m
Multiple Airlines
Fri 8/712:10 pm
ORF
- HPN
2 stops23h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/76:51 pm
HPN
- ORF
1 stop4h 17m
American Airlines
Mon 8/105:42 pm
ORF
- HPN
1 stop5h 47m
American Airlines
Deal found 7/3![American Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 6/29. 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 8/86:51 pm
HPN
- ORF
1 stop4h 17m
American Airlines
Fri 8/146:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 6/29![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/146:30 am
HPN
- ORF
1 stop4h 40m
American Airlines
Fri 8/216:00 am
ORF
- HPN
1 stop4h 30m
American Airlines
Deal found 7/1![American Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/2710:00 am
HPN
- ORF
1 stop5h 08m
American Airlines
Sun 8/305:03 am
ORF
- HPN
1 stop4h 26m
American Airlines
Deal found 6/30![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 am
HPN
- ORF
2 stops15h 53m
Multiple Airlines
Sun 8/309:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/308:00 am
HPN
- ORF
2 stops28h 25m
Multiple Airlines
Thu 9/39:52 pm
ORF
- HPN
1 stop23h 08m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$349
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 July 3, 2026.
Search for one-way flight options from White Plains to Chesapeake. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Mon 9/78:00 am
HPN
- ORF
1 stop25h 20m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Sun 9/68:00 am
HPN
- ORF
2 stops28h 25m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Thu 7/308:00 am
HPN
- ORF
2 stops27h 15m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:00 pm
HPN
- ORF
2 stops23h 15m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Fri 10/97:40 pm
HPN
- ORF
2 stops16h 22m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/1412:27 pm
HPN
- ORF
2 stops32h 12m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Sun 9/612:07 pm
HPN
- ORF
1 stop5h 06m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Mon 9/71:24 pm
HPN
- ORF
3 stops23h 01m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Sat 7/1812:00 pm
HPN
- ORF
2 stops23h 15m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$221
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 July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (American Airlines) |
One-way from | $146 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $282 |
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 July 3, 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
Tue 7/28
11:00 am-5:12 pm
1 stop6h 12m
Norfolk
Tue 8/18
11:40 am-2:51 pm
1 stop3h 11m
$283
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Sat 8/1
6:59 pm-12:18 am
1 stop5h 19m
Norfolk
Sat 8/8
6:00 am-10:30 am
1 stop4h 30m
$283
Quickest round-trip
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 8/14
6:30 am-11:10 am
1 stop4h 40m
Norfolk
Fri 8/21
6:00 am-10:30 am
1 stop4h 30m
$343
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 9/4
7:55 am-3:08 pm
1 stop7h 13m
Norfolk
Mon 9/7
11:40 am-2:51 pm
1 stop3h 11m
$349
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Tue 7/28
12:27 pm-8:39 pm
2 stops8h 12m
Norfolk
Thu 7/30
9:52 pm-9:00 pm
1 stop23h 08m
$394
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Mon 7/13
8:00 am-9:20 am
1 stop25h 20m
Norfolk
Thu 7/16
12:10 pm-5:29 pm
2 stops29h 19m
$464
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Sun 8/16
3:22 pm-9:48 pm
1 stop6h 26m
Norfolk
Fri 8/21
6:00 am-10:30 am
1 stop4h 30m
$487
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 8/28
8:00 am-8:26 am
2 stops24h 26m
Norfolk
Mon 8/31
12:04 pm-11:27 am
2 stops23h 23m
$589
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Fri 9/4
8:30 am-9:09 pm
1 stop12h 39m
Norfolk
Mon 9/7
3:35 pm-11:57 am
2 stops20h 22m
$593
White PlainsNorfolk
HPN - ORF
HPNORF
White Plains Westchester County
Thu 9/24
1:08 pm-9:06 pm
2 stops7h 58m
Norfolk
Mon 9/28
6:00 am-11:27 am
2 stops29h 27m
$614
Showing 1-10 of 23 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
No data available for this route at this time. Please check back soon.
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 July 3, 2026.
See what other customers who have flown with 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
7.1
Comfort
7.2
Food
6.4
Crew
7.9
Boarding
7.5
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreHiram K,Sep 2023
JFK - CLT
Overall
7.1
Comfort
7.2
Food
6.4
Crew
7.9
Boarding
7.5
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreHiram K,Sep 2023
JFK - CLT
Related info for your journey
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Alternative routes for White Plains to Chesapeake
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Complete your trip
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White Plains and Chesapeake flights
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White Plains to Chesapeake flights
Consider these flights traveling from White Plains to Chesapeake.
Top airline flying from White Plains to Chesapeake
Discover the top airline 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$447 | FlexibilityNo cancel fee | On-time71% |