$89+ Cheap flights from Chesapeake, VA to Westchester County
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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HPN
Apr 22 — Apr 291
1 adult, Economy
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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 Chesapeake to Westchester County
Keep the following information in mind while searching for Chesapeake to Westchester County flight deals. Data was last updated April 17, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $209 (American Airlines) |
One-way from | $89 (Priceline) |
Popular in | July |
Cheapest in | September |
Average price | $247 |
Find flight deals from Chesapeake to Westchester County
Cheapest flights from Chesapeake to Westchester CountyExplore the most affordable flight options available from Chesapeake to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.
Explore the most affordable flight options available from Chesapeake to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/15:49 amORF - HPN
1 stop4h 53mAmerican Airlines
Mon 5/56:32 pmHPN - ORF
1 stop5h 23mAmerican Airlines
Deal found 4/16![American Airlines logo]()
$209
This Priceline deal was found by Cheapflights users on 4/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/103:58 pmORF - HPN
1 stop4h 32mBreeze Airways
Thu 6/1212:05 pmHPN - ORF
1 stop5h 00mBreeze Airways
Deal found 4/17![Breeze Airways logo]()
$304
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/18:56 pmORF - HPN
2 stops14h 25mMultiple Airlines
Mon 5/512:06 pmHPN - ORF
2 stops28h 05mMultiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$534
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Westchester County 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 17, 2025.
Use the filters below to find and compare flights from Chesapeake to Westchester County that are best for you.
Fly from
Chesapeake
Fly to
Westchester County
Route
Depart
Return
Price
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Thu 5/1
5:49 am-10:42 am
1 stop4h 53m
White Plains Westchester County
Mon 5/5
6:32 pm-11:55 pm
1 stop5h 23m
$209
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Tue 6/10
3:58 pm-8:30 pm
1 stop4h 32m
White Plains Westchester County
Thu 6/12
12:05 pm-5:05 pm
1 stop5h 00m
$304
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Thu 5/1
8:56 pm-11:21 am
2 stops14h 25m
White Plains Westchester County
Mon 5/5
12:06 pm-4:11 pm
2 stops28h 05m
$534
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Tue 6/17
3:58 pm-8:30 pm
1 stop4h 32m
$89
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Fri 5/16
6:40 am-10:50 am
1 stop4h 10m
$206
NorfolkWhite Plains
ORF - HPN
ORFHPN
Norfolk
Wed 6/4
12:13 pm-11:25 am
2 stops23h 12m
$209
Best time to book a flight from Chesapeake to Westchester County
Have a flexible travel schedule? Discover the best time to fly to Westchester County from Chesapeake with our price prediction graph.
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 Chesapeake to Westchester County
What is the cheapest month to book a flight from Chesapeake to Westchester County?
Currently, January is the cheapest month in which you can book a flight from Chesapeake to Westchester County (average of $276). Flying from Chesapeake to Westchester County in March is currently the most expensive (average of $341). 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.
What is the cheapest time of day to fly from C6E to REU?
Find hourly flight availability from Chesapeake to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.
When flying from Chesapeake to Westchester County, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Westchester County
Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated April 17, 2025.
Entertainment
6.6
Boarding
8.3
Comfort
8.2
Overall
8.1
Crew
8.8
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Entertainment
6.6
Boarding
8.3
Comfort
8.2
Overall
8.1
Crew
8.8
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Entertainment
6.6
Boarding
8.3
Comfort
8.2
Overall
8.1
Crew
8.8
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Westchester County. 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 Chesapeake to Westchester County
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Chesapeake to Westchester County
Discover the top airline that operate flights from Chesapeake to Westchester County. 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 17, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$428 | FlexibilityNo cancel fee | On-time71% |