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Cheap flights from Chesapeake, VA to Westchester County from $118

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
RIC — HPN
May 14 — May 211
From?
To?
Tue 5/14
Tue 5/21
1 adult, Economy
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How far in advance should I book a flight from Chesapeake to Westchester County?

Travelers have found it’s best to book a flight 59 days in advance to save up to 47% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 59 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chesapeake to Westchester County 1-2 weeks in advance for as low as $178, or $242 for flights within the next 24 hours.

What is the cheapest month to fly from Chesapeake to Westchester County?

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, August can be a great choice for travel to Westchester County. Flights to Westchester County from Chesapeake in August are about $207 on average during August, but can be found for as low as $109.

When is the cheapest time to fly from Chesapeake to Westchester County (C6E - REU)?

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.

Cheap American Airlines flights from Chesapeake to Westchester County

Explore cheap flight options specifically provided by American Airlines for the route between Chesapeake and Westchester County. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
Take a peek at the cheapest American Airlines flights we've detected traveling from Chesapeake to Westchester County. Make sure to double check the flight details before booking.
Wed 7/107:05 pmORF - HPN
1 stop4h 18mAmerican Airlines
Tue 7/165:25 pmHPN - ORF
1 stop5h 40mAmerican Airlines
Deal found 5/9$178
Fri 6/287:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Tue 7/27:59 amHPN - ORF
1 stop4h 40mAmerican Airlines
Deal found 5/8$336
Fri 6/217:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Thu 6/276:30 amHPN - ORF
1 stop3h 05mAmerican Airlines
Deal found 5/8$338
Sat 5/1810:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Mon 5/206:59 pmHPN - ORF
1 stop4h 47mAmerican Airlines
Deal found 5/7$488
Thu 7/185:16 amORF - HPN
1 stop4h 13mAmerican Airlines
Mon 7/226:00 amHPN - ORF
1 stop4h 12mAmerican Airlines
Deal found 5/7$505
Fri 6/147:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Sat 6/156:46 pmHPN - ORF
1 stop5h 06mAmerican Airlines
Deal found 5/8$506
Fri 5/175:18 amORF - HPN
1 stop4h 11mAmerican Airlines
Sun 5/196:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$579
Wed 7/105:04 pmORF - HPN
2 stops6h 19mAmerican Airlines
Tue 7/165:25 pmHPN - ORF
1 stop5h 40mAmerican Airlines
Deal found 5/9$599
Mon 5/136:15 pmORF - HPN
1 stop4h 28mAmerican Airlines
Mon 5/206:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/9$639

Cheap Breeze Airways flights from Chesapeake to Westchester County

Explore cheap flight options specifically provided by Breeze Airways for the route between Chesapeake and Westchester County. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
Some of the lowest-priced Breeze Airways flights we've found at this time heading from Chesapeake to Westchester County. Ensure the flight price, dates, time, and airline match your criteria before you book.
Fri 6/2810:10 amORF - HPN
Nonstop1h 19mBreeze Airways
Mon 7/18:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/9$118
Wed 6/197:40 pmORF - HPN
Nonstop1h 19mBreeze Airways
Mon 6/248:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/8$122

Cheap Chesapeake to Westchester County flights in May & June 2024

Find cheap flight options from Chesapeake to Westchester County specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,717,708 searches. Prices were last updated on May 9, 2024.
Check out some of the best flight deals from Chesapeake to Westchester County in 2024. More deals are always being added, so be sure to check back regularly.
Fri 6/2810:10 amORF - HPN
Nonstop1h 19mBreeze Airways
Mon 7/18:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/9$118
Wed 6/197:40 pmORF - HPN
Nonstop1h 19mBreeze Airways
Mon 6/248:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/8$122
Thu 5/95:53 amORF - HPN
1 stop5h 06mAmerican Airlines
Sun 5/126:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$298
Thu 5/93:19 pmORF - HPN
1 stop3h 01mAmerican Airlines
Sat 5/116:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$336
Fri 6/217:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Thu 6/276:30 amHPN - ORF
1 stop3h 05mAmerican Airlines
Deal found 5/8$338
Sat 5/1810:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Mon 5/206:59 pmHPN - ORF
1 stop4h 47mAmerican Airlines
Deal found 5/7$488
Fri 6/147:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Sat 6/156:46 pmHPN - ORF
1 stop5h 06mAmerican Airlines
Deal found 5/8$506
Fri 5/175:18 amORF - HPN
1 stop4h 11mAmerican Airlines
Sun 5/196:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$579
Mon 5/136:15 pmORF - HPN
1 stop4h 28mAmerican Airlines
Mon 5/206:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/9$639

Chesapeake to Westchester County 2024 flight deals

Discover exclusive flight deals for travel between Chesapeake and Westchester County in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
Check out some of the best flight deals from Chesapeake to Westchester County in 2024. More deals are always being added, so be sure to check back regularly.
Fri 6/2810:10 amORF - HPN
Nonstop1h 19mBreeze Airways
Mon 7/18:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/9$118
Fri 9/2010:10 amORF - HPN
Nonstop1h 19mBreeze Airways
Mon 9/238:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/8$122
Wed 7/107:05 pmORF - HPN
1 stop4h 18mAmerican Airlines
Tue 7/165:25 pmHPN - ORF
1 stop5h 40mAmerican Airlines
Deal found 5/9$178
Thu 5/95:53 amORF - HPN
1 stop5h 06mAmerican Airlines
Sun 5/126:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$298
Thu 5/93:19 pmORF - HPN
1 stop3h 01mAmerican Airlines
Sat 5/116:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$336
Fri 6/217:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Thu 6/276:30 amHPN - ORF
1 stop3h 05mAmerican Airlines
Deal found 5/8$338
Sat 5/1810:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Mon 5/206:59 pmHPN - ORF
1 stop4h 47mAmerican Airlines
Deal found 5/7$488
Thu 7/185:16 amORF - HPN
1 stop4h 13mAmerican Airlines
Mon 7/226:00 amHPN - ORF
1 stop4h 12mAmerican Airlines
Deal found 5/7$505
Fri 6/147:03 pmORF - HPN
1 stop4h 20mAmerican Airlines
Sat 6/156:46 pmHPN - ORF
1 stop5h 06mAmerican Airlines
Deal found 5/8$506

Non-stop flights to Westchester County from Chesapeake

Discover non-stop flight options from Chesapeake to Westchester County. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
If you're seeking options on non-stop flights from Chesapeake to Westchester County, check out these fares. Those looking to potentially save on 1 or 2-stop flights from Chesapeake to Westchester County should utilize the search form at the the top of the page.
Fri 6/2810:10 amORF - HPN
Nonstop1h 19mBreeze Airways
Mon 7/18:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/9$118
Wed 6/197:40 pmORF - HPN
Nonstop1h 19mBreeze Airways
Mon 6/248:00 amHPN - ORF
Nonstop1h 25mBreeze Airways
Deal found 5/8$122

Chesapeake to Westchester County flights leaving soon

Find last-minute flight options from Chesapeake to Westchester County for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
Consider one of these great deals we found on last-minute flights from Chesapeake to Westchester County. Users should examine the flight details to ensure there are no surprises.
Sat 5/1810:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Mon 5/206:59 pmHPN - ORF
1 stop4h 47mAmerican Airlines
Deal found 5/7$488
Fri 5/175:18 amORF - HPN
1 stop4h 11mAmerican Airlines
Sun 5/196:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/8$579
Mon 5/136:15 pmORF - HPN
1 stop4h 28mAmerican Airlines
Mon 5/206:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/9$639
Tue 5/145:18 amORF - HPN
1 stop4h 11mAmerican Airlines
Mon 5/206:30 amHPN - ORF
1 stop3h 06mAmerican Airlines
Deal found 5/9$640
Fri 5/177:17 amORF - HPN
2 stops11h 03mAmerican Airlines
Sun 5/196:00 amHPN - ORF
1 stop4h 17mAmerican Airlines
Deal found 5/9$812
Sat 5/1810:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Mon 5/2011:29 amHPN - ORF
2 stops11h 16mAmerican Airlines
Deal found 5/7$814
Fri 5/177:17 amORF - HPN
2 stops7h 25mAmerican Airlines
Sun 5/197:30 amHPN - ORF
1 stop6h 40mAmerican Airlines
Deal found 5/8$893
Fri 5/172:55 pmORF - HPN
2 stops8h 25mAmerican Airlines
Sun 5/196:00 amHPN - ORF
2 stops8h 49mAmerican Airlines
Deal found 5/8$2,105

One-way flights to Westchester County from Chesapeake

Search for one-way flight options from Chesapeake to Westchester County. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,717,708 searches. Data last updated May 9, 2024.
Users in need of a one-way flight from Chesapeake to Westchester County can choose from these deals. For those needing a return trip from Chesapeake, there is a search form available above.
Tue 6/259:58 amORF - HPN
2 stops9h 02mBreeze Airways
Deal found 5/7$168
Thu 5/167:51 pmORF - HPN
2 stops23h 17mMultiple Airlines
Deal found 5/7$187
Tue 6/257:03 pmORF - HPN
1 stop15h 56mAmerican Airlines
Deal found 5/7$230
Thu 5/1610:07 amORF - HPN
1 stop4h 35mAmerican Airlines
Deal found 5/7$291
Thu 5/167:51 pmORF - HPN
3 stops23h 17mMultiple Airlines
Deal found 5/7$293
Sun 5/126:40 amORF - HPN
1 stop6h 30mAmerican Airlines
Deal found 5/8$703
Sun 5/121:00 pmORF - HPN
2 stops5h 20mAmerican Airlines
Deal found 5/8$1,015

Find flights from Chesapeake to Westchester County within your budget

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 2,717,708 searches. Data last updated May 9, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$118 - $1,064

Route

Depart

Return

Price

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Fri 6/28

Nonstop1h 19m

White Plains Westchester County

Mon 7/1

Nonstop1h 25m

$118

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Wed 6/19

Nonstop1h 19m

White Plains Westchester County

Mon 6/24

Nonstop1h 25m

$122

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Wed 7/10

1 stop4h 18m

White Plains Westchester County

Tue 7/16

1 stop5h 40m

$178

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Fri 6/28

1 stop4h 20m

White Plains Westchester County

Tue 7/2

1 stop4h 40m

$336

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Fri 6/21

1 stop4h 20m

White Plains Westchester County

Thu 6/27

1 stop3h 05m

$338

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Sat 5/18

1 stop4h 35m

White Plains Westchester County

Mon 5/20

1 stop4h 47m

$488

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Thu 7/18

1 stop4h 13m

White Plains Westchester County

Mon 7/22

1 stop4h 12m

$505

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Fri 6/14

1 stop4h 20m

White Plains Westchester County

Sat 6/15

1 stop5h 06m

$506

NorfolkWhite Plains Westchester County

ORF - HPN

ORFHPN

Norfolk

Thu 6/27

1 stop5h 47m

White Plains Westchester County

Sat 6/29

1 stop5h 41m

$1,064

Flights are sorted by cheapest first

Deals found on 5/9

No data available for this route at this time. Please check back soon.

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 May 9, 2024.
Read through reviews of airlines operating flights from Chesapeake to Westchester County, such as American Airlines and Breeze Airways. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,778 reviews
Check prices

Entertainment

8.0

Food

7.4

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Delta
8.0
Very good
10,778 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Entertainment

8.0

Food

7.4

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Breeze Airways
8.0
Very good
76 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Entertainment

8.0

Food

7.4

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

American Airlines
7.3
Good
14,665 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Entertainment

8.0

Food

7.4

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

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.

  • Can I find flights from Chesapeake to Westchester County for under $200 on Cheapflights?

    Yes, there are multiple flights from Chesapeake to Westchester County for under $200. The cheapest flight booked recently is on Breeze Airways for just $118, but on average you can expect to pay $652.

  • Are there nonstop flights from Chesapeake to Westchester County for under $200 on Cheapflights?

    Cheapflights has at least 2 direct flights from Chesapeake to Westchester County under $200. A good price for a nonstop flight from Chesapeake to Westchester County is less than $120.

  • Are there last-minute flights available from Chesapeake to Westchester County for under $500?

    There are currently 8+ open flights from Chesapeake to Westchester County within the next 7 days for less than $500.

  • What does RIC to HPN mean?

    RIC stands for Richmond Byrd Intl Airport, while HPN stands for White Plains Westchester County Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Norfolk Airport (ORF), Newport News Intl Airport (PHF), Pitt-Greenville Airport (PGV).

  • Can I find deals for flights from Chesapeake to Westchester County that include extra baggage allowance?

    The amount of baggage you can bring on your Chesapeake to Westchester County flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chesapeake to Westchester County with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chesapeake to Westchester County flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chesapeake to Westchester County that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Westchester County?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Westchester County.

  • Can I find deals for business class flights from Chesapeake to Westchester County?

    Yes. Cheapflights offers flight deals from Chesapeake to Westchester County by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chesapeake to Westchester County that allow pets onboard?

    Many airlines flying from Chesapeake to Westchester County offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chesapeake to Westchester County?

    Yes, you can often find last-minute deals on Chesapeake to Westchester County flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chesapeake to Westchester County flight deals updated?

    The Chesapeake to Westchester County flight deals you see on this page were last updated on 5/9.

See more FAQs

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Alternative routes for Chesapeake to Westchester County
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Top 3 airlines flying from Chesapeake to Westchester County

Discover the top 3 airlines 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 2,717,708 searches. Data last updated May 9, 2024.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$106FlexibilityNo cancel feeOn-timeN/A
Search Breeze Airways flights
DeltaCheapest$148Average$219FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$180Average$398FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
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Search flights from Chesapeake to Westchester County by cabin class

Find flights from Chesapeake to Westchester County, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chesapeake to Westchester County?

Cheapflights helps you search for flights from Chesapeake to Westchester County via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chesapeake to Westchester County?

Cheapflights simply makes it quick and affordable to book flights from Chesapeake to Westchester County by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chesapeake to Westchester County with no change fees?

Need flexible booking options for your flight to Westchester County from Chesapeake? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chesapeake to Westchester County become cheaper?

Of course! You can now track prices for flights from Chesapeake to Westchester County and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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