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$280 Cheap Flights from White Plains (HPN) to Hilton Head Island (HHH)

View $280 flight on Wed, Sep 30, 2026Opens in a new window

Popular airlines from Westchester County Airport (HPN) to Hilton Head Island Airport (HHH)

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Cheap Flights from White Plains to Hilton Head Island (HPN-HHH)

Prices were available within the past 7 days and start at $280 for one-way flights and $429 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Nov 14 - Sat, Nov 21
HPN
White Plains
HHH
Hilton Head Island
$429 Roundtrip, found 1 day ago
$429
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 14 from White Plains to Hilton Head Island, returning Sat, Nov 21, priced at $429 found 1 day ago
American Airlines
Fri, Oct 30 - Tue, Nov 3
HPN
White Plains
HHH
Hilton Head Island
$479 Roundtrip, found 8 hours ago
$479
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Oct 30 from White Plains to Hilton Head Island, returning Tue, Nov 3, priced at $479 found 8 hours ago
American Airlines
Sat, Jul 10 - Tue, Jul 13
HPN
White Plains
HHH
Hilton Head Island
$480 Roundtrip, found 1 day ago
$480
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 10 from White Plains to Hilton Head Island, returning Tue, Jul 13, priced at $480 found 1 day ago
American Airlines
Wed, Mar 31 - Sat, Apr 3
HPN
White Plains
HHH
Hilton Head Island
$500 Roundtrip, found 1 day ago
$500
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 31 from White Plains to Hilton Head Island, returning Sat, Apr 3, priced at $500 found 1 day ago
Delta
Fri, Oct 30 - Tue, Nov 3
HPN
White Plains
HHH
Hilton Head Island
$518 Roundtrip, found 8 hours ago
$518
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Oct 30 from White Plains to Hilton Head Island, returning Tue, Nov 3, priced at $518 found 8 hours ago
American Airlines
Sat, Nov 14 - Sat, Nov 21
HPN
White Plains
HHH
Hilton Head Island
$519 Roundtrip, found 1 day ago
$519
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 14 from White Plains to Hilton Head Island, returning Sat, Nov 21, priced at $519 found 1 day ago
American Airlines
Thu, Apr 15 - Sun, Apr 18
HPN
White Plains
HHH
Hilton Head Island
$529 Roundtrip, found 1 hour ago
$529
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Apr 15 from White Plains to Hilton Head Island, returning Sun, Apr 18, priced at $529 found 1 hour ago
American Airlines
Thu, Nov 12 - Sat, Nov 14
HPN
White Plains
HHH
Hilton Head Island
$530 Roundtrip, found 2 days ago
$530
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 12 from White Plains to Hilton Head Island, returning Sat, Nov 14, priced at $530 found 2 days ago
Delta
Fri, Oct 30 - Tue, Nov 3
HPN
White Plains
HHH
Hilton Head Island
$548 Roundtrip, found 8 hours ago
$548
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Oct 30 from White Plains to Hilton Head Island, returning Tue, Nov 3, priced at $548 found 8 hours ago
American Airlines
Sun, Apr 25 - Sat, May 1
HPN
White Plains
HHH
Hilton Head Island
$550 Roundtrip, found 17 hours ago
$550
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, Apr 25 from White Plains to Hilton Head Island, returning Sat, May 1, priced at $550 found 17 hours ago

Alternative airports near Hilton Head Island

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Savannah - Hilton Head Intl. SAV. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $368
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $368

Find the cheapest month to fly from White Plains (HPN) to Hilton Head Island (HHH)

February is typically the cheapest month to fly

From $197 - $592 per traveler.

What you need to know for your flight from Westchester County to Hilton Head Island

White Plains (HPN) to Hilton Head Island (HHH) at a glance

Embark on your journey from White Plains (HPN) to Hilton Head Island (HHH) with a selection of airlines catering to this domestic short-haul route. Explore various options from full-service carriers to find the perfect flight that aligns with your budget, schedule, and travel preferences as you discover the iconic attractions and neighborhoods of Hilton Head Island. Here, you'll find essential information for flights between Westchester County Airport (HPN) and Hilton Head Island Airport (HHH).

  • Fastest flight duration: around 3h 15m in-flight, plus roughly 1 hour layover with one stop
  • Route distance: roughly 700 miles (1,130 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $115–$470, depending on seasonality and how far ahead you book

Flights from Westchester County Airport (HPN) to Hilton Head Island Airport (HHH)

Based on recent traveler bookings, here are the top airlines favored for one-stop flights from White Plains to Hilton Head Island, with common layovers at Charlotte-Douglas International Airport (CLT) for about an hour and Ronald Reagan Washington National Airport (DCA) for around 55 minutes. These options allow you to tailor your journey by balancing price, total travel time, and cabin class to discover the ideal itinerary for your trip.

  • American Airlines: This major airline offers comprehensive service with one-stop flights, typically pricing one-way tickets between $115 and $470. It dominates the route with about 98% of departures. Expect an in-flight duration of 3 hours and 15 minutes, leading to a total travel time of approximately 4 hours and 15 minutes, including layover time.

Alternative routes from White Plains (HPN) to Hilton Head Island (HHH)

  • White Plains to Savannah (HPN-SAV): Savannah - Hilton Head International Airport (SAV) is located approximately 31 miles from Hilton Head Island Airport (HHH). The typical range for one-way economy tickets on this route is between $70 and $320, influenced by the time of year and how far in advance you book. Passengers can choose from both non-stop and one-stop flights, with common layover points at Ronald Reagan Washington National Airport (DCA) and Charlotte-Douglas International Airport (CLT). Major airlines operating this route include American Airlines and Breeze, a budget-friendly carrier. First-class service is also available.
  • New York to Hilton Head Island (LGA-HHH): LaGuardia Airport (LGA) is situated approximately 22 miles from Westchester County Airport (HPN). One-way economy fares on this journey generally fall between $90 and $330, varying by season and booking timeframe. This route is serviced by both non-stop and one-stop flights. Prominent airlines for this route include Delta and American Airlines, and there's the option for first-class service as well.
  • White Plains to Charleston (HPN-CHS): Charleston International Airport (CHS) is located around 60 miles from Hilton Head Island Airport (HHH). One-way economy fares typically range from $60 to $320, depending on the season and booking period. Travelers can find both non-stop and one-stop flight options on this route. Breeze, a low-cost carrier, and American Airlines are the leading airlines serving this route. Additionally, both business and first-class service are offered.

How to find the best prices for flights from White Plains (HPN) to Hilton Head Island (HHH)

Getting some of the best deals on flights from White Plains to Hilton Head Island is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which is also when most travelers plan their trips. Morning departures (5 am-12 pm) tend to be more affordable and are popular flight times, while flying on Thursday generally offers lower prices, even though Friday is the most sought-after travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Hilton Head Island hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Hilton Head Island Airport from Westchester County Airport

Hilton Head Island welcomes travelers from White Plains with a range of transport options based on price, convenience, and proximity. For departures, Westchester County Airport is roughly a 10-minute drive (covering about 7 miles) from central White Plains. Here's how to reach Hilton Head Island efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Hilton Head Island, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Hilton Head Island Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hilton Head Island Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Hilton Head Island Airport, St Phillips Island Seaport, a seaport, is located about 6.4 miles from the airport, providing convenient access to coastal activities.

Frequently asked questions

How much does a flight from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) cost?
You can find cheap one-way flights from $280 and cheap return flights from $429 White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) with Expedia. One-way flights generally range between $118 and $647, and roundtrip flights usually range from $266 to $941. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
The cheapest month to fly from HPN to HHH is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
Enter HPN to HHH and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
American Airlines is one of the cheapest airlines offering connecting flights from White Plains, NY (HPN) to Hilton Head Island, SC (HHH), with round-trip tickets starting from around $510 with a layover in Ronald Reagan Washington National (DCA). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
To find a cheap flight from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from HPN to HHH. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
The most popular departure times for flights from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) are in the early morning, from 6am to 9am. About 47% of passengers prefer this time window. Many major carriers, including American Airlines and Delta Airlines, offer flights during this window. This timing is favored as it allows you to arrive in Hilton Head early to enjoy the day.
How long does it take to fly from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
Flights from HPN to HHH with one stop typically take around 4 hours 20 minutes, covering approximately 723 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
First class seats are offered on the HPN to HHH route with American Airlines and Delta Air Lines.
How do I earn miles on a White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) flight with Expedia?
It's easy to earn miles on a White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) at the last minute?
Typically, booking a last minute flight from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) flight and hotel package?
Securing a White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) Hilton Head Island Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH)?
If you booked your White Plains, NY (HPN-Westchester County) to Hilton Head Island, SC (HHH) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Westchester County
Destination airport
Hilton Head Island
Airlines serving
American Airlines, Delta
Roundtrip price
$428
Distance
722 mi

Book with confidence

White Plains to Hilton Head Island Flights

The cheapest times to fly from White Plains to Hilton Head Island

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from White Plains to Hilton Head Island are during the month of November. You can find some of the cheapest flights from White Plains to Hilton Head Island with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from White Plains to Hilton Head Island

Sunday is one of the best days to book for cheap flights from White Plains to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from White Plains to Hilton Head Island

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from White Plains to Hilton Head Island in 2026. You can also book with separate airlines for your outbound and return journeys, from $280 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap White Plains to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your White Plains to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

White Plains to Hilton Head Island Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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