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Hilton Head Island

$369+ Cheap flights from Westchester County to Hilton Head Island (HHH)

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — HHH
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Westchester County to Hilton Head Island

Cheapest flights from Westchester County to Hilton Head Island
Explore the most affordable flight options available from Westchester County to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 11/137:59 amHPN - HHH
1 stop6h 20mAmerican Airlines
Sat 11/1511:46 amHHH - HPN
1 stop5h 05mAmerican Airlines
Deal found 11/2$377
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/286:30 amHPN - HHH
1 stop4h 32mAmerican Airlines
Wed 12/33:27 pmHHH - HPN
1 stop7h 03mAmerican Airlines
Deal found 11/2$439
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 11/207:59 amHPN - HHH
1 stop6h 20mAmerican Airlines
Sun 11/236:40 pmHHH - HPN
1 stop4h 07mAmerican Airlines
Deal found 11/3$461
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/216:30 amHPN - HHH
1 stop4h 32mAmerican Airlines
Sun 11/236:40 pmHHH - HPN
1 stop4h 07mAmerican Airlines
Deal found 11/3$484
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/216:30 amHPN - HHH
1 stop4h 32mAmerican Airlines
Mon 11/241:02 pmHHH - HPN
2 stops7h 09mAmerican Airlines
Deal found 11/2$489

Cheap flight deals from Westchester County to Hilton Head Island

Keep the following information in mind while searching for Westchester County to Hilton Head Island flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$369
(American Airlines)

Popular in

October

Cheapest in

September

Average price

$300
Provider with most accurate pricing for New York (NYC)-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Hilton Head Island flights.
Search Deals
From Westchester County to Hilton Head Island
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Hilton Head Island 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 November 3, 2025.
Use the filters below to find and compare flights from Westchester County to Hilton Head Island that are best for you.

Fly from

Westchester County

Fly to

Hilton Head Island

Route

Depart

Return

Price

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 3/3

10:05 am-4:50 pm

1 stop6h 45m

Hilton Head Island

Sat 3/7

6:22 pm-11:00 pm

1 stop4h 38m

$369

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Thu 11/13

7:59 am-2:19 pm

1 stop6h 20m

Hilton Head Island

Sat 11/15

11:46 am-4:51 pm

1 stop5h 05m

$377

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 11/28

6:30 am-11:02 am

1 stop4h 32m

Hilton Head Island

Wed 12/3

3:27 pm-10:30 pm

1 stop7h 03m

$439

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Thu 11/20

7:59 am-2:19 pm

1 stop6h 20m

Hilton Head Island

Sun 11/23

6:40 pm-10:47 pm

1 stop4h 07m

$461

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 11/21

6:30 am-11:02 am

1 stop4h 32m

Hilton Head Island

Mon 11/24

11:32 am-6:13 pm

1 stop6h 41m

$484

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 11/26

4:30 pm-10:24 am

2 stops17h 54m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Best time to book a flight from Westchester County to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Westchester County 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 Westchester County to Hilton Head Island

What is the cheapest month to book a flight from Westchester County to Hilton Head Island?

Currently, October is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $51). Flying from Westchester County to Hilton Head Island in May is currently the most expensive (average of $139). 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.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated November 3, 2025.
Read reviews from past customers who have flown American Airlines from Westchester County to Hilton Head Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,038 reviews

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Westchester County?

    For a flight from Westchester County to Hilton Head Island, you will be flying into Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city.

  • How long is the flight from Westchester County to Hilton Head Island?

    A quick flight from Westchester County to Hilton Head Island can take about 6h 45m. American Airlines provides one of the quickest options available for as low as $369. Airlines will cover a distance of 722 mi.

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

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

  • How can I find direct flights from Westchester County to Hilton Head Island?

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

  • Can I find deals for business class flights from Westchester County to Hilton Head Island?

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

  • What is the cheapest month to book a flight from Westchester County to Hilton Head Island?

    Currently, October is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $51). Flying from Westchester County to Hilton Head Island in May is currently the most expensive (average of $139). 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.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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Top airline flying from Westchester County to Hilton Head Island

Discover the top airline that operate flights from Westchester County to Hilton Head Island. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$348FlexibilityNo cancel feeOn-time71%

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