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Hilton Head Island

$144+ Cheap flights from Westchester County to Hilton Head Island (HHH)

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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — HHH
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$144
(Delta)

Popular in

May

Cheapest in

March

Average price

$326
From Westchester County to Hilton Head Island
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One-way flight from Westchester County to Hilton Head Island
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Highest demand for flights based on searches. 12% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 11/146:30 amHPN - HHH
1 stop4h 28mAmerican Airlines
Mon 11/1711:28 amHHH - HPN
1 stop6h 45mAmerican Airlines
Deal found 9/15$217
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/116:30 amHPN - HHH
1 stop4h 16mAmerican Airlines
Sat 10/183:02 pmHHH - HPN
1 stop5h 27mAmerican Airlines
Deal found 9/16$298
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/306:30 amHPN - HHH
2 stops8h 26mAmerican Airlines
Sat 10/43:26 pmHHH - HPN
1 stop4h 34mAmerican Airlines
Deal found 9/15$322
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/2410:00 amHPN - HHH
1 stop6h 47mAmerican Airlines
Sat 9/2711:17 amHHH - HPN
1 stop7h 03mAmerican Airlines
Deal found 9/15$337
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 9/237:42 amHPN - HHH
1 stop4h 35mAmerican Airlines
Mon 9/293:26 pmHHH - HPN
2 stops8h 00mAmerican Airlines
Deal found 9/16$342
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/46:30 amHPN - HHH
1 stop4h 09mAmerican Airlines
Mon 10/611:16 amHHH - HPN
1 stop3h 35mAmerican Airlines
Deal found 9/15$382
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/131:30 pmHPN - HHH
1 stop4h 39mAmerican Airlines
Sat 11/1511:46 amHHH - HPN
1 stop5h 05mAmerican Airlines
Deal found 9/15$398

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 September 17, 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

Fri 11/14

6:30 am-10:58 am

1 stop4h 28m

Hilton Head Island

Mon 11/17

11:28 am-6:13 pm

1 stop6h 45m

$217

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sat 10/11

6:30 am-10:46 am

1 stop4h 16m

Hilton Head Island

Sat 10/18

3:02 pm-8:29 pm

1 stop5h 27m

$298

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sat 10/11

6:30 am-10:46 am

1 stop4h 16m

Hilton Head Island

Tue 10/14

12:45 pm-4:59 pm

1 stop4h 14m

$317

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 9/30

7:42 am-2:56 pm

1 stop7h 14m

Hilton Head Island

Sat 10/4

3:26 pm-8:00 pm

1 stop4h 34m

$317

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 9/23

7:42 am-12:17 pm

1 stop4h 35m

Hilton Head Island

Mon 9/29

3:26 pm-8:00 pm

1 stop4h 34m

$337

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 9/24

10:00 am-4:47 pm

1 stop6h 47m

Hilton Head Island

Sat 9/27

11:17 am-6:20 pm

1 stop7h 03m

$337

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sat 10/4

6:30 am-10:39 am

1 stop4h 09m

Hilton Head Island

Mon 10/6

11:16 am-2:51 pm

1 stop3h 35m

$382

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 10/22

10:24 am-3:30 pm

1 stop5h 06m

$144

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 9/28

6:30 am-10:34 am

1 stop4h 04m

$169

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 10/19

10:24 am-3:30 pm

1 stop5h 06m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 results
1
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, January is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $275). Flying from Westchester County to Hilton Head Island in March is currently the most expensive (average of $479). 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 September 17, 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
10,000 reviews

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

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 4h 28m. American Airlines provides one of the quickest options available for as low as $217. 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, January is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $275). Flying from Westchester County to Hilton Head Island in March is currently the most expensive (average of $479). 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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Alternative routes for Westchester County to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$266Average$351FlexibilityNo cancel feeOn-time71%

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