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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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — HHH
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap 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 March 28, 2026.

This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2610:29 am
HPN
-
HHH
1 stop4h 51m
Delta
Wed 4/2912:08 pm
HHH
-
HPN
1 stop6h 08m
Delta
Deal found 3/28$262
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Sun 4/1211:00 am
HPN
-
HHH
1 stop4h 14m
American Airlines
Thu 4/166:39 pm
HHH
-
HPN
1 stop4h 21m
American Airlines
Deal found 3/28$267
This American Airlines deal was found by Cheapflights users on 3/23. 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 4/2911:00 am
HPN
-
HHH
1 stop4h 14m
American Airlines
Mon 5/46:39 pm
HHH
-
HPN
1 stop4h 21m
American Airlines
Deal found 3/23$277
This American Airlines deal was found by Cheapflights users on 3/25. 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 4/227:49 am
HPN
-
HHH
1 stop6h 37m
American Airlines
Fri 4/246:39 pm
HHH
-
HPN
1 stop4h 21m
American Airlines
Deal found 3/25$282
This American Airlines deal was found by Cheapflights users on 3/23. 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 4/2411:00 am
HPN
-
HHH
1 stop4h 14m
American Airlines
Fri 5/13:44 pm
HHH
-
HPN
1 stop4h 43m
American Airlines
Deal found 3/23$287
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Sun 5/106:30 am
HPN
-
HHH
2 stops7h 56m
American Airlines
Fri 5/153:44 pm
HHH
-
HPN
1 stop4h 43m
American Airlines
Deal found 3/25$292
This American Airlines deal was found by Cheapflights users on 3/26. 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 5/811:00 am
HPN
-
HHH
1 stop4h 14m
American Airlines
Sat 5/162:10 pm
HHH
-
HPN
1 stop4h 17m
American Airlines
Deal found 3/26$297
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/1811:00 am
HPN
-
HHH
1 stop4h 40m
American Airlines
Sat 4/255:04 pm
HHH
-
HPN
1 stop5h 56m
American Airlines
Deal found 3/27$388
This American Airlines deal was found by Cheapflights users on 3/28. 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 4/1111:00 am
HPN
-
HHH
1 stop4h 40m
American Airlines
Sat 4/182:10 pm
HHH
-
HPN
1 stop4h 17m
American Airlines
Deal found 3/28$393
This American Airlines deal was found by Cheapflights users on 3/24. 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 4/116:30 am
HPN
-
HHH
1 stop7h 10m
American Airlines
Wed 4/155:04 pm
HHH
-
HPN
1 stop5h 56m
American Airlines
Deal found 3/24$399
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Sun 4/266:30 am
HPN
-
HHH
2 stops7h 56m
American Airlines
Wed 4/296:39 pm
HHH
-
HPN
1 stop4h 21m
American Airlines
Deal found 3/28$403
This American Airlines deal was found by Cheapflights users on 3/23. 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 4/711:00 am
HPN
-
HHH
1 stop4h 38m
American Airlines
Sat 4/116:50 pm
HHH
-
HPN
1 stop4h 10m
American Airlines
Deal found 3/23$404

Find 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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$287
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
One-way flight from Westchester County to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 28, 2026.
Use the filters below to find and compare flights from Westchester County to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 4/26

10:29 am-3:20 pm

1 stop4h 51m

Hilton Head Island

Wed 4/29

12:08 pm-6:16 pm

1 stop6h 08m

$262

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Mon 4/13

1:30 pm-6:09 pm

1 stop4h 39m

Hilton Head Island

Thu 4/16

6:39 pm-11:00 pm

1 stop4h 21m

$267

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 4/22

7:49 am-2:26 pm

1 stop6h 37m

Hilton Head Island

Fri 4/24

6:39 pm-11:00 pm

1 stop4h 21m

$282

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 5/10

7:49 am-2:26 pm

1 stop6h 37m

Hilton Head Island

Fri 5/15

3:44 pm-8:27 pm

1 stop4h 43m

$287

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 4/24

11:00 am-3:14 pm

1 stop4h 14m

Hilton Head Island

Fri 5/1

3:44 pm-8:27 pm

1 stop4h 43m

$287

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 5/8

11:00 am-3:14 pm

1 stop4h 14m

Hilton Head Island

Sat 5/16

2:10 pm-6:27 pm

1 stop4h 17m

$297
Quickest round-trip

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 4/15

11:00 am-3:14 pm

1 stop4h 14m

Hilton Head Island

Sat 4/18

6:50 pm-11:00 pm

1 stop4h 10m

$404

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 4/7

11:00 am-3:38 pm

1 stop4h 38m

Hilton Head Island

Sat 4/11

6:50 pm-11:00 pm

1 stop4h 10m

$404

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 5/1

7:49 am-2:26 pm

1 stop6h 37m

Hilton Head Island

Mon 5/4

6:39 pm-11:00 pm

1 stop4h 21m

$494
Cheapest one-way

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 7/28

10:29 am-3:29 pm

1 stop5h 00m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 18 resultsSorted by cheapest first
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 $93). Flying from Westchester County to Hilton Head Island in November is currently the most expensive (average of $155). 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 March 28, 2026.
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
7.1
Good
11,520 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Overall

7.1

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,520 reviews
American Airlines
7.1
Good
11,520 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Overall

7.1

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 39m. American Airlines provides one of the quickest options available for as low as $267. 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 $93). Flying from Westchester County to Hilton Head Island in November is currently the most expensive (average of $155). 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

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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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$377FlexibilityNo cancel feeOn-time71%

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