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Hilton Head Island

$124+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — HHH
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/4. 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.
Mon 3/211:28 am
HPN
-
HHH
1 stop4h 13m
American Airlines
Thu 3/54:11 pm
HHH
-
HPN
1 stop3h 57m
American Airlines
Deal found 2/4$222
This American Airlines deal was found by Cheapflights users on 2/4. 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 2/1911:28 am
HPN
-
HHH
1 stop4h 13m
American Airlines
Mon 2/234:11 pm
HHH
-
HPN
1 stop3h 57m
American Airlines
Deal found 2/4$267
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/611:28 am
HPN
-
HHH
1 stop4h 13m
American Airlines
Fri 3/134:11 pm
HHH
-
HPN
1 stop3h 57m
American Airlines
Deal found 2/3$268
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/311:28 am
HPN
-
HHH
1 stop4h 13m
American Airlines
Sat 3/711:03 am
HHH
-
HPN
1 stop5h 57m
American Airlines
Deal found 2/3$272
This American Airlines deal was found by Cheapflights users on 2/4. 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 2/2410:05 am
HPN
-
HHH
1 stop4h 56m
American Airlines
Thu 3/194:11 pm
HHH
-
HPN
1 stop3h 57m
American Airlines
Deal found 2/4$287
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Sun 3/811:29 am
HPN
-
HHH
1 stop4h 12m
American Airlines
Sat 3/146:15 pm
HHH
-
HPN
1 stop4h 44m
American Airlines
Deal found 2/3$303

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(American Airlines)

One-way from

$124
(American Airlines)

Popular in

December

Cheapest in

November

Average price

$342
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 ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 4, 2026.
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

Mon 3/2

11:28 am-3:41 pm

1 stop4h 13m

Hilton Head Island

Thu 3/5

4:11 pm-8:08 pm

1 stop3h 57m

$232

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Fri 3/6

11:28 am-3:41 pm

1 stop4h 13m

Hilton Head Island

Fri 3/13

4:11 pm-8:08 pm

1 stop3h 57m

$268

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Thu 2/19

11:28 am-5:44 pm

2 stops6h 16m

Hilton Head Island

Mon 2/23

4:11 pm-8:08 pm

1 stop3h 57m

$272

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 3/3

11:28 am-3:41 pm

1 stop4h 13m

Hilton Head Island

Sat 3/7

11:03 am-5:00 pm

1 stop5h 57m

$272

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 3/8

11:29 am-3:41 pm

1 stop4h 12m

Hilton Head Island

Sat 3/14

6:15 pm-10:59 pm

1 stop4h 44m

$303

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Wed 4/1

11:29 am-3:41 pm

1 stop4h 12m

$124

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Mon 5/11

10:29 am-3:22 pm

1 stop4h 53m

$270

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Mon 2/9

7:30 am-2:59 pm

1 stop7h 29m

$453

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Thu 4/2

1:37 pm-5:44 pm

1 stop4h 07m

$453

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Mon 5/11

6:30 am-4:34 pm

2 stops10h 04m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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, March is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $85). 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 February 4, 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
7.2
Good
11,222 reviews

Food

6.4

Overall

7.2

Crew

8.0

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,222 reviews
American Airlines
7.2
Good
11,222 reviews

Food

6.4

Overall

7.2

Crew

8.0

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 13m. American Airlines provides one of the quickest options available for as low as $232. 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, March is the cheapest month in which you can book a flight from Westchester County to Hilton Head Island (average of $85). 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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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$367FlexibilityNo cancel feeOn-time71%

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