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Hilton Head Island

$247+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — HHH
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$447
Provider with most accurate pricing for New York (NYC)-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Hilton Head Island flights.
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From Westchester County to Hilton Head Island
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 7/16:30 amHPN - HHH
1 stop4h 03mAmerican Airlines
Wed 7/911:56 amHHH - HPN
1 stop5h 03mAmerican Airlines
Deal found 4/29$247
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 7/2210:26 amHPN - HHH
1 stop4h 49mDelta
Tue 7/2912:03 pmHHH - HPN
1 stop4h 32mDelta
Deal found 4/29$252

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 April 30, 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 7/1

6:30 am-10:33 am

1 stop4h 03m

Hilton Head Island

Wed 7/9

11:56 am-4:59 pm

1 stop5h 03m

$247

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Tue 7/22

10:26 am-3:15 pm

1 stop4h 49m

Hilton Head Island

Tue 7/29

12:03 pm-4:35 pm

1 stop4h 32m

$252

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sun 5/11

10:29 am-3:20 pm

1 stop4h 51m

$290

White PlainsHilton Head Island

HPN - HHH

HPNHHH

White Plains Westchester County

Sat 5/3

6:30 am-11:03 am

1 stop4h 33m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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 April 30, 2025.
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • 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 Westchester County?

Book flights to Westchester County if you plan to visit one of these locations
Beaufort
Bluffton

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Alternative routes for Westchester County to Hilton Head Island

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$231Average$362FlexibilityNo cancel feeOn-time71%

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