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Hilton Head Island

$269+ Cheap flights from Virginia Beach, VA 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HHH
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Virginia Beach to Hilton Head Island

Keep the following information in mind while searching for Virginia Beach to Hilton Head Island flight deals. Data was last updated September 15, 2025.

Round-trip from

$239
(American Airlines)
From Virginia Beach to Hilton Head Island
Search Deals

Find flight deals from Virginia Beach to Hilton Head Island

Cheapest flights from Virginia Beach to Hilton Head Island
Explore the most affordable flight options available from Virginia Beach to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 9/2011:14 amORF - HHH
1 stop5h 33mAmerican Airlines
Thu 9/2512:00 pmHHH - ORF
1 stop5h 00mAmerican Airlines
Deal found 9/13$269
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 9/1910:13 amORF - HHH
1 stop5h 12mDelta
Tue 9/2312:14 pmHHH - ORF
1 stop4h 36mDelta
Deal found 9/14$279
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/198:30 amORF - HHH
2 stops8h 17mAmerican Airlines
Tue 9/233:26 pmHHH - ORF
2 stops7h 34mAmerican Airlines
Deal found 9/14$289
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:00 amORF - HHH
1 stop5h 25mUnited Airlines
Thu 9/2511:57 amHHH - ORF
1 stop4h 36mUnited Airlines
Deal found 9/15$339
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/295:30 amORF - HHH
2 stops9h 26mAmerican Airlines
Fri 10/33:26 pmHHH - ORF
1 stop3h 11mAmerican Airlines
Deal found 9/13$444

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach 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 15, 2025.
Use the filters below to find and compare flights from Virginia Beach to Hilton Head Island that are best for you.

Fly from

Virginia Beach

Fly to

Hilton Head Island

Route

Depart

Return

Price

NorfolkHilton Head Island

ORF - HHH

ORFHHH

Norfolk

Mon 9/29

5:30 am-2:56 pm

2 stops9h 26m

Hilton Head Island

Fri 10/3

3:26 pm-6:37 pm

1 stop3h 11m

$444

NorfolkHilton Head Island

ORF - HHH

ORFHHH

Norfolk

Mon 9/29

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Fri 10/3

11:57 am-6:30 pm

1 stop6h 33m

$467

NorfolkHilton Head Island

ORF - HHH

ORFHHH

Norfolk

Fri 9/26

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Fri 10/3

11:57 am-6:30 pm

1 stop6h 33m

$556

NorfolkHilton Head Island

ORF - HHH

ORFHHH

Norfolk

Fri 10/17

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Mon 10/20

11:57 am-4:33 pm

1 stop4h 36m

$1,065

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Best time to book a flight from Virginia Beach to Hilton Head Island

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

What is the cheapest month to book a flight from Virginia Beach to Hilton Head Island?

Currently, January is the cheapest month in which you can book a flight from Virginia Beach to Hilton Head Island (average of $275). Flying from Virginia Beach to Hilton Head Island in March is currently the most expensive (average of $480). 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 15, 2025.
Get a feel of what it's like to fly with American Airlines from Virginia Beach to Hilton Head Island by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

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

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

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 Virginia Beach 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 Virginia Beach?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Virginia Beach to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Virginia Beach; the airport handles an average of 0 inbound flights from Virginia Beach per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Hilton Head Island airport from Virginia Beach. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

  • How long is the flight from Virginia Beach to Hilton Head Island?

    American Airlines and United Airlines can get you from Virginia Beach to Hilton Head Island in just under 5h 16m. Your travel time can differ by up to 4h 10m. Virginia Beach and Hilton Head Island are separated by a distance of 412 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

  • How can I find direct flights from Virginia Beach 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 Virginia Beach to Hilton Head Island.

  • Can I find deals for business class flights from Virginia Beach to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Virginia Beach 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 Virginia Beach to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Virginia Beach to Hilton Head Island (average of $275). Flying from Virginia Beach to Hilton Head Island in March is currently the most expensive (average of $480). 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 Virginia Beach to Hilton Head Island

Discover the top airline that operate flights from Virginia Beach 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$516FlexibilityNo cancel feeOn-time71%

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