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$144 Find Cheap Flights to Hilton Head Island - Compare and Save

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Everything you should know

Cheapest round-trip
$279
Typical prices: $349-$588
United Airlines
Wed 10/3Wed 10/10
ORD - HHH • Non-stop
Cheapest non-stop
$279
Typical prices: $312-$529
United Airlines
Fri 9/7Wed 9/12
ORD - HHH • Non-stop
Nonstop flights
You can fly direct with American Airlines, Delta and United Airlines. Average duration is 1h 48m
FAQs
FAQs
Top airlines
Most flights • 29 per week
Best reviews • 7.8 score
Airline reviews
+1
Airline reviews
+1
Top routes
Cheapest • 16% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 10 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 12% price drop
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Hilton Head Island!
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Booking Insights
Expert advice
Flight Deals

Cheap Flights to Hilton Head Island

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Hilton Head Island

Sat, Oct 3 - Sat, Oct 10
United Airlines Logo
10:35 am - 2:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 35mnonstop
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$279United Airlines
Tue, Sep 15 - Tue, Sep 22
United Airlines Logo
10:25 am - 2:03 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 38mnonstop
United Airlines Logo
2:48 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 17mnonstop
$279United Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
9:55 am - 1:20 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 25mnonstop
American Airlines Logo
1:55 pm - 3:39 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 44mnonstop
$279American Airlines
Mon, Sep 7 - Sat, Sep 12
United Airlines Logo
10:25 am - 2:03 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 38mnonstop
United Airlines Logo
2:48 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 17mnonstop
$279United Airlines
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
8:05 am - 2:03 pmLGA  New York LaGuardia-HHH Hilton Head Island
5h 58m1 stop Chicago O'Hare Intl
United Airlines Logo
2:48 pm - 9:54 pmHHH  Hilton Head Island-LGA New York LaGuardia
7h 06m1 stop Chicago O'Hare Intl
$287United Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
12:05 pm - 5:40 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 35m1 stop Charlotte Douglas
American Airlines Logo
1:55 pm - 3:39 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 44mnonstop
$289American Airlines
Sat, Oct 24 - Sun, Nov 1
American Airlines Logo
9:55 am - 1:20 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 25mnonstop
American Airlines Logo
5:54 pm - 10:32 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
5h 38m1 stop Charlotte Douglas
$289American Airlines
Sat, Sep 12 - Wed, Sep 16
Delta Logo
8:05 am - 3:27 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:17 pm - 10:18 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 01m1 stop New York LaGuardia
$299Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
9:03 am - 11:29 amLGA  New York LaGuardia-HHH Hilton Head Island
2h 26mnonstop
Delta Logo
4:17 pm - 6:21 pmHHH  Hilton Head Island-LGA New York LaGuardia
2h 04mnonstop
$299Delta
Tue, Sep 22 - Sat, Sep 26
Delta Logo
9:03 am - 11:29 amLGA  New York LaGuardia-HHH Hilton Head Island
2h 26mnonstop
Delta Logo
4:17 pm - 6:21 pmHHH  Hilton Head Island-LGA New York LaGuardia
2h 04mnonstop
$299Delta
Booking Insights

KAYAK's insights & trends for flights to Hilton Head Island

Get data-powered insights and trends for flights to Hilton Head Island to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Hilton Head Island?

Chicago O'Hare Intl Airport to Hilton Head Island is the cheapest route at $279 round-trip, found in the past 5 days on KAYAK. New York LaGuardia Airport to Hilton Head Island is the most popular connection with round-trip deals from $287.

How much is a flight to Hilton Head Island?

A round-trip flight to Hilton Head Island costs $446 on average, based on data over the past 12 months on KAYAK. Round-trip fares from New York average $380, while Boston runs a bit higher at $397.

What is the cheapest day to fly to Hilton Head Island?

Tuesday is the cheapest day to fly to Hilton Head Island at $409 round-trip on average over the past 12 months on KAYAK. Sunday is the most expensive at $520.

What is the cheapest month to fly to Hilton Head Island?

  • January and September are the cheapest months to fly to Hilton Head Island with an average price of $392 round-trip.
  • April ($484) and March ($484) are the most expensive.
  • Based on KAYAK data over the past 12 months.

What is the cheapest time of day to fly to Hilton Head Island?

Afternoon flights to Hilton Head Island are the cheapest at $452 round-trip on average. Evening flights are the most expensive at $1,078.

What is a good deal for flights to Hilton Head Island?

Flights under $349 are considered a good deal. 25% of KAYAK users found round-trip flights to Hilton Head Island at or below these prices, with the lowest fares from:

  • New York $287
  • Boston $317
  • Chicago $323
.

When are flights to Hilton Head Island the cheapest?

Flights to Hilton Head Island are cheapest 10 weeks before departure. Booking in this window typically costs about 25% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight to Hilton Head Island

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Delta

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Key details for flights to Hilton Head Island

Low season

January

Cheapest flight

$144
Best time to beat the crowds with an average 12% drop in price.
Flight from New York John F Kennedy Intl Airport to Hilton Head Island

When to book flights to Hilton Head Island

Are your dates flexible? Find out the best times to travel to Hilton Head Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your questions about flights to Hilton Head Island, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • How do I transfer from the airport in Hilton Head Island?

    There are no public transportation options at Hilton Head Island Airport so your best bet is to take a taxi that will cost you about $20 when going into the city. For the most convenient option you can also try to book a hotel that offers shuttle services for the guests.

  • Are there hotels near the airport in Hilton Head Island?

    Yes, people who have late flights to Hilton Head Island or want to stay close to the airport have a few accommodation options that they can pick from. For example, Hampton Inn Hilton Head is only a short drive from the airport, while Marriott’s Barony Beach Club and the Westin Hilton Head Island Resort & Spa are about a 10-minute drive away.

  • Is it possible to store luggage at the airport in Hilton Head Island?

    It is not possible to store luggage at the airport, but there is a self-service storage next to the airport, on Matthews Drive.

  • Are there any restaurants at Hilton Head Island Airport?

    There are no restaurants inside of the airport, but you will be able to buy some snacks from the vending machines after landing at Hilton Head Island Airport; they are next to the Security Check Point. Because the airport is small, you can also easily stop by one of the restaurants nearby, such as Robber’s Row Grille, the Carolina Room, or Bella Italia Bistro & Pizzeria. All of these dining spots are within a short walk from the airport.

  • Which other cities can I fly to from Hilton Head Island Airport?

    HHH is a small regional airport with flights to other major cities in the U.S., like Atlanta, Washington D.C., Charlotte, Chicago, and New York City. Multiple airlines operate from this airport, with flights to various destinations on a seasonal or occasional basis.

  • Are there parking options where my ride can wait for me at Hilton Head Island Airport?

    Hilton Head Island Airport has one parking lot charging a flat rate of around $10 per day through their automated parking machine kiosks outside the middle entrance. Parking is free for the first 2 hours, which is ideal for pick-ups or drop-offs.

  • How do I connect to international flights from Hilton Head Island Airport?

    If you wish to connect to an international flight from Hilton Head Island Airport, you’ll find flights to other international airports within the U.S. Alternatively; you can head to Savannah/Hilton Head International Airport (SAV), approximately 45 miles southwest of HHH.

  • Which hotels provide shuttle services from Hilton Head Island Airport?

    Hotels in Hilton Head Island do not provide shuttle services to arriving guests from HHH. You can book a car rental or hire a taxi outside the Terminal’s exit. Rental counters are inside the Terminal close to the Baggage Claim area.

  • What is the difference between the most popular and the most frequent airline at Hilton Head Island?

    American Airlines operates the most flights from the United States to Hilton Head Island at 29 per week, and for this route American Airlines is also the airline most often selected by KAYAK users searching for flights from the United States to Hilton Head Island. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveler choice.

  • How long are nonstop flights to Hilton Head Island from different departure cities?

    Nonstop flight time to Hilton Head Island varies depending on your departure city:
    • from Chicago: 2h 21m
    • from Charlotte: 1h 14m
    • from Boston: 2h 51m
    • from Atlanta: 1h 11m
    • from Washington, D.C.: 2h 04m

  • Where can I fly from to get the cheapest fares to Hilton Head Island?

    Based on fares booked in the past 5 days, the cheapest flights to Hilton Head Island are from:
    • Chicago, from $279 round-trip
    • New York, from $287 round-trip

  • How many flights serve Hilton Head Island?

    Hilton Head Island receives 7 flights per day and 50 per week from across the world. Charlotte has the most flights to Hilton Head Island, with 21 weekly flights.

  • How do I know if a flight to Hilton Head Island is a good deal?

    A good deal on a flight to Hilton Head Island is around $349 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • How expensive are last-minute flights to Hilton Head Island?

    Last-minute fares to Hilton Head Island – booked within 2 weeks of departure – run 17% above the average round-trip fare of $446.

Your guide to booking Hilton Head Island flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Hilton Head Island, aim to book around 10 weeks before you fly. That window historically saves about 25% versus last-minute pricing based on KAYAK booking data over the last 12 months.
  • For flights to Hilton Head Island, recent KAYAK data shows that stronger deals tend to land around $349 round-trip. If you see a fare below that threshold, it's a strong deal – book before the price climbs back up.
  • If you can choose when to go, time your trip to Hilton Head Island around January. Round-trip fares historically average $392 that month – typically the cheapest month to travel based on the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat-selection costs on budget carriers.
    • Verify whether you need any travel documents beyond ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to noon to save up to $626 per round-trip. Noon flights to Hilton Head Island average $452 compared to $1,078 for afternoon flights. See the time-of-day chart above for the full breakdown.
  • Bag allowances vary by airline, fare type, cabin class and route. On flights to Hilton Head Island, some airlines may include bags at no extra cost. For example, American Airlines includes a cabin bag and a checked bag in Economy Class, United Airlines includes a cabin bag and a checked bag in Economy Class and Delta includes a cabin bag and a checked bag in Economy Class. Always check the fare details before booking, since bag policies can change by ticket type.
  • Once you arrive in Hilton Head Island, a great place to start is Harbour Town Lighthouse. It is popular with first-time visitors and can give you a good feel for the area.
  • Going for vacation to Hilton Head Island? Hilton Head Island Airport (HHH) is the only airport on the island and it will make the travel there hassle-free for you as it is convenient, spacious and simple to navigate. Keep in mind that Hilton Head Island Airport is fairly small and has a limited number of connections, so if you prefer airports with a lot of amenities and more flights, Savannah/Hilton Head International Airport (SAV), located about 43 miles away, may be a better solution for you.
  • If you need to charge your mobile or other electronics immediately after your flight to Hilton Head Island, you will be able to find a few power outlets near the chairs in the main hall’s sitting area.
  • There is no pubic transportation available on Hilton Head Island so it might be a good idea to rent a car for the duration of your stay there to be able to move around it easily. It is possible to rent the car after landing at Hilton Head Island Airport from car rentals like Alamo, Enterprise, Dollar, and Thrifty. All of them are located only a few steps from the terminal building.
  • Although there are no shops inside of the airport in Hilton Head, there are vending machines with some basic products and you can also easily leave the airport and find shops within a few minutes’ walk from the airport grounds.
  • Feel like you have to unwind and rest a bit after the flight to Hilton Head Island? Take your time on the rocking chairs scattered throughout the terminal and enjoy the peaceful atmosphere of this small airport.
  • If you’re flying to Hilton Head Island Airport (HHH) from New York, you’ll find direct flights from LaGuardia Airport and Newark Liberty International Airport (EWR). Airlines offering direct flights from New York to HHH include United Airlines and Delta Airlines. One-stop flights with layovers at Charlotte Douglas International Airport (CLT) are also available at these airports and JFK.
  • From the West Coast, you can take a connecting flight to HHH from San Francisco International Airport (SFO) or John Wayne Airport (SNA) in Orange County, California. There are no direct flights to HHH from the West Coast, but you’ll find one-stop flights from providers like Delta Airlines, United Airlines, and American Airlines.

Reviews of the top 4 airlines flying to Hilton Head Island

 
Need help choosing which airline to fly with to Hilton Head Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8504 reviews
8.1Boarding
7.8Entertainment
7.8Comfort
8.5Crew
7.2Food
Airline reviews

They announced a mechanical issue prior to boarding Said it was fixed, we boarded Waited Then learned it was not fixed Had to deplane and go to new gate Bought wifi on plane and it never worked

2.0 MediocreJames, Aug 2026
Read more Delta reviews

They announced a mechanical issue prior to boarding Said it was fixed, we boarded Waited Then learned it was not fixed Had to deplane and go to new gate Bought wifi on plane and it never worked

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

I am still at the Airport! Delayed Delayed and Delyaed

The landing was the worst I’ve experienced with a flight.

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

All good on Delta's part. Passengers could be a little more courteous to each other.

The pilots were good. Disappointing when planes don't have electrical ports

No complaints - left 20 minutes later than planned but still arrived on time.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

Awful. No counter attendants. No dinner offered due to delays.

The plane was late getting to Ontario by half an hour which makes it inconvenient when you have people waiting for you.

Luggage handling and communication is extremely poor. I landed in india 15th and recived luggage today. Based on my itag the luggage was in Germany. They kept me in dark. Etihad num er in india was non operatuonal. Had to call USA etihad. It should not be so difficullt. I came for 1 week business trip everything was screwed . This is the first and also will be last for me

There was no service on the flight even though there was no turbulence or any other issues on the flight. Nobody greeted at the entry or leaving the airplane, staff crew looked annoyed and not helpful at all.

mechanical problem delayed more than 2 hours on the run way.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Multiple gate changes and significant delay leaving DFW. Made for a late arrival

For the price of the ticket you get nothing. The plane had 1 bathroom in the back and when the flight attendant did service no one could use it. No announcement just was told to go back to my seat. Ridiculous and rude.

In-flight Wi-Fi didn’t work and the flight was 25 minutes late. The Embraer plane I was on was pretty old and the tray table was broken.

American Airlines no longer has Bischoff biscuits. This is intolerable.

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

Everything you need to know for your flight to Hilton Head Island

Flights with popular airlines flying to Hilton Head Island