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$264 Cheap Flights from Lexington (LEX) to Hilton Head Island (HHH)

View $264 flight on Tue, Sep 29, 2026Opens in a new window

Popular airlines from Blue Grass Airport (LEX) to Hilton Head Island Airport (HHH)

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Cheap Flights from Lexington to Hilton Head Island (LEX-HHH)

Prices were available within the past 7 days and start at $264 for one-way flights and $314 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Sep 16 - Wed, Sep 23
LEX
Lexington
HHH
Hilton Head Island
$314 Roundtrip, found 4 days ago
$314
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 16 from Lexington to Hilton Head Island, returning Wed, Sep 23, priced at $314 found 4 days ago
Delta
Wed, Sep 16 - Wed, Sep 23
LEX
Lexington
HHH
Hilton Head Island
$314 Roundtrip, found 4 days ago
$314
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 16 from Lexington to Hilton Head Island, returning Wed, Sep 23, priced at $314 found 4 days ago
American Airlines
Fri, Nov 13 - Tue, Nov 17
LEX
Lexington
HHH
Hilton Head Island
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Nov 13 from Lexington to Hilton Head Island, returning Tue, Nov 17, priced at $328 found 1 day ago
United
Wed, Sep 16 - Wed, Sep 23
LEX
Lexington
HHH
Hilton Head Island
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Select United flight, departing Wed, Sep 16 from Lexington to Hilton Head Island, returning Wed, Sep 23, priced at $329 found 4 days ago
American Airlines
Wed, Sep 23 - Mon, Sep 28
LEX
Lexington
HHH
Hilton Head Island
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 23 from Lexington to Hilton Head Island, returning Mon, Sep 28, priced at $334 found 4 days ago
American Airlines
Wed, Sep 16 - Wed, Sep 23
LEX
Lexington
HHH
Hilton Head Island
$349 Roundtrip, found 4 days ago
$349
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 16 from Lexington to Hilton Head Island, returning Wed, Sep 23, priced at $349 found 4 days ago
American Airlines
Fri, Nov 13 - Tue, Nov 17
LEX
Lexington
HHH
Hilton Head Island
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Nov 13 from Lexington to Hilton Head Island, returning Tue, Nov 17, priced at $363 found 1 day ago
United
Sat, Oct 3 - Sat, Oct 10
LEX
Lexington
HHH
Hilton Head Island
$370 Roundtrip, found 13 hours ago
$370
Roundtrip
found 13 hours ago
Select United flight, departing Sat, Oct 3 from Lexington to Hilton Head Island, returning Sat, Oct 10, priced at $370 found 13 hours ago
American Airlines
Fri, Nov 13 - Tue, Nov 17
LEX
Lexington
HHH
Hilton Head Island
$387 Roundtrip, found 1 day ago
$387
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Nov 13 from Lexington to Hilton Head Island, returning Tue, Nov 17, priced at $387 found 1 day ago
United
Wed, Sep 16 - Wed, Sep 23
LEX
Lexington
HHH
Hilton Head Island
$399 Roundtrip, found 4 days ago
$399
Roundtrip
found 4 days ago
Select United flight, departing Wed, Sep 16 from Lexington to Hilton Head Island, returning Wed, Sep 23, priced at $399 found 4 days ago

Alternative airports near Hilton Head Island

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Savannah - Hilton Head Intl. SAV. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $457
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $457

Find the cheapest month to fly from Lexington (LEX) to Hilton Head Island (HHH)

May is typically the cheapest month to fly

From $249 - $555 per traveler.

What you need to know for your flight from Blue Grass to Hilton Head Island

Lexington (LEX) to Hilton Head Island (HHH) at a glance

Travel between Lexington (LEX) and Hilton Head Island (HHH) with a variety of airlines on this short domestic route. Discover options for flights from Lexington that cater to different budgets and schedules, making it easier to plan your visit to Hilton Head Island’s renowned attractions and neighborhoods. Whether you're on the lookout for cheap flights from Lexington or full-service options, find all the essential details for your journey from Blue Grass Airport to Hilton Head Island Airport.

  • Fastest flight duration: around 2h 45m in-flight, plus roughly 2 hours layover with one stop
  • Route distance: roughly 450 miles (725 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $150–$365, depending on seasonality and how far ahead you book

Flights from Blue Grass Airport (LEX) to Hilton Head Island Airport (HHH)

According to recent traveler bookings, the top airlines flying from Lexington to Hilton Head Island are typically favored for their one-stop services. Common layover points include Charlotte-Douglas International Airport (CLT) with an approximate 2-hour layover and Hartsfield-Jackson Atlanta International Airport (ATL) with about a 2-hour and 15-minute layover. This allows you to customize your travel experience by balancing price, overall travel time, and cabin class to secure the ideal itinerary.

  • American Airlines: This established full-service airline provides one-stop flights, with one-way ticket prices generally falling between $150 and $370. It handles around 93% of the departures for this route, featuring an in-flight duration of 2 hours and 45 minutes, and a total travel time of approximately 4 hours and 45 minutes, including layover time.

Alternative route from Lexington (LEX) to Hilton Head Island (HHH)

  • Lexington to Savannah (LEX-SAV): Savannah - Hilton Head International Airport (SAV) is located approximately 31 miles from Hilton Head Island Airport (HHH). One-way economy ticket prices for this route generally fall between $115 and $380, influenced by the time of year and when you book. Travelers typically encounter one-stop options, with common layover points at Charlotte-Douglas International Airport (CLT) and Hartsfield-Jackson Atlanta International Airport (ATL). Leading airlines operating on this route include American Airlines and Delta, with first-class service also available.

How to find the best prices for flights from Lexington (LEX) to Hilton Head Island (HHH)

Getting some of the best deals on flights from Lexington to Hilton Head Island is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are typically available when booking at least two months in advance, although most travelers reserve their flights two to eight weeks ahead. Morning departures between 5 a.m. and noon often provide lower prices and are the most sought-after. Additionally, flying on Friday usually offers cheaper rates, while Wednesday remains the most popular travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Hilton Head Island hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Hilton Head Island Airport from Blue Grass Airport

Hilton Head Island welcomes travelers from Lexington with a range of transport options based on price, convenience, and proximity. Here's how to reach Hilton Head Island efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Hilton Head Island, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Hilton Head Island Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hilton Head Island Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Hilton Head Island Airport, St Phillips Island Seaport, a seaport, is located about 6.4 miles from the airport.

Frequently asked questions

How much does a flight from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) cost?
You can find cheap one-way flights from $264 and cheap return flights from $314 Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) with Expedia. One-way flights generally range between $248 and $504, and roundtrip flights usually range from $332 to $1027. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
The cheapest month to fly from LEX to HHH is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
Enter LEX to HHH and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
American Airlines is one of the cheapest airlines offering connecting flights from Lexington, KY (LEX) to Hilton Head Island, SC (HHH) with a layover in Dallas-Fort Worth Intl. (DFW), starting from around $619. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
To find a cheap flight from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from LEX to HHH. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
The most popular departure times for flights from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) are in the early morning, from 6am to 9am. About 50% of passengers prefer this time window. Many major carriers, including American Airlines, Delta and Delta, offer flights during this window. This timing works well because it allows you to start your day early and arrive at your destination with plenty of time to enjoy the afternoon.
How long does it take to fly from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
Flying from LEX to HHH with a connection usually takes about 4 hours 30 minutes, traveling roughly 458 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
You can fly first class between LEX and HHH. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United Airlines

How do I earn miles on a Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) flight with Expedia?
It's easy to earn miles on a Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) at the last minute?
Typically, booking a last minute flight from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) flight and hotel package?
Securing a Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) Hilton Head Island Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH)?
If you booked your Lexington, KY (LEX-Blue Grass) to Hilton Head Island, SC (HHH) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Blue Grass
Destination airport
Hilton Head Island
Airlines serving
American Airlines, Delta, United
Roundtrip price
$313
Distance
457 mi

Book with confidence

Lexington to Hilton Head Island Flights

The cheapest times to fly from Lexington to Hilton Head Island

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Lexington to Hilton Head Island are during the month of September. You can find some of the cheapest flights from Lexington to Hilton Head Island with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Lexington to Hilton Head Island

Sunday is one of the best days to book for cheap flights from Lexington to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Lexington to Hilton Head Island

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Lexington to Hilton Head Island in 2026. You can also book with separate airlines for your outbound and return journeys, from $264 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Lexington to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Lexington to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Lexington to Hilton Head Island Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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