$224 Cheap Flights from Key West (EYW) to Hilton Head Island (HHH)

View $224 flight on Sat, Feb 14, 2026Opens in a new window

Popular airlines from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Key West to Hilton Head Island (EYW-HHH)

Prices were available within the past 7 days and start at $224 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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 $780
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $780

Frequently asked questions

How much does a flight from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH) cost?
Secure a cheap one-way flight from $224 or cheap return flight from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)?
The cheapest month to fly from EYW to HHH is , when demand is low. Off-peak season is often when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest EYW to HHH flight.
How many flights per day from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)?
You'll need to hop on a flight with a layover if you're traveling from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from EYW to HHH?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)?
Select a flight from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH) that takes off before 3 PM to reduce the risk of cancellations and delays. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH) last-minute?
Waiting until just before your trip to book a flight from EYW to HHH often results in higher prices. While you may come across some last-minute discounts, they aren't always guaranteed. Be flexible with your travel plans for the best chance of snagging a bargain.
Is it cheaper to book an EYW to HHH flight and hotel package?
You'll typically save money by booking an EYW to HHH flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've selected your ideal accommodations and flights, consider adding extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Key West Intl. Airport (EYW) to Hilton Head Island Airport (HHH)?
If you reserved your EYW to HHH flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Origin airport
Key West Intl.
Destination airport
Hilton Head Island
Distance
533 mi

Book with confidence

Key West to Hilton Head Island Flights

The cheapest times to fly from Key West 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 Key West to Hilton Head Island are during the month of . You can find some of the cheapest flights from Key West to Hilton Head Island with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Key West to Hilton Head Island

Sunday is one of the best days to book for cheap flights from Key West 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 Key West 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 Key West to Hilton Head Island in 2026. You can also book with separate airlines for your outbound and return journeys, from $224 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 Key West 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 Key West 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.

 

Key West to Hilton Head Island Flights

Explore a world of travel with Expedia

*Available to One Key members.