$289 Cheap Flights from Hilton Head Island (HHH) to Key West (EYW)

View $289 flight on Thu, Apr 9, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $289 for one-way flights and $377 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jan 27 - Sat, Jan 31
HHH
Hilton Head Island
EYW
Key West
$377 Roundtrip, found 5 days ago
$377
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 27 from Hilton Head Island to Key West, returning Sat, Jan 31, priced at $377 found 5 days ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
HHH
Hilton Head Island
EYW
Key West
$447 Roundtrip, found 5 days ago
$447
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 27 from Hilton Head Island to Key West, returning Sat, Jan 31, priced at $447 found 5 days ago
American Airlines
Tue, Jan 27 - Tue, Feb 3
HHH
Hilton Head Island
EYW
Key West
$452 Roundtrip, found 5 days ago
$452
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 27 from Hilton Head Island to Key West, returning Tue, Feb 3, priced at $452 found 5 days ago
American Airlines
Sun, Jan 25 - Sat, Jan 31
HHH
Hilton Head Island
EYW
Key West
$457 Roundtrip, found 5 days ago
$457
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Jan 25 from Hilton Head Island to Key West, returning Sat, Jan 31, priced at $457 found 5 days ago
American Airlines
Sun, Jan 25 - Tue, Feb 3
HHH
Hilton Head Island
EYW
Key West
$462 Roundtrip, found 5 days ago
$462
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Jan 25 from Hilton Head Island to Key West, returning Tue, Feb 3, priced at $462 found 5 days ago
American Airlines
Wed, Jan 7 - Sat, Jan 10
HHH
Hilton Head Island
EYW
Key West
$498 Roundtrip, found 2 days ago
$498
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jan 7 from Hilton Head Island to Key West, returning Sat, Jan 10, priced at $498 found 2 days ago
American Airlines
Fri, Jan 30 - Sat, Jan 31
HHH
Hilton Head Island
EYW
Key West
$508 Roundtrip, found 5 days ago
$508
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 30 from Hilton Head Island to Key West, returning Sat, Jan 31, priced at $508 found 5 days ago
American Airlines
Fri, Jan 30 - Tue, Feb 3
HHH
Hilton Head Island
EYW
Key West
$513 Roundtrip, found 5 days ago
$513
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 30 from Hilton Head Island to Key West, returning Tue, Feb 3, priced at $513 found 5 days ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
HHH
Hilton Head Island
EYW
Key West
$547 Roundtrip, found 5 days ago
$547
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 27 from Hilton Head Island to Key West, returning Sat, Jan 31, priced at $547 found 5 days ago
Delta
Fri, Oct 24 - Sat, Oct 25
HHH
Hilton Head Island
EYW
Key West
$712 Roundtrip, found 2 days ago
$712
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 24 from Hilton Head Island to Key West, returning Sat, Oct 25, priced at $712 found 2 days ago

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW) cost?
Grab a cheap one-way flight from $289 or cheap return flight from $377 from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW)?
The cheapest month to fly from HHH to EYW is January, when demand is low. Off-peak season is usually when better flight deals are available between these airports.
What is the cheapest airline that flies from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from HHH to EYW. Then, sort your results by "Price (lowest to highest)" to snap up a good deal.
How many flights per day from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW)?
You'll have to take a flight with a layover if you're traveling from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW). 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 HHH to EYW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary based on various factors, such as the airline 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 Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW)?
Book a flight from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW) that leaves before 3 PM to reduce the likelihood of delays. Departures after this hour 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 Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW) last-minute?
Last-minute bookings from HHH to EYW are usually more expensive. To lock in the best rates, start searching for flights ahead of time. That said, if you can play around with your travel dates, it's possible to find a cheap fare right before your journey.
Is it cheaper to book a HHH to EYW flight and hotel package?
Booking a HHH to EYW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our wide range of accommodations and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Hilton Head Island Airport (HHH) to Key West Intl. Airport (EYW)?
If you booked your HHH to EYW flight in 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, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Hilton Head Island
Destination airport
Key West Intl.
Airlines serving
American Airlines
Roundtrip price
$376
Distance
533 mi

Book with confidence

Hilton Head Island to Key West Flights

The cheapest times to fly from Hilton Head Island to Key West

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

 

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

Sunday is one of the best days to book for cheap flights from Hilton Head Island to Key West: 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 Hilton Head Island to Key West

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 Hilton Head Island to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $289 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 Hilton Head Island to Key West 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 Hilton Head Island to Key West 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.

 

Hilton Head Island to Key West Flights

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*Available to One Key members.