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$447+ Cheap flights from Hilton Head Island to Key West (HHH - EYW)

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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 11, 2025.

Round-trip from

$447
(American Airlines)
From Hilton Head Island to Key West
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Find flight deals from Hilton Head Island to Key West

Cheapest flights from Hilton Head Island to Key West
Explore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/9. 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.
sáb. 12/132:17 pmHHH - EYW
1 stop7h 33mAmerican Airlines
mar. 12/167:30 amEYW - HHH
1 stop4h 52mAmerican Airlines
Deal found 9/9$447
This American Airlines deal was found by Cheapflights users on 9/10. 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.
vie. 10/312:56 pmHHH - EYW
1 stop4h 50mAmerican Airlines
mar. 10/77:52 pmEYW - HHH
2 stops20h 59mAmerican Airlines
Deal found 9/10$512

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Key West 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 septiembre 11, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Key West that are best for you.

Fly from

Hilton Head Island

Fly to

Key West

Route

Depart

Return

Price

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

sáb. 12/13

2:17 pm-9:50 pm

1 stop7h 33m

Key West

mar. 12/16

7:30 am-12:22 pm

1 stop4h 52m

$447

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

vie. 10/3

12:56 pm-5:46 pm

1 stop4h 50m

Key West

mar. 10/7

7:52 pm-4:51 pm

2 stops20h 59m

$512

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Best time to book a flight from Hilton Head Island to Key West

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

What is the cheapest month to book a flight from Hilton Head Island to Key West?

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $328). Flying from Hilton Head Island to Key West in March is currently the most expensive (average of $491). 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Hilton Head Island to Key West?

    For as low as $447, American Airlines can have you in Key West from Hilton Head Island in 7h 33m. Airlines will cover a distance of 533 mi.

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

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

  • How can I find direct flights from Hilton Head Island to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Key West.

  • Can I find deals for business class flights from Hilton Head Island to Key West?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Key West 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 Hilton Head Island to Key West?

    Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $328). Flying from Hilton Head Island to Key West in March is currently the most expensive (average of $491). 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

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