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$387+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Key West

Best flights from Hilton Head Island to Key West
Discover carefully curated flight deals from Hilton Head Island to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 1/293:29 pmHHH - EYW
1 stop6h 18mAmerican Airlines
Thu 2/57:08 amEYW - HHH
1 stop5h 12mAmerican Airlines
Deal found 12/15$387
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 2/266:22 pmHHH - EYW
1 stop4h 21mAmerican Airlines
Sun 3/17:54 pmEYW - HHH
2 stops18h 33mAmerican Airlines
Deal found 12/15$561

Find 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 December 16, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$387
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Key West flights.
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From Hilton Head Island to Key West
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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 December 16, 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

Thu 1/29

3:29 pm-9:47 pm

1 stop6h 18m

Key West

Thu 2/5

7:08 am-12:20 pm

1 stop5h 12m

$387

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Thu 2/26

6:22 pm-10:43 pm

1 stop4h 21m

Key West

Sun 3/1

7:54 pm-2:27 pm

2 stops18h 33m

$561

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

  • Most accurate provider: When it comes to deals on Hilton Head Island-Key West flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Hilton Head Island-Key West flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Hilton Head Island-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Key West flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Hilton Head Island-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, February is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $64). Flying from Hilton Head Island to Key West in April is currently the most expensive (average of $454). 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 $392, American Airlines can have you in Key West from Hilton Head Island in 8h 27m. 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, February is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $64). Flying from Hilton Head Island to Key West in April is currently the most expensive (average of $454). 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.

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