$289+ Cheap flights from Hilton Head Island to Key West (HHH - EYW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
nov. 28 — dic. 51
1 adult, Economy
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One-way flights from Hilton Head Island to Key WestSearch for one-way flight options from Hilton Head Island to Key West. Find affordable one-way fares based on user searches. Data last updated octubre 29, 2025.
Search for one-way flight options from Hilton Head Island to Key West. Find affordable one-way fares based on user searches. Data last updated octubre 29, 2025.
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 12/112:17 pmHHH - EYW
1 stop7h 28mAmerican Airlines
Deal found 10/27![American Airlines logo]()
$289
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 octubre 29, 2025.
Most accurate provider | Expedia 2 stars |
|---|---|
Most trusted provider | Expedia 3 stars |
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 octubre 29, 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
jue. 12/11
2:17 pm-9:45 pm
1 stop7h 28m
$289
- 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.