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$445+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
mai 30 — juin 61
sam. 5/30
sam. 6/6
1 adult, Economy
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Cheap 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 avril 30, 2026.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
mar. 4/282:54 pm
HHH
-
EYW
1 stop6h 59m
American Airlines
mar. 5/511:56 am
EYW
-
HHH
1 stop5h 25m
American Airlines
Deal found 4/28$467
This American Airlines deal was found by Cheapflights users on 4/29. 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.
jeu. 5/145:04 pm
HHH
-
EYW
1 stop5h 32m
American Airlines
lun. 5/188:05 am
EYW
-
HHH
1 stop4h 32m
American Airlines
Deal found 4/29$547
This American Airlines deal was found by Cheapflights users on 4/29. 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.
jeu. 5/285:21 pm
HHH
-
EYW
2 stops20h 20m
American Airlines
mar. 6/27:29 pm
EYW
-
HHH
2 stops14h 58m
American Airlines
Deal found 4/29$690
This American Airlines deal was found by Cheapflights users on 4/27. 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.
mar. 5/1211:17 am
HHH
-
EYW
1 stop5h 18m
American Airlines
sam. 5/168:05 am
EYW
-
HHH
1 stop6h 19m
American Airlines
Deal found 4/27$728
This American Airlines deal was found by Cheapflights users on 4/28. 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.
mar. 5/123:44 pm
HHH
-
EYW
1 stop23h 40m
American Airlines
mar. 5/265:37 pm
EYW
-
HHH
2 stops17h 33m
American Airlines
Deal found 4/28$796

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 avril 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$547
(American Airlines)

One-way from

$445
(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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One-way flight 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 avril 30, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

jeu. 5/14

1:08 pm-10:58 pm

2 stops9h 50m

Key West

lun. 5/18

6:45 am-6:09 pm

2 stops11h 24m

$687

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

jeu. 5/28

5:21 pm-1:41 pm

2 stops20h 20m

Key West

mar. 6/2

7:29 pm-10:27 am

2 stops14h 58m

$690
Quickest round-trip

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

mar. 5/12

11:17 am-4:35 pm

1 stop5h 18m

Key West

sam. 5/16

8:05 am-2:24 pm

1 stop6h 19m

$728

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

mar. 5/12

3:44 pm-3:24 pm

1 stop23h 40m

Key West

mar. 5/26

5:37 pm-11:10 am

2 stops17h 33m

$796
Cheapest one-way
Quickest one-way

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

dim. 5/10

1:08 pm-10:58 pm

2 stops9h 50m

$450

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

dim. 5/10

4:39 pm-3:07 pm

3 stops22h 28m

$1,556

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Sorted by cheapest first

Compare providers for flights from Hilton Head Island to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hilton Head Island to Key West in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Hilton Head Island-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Key West flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 $547, American Airlines can have you in Key West from Hilton Head Island in 5h 32m. 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.

See more FAQs

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