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$427+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This American Airlines deal was found by Cheapflights users on 3/13. 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 5/711:03 am
HHH
-
EYW
1 stop4h 37m
American Airlines
Sun 5/108:05 am
EYW
-
HHH
1 stop6h 21m
American Airlines
Deal found 3/13$427
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sat 11/710:47 am
HHH
-
EYW
1 stop5h 25m
American Airlines
Mon 11/1612:40 pm
EYW
-
HHH
1 stop5h 29m
American Airlines
Deal found 3/15$497
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 11/910:47 am
HHH
-
EYW
2 stops8h 42m
American Airlines
Mon 11/168:06 am
EYW
-
HHH
1 stop6h 13m
American Airlines
Deal found 3/15$502
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 11/810:47 am
HHH
-
EYW
1 stop5h 25m
American Airlines
Mon 11/168:06 am
EYW
-
HHH
1 stop6h 13m
American Airlines
Deal found 3/15$517
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sat 11/710:47 am
HHH
-
EYW
1 stop5h 25m
American Airlines
Sat 11/1412:40 pm
EYW
-
HHH
1 stop5h 29m
American Airlines
Deal found 3/15$528
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sat 11/72:51 pm
HHH
-
EYW
1 stop6h 56m
American Airlines
Sun 11/158:06 am
EYW
-
HHH
1 stop6h 13m
American Airlines
Deal found 3/15$548
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 11/82:51 pm
HHH
-
EYW
1 stop6h 56m
American Airlines
Sun 11/158:06 am
EYW
-
HHH
1 stop6h 13m
American Airlines
Deal found 3/15$568

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$427
(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.
Search Deals
From Hilton Head Island to Key West
Search Deals

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 March 17, 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
Quickest round-trip

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Thu 5/7

11:03 am-3:40 pm

1 stop4h 37m

Key West

Sun 5/10

8:05 am-2:26 pm

1 stop6h 21m

$427

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sat 4/25

4:11 pm-3:57 pm

2 stops23h 46m

Key West

Wed 4/29

3:52 pm-2:11 pm

1 stop22h 19m

$973

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 4/1

4:11 pm-2:51 pm

3 stops22h 40m

Key West

Sun 4/5

4:38 pm-2:16 pm

2 stops21h 38m

$1,543

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

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 March.
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.

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, January is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $78). Flying from Hilton Head Island to Key West in April is currently the most expensive (average of $367). 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 $427, American Airlines can have you in Key West from Hilton Head Island in 4h 37m. Airlines will cover a distance of 533 mi. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $78). Flying from Hilton Head Island to Key West in April is currently the most expensive (average of $367). 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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