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Hilton Head Island

$154+ Cheap flights from Clearwater, FL to Hilton Head Island (HHH)

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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap flight deals from Clearwater to Hilton Head Island

Keep the following information in mind while searching for Clearwater to Hilton Head Island flight deals. Data was last updated November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$317
(American Airlines)

One-way from

$154
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$399
Provider with most accurate pricing for Tampa-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Tampa-Hilton Head Island flights.
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From Clearwater to Hilton Head Island
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One-way flight from Clearwater to Hilton Head Island
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Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Clearwater to Hilton Head Island

Cheapest flights from Clearwater to Hilton Head Island
Explore the most affordable flight options available from Clearwater to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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.
Tue 11/256:00 amTPA - HHH
1 stop5h 49mAmerican Airlines
Fri 11/2812:19 pmHHH - TPA
1 stop6h 37mAmerican Airlines
Deal found 11/18$507
This American Airlines deal was found by Cheapflights users on 11/17. 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 12/17:01 amTPA - HHH
1 stop4h 48mAmerican Airlines
Fri 12/512:52 pmHHH - TPA
1 stop4h 23mAmerican Airlines
Deal found 11/17$535
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 11/2110:20 amTPA - HHH
1 stop3h 59mAmerican Airlines
Sun 11/236:40 pmHHH - TPA
1 stop5h 34mAmerican Airlines
Deal found 11/19$547
This American Airlines deal was found by Cheapflights users on 11/18. 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 11/229:41 amTPA - HHH
2 stops8h 28mAmerican Airlines
Mon 11/243:27 pmHHH - TPA
2 stops8h 32mAmerican Airlines
Deal found 11/18$557

Cheapflights Fare Finder

 
Customize your flight search to find flights from Clearwater to Hilton Head Island 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 November 20, 2025.
Use the filters below to find and compare flights from Clearwater to Hilton Head Island that are best for you.

Fly from

Clearwater

Fly to

Hilton Head Island

Route

Depart

Return

Price

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 1/9

8:00 am-12:20 pm

1 stop4h 20m

Hilton Head Island

Tue 1/13

12:51 pm-5:15 pm

1 stop4h 24m

$317

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Sat 2/21

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Wed 2/25

3:39 pm-9:17 pm

1 stop5h 38m

$367

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 12/1

7:01 am-11:49 am

1 stop4h 48m

Hilton Head Island

Fri 12/5

12:52 pm-5:15 pm

1 stop4h 23m

$535

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 11/27

6:00 am-10:24 am

1 stop4h 24m

$154

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Wed 11/26

8:26 am-2:19 pm

1 stop5h 53m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Best time to book a flight from Clearwater to Hilton Head Island

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

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

Currently, February is the cheapest month in which you can book a flight from Clearwater to Hilton Head Island (average of $63). Flying from Clearwater to Hilton Head Island in March is currently the most expensive (average of $119). 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.

What is the cheapest time of day to fly from CL9 to HHH?

Find hourly flight availability from Clearwater to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2025.

One of the essential ways to save on airfare from Clearwater to Hilton Head Island is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 68% on airfare.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated November 20, 2025.
See what other customers who have flown with American Airlines from Clearwater to Hilton Head Island have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,047 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Crew

8.0

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Crew

8.0

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

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

  • What airport do you fly into for flights to Hilton Head Island from Clearwater?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly into when you book flights from Clearwater to Hilton Head Island. 1 airline have flights to Hilton Head from Clearwater on a regular basis. Booking flights from Clearwater to Hilton Head Island should not be difficult; the airport handles an average of 0 inbound flights from Clearwater per day.

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

    American Airlines can get you from Clearwater to Hilton Head Island in just under 4h 20m. Your travel time can differ by up to . The distance from Clearwater to Hilton Head Island is about 313 mi.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Clearwater to Hilton Head Island (average of $63). Flying from Clearwater to Hilton Head Island in March is currently the most expensive (average of $119). 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

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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Top airline flying from Clearwater to Hilton Head Island

Discover the top airline that operate flights from Clearwater to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$376FlexibilityNo cancel feeOn-time71%

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