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Hilton Head Island

$253+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 September 19, 2025.

Round-trip from

$287
(American Airlines)

One-way from

$253
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$292
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. 2% potential increase in price ($10 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 September 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 September 19, 2025.

This American Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 11/1810:57 amTPA - HHH
1 stop4h 00mAmerican Airlines
Tue 12/27:07 pmHHH - TPA
1 stop4h 07mAmerican Airlines
Deal found 9/17$287
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/136:03 amTPA - HHH
1 stop5h 29mAmerican Airlines
Thu 10/165:57 pmHHH - TPA
1 stop4h 03mAmerican Airlines
Deal found 9/17$297
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 11/216:00 amTPA - HHH
1 stop5h 49mAmerican Airlines
Sat 12/66:48 pmHHH - TPA
1 stop5h 21mAmerican Airlines
Deal found 9/18$312
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/166:00 amTPA - HHH
2 stops11h 27mAmerican Airlines
Mon 10/205:57 pmHHH - TPA
1 stop4h 00mAmerican Airlines
Deal found 9/17$362
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/177:13 amTPA - HHH
1 stop4h 19mAmerican Airlines
Mon 10/205:57 pmHHH - TPA
1 stop6h 09mAmerican Airlines
Deal found 9/17$382
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/276:00 amTPA - HHH
1 stop4h 44mAmerican Airlines
Wed 12/3111:14 amHHH - TPA
2 stops9h 42mAmerican Airlines
Deal found 9/16$387
This American Airlines deal was found by Cheapflights users on 9/16. 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 9/307:15 amTPA - HHH
1 stop5h 02mAmerican Airlines
Fri 10/312:56 pmHHH - TPA
1 stop4h 48mAmerican Airlines
Deal found 9/16$419
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/1511:08 amTPA - HHH
1 stop5h 43mAmerican Airlines
Sat 10/185:57 pmHHH - TPA
1 stop6h 09mAmerican Airlines
Deal found 9/17$428

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 September 19, 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

Tue 11/18

10:57 am-2:57 pm

1 stop4h 00m

Hilton Head Island

Tue 12/2

7:07 pm-11:14 pm

1 stop4h 07m

$287

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 10/13

7:13 am-11:32 am

1 stop4h 19m

Hilton Head Island

Thu 10/16

3:02 pm-11:59 pm

2 stops8h 57m

$302

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 11/21

6:00 am-11:49 am

1 stop5h 49m

Hilton Head Island

Sat 12/6

6:48 pm-12:09 am

1 stop5h 21m

$312

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 10/16

6:00 am-5:27 pm

2 stops11h 27m

Hilton Head Island

Mon 10/20

5:57 pm-9:57 pm

1 stop4h 00m

$362

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 9/30

7:15 am-12:17 pm

1 stop5h 02m

Hilton Head Island

Fri 10/3

12:56 pm-5:44 pm

1 stop4h 48m

$419

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Wed 10/15

11:08 am-4:51 pm

1 stop5h 43m

Hilton Head Island

Sat 10/18

5:57 pm-12:06 am

1 stop6h 09m

$428

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 10/16

6:03 am-11:32 am

1 stop5h 29m

$253

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 9/22

11:14 am-4:47 pm

1 stop5h 33m

$344

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 10/16

6:22 pm-11:16 am

3 stops16h 54m

$607

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Sat 9/27

1:30 pm-11:16 am

2 stops21h 46m

$699

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

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, January is the cheapest month in which you can book a flight from Clearwater to Hilton Head Island (average of $275). Flying from Clearwater to Hilton Head Island in March is currently the most expensive (average of $479). 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 September 19, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Clearwater to Hilton Head Island as you normally would.

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 September 19, 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
10,000 reviews

Crew

8.0

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Entertainment

6.9

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Entertainment

6.9

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. 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, January is the cheapest month in which you can book a flight from Clearwater to Hilton Head Island (average of $275). Flying from Clearwater to Hilton Head Island in March is currently the most expensive (average of $479). 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$369FlexibilityNo cancel feeOn-time71%

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