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Hilton Head Island

$170+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/29. 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.
Sat 3/76:00 am
TPA
-
HHH
1 stop4h 33m
American Airlines
Tue 3/103:31 pm
HHH
-
TPA
1 stop5h 44m
American Airlines
Deal found 1/29$317
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 5/167:15 am
TPA
-
HHH
1 stop5h 22m
American Airlines
Sat 5/235:54 pm
HHH
-
TPA
1 stop6h 23m
American Airlines
Deal found 1/28$373
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/1011:00 am
TPA
-
HHH
1 stop3h 59m
American Airlines
Sat 2/142:58 pm
HHH
-
TPA
1 stop3h 47m
American Airlines
Deal found 1/26$407
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 10/2212:11 pm
TPA
-
HHH
1 stop5h 21m
American Airlines
Sun 10/256:13 pm
HHH
-
TPA
1 stop5h 53m
American Airlines
Deal found 1/27$419
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 3/1311:53 am
TPA
-
HHH
1 stop5h 51m
American Airlines
Fri 3/202:58 pm
HHH
-
TPA
1 stop7h 01m
American Airlines
Deal found 1/27$475
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 7/1210:12 am
TPA
-
HHH
1 stop4h 06m
American Airlines
Fri 7/1711:40 am
HHH
-
TPA
1 stop5h 37m
American Airlines
Deal found 1/27$495

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(American Airlines)

One-way from

$170
(American Airlines)

Popular in

June

Cheapest in

September
Provider with most accurate pricing for Tampa-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Hilton Head Island flights.
Search Deals
From Clearwater to Hilton Head Island
Search Deals
One-way flight from Clearwater to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals

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 January 29, 2026.
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

Sat 3/7

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Tue 3/10

3:31 pm-9:15 pm

1 stop5h 44m

$317

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Sat 5/16

7:15 am-12:37 pm

1 stop5h 22m

Hilton Head Island

Sat 5/23

5:54 pm-12:17 am

1 stop6h 23m

$373

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 2/10

11:00 am-2:59 pm

1 stop3h 59m

Hilton Head Island

Sat 2/14

2:58 pm-6:45 pm

1 stop3h 47m

$407

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 3/13

11:53 am-5:44 pm

1 stop5h 51m

Hilton Head Island

Fri 3/20

2:58 pm-9:59 pm

1 stop7h 01m

$475

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Sun 7/12

10:12 am-2:18 pm

1 stop4h 06m

Hilton Head Island

Fri 7/17

11:40 am-5:17 pm

1 stop5h 37m

$495

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 3/5

1:51 pm-5:44 pm

1 stop3h 53m

$170

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 3/6

7:25 am-2:22 pm

1 stop6h 57m

$208

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Sun 2/22

7:25 am-2:22 pm

1 stop6h 57m

$228

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 4/13

8:35 am-3:20 pm

1 stop6h 45m

$320

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 3/6

12:05 pm-1:59 pm

3 stops25h 54m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 11 results
1
2

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 $121). 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.

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 January 29, 2026.
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
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 33m. 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 $121). 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

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$351FlexibilityNo cancel feeOn-time71%

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