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Hilton Head Island

$186+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
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 May 7, 2026.

This American Airlines deal was found by Cheapflights users on 5/3. 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 6/1710:24 am
TPA
-
HHH
1 stop3h 49m
American Airlines
Wed 6/242:43 pm
HHH
-
TPA
1 stop5h 07m
American Airlines
Deal found 5/3$349
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/910:24 am
TPA
-
HHH
1 stop3h 49m
American Airlines
Mon 6/1511:40 am
HHH
-
TPA
1 stop5h 37m
American Airlines
Deal found 5/3$357
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/128:30 am
TPA
-
HHH
1 stop3h 56m
American Airlines
Mon 6/152:43 pm
HHH
-
TPA
2 stops9h 57m
American Airlines
Deal found 5/3$372
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/148:30 am
TPA
-
HHH
1 stop3h 56m
American Airlines
Wed 6/172:43 pm
HHH
-
TPA
1 stop5h 07m
American Airlines
Deal found 5/4$406
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/107:15 am
TPA
-
HHH
1 stop3h 55m
American Airlines
Fri 6/1212:56 pm
HHH
-
TPA
1 stop6h 54m
American Airlines
Deal found 5/5$412

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$186
(Delta)
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
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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 May 7, 2026.
Use the filters below to find and compare flights from Clearwater to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 6/9

10:24 am-2:13 pm

1 stop3h 49m

Hilton Head Island

Mon 6/15

11:40 am-5:17 pm

1 stop5h 37m

$357

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Fri 6/26

7:15 am-2:13 pm

1 stop6h 58m

Hilton Head Island

Mon 6/29

2:43 pm-7:50 pm

1 stop5h 07m

$367

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Wed 6/10

8:30 am-2:13 pm

1 stop5h 43m

Hilton Head Island

Fri 6/12

12:56 pm-7:50 pm

1 stop6h 54m

$412

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 8/24

9:59 am-3:30 pm

1 stop5h 31m

Hilton Head Island

Thu 8/27

12:11 pm-5:52 pm

1 stop5h 41m

$441

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 8/24

11:22 am-4:38 pm

1 stop5h 16m

Hilton Head Island

Thu 8/27

2:48 pm-12:02 am

2 stops9h 14m

$446

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Mon 5/18

8:15 am-12:37 pm

1 stop4h 22m

Hilton Head Island

Fri 5/22

12:56 pm-7:50 pm

1 stop6h 54m

$559
Cheapest one-way

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 6/16

9:58 am-3:32 pm

1 stop5h 34m

$186

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 6/16

6:00 am-2:13 pm

2 stops8h 13m

$191
Quickest one-way

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Tue 6/2

11:54 am-4:32 pm

1 stop4h 38m

$192

TampaHilton Head Island

TPA - HHH

TPAHHH

Tampa

Thu 6/4

8:30 am-2:13 pm

1 stop5h 43m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 11 resultsSorted by cheapest first
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
No data available for this route at this time. Please check back soon.

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 May 7, 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
7.1
Good
11,669 reviews

Crew

7.9

Overall

7.1

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,669 reviews
American Airlines
7.1
Good
11,669 reviews

Crew

7.9

Overall

7.1

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 and Delta can get you from Clearwater to Hilton Head Island in just under 3h 49m. Your travel time can differ by up to 1h 42m. The distance from Clearwater to Hilton Head Island is about 313 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$365FlexibilityNo cancel feeOn-time71%

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