$179+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Sep 15 — Sep 221
Round-trip
1 adult, Economy
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Find cheap flights from Clearwater to Hilton Head Island with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Clearwater to Hilton Head Island
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Cheapest flights from Clearwater to Hilton Head IslandExplore 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 August 16, 2026.
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 August 16, 2026.
This American Airlines deal was found by Cheapflights users on 8/12. 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 11/195:35 am -
1 stop5h 01m
Sun 11/222:51 pm -
1 stop7h 10m
Deal found 8/12![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/106:00 am -
1 stop5h 05m
Sat 10/176:13 pm -
1 stop6h 22m
Deal found 8/14![American Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/512:00 pm -
1 stop5h 05m
Fri 9/1112:50 pm -
1 stop6h 37m
Deal found 8/15![American Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/295:44 am -
1 stop6h 31m
Sat 10/312:50 pm -
1 stop6h 37m
Deal found 8/14![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/87:00 am -
1 stop4h 05m
Tue 10/135:11 pm -
1 stop4h 15m
Deal found 8/14![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:10 am -
1 stop4h 22m
Tue 9/112:15 pm -
1 stop6h 38m
Deal found 8/13![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/128:01 am -
1 stop4h 24m
Thu 9/175:15 pm -
1 stop6h 11m
Deal found 8/11![American Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/238:54 am -
1 stop4h 51m
Sat 9/265:15 pm -
1 stop3h 45m
Deal found 8/12![American Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/296:00 am -
1 stop5h 09m
Wed 9/23:27 pm -
1 stop5h 54m
Deal found 8/14![American Airlines logo]()
$457
Best flights from Clearwater to Hilton Head IslandDiscover carefully curated flight deals from Clearwater to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
Discover carefully curated flight deals from Clearwater to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 16, 2026.
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/512:00 pm -
1 stop5h 05m
Fri 9/1112:50 pm -
1 stop6h 37m
Deal found 8/15![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:10 am -
1 stop4h 22m
Tue 9/112:15 pm -
1 stop6h 38m
Deal found 8/13![Delta logo]()
$432
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:23 pm -
1 stop21h 40m
Wed 9/162:48 pm -
2 stops24h 40m
Deal found 8/11![United Airlines logo]()
$616
This American Airlines deal was found by Cheapflights users on 8/14. 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 2/58:03 am -
1 stop6h 56m
Mon 2/83:29 pm -
2 stops16h 28m
Deal found 8/14![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 8/11. 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 1/18:12 am -
1 stop6h 17m
Tue 1/53:02 pm -
2 stops7h 57m
Deal found 8/11![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:10 am -
1 stop4h 22m
Mon 8/3112:15 pm -
1 stop4h 33m
Deal found 8/14![Delta logo]()
$517
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/106:00 am -
2 stops7h 45m
Wed 9/1612:50 pm -
1 stop4h 32m
Deal found 8/11![American Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:03 am -
1 stop4h 28m
Tue 10/1312:23 pm -
1 stop4h 15m
Deal found 8/14![Delta logo]()
$623
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/86:00 am -
2 stops8h 26m
Tue 10/135:11 pm -
1 stop6h 10m
Deal found 8/14![American Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Wed 9/231:05 pm -
1 stop3h 40m
Sun 9/276:29 pm -
1 stop6h 00m
Deal found 8/15![American Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 8/287:43 pm -
2 stops15h 26m
Tue 9/15:16 pm -
2 stops6h 43m
Deal found 8/13![American Airlines logo]()
$629
Last-minute flights from Clearwater to Hilton Head IslandDiscover last-minute flight deals from Clearwater to Hilton Head Island. Data last updated August 16, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Hilton Head Island. Data last updated August 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:10 am -
1 stop4h 22m
Tue 9/112:15 pm -
1 stop6h 38m
Deal found 8/13![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 8/288:00 am -
1 stop6h 57m
Tue 9/15:16 pm -
2 stops6h 43m
Deal found 8/13![American Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/296:00 am -
1 stop5h 09m
Wed 9/23:27 pm -
1 stop5h 54m
Deal found 8/14![American Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/512:00 pm -
1 stop5h 05m
Fri 9/1112:50 pm -
1 stop6h 37m
Deal found 8/15![American Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/105:44 am -
1 stop6h 31m
Wed 9/1612:50 pm -
1 stop6h 37m
Deal found 8/11![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/128:01 am -
1 stop4h 24m
Thu 9/175:15 pm -
1 stop6h 11m
Deal found 8/11![American Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/238:54 am -
1 stop4h 51m
Sat 9/265:15 pm -
1 stop3h 45m
Deal found 8/12![American Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/238:54 am -
1 stop4h 51m
Sun 9/276:29 pm -
1 stop6h 00m
Deal found 8/12![American Airlines logo]()
$514
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/295:44 am -
1 stop6h 31m
Sat 10/312:50 pm -
1 stop6h 37m
Deal found 8/14![American Airlines logo]()
$417
One-way flights from Clearwater to Hilton Head IslandSearch for one-way flight options from Clearwater to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
Search for one-way flight options from Clearwater to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Tue 9/155:44 am -
1 stop6h 31m
Deal found 8/13![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/26:00 am -
1 stop5h 09m
Deal found 8/11![American Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm -
1 stop19h 29m
Deal found 8/15![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2711:05 am -
1 stop4h 22m
Deal found 8/15![Delta logo]()
$246
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/288:01 am -
1 stop4h 14m
Deal found 8/15![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/2612:02 pm -
2 stops23h 16m
Deal found 8/15![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/37:50 pm -
2 stops15h 28m
Deal found 8/14![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:59 pm -
2 stops18h 28m
Deal found 8/15![Delta logo]()
$354
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 August 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $367 (American Airlines) |
One-way from | $179 (American Airlines) |
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 August 16, 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
Cheapest round-trip
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Sat 9/5
12:00 pm-5:05 pm
1 stop5h 05m
Hilton Head Island
Fri 9/11
12:50 pm-7:27 pm
1 stop6h 37m
$405
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Fri 8/28
11:10 am-3:32 pm
1 stop4h 22m
Hilton Head Island
Tue 9/1
12:15 pm-6:53 pm
1 stop6h 38m
$432
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Fri 2/5
8:03 am-2:59 pm
1 stop6h 56m
Hilton Head Island
Mon 2/8
3:29 pm-7:57 am
2 stops16h 28m
$435
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Fri 1/1
8:12 am-2:29 pm
1 stop6h 17m
Hilton Head Island
Tue 1/5
3:02 pm-10:59 pm
2 stops7h 57m
$456
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Thu 8/27
11:10 am-3:32 pm
1 stop4h 22m
Hilton Head Island
Mon 8/31
12:15 pm-4:48 pm
1 stop4h 33m
$517
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Thu 9/10
6:00 am-1:45 pm
2 stops7h 45m
Hilton Head Island
Wed 9/16
12:50 pm-5:22 pm
1 stop4h 32m
$546
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Thu 10/8
6:00 am-2:26 pm
2 stops8h 26m
Hilton Head Island
Tue 10/13
5:11 pm-11:21 pm
1 stop6h 10m
$546
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Wed 9/23
1:05 pm-4:45 pm
1 stop3h 40m
Hilton Head Island
Sun 9/27
6:29 pm-12:29 am
1 stop6h 00m
$569
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Thu 9/10
4:23 pm-2:03 pm
1 stop21h 40m
Hilton Head Island
Wed 9/16
2:48 pm-3:28 pm
2 stops24h 40m
$616
Quickest round-trip
TampaHilton Head Island
TPA Tampa - HHH Hilton Head Island
TPAHHH
Tampa
Thu 10/8
11:03 am-3:31 pm
1 stop4h 28m
Hilton Head Island
Tue 10/13
12:23 pm-4:38 pm
1 stop4h 15m
$623
Showing 1-10 of 18 resultsSorted by cheapest first
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.
TPA-HHH
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
CL9-HHH
TPA-HHH
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 August 16, 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.
Comfort
7.2
Entertainment
6.8
Crew
7.9
Boarding
7.5
Food
6.4
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Comfort
7.2
Entertainment
6.8
Crew
7.9
Boarding
7.5
Food
6.4
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
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.
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
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Other flights to Hilton Head Island
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Consider these flights traveling from Clearwater to Hilton Head Island.
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 August 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$306 | Average$476 | FlexibilityNo cancel fee | On-time71% |