$184+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
jul. 20 — jul. 271
Round-trip
1 adult, Economy
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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 junio 20, 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 junio 20, 2026.
This American Airlines deal was found by Cheapflights users on 6/16. 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.
jue. 7/167:15 am
TPA
- HHH
1 stop4h 02m
American Airlines
jue. 7/232:48 pm
HHH
- TPA
1 stop5h 03m
American Airlines
Deal found 6/16![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2911:14 am
TPA
- HHH
1 stop4h 15m
Delta
lun. 8/34:18 pm
HHH
- TPA
1 stop17h 43m
Delta
Deal found 6/17![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/18. 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.
mar. 11/36:00 am
TPA
- HHH
2 stops12h 09m
American Airlines
mié. 11/46:40 pm
HHH
- TPA
1 stop5h 32m
American Airlines
Deal found 6/18![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/3010:00 am
TPA
- HHH
1 stop5h 29m
Delta
mié. 8/512:15 pm
HHH
- TPA
1 stop12h 15m
Delta
Deal found 6/16![Delta logo]()
$406
This American Airlines deal was found by Cheapflights users on 6/16. 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.
lun. 9/78:00 am
TPA
- HHH
1 stop6h 57m
American Airlines
dom. 9/1311:48 am
HHH
- TPA
1 stop6h 38m
American Airlines
Deal found 6/16![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 6/16. 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.
lun. 7/207:15 am
TPA
- HHH
1 stop4h 02m
American Airlines
mié. 7/2211:47 am
HHH
- TPA
1 stop5h 54m
American Airlines
Deal found 6/16![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 6/16. 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.
sáb. 7/118:38 am
TPA
- HHH
1 stop6h 26m
American Airlines
mar. 7/144:55 pm
HHH
- TPA
1 stop5h 04m
American Airlines
Deal found 6/16![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 6/19. 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.
sáb. 7/47:15 am
TPA
- HHH
1 stop3h 50m
American Airlines
mié. 7/811:47 am
HHH
- TPA
1 stop5h 54m
American Airlines
Deal found 6/19![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 6/15. 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.
jue. 10/112:00 pm
TPA
- HHH
1 stop5h 59m
American Airlines
dom. 10/46:29 pm
HHH
- TPA
1 stop6h 00m
American Airlines
Deal found 6/15![American Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 6/18. 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.
lun. 10/268:41 am
TPA
- HHH
1 stop5h 41m
American Airlines
lun. 11/26:40 pm
HHH
- TPA
2 stops12h 59m
American Airlines
Deal found 6/18![American Airlines logo]()
$432
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 junio 20, 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 junio 20, 2026.
This American Airlines deal was found by Cheapflights users on 6/16. 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.
jue. 7/167:15 am
TPA
- HHH
1 stop4h 02m
American Airlines
jue. 7/232:48 pm
HHH
- TPA
1 stop5h 03m
American Airlines
Deal found 6/16![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2911:14 am
TPA
- HHH
1 stop4h 15m
Delta
lun. 8/34:18 pm
HHH
- TPA
1 stop17h 43m
Delta
Deal found 6/17![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/16. 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.
lun. 9/78:00 am
TPA
- HHH
1 stop6h 57m
American Airlines
dom. 9/1311:48 am
HHH
- TPA
1 stop6h 38m
American Airlines
Deal found 6/16![American Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2911:14 am
TPA
- HHH
1 stop4h 15m
Delta
dom. 8/212:11 pm
HHH
- TPA
1 stop21h 53m
Delta
Deal found 6/17![Delta logo]()
$445
This American Airlines deal was found by Cheapflights users on 6/16. 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.
sáb. 7/118:38 am
TPA
- HHH
1 stop6h 26m
American Airlines
mar. 7/144:55 pm
HHH
- TPA
1 stop5h 04m
American Airlines
Deal found 6/16![American Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/308:45 am
TPA
- HHH
1 stop6h 44m
Delta
mar. 8/412:15 pm
HHH
- TPA
1 stop7h 56m
Delta
Deal found 6/16![Delta logo]()
$446
This American Airlines deal was found by Cheapflights users on 6/19. 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.
sáb. 7/47:15 am
TPA
- HHH
1 stop3h 50m
American Airlines
mié. 7/811:47 am
HHH
- TPA
1 stop5h 54m
American Airlines
Deal found 6/19![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/308:45 am
TPA
- HHH
1 stop6h 44m
Delta
lun. 8/34:18 pm
HHH
- TPA
1 stop17h 43m
Delta
Deal found 6/17![Delta logo]()
$449
This American Airlines deal was found by Cheapflights users on 6/14. 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.
lun. 7/138:36 am
TPA
- HHH
1 stop5h 40m
American Airlines
dom. 7/1912:50 pm
HHH
- TPA
1 stop7h 01m
American Airlines
Deal found 6/14![American Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/258:45 am
TPA
- HHH
1 stop6h 47m
Delta
sáb. 6/2712:17 pm
HHH
- TPA
1 stop4h 33m
Delta
Deal found 6/19![Delta logo]()
$522
Last-minute flights from Clearwater to Hilton Head IslandDiscover last-minute flight deals from Clearwater to Hilton Head Island. Data last updated junio 20, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Hilton Head Island. Data last updated junio 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/19. 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.
sáb. 7/47:15 am
TPA
- HHH
1 stop3h 50m
American Airlines
mié. 7/811:47 am
HHH
- TPA
1 stop5h 54m
American Airlines
Deal found 6/19![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 6/16. 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.
sáb. 7/118:38 am
TPA
- HHH
1 stop6h 26m
American Airlines
mar. 7/144:55 pm
HHH
- TPA
1 stop5h 04m
American Airlines
Deal found 6/16![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 6/16. 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.
jue. 7/167:15 am
TPA
- HHH
1 stop4h 02m
American Airlines
jue. 7/232:48 pm
HHH
- TPA
1 stop5h 03m
American Airlines
Deal found 6/16![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/16. 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.
lun. 7/207:15 am
TPA
- HHH
1 stop4h 02m
American Airlines
mié. 7/2211:47 am
HHH
- TPA
1 stop5h 54m
American Airlines
Deal found 6/16![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2911:14 am
TPA
- HHH
1 stop4h 15m
Delta
lun. 8/34:18 pm
HHH
- TPA
1 stop17h 43m
Delta
Deal found 6/17![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/3010:00 am
TPA
- HHH
1 stop5h 29m
Delta
mié. 8/512:15 pm
HHH
- TPA
1 stop12h 15m
Delta
Deal found 6/16![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/308:45 am
TPA
- HHH
1 stop6h 44m
Delta
mar. 8/412:15 pm
HHH
- TPA
1 stop7h 56m
Delta
Deal found 6/16![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/308:45 am
TPA
- HHH
1 stop6h 44m
Delta
lun. 8/34:18 pm
HHH
- TPA
1 stop17h 43m
Delta
Deal found 6/17![Delta logo]()
$449
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 junio 20, 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 junio 20, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. 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.
mié. 8/2611:22 am
TPA
- HHH
1 stop5h 16m
American Airlines
Deal found 6/17![American Airlines logo]()
$184
This American Airlines deal was found by Cheapflights users on 6/17. 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.
mié. 7/111:55 am
TPA
- HHH
1 stop4h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/262:00 pm
TPA
- HHH
3 stops24h 03m
United Airlines
Deal found 6/17![United Airlines logo]()
$841
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/87:50 am
TPA
- HHH
1 stop6h 31m
United Airlines
Deal found 6/18![United Airlines logo]()
$877
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 junio 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $367 (American Airlines) |
One-way from | $184 (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 junio 20, 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
Quickest round-trip
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
jue. 7/16
7:15 am-11:17 am
1 stop4h 02m
Hilton Head Island
jue. 7/23
2:48 pm-7:51 pm
1 stop5h 03m
$367
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
mié. 7/29
11:14 am-3:29 pm
1 stop4h 15m
Hilton Head Island
lun. 8/3
4:18 pm-10:01 am
1 stop17h 43m
$399
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
lun. 9/7
8:00 am-2:57 pm
1 stop6h 57m
Hilton Head Island
dom. 9/13
11:48 am-6:26 pm
1 stop6h 38m
$407
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
sáb. 7/11
8:38 am-3:04 pm
1 stop6h 26m
Hilton Head Island
mar. 7/14
4:55 pm-9:59 pm
1 stop5h 04m
$416
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
sáb. 7/4
7:15 am-11:05 am
1 stop3h 50m
Hilton Head Island
mié. 7/8
11:47 am-5:41 pm
1 stop5h 54m
$425
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
mié. 7/29
11:14 am-3:29 pm
1 stop4h 15m
Hilton Head Island
dom. 8/2
12:11 pm-10:04 am
1 stop21h 53m
$445
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
jue. 7/30
8:45 am-3:29 pm
1 stop6h 44m
Hilton Head Island
mar. 8/4
12:15 pm-8:11 pm
1 stop7h 56m
$446
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
jue. 7/30
8:45 am-3:29 pm
1 stop6h 44m
Hilton Head Island
lun. 8/3
4:18 pm-10:01 am
1 stop17h 43m
$449
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
lun. 7/13
8:36 am-2:16 pm
1 stop5h 40m
Hilton Head Island
dom. 7/19
12:50 pm-7:51 pm
1 stop7h 01m
$478
TampaHilton Head Island
TPA - HHH
TPAHHH
Tampa
jue. 6/25
8:45 am-3:32 pm
1 stop6h 47m
Hilton Head Island
sáb. 6/27
12:17 pm-4:50 pm
1 stop4h 33m
$522
Showing 1-10 of 14 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 junio 20, 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.
Boarding
7.5
Comfort
7.2
Overall
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
Boarding
7.5
Comfort
7.2
Overall
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
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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Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on junio 20, 2026.
Clearwater and Hilton Head Island flights
Browse other Clearwater and Hilton Head Island flight options. Last updated on junio 20, 2026.
Popular flight searches
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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 junio 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$262 | Average$422 | FlexibilityNo cancel fee | On-time71% |