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Hilton Head Island

$249+ Cheap flights from Cleveland to Hilton Head Island (CLE - HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — HHH
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Hilton Head Island are usually found in December or September, booked 73 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Cleveland to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(American Airlines)

Popular in

March

Cheapest in

December

Average price

$428
Provider with most accurate pricing for Cleveland Hopkins Intl-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Hilton Head Island flights.
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From Cleveland Hopkins Intl to Hilton Head Island
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Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Cleveland to Hilton Head Island

Cheapest flights from Cleveland to Hilton Head Island
Explore the most affordable flight options available from Cleveland to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 12/181:28 pmCLE - HHH
1 stop4h 15mAmerican Airlines
mar. 12/236:13 pmHHH - CLE
1 stop6h 12mAmerican Airlines
Deal found 10/27$249
This American Airlines deal was found by Cheapflights users on 10/26. 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.
mié. 12/106:01 amCLE - HHH
1 stop4h 58mAmerican Airlines
mié. 12/173:27 pmHHH - CLE
1 stop4h 51mAmerican Airlines
Deal found 10/26$250
This American Airlines deal was found by Cheapflights users on 10/26. 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.
jue. 12/116:17 amCLE - HHH
1 stop5h 34mAmerican Airlines
mar. 12/1612:52 pmHHH - CLE
2 stops10h 07mAmerican Airlines
Deal found 10/26$254
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 11/206:00 amCLE - HHH
1 stop5h 02mAmerican Airlines
dom. 11/236:40 pmHHH - CLE
1 stop6h 03mAmerican Airlines
Deal found 10/27$338
This American Airlines deal was found by Cheapflights users on 10/26. 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.
jue. 10/306:00 amCLE - HHH
2 stops10h 51mAmerican Airlines
jue. 11/66:40 pmHHH - CLE
1 stop4h 02mAmerican Airlines
Deal found 10/26$349
This American Airlines deal was found by Cheapflights users on 10/26. 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.
vie. 11/71:14 pmCLE - HHH
1 stop5h 30mAmerican Airlines
vie. 11/147:07 pmHHH - CLE
1 stop4h 42mAmerican Airlines
Deal found 10/26$401

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland 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 octubre 28, 2025.
Use the filters below to find and compare flights from Cleveland to Hilton Head Island that are best for you.

Fly from

Cleveland

Fly to

Hilton Head Island

Route

Depart

Return

Price

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

jue. 12/18

1:28 pm-5:43 pm

1 stop4h 15m

Hilton Head Island

mar. 12/23

6:13 pm-9:59 pm

1 stop3h 46m

$249

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

jue. 12/11

6:01 am-10:59 am

1 stop4h 58m

Hilton Head Island

mar. 12/16

3:27 pm-8:18 pm

1 stop4h 51m

$249

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

jue. 2/12

8:00 am-2:28 pm

1 stop6h 28m

Hilton Head Island

lun. 2/23

6:22 pm-10:05 pm

1 stop3h 43m

$249

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

mié. 12/10

6:01 am-10:59 am

1 stop4h 58m

Hilton Head Island

mié. 12/17

3:27 pm-8:18 pm

1 stop4h 51m

$250

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

mié. 1/28

10:48 am-2:59 pm

1 stop4h 11m

Hilton Head Island

jue. 2/5

12:51 pm-11:57 pm

2 stops11h 06m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Cleveland to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cleveland to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cleveland-Hilton Head Island flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Hilton Head Island flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Cleveland-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cleveland-Hilton Head Island flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cleveland-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Cleveland to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Cleveland 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 Cleveland to Hilton Head Island

How far ahead should I book a flight from Cleveland to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Hilton Head Island. Price data was last updated on October 24, 2025.

Booking 72 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Hilton Head Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Cleveland to Hilton Head Island?

Currently, October is the cheapest month in which you can book a flight from Cleveland to Hilton Head Island (average of $73). Flying from Cleveland to Hilton Head Island in July is currently the most expensive (average of $105). 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 CLE to HHH?

Find hourly flight availability from Cleveland 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 octubre 28, 2025.

One of the essential ways to save on airfare from Cleveland to Hilton Head Island is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 57% on airfare.

How much does it cost to fly round-trip from Cleveland to Hilton Head Island?

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 octubre 28, 2025.
See what other customers who have flown with Delta and American Airlines from Cleveland 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.
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,996 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Cleveland 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.

  • How long is the flight from Cleveland to Hilton Head Island?

    American Airlines can get you from Cleveland to Hilton Head Island in just under 4h 15m. Your travel time can differ by up to . There are 638 mi between Cleveland and Hilton Head Island.

  • What are the cheapest airlines flying from Cleveland to Hilton Head Island round-trip?

    Flying on Delta is currently your cheapest option to Hilton Head Island, with prices starting at $207. Another option worth looking into is American Airlines, starting at $248 round trip. Users have found that Delta is 47% cheaper than the other options available to this destination.

  • Can I find deals for flights from Cleveland to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Cleveland to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland 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 Cleveland to Hilton Head Island.

  • Can I find deals for business class flights from Cleveland to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Cleveland 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 Cleveland to Hilton Head Island?

    Currently, October is the cheapest month in which you can book a flight from Cleveland to Hilton Head Island (average of $73). Flying from Cleveland to Hilton Head Island in July is currently the most expensive (average of $105). 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 2 airlines flying from Cleveland to Hilton Head Island

Discover the top 2 airlines that operate flights from Cleveland 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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$207Average$313FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$405FlexibilityNo cancel feeOn-time71%

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