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Cheap flights from Cleveland to Hilton Head Island from $249

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Hilton Head Island departing on 12/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Cleveland to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:28 pm - 5:43 pmCLE-HHH
4h 15m1 stop
American Airlines Logo
6:13 pm - 12:25 amHHH-CLE
6h 12m1 stop
$249American Airlines
Find Deal
Thu, Dec 18 - Tue, Dec 23
American Airlines Logo
1:14 pm - 6:33 pmCLE-HHH
5h 19m1 stop
American Airlines Logo
7:08 pm - 11:49 pmHHH-CLE
4h 41m1 stop
$250American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:01 am - 11:51 amCLE-HHH
5h 50m2 stops
American Airlines Logo
11:30 am - 3:26 pmHHH-CLE
3h 56m1 stop
$254American Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
American Airlines Logo
6:01 am - 2:57 pmCLE-HHH
8h 56m2 stops
American Airlines Logo
3:27 pm - 8:18 pmHHH-CLE
4h 51m1 stop
$256American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:01 am - 1:47 pmCLE-HHH
7h 46m2 stops
American Airlines Logo
3:27 pm - 11:47 pmHHH-CLE
8h 20m2 stops
$259American Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
American Airlines Logo
11:00 am - 6:33 pmCLE-HHH
7h 33m2 stops
American Airlines Logo
12:52 pm - 9:20 pmHHH-CLE
8h 28m2 stops
$261American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:24 am - 6:37 pmCLE-HHH
12h 13m2 stops
American Airlines Logo
12:38 pm - 7:32 pmHHH-CLE
6h 54m1 stop
$264American Airlines
Find Deal
Tue, Nov 4 - Sat, Nov 8
American Airlines Logo
6:00 am - 11:02 amCLE-HHH
5h 02m1 stop
American Airlines Logo
6:40 pm - 12:43 amHHH-CLE
6h 03m1 stop
$294American Airlines
Find Deal
Tue, Nov 25 - Fri, Nov 28
American Airlines Logo
5:30 am - 10:46 amCLE-HHH
5h 16m1 stop
American Airlines Logo
1:55 pm - 7:14 pmHHH-CLE
5h 19m1 stop
$309American Airlines
Find Deal
Thu, Oct 30 - Sat, Nov 1
Delta Logo
10:25 am - 3:18 pmCLE-HHH
4h 53m1 stop
Delta Logo
4:00 pm - 9:30 pmHHH-CLE
5h 30m1 stop
$598Delta
Find Deal
Fri, Apr 17 - Mon, Apr 20

American Airlines flights from Cleveland to Hilton Head Island

Our best American Airlines deals on Cleveland to Hilton Head Island flight tickets
American Airlines
Dec 18
CLE1:28 pmCleveland Hopkins Intl
4h 15m
1 stop
HHH5:43 pmHilton Head Island
Dec 23
HHH6:13 pmHilton Head Island
6h 12m
1 stop
CLE12:25 amCleveland Hopkins Intl
$249
Find similar
American Airlines
Dec 3
CLE1:14 pmCleveland Hopkins Intl
5h 19m
1 stop
HHH6:33 pmHilton Head Island
Dec 10
HHH7:08 pmHilton Head Island
4h 41m
1 stop
CLE11:49 pmCleveland Hopkins Intl
$250
Find similar
American Airlines
Dec 11
CLE6:01 amCleveland Hopkins Intl
5h 50m
2 stops
HHH11:51 amHilton Head Island
Dec 16
HHH11:30 amHilton Head Island
3h 56m
1 stop
CLE3:26 pmCleveland Hopkins Intl
$254
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated October 20, 2025.
Use the filters below to find and compare flights from Cleveland to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Thu 12/18

1:28 pm-5:43 pm

1 stop4h 15m

Hilton Head Island

Tue 12/23

6:13 pm-12:25 am

1 stop6h 12m

$249

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Wed 12/3

1:14 pm-6:33 pm

1 stop5h 19m

Hilton Head Island

Wed 12/10

7:08 pm-11:49 pm

1 stop4h 41m

$250

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Thu 12/11

6:01 am-11:51 am

2 stops5h 50m

Hilton Head Island

Tue 12/16

11:30 am-3:26 pm

1 stop3h 56m

$254

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Wed 12/3

6:01 am-2:57 pm

2 stops8h 56m

Hilton Head Island

Wed 12/10

3:27 pm-8:18 pm

1 stop4h 51m

$256

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Thu 12/11

6:01 am-1:47 pm

2 stops7h 46m

Hilton Head Island

Tue 12/16

3:27 pm-11:47 pm

2 stops8h 20m

$259

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Wed 12/3

11:00 am-6:33 pm

2 stops7h 33m

Hilton Head Island

Wed 12/10

12:52 pm-9:20 pm

2 stops8h 28m

$261

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Tue 11/4

6:24 am-6:37 pm

2 stops12h 13m

Hilton Head Island

Sat 11/8

12:38 pm-7:32 pm

1 stop6h 54m

$264

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Tue 11/25

6:00 am-11:02 am

1 stop5h 02m

Hilton Head Island

Fri 11/28

6:40 pm-12:43 am

1 stop6h 03m

$294

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Thu 10/30

5:30 am-10:46 am

1 stop5h 16m

Hilton Head Island

Sat 11/1

1:55 pm-7:14 pm

1 stop5h 19m

$309

ClevelandHilton Head Island

CLE - HHH

CLEHHH

Cleveland Hopkins Intl

Fri 4/17

10:25 am-3:18 pm

1 stop4h 53m

Hilton Head Island

Mon 4/20

4:00 pm-9:30 pm

1 stop5h 30m

$598

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Cleveland to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in December, then you should wait until September to fly from Cleveland, when ticket prices are also cheap, with an average price of $314.

What is the cheapest day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Cleveland to Hilton Head Island is on a Tuesday. Travelers who choose to depart for Hilton Head Island on a Tuesday will often find tickets for as low as $364. On the other hand, Sunday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $499.

What is the cheapest time of day to depart on your flight to Hilton Head Island?

Flying to Hilton Head Island from Cleveland in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $174 when looking at flights departing in the afternoon. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $405 on average. Flights to Hilton Head Island from Cleveland at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

How far in advance should I book a flight to Hilton Head Island?

You are more likely to see cheaper flights to Hilton Head Island from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $393 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hilton Head Island from Cleveland for as low as $248 on momondo.

How have Cleveland to Hilton Head Island flight prices changed over time?

When to book flights from Cleveland to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to Hilton Head Island (CLE to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Hilton Head Island

Direct flights

None
There are no direct flights from Cleveland to Hilton Head Island. There are no popular flight routes from Cleveland to Hilton Head Island.
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  • How far is Cleveland Hopkins Intl to Hilton Head Island by plane?

    A flight from Cleveland Hopkins Intl to Hilton Head Island will travel around 643.0 mi. A reasonable flight in good conditions will take 3h 32m.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Hilton Head Island Airport?

    Prices for flights from Cleveland Hopkins Intl Airport to Hilton Head Island Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Hilton Head Island Airport?

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The travel and health documents required for your trip to Hilton Head Island Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hilton Head Island Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Cleveland to Hilton Head Island?

Best airlines flying from Cleveland to Hilton Head Island

Compare and see reviews for airlines that fly from Cleveland to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $207Free CancellationRating
7.9
7,978 reviews
Search Delta flights
American AirlinesPriceFrom $248Free CancellationRating
7.2
11,024 reviews
Search American Airlines flights

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
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Hilton Head Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Cleveland to Hilton Head Island. momondo saves you time and could save you money on your trip.

Can I find flights from Cleveland to Hilton Head Island with flexible booking policies on momondo?

Yes. All flights to Hilton Head Island from Cleveland on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Cleveland to Hilton Head Island?

Once all potential Cleveland to Hilton Head Island flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Cleveland to Hilton Head Island right now. Can momondo alert me if prices change?

Price alerts on flights to Hilton Head Island from Cleveland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Hilton Head Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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