Cheap flights from CLE to HHH (Hopkins Intl. to Hilton Head Island)

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Cheap Flights from CLE to HHH starting at $141 One Way, $253 Round Trip

Prices starting at $253 for return flights and $141 for one-way flights to Hilton Head Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Sep 22 - Tue, Sep 30
CLE
Cleveland
HHH
Hilton Head Island
$253 Roundtrip, found 1 hour ago
$253
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Sep 22 from Cleveland to Hilton Head Island, returning Tue, Sep 30, priced at $253 found 1 hour ago
Wed, Aug 6 - Tue, Aug 19
CLE
Cleveland
HHH
Hilton Head Island
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 6 from Cleveland to Hilton Head Island, returning Tue, Aug 19, priced at $259 found 6 days ago
Wed, Aug 6 - Tue, Aug 12
CLE
Cleveland
HHH
Hilton Head Island
$264 Roundtrip, found 6 days ago
$264
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 6 from Cleveland to Hilton Head Island, returning Tue, Aug 12, priced at $264 found 6 days ago
Mon, Sep 22 - Sat, Oct 4
CLE
Cleveland
HHH
Hilton Head Island
$273 Roundtrip, found 1 hour ago
$273
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Sep 22 from Cleveland to Hilton Head Island, returning Sat, Oct 4, priced at $273 found 1 hour ago
Wed, Aug 6 - Thu, Aug 14
CLE
Cleveland
HHH
Hilton Head Island
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 6 from Cleveland to Hilton Head Island, returning Thu, Aug 14, priced at $274 found 6 days ago

Hotel Ideas near Hilton Head Island

Airport Hotels near Hilton Head Island

Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road, Hilton Head Island, SC
$119 nightly
The price is $131 total per night from Aug 10 to Aug 11
$131 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this golf hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,013 reviews)
"Great place"

Reviewed on Jul 26, 2025

Hampton Inn Hilton Head
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave, Hilton Head Island, SC
$266 nightly
The price is $292 total per night from Aug 24 to Aug 25
$292 total
Aug 24 - Aug 25
Total includes taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (1,016 reviews)
"Good"

Reviewed on Jul 25, 2025

The Westin Hilton Head Island Resort & Spa
Island Links Resort by Palmera

Island Links Resort by Palmera

3 out of 5
1 Coggins Point Road, Hilton Head Island, SC
Stay at this 3-star golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (308 reviews)
"Great place to stay. Kids really enjoy it. Staff were amazing! Golf courses around were fantastic."

Reviewed on Jul 19, 2025

Get rates
Island Links Resort by Palmera
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Hilton Head Island

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive, Hilton Head Island, SC
$277 nightly
The price is $305 total per night from Aug 24 to Aug 25
$305 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (1,001 reviews)
"The property was convenient and great for the kids. A few roudy guests on our floor were the only issue."

Reviewed on Jul 30, 2025

Sonesta Resort Hilton Head Island
Hilton Beachfront Resort & Spa Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

4.5 out of 5
1 Hotel Circle, Hilton Head Island, SC
$261 nightly
The price is $288 total per night from Aug 11 to Aug 12
$288 total
Aug 11 - Aug 12
Total includes taxes and fees
Stay at this 4.5-star luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in ...
8.4/10 Very Good! (1,321 reviews)
"Great service!"

Reviewed on Jul 28, 2025

Hilton Beachfront Resort & Spa Hilton Head Island
Beach House Resort Hilton Head

Beach House Resort Hilton Head

4 out of 5
1 South Forest Beach Drive, Hilton Head Island, SC
$264 nightly
The price is $291 total per night from Aug 19 to Aug 20
$291 total
Aug 19 - Aug 20
Total includes taxes and fees
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the bar in our ...
8.8/10 Excellent! (735 reviews)
"Safe place. Great for families. Good environment for all ages. Pool could be cleaner."

Reviewed on Jul 28, 2025

Beach House Resort Hilton Head
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Head Island Hotels With Airport Transportation

Hilton Head Health - Weight Loss Resort and Health Spa

Hilton Head Health - Weight Loss Resort and Health Spa

4 out of 5
14 Valencia Road, Hilton Head Island, SC
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Palmetto Dunes ...
Get rates
Hilton Head Health - Weight Loss Resort and Health Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Hilton Head Island Hotels

Red Roof Inn Hilton Head Island

Red Roof Inn Hilton Head Island

2 out of 5
5 Regency Pkwy, Us 278, 30 Miles From I-95, Hilton Head Island, SC
$85 nightly
The price is $93 total per night from Aug 10 to Aug 11
$93 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.2/10 (1,000 reviews)
"Great"

Reviewed on Jul 21, 2025

Red Roof Inn Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln, Hilton Head Island, SC
$189 nightly
The price is $208 total per night from Aug 3 to Aug 4
$208 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this 3-star hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,088 reviews)
"Breakfast was excellent with variety. They never ran out of food even during the busiest times."

Reviewed on Jul 29, 2025

Palmera Inn and Suites
Hotel Carolina, a Days Inn by Wyndham

Hotel Carolina, a Days Inn by Wyndham

2 out of 5
9 Marina Side Drive, Hilton Head Island, SC
$93 nightly
The price is $102 total per night from Aug 3 to Aug 4
$102 total
Aug 3 - Aug 4
Total includes taxes and fees
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and ...
6.6/10 (1,017 reviews)
10/10
"everything was cool! loved the room & how clean it was!!!"

Reviewed on Jul 27, 2025

Hotel Carolina, a Days Inn by Wyndham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Hilton Head Island

Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane, Hilton Head Island, SC
$358 nightly
The price is $389 total per night from Aug 25 to Aug 26
$389 total
Aug 25 - Aug 26
Total includes taxes and fees
Stay at this 4-star beach resort in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,016 reviews)

Families like: Outdoor pools, kids club, kitchenette, playground

Travelers say...
"Beautiful setting right on a wide expanse of beach. The rooms are clean and thoughtfully equipped. Food options on site are pretty good, and many good restaurants are a short drive away. The staff was extraordinarily friendly and attentive. In all, a great place for a stress-free beach vacation."

Reviewed on Jul 26, 2025

Omni Hilton Head Oceanfront Resort
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive, Hilton Head Island, SC
$277 nightly
The price is $305 total per night from Aug 24 to Aug 25
$305 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (1,001 reviews)

Families like: Outdoor pool, kids club, on the beach, bicycle rentals

Travelers say...
"The property was convenient and great for the kids. A few roudy guests on our floor were the only issue."

Reviewed on Jul 30, 2025

Sonesta Resort Hilton Head Island
Hilton Head Island Beach & Tennis Resort

Hilton Head Island Beach & Tennis Resort

3.5 out of 5
40 Folly Field Rd, Hilton Head Island, SC
Stay at this 3.5-star beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Palmetto Dunes Club and Coligny ...
7.6/10 Good! (1,002 reviews)

Families like: Outdoor pools, kitchen, playground, on the beach

Been before will continue to book here!
"For the price, the location, the restaurants, bar, pool, and access to the beach, you cant go wrong!"

Reviewed on Jul 20, 2025

Get rates
Hilton Head Island Beach & Tennis Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

CLE to HHH Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Cleveland Hopkins Intl. Airport to Hilton Head Airport?
While you won't be able to fly nonstop from CLE to Hilton Head Island Airport (HHH) at this point in time, there are several carriers that operate on this route with just a single stopover. Why not see if the dates and times offered by American Airlines or United Airlines work with your travel plans? If not, you could always check out Delta Air Lines.
What is the shortest flight from Cleveland Hopkins Intl. Airport to Hilton Head Island Airport (HHH)?
There's nothing as exciting as an impromptu getaway. With the flight from Cleveland to Hilton Head Island being a mere 2 hours and 55 minutes, you'll have to come up with excuses not to take one.
How many hours flight from Cleveland Hopkins Intl. Airport to HHH?
Get cozy, because the average journey from Cleveland Hopkins Intl. Airport to Hilton Head Airport is 3 hours. Watch a movie or two, put your nose in a book ... You'll have plenty of time to relax and unwind.
What airlines have the most flights from Cleveland Hopkins Intl. Airport to HHH?
If you're hoping to book with an airline that offers direct flights from Cleveland Hopkins Intl. Airport to HHH, you won't have much luck. You'll need to book a flight with at least one stopover to get to your destination.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.