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Hilton Head Island

$177+ Cheap flights from Kentucky 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — HHH
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Kentucky to Hilton Head Island

Keep the following information in mind while searching for Kentucky to Hilton Head Island flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(American Airlines)

One-way from

$177
(American Airlines)

Popular in

October

Cheapest in

May

Average price

$562
Provider with most accurate pricing for Louisville Intl-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Hilton Head Island flights.
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From Kentucky to Hilton Head Island
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One-way flight from Kentucky to Hilton Head Island
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Highest demand for flights based on searches. 19% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Kentucky to Hilton Head Island

Cheapest flights from Kentucky to Hilton Head Island
Explore the most affordable flight options available from Kentucky to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/2. 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 12/46:25 amSDF - HHH
1 stop5h 26mAmerican Airlines
Mon 12/83:27 pmHHH - SDF
1 stop6h 22mAmerican Airlines
Deal found 11/2$229
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/86:08 amSDF - HHH
2 stops8h 49mAmerican Airlines
Sat 12/132:17 pmHHH - SDF
2 stops7h 26mAmerican Airlines
Deal found 11/3$239
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/146:01 amSDF - HHH
1 stop4h 57mAmerican Airlines
Tue 11/1811:28 amHHH - SDF
1 stop5h 01mAmerican Airlines
Deal found 11/1$279
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/317:30 amBNA - HHH
1 stop5h 46mAmerican Airlines
Fri 1/26:13 pmHHH - BNA
1 stop6h 25mAmerican Airlines
Deal found 11/1$282
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/56:01 amSDF - HHH
1 stop4h 57mAmerican Airlines
Sat 11/812:38 pmHHH - SDF
1 stop4h 17mAmerican Airlines
Deal found 11/1$309
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/138:30 amCVG - HHH
1 stop5h 49mAmerican Airlines
Sat 11/1511:46 amHHH - CVG
1 stop5h 35mAmerican Airlines
Deal found 11/1$309
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/235:15 amBNA - HHH
1 stop4h 29mAmerican Airlines
Sat 12/276:13 pmHHH - BNA
1 stop6h 28mAmerican Airlines
Deal found 11/3$314
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/2510:31 amCVG - HHH
1 stop3h 48mAmerican Airlines
Wed 12/312:52 pmHHH - CVG
2 stops9h 21mAmerican Airlines
Deal found 11/3$324
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/1910:15 amBNA - HHH
1 stop3h 42mAmerican Airlines
Sun 11/236:40 pmHHH - BNA
1 stop6h 00mAmerican Airlines
Deal found 11/1$329
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/138:10 amSDF - HHH
1 stop6h 09mAmerican Airlines
Sun 11/166:40 pmHHH - SDF
1 stop5h 42mAmerican Airlines
Deal found 11/3$349
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/156:00 amCVG - HHH
1 stop6h 22mAmerican Airlines
Thu 12/1811:14 amHHH - CVG
1 stop3h 35mAmerican Airlines
Deal found 11/1$367
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/1211:16 amCVG - HHH
1 stop3h 41mAmerican Airlines
Mon 11/1711:28 amHHH - CVG
1 stop6h 32mAmerican Airlines
Deal found 11/3$379

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky 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 November 3, 2025.
Use the filters below to find and compare flights from Kentucky to Hilton Head Island that are best for you.

Fly from

Kentucky

Fly to

Hilton Head Island

Route

Depart

Return

Price

LouisvilleHilton Head Island

SDF - HHH

SDFHHH

Louisville Intl

Fri 12/5

8:47 am-2:57 pm

1 stop6h 10m

Hilton Head Island

Tue 12/9

12:52 pm-6:12 pm

1 stop5h 20m

$229

LouisvilleHilton Head Island

SDF - HHH

SDFHHH

Louisville Intl

Mon 12/8

8:47 am-12:22 pm

1 stop3h 35m

Hilton Head Island

Sat 12/13

11:47 am-5:28 pm

1 stop5h 41m

$229

LouisvilleHilton Head Island

SDF - HHH

SDFHHH

Louisville Intl

Thu 12/4

8:30 am-1:47 pm

1 stop5h 17m

Hilton Head Island

Mon 12/8

7:08 pm-11:54 pm

1 stop4h 46m

$229

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

Sun 2/1

8:54 am-2:59 pm

1 stop6h 05m

Hilton Head Island

Sat 2/7

12:54 pm-4:41 pm

1 stop3h 47m

$249

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

Sat 2/7

7:03 am-12:20 pm

1 stop5h 17m

Hilton Head Island

Wed 2/11

12:51 pm-10:59 pm

2 stops10h 08m

$254

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

Sat 2/7

6:30 am-2:59 pm

2 stops8h 29m

Hilton Head Island

Tue 2/10

3:29 pm-9:27 pm

1 stop5h 58m

$254

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

Mon 2/2

7:03 am-12:20 pm

1 stop5h 17m

Hilton Head Island

Sat 2/7

12:54 pm-10:00 pm

2 stops9h 06m

$254

LouisvilleHilton Head Island

SDF - HHH

SDFHHH

Louisville Intl

Thu 11/20

8:10 am-2:19 pm

1 stop6h 09m

Hilton Head Island

Tue 11/25

6:40 pm-12:22 am

1 stop5h 42m

$279

LouisvilleHilton Head Island

SDF - HHH

SDFHHH

Louisville Intl

Fri 11/14

6:01 am-10:58 am

1 stop4h 57m

Hilton Head Island

Tue 11/18

11:28 am-4:29 pm

1 stop5h 01m

$279

NashvilleHilton Head Island

BNA - HHH

BNAHHH

Nashville Intl

Wed 12/31

7:30 am-2:16 pm

1 stop5h 46m

Hilton Head Island

Fri 1/2

6:13 pm-11:38 pm

1 stop6h 25m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 34 results
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Best time to book a flight from Kentucky to Hilton Head Island

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

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

Currently, July is the cheapest month in which you can book a flight from Kentucky to Hilton Head Island (average of $78). Flying from Kentucky to Hilton Head Island in April is currently the most expensive (average of $216). 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 KY to HHH?

Find hourly flight availability from Kentucky 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 November 3, 2025.

One of the essential ways to save on airfare from Kentucky 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 66% on airfare.

Related info for your journey

Find useful and relevant information for your journey from Kentucky 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.

  • What airport do you fly into for flights to Hilton Head Island from Kentucky?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Kentucky to Hilton Head Island. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

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

    Airlines like American Airlines fly from Kentucky to Hilton Head Island in about 6h 10m. The time it takes to get you to your destination can typically vary by up to . There are 499 mi between Kentucky and Hilton Head Island.

  • What are the most popular routes from Kentucky to Hilton Head Island?

    When deciding which route to take from Kentucky to Hilton Head Island consider Cincinnati Cinci./N. Kentucky - Hilton Head Island, Louisville Intl - Hilton Head Island or Nashville Intl - Hilton Head Island as they are the most popular.

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Kentucky to Hilton Head Island (average of $78). Flying from Kentucky to Hilton Head Island in April is currently the most expensive (average of $216). 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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Alternative routes for Kentucky to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Kentucky to Hilton Head Island

Discover the top airline that operate flights from Kentucky 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$391FlexibilityNo cancel feeOn-time71%

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