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Hilton Head Island

$164+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — HHH
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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 septiembre 16, 2025.

Round-trip from

$234
(American Airlines)

One-way from

$164
(American Airlines)

Popular in

October

Cheapest in

May

Average price

$330
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. 14% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 12/195:00 amSDF - HHH
1 stop5h 44mAmerican Airlines
mar. 12/236:13 pmHHH - SDF
1 stop4h 01mAmerican Airlines
Deal found 9/14$259
This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 9/191:09 pmSDF - HHH
1 stop3h 38mAmerican Airlines
lun. 9/223:26 pmHHH - SDF
1 stop6h 10mAmerican Airlines
Deal found 9/14$279
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/146:00 amCVG - HHH
1 stop5h 37mDelta
mar. 10/214:10 pmHHH - CVG
1 stop6h 46mDelta
Deal found 9/14$283
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/146:00 amCVG - HHH
1 stop4h 46mAmerican Airlines
mar. 10/2112:45 pmHHH - CVG
2 stops10h 34mAmerican Airlines
Deal found 9/14$288
This American Airlines deal was found by Cheapflights users on 9/13. 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. 11/88:47 amBNA - HHH
1 stop4h 32mAmerican Airlines
mar. 11/117:07 pmHHH - BNA
1 stop4h 34mAmerican Airlines
Deal found 9/13$289
This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 11/1411:21 amLEX - HHH
1 stop3h 36mAmerican Airlines
lun. 11/177:07 pmHHH - LEX
1 stop4h 09mAmerican Airlines
Deal found 9/14$289
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 12/166:30 amSDF - HHH
2 stops8h 27mAmerican Airlines
mié. 12/312:46 pmHHH - SDF
1 stop3h 35mAmerican Airlines
Deal found 9/14$294
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 11/1211:04 amLEX - HHH
2 stops7h 33mAmerican Airlines
mar. 11/187:07 pmHHH - LEX
1 stop4h 09mAmerican Airlines
Deal found 9/14$294
This American Airlines deal was found by Cheapflights users on 9/15. 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.
mié. 9/246:47 amBNA - HHH
1 stop4h 30mAmerican Airlines
dom. 9/286:20 pmHHH - BNA
1 stop6h 17mAmerican Airlines
Deal found 9/15$314
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/16:04 amCVG - HHH
1 stop5h 26mDelta
mié. 10/154:10 pmHHH - CVG
1 stop6h 46mDelta
Deal found 9/15$316
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 10/17:48 amCVG - HHH
2 stops8h 59mAmerican Airlines
mié. 10/1511:16 amHHH - CVG
1 stop7h 20mAmerican Airlines
Deal found 9/14$321
This American Airlines deal was found by Cheapflights users on 9/16. 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.
mar. 11/186:00 amCVG - HHH
1 stop6h 29mAmerican Airlines
dom. 11/236:40 pmHHH - CVG
1 stop5h 18mAmerican Airlines
Deal found 9/16$325

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 septiembre 16, 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

vie. 12/19

5:00 am-10:44 am

1 stop5h 44m

Hilton Head Island

mar. 12/23

6:13 pm-10:14 pm

1 stop4h 01m

$259

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

mar. 10/14

6:00 am-11:37 am

1 stop5h 37m

Hilton Head Island

mar. 10/21

4:10 pm-10:56 pm

1 stop6h 46m

$283

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

vie. 10/31

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

mar. 11/4

11:28 am-6:08 pm

1 stop6h 40m

$283

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

mié. 10/15

6:00 am-11:37 am

1 stop5h 37m

Hilton Head Island

mié. 10/22

12:17 pm-4:59 pm

1 stop4h 42m

$283

CincinnatiHilton Head Island

CVG - HHH

CVGHHH

Cincinnati Cinci./N. Kentucky

mié. 10/15

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

mié. 10/22

12:45 pm-11:19 pm

2 stops10h 34m

$288

NashvilleHilton Head Island

BNA - HHH

BNAHHH

Nashville Intl

sáb. 11/8

8:47 am-2:19 pm

1 stop4h 32m

Hilton Head Island

mar. 11/11

7:07 pm-10:41 pm

1 stop4h 34m

$289

LexingtonHilton Head Island

LEX - HHH

LEXHHH

Lexington Blue Grass

vie. 11/14

11:21 am-2:57 pm

1 stop3h 36m

Hilton Head Island

lun. 11/17

7:07 pm-11:16 pm

1 stop4h 09m

$289

LexingtonHilton Head Island

LEX - HHH

LEXHHH

Lexington Blue Grass

mié. 11/12

11:04 am-6:37 pm

2 stops7h 33m

Hilton Head Island

lun. 11/17

7:07 pm-11:16 pm

1 stop4h 09m

$294

LexingtonHilton Head Island

LEX - HHH

LEXHHH

Lexington Blue Grass

mié. 11/12

11:04 am-6:37 pm

2 stops7h 33m

Hilton Head Island

mar. 11/18

7:07 pm-11:16 pm

1 stop4h 09m

$294

LexingtonHilton Head Island

LEX - HHH

LEXHHH

Lexington Blue Grass

sáb. 11/15

6:00 am-6:17 pm

2 stops12h 17m

Hilton Head Island

mar. 11/18

7:07 pm-11:16 pm

1 stop4h 09m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 43 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, January is the cheapest month in which you can book a flight from Kentucky to Hilton Head Island (average of $275). Flying from Kentucky to Hilton Head Island in March is currently the most expensive (average of $479). 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 septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Hilton Head Island as you normally would.

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 and Delta fly from Kentucky to Hilton Head Island in about 5h 37m. The time it takes to get you to your destination can typically vary by up to 07m. There are 521 mi between Kentucky and Hilton Head Island. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Kentucky to Hilton Head Island one-way?

    The cheapest airlines for a one-way flight from Kentucky to Hilton Head Island are American Airlines ($164), Delta ($269), and United Airlines ($333).

  • 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 Lexington Blue Grass - 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, January is the cheapest month in which you can book a flight from Kentucky to Hilton Head Island (average of $275). Flying from Kentucky to Hilton Head Island in March is currently the most expensive (average of $479). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$412FlexibilityNo cancel feeOn-time71%

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