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$224+ Cheap flights from Hilton Head Island (HHH) to Kentucky

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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SDF
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find flight deals from Hilton Head Island to Kentucky

Cheapest flights from Hilton Head Island to Kentucky
Explore the most affordable flight options available from Hilton Head Island to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 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 12/252:46 pmHHH - SDF
1 stop3h 35mAmerican Airlines
Fri 1/28:00 amSDF - HHH
1 stop6h 16mAmerican Airlines
Deal found 11/2$224
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Sat 11/156:48 pmHHH - BNA
1 stop5h 52mAmerican Airlines
Wed 11/1910:15 amBNA - HHH
1 stop3h 42mAmerican Airlines
Deal found 10/31$259
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.
Sat 12/206:13 pmHHH - SDF
1 stop6h 08mAmerican Airlines
Wed 12/245:00 amSDF - HHH
1 stop5h 44mAmerican Airlines
Deal found 11/1$278
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.
Wed 11/127:07 pmHHH - SDF
1 stop4h 52mAmerican Airlines
Sun 11/166:25 amSDF - HHH
1 stop5h 24mAmerican Airlines
Deal found 11/2$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.
Fri 11/77:14 pmHHH - BNA
1 stop4h 27mAmerican Airlines
Mon 11/1010:11 amBNA - HHH
1 stop3h 46mAmerican Airlines
Deal found 11/1$309
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.
Fri 12/123:27 pmHHH - TYS
1 stop5h 55mAmerican Airlines
Mon 12/1512:02 pmTYS - HHH
1 stop6h 31mAmerican Airlines
Deal found 11/2$357
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 11/173:27 pmHHH - BNA
1 stop5h 25mAmerican Airlines
Fri 11/218:28 amBNA - HHH
1 stop4h 51mAmerican Airlines
Deal found 11/1$411
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.
Sun 11/166:40 pmHHH - SDF
1 stop5h 42mAmerican Airlines
Thu 11/206:00 amSDF - HHH
1 stop5h 02mAmerican Airlines
Deal found 11/1$499
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.
Wed 11/266:40 pmHHH - TYS
1 stop4h 14mAmerican Airlines
Sun 11/306:30 amTYS - HHH
1 stop5h 19mAmerican Airlines
Deal found 11/2$583
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 11/66:40 pmHHH - BNA
1 stop6h 00mAmerican Airlines
Mon 11/107:32 amBNA - HHH
2 stops10h 05mAmerican Airlines
Deal found 11/1$591
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 12/196:13 pmHHH - SDF
1 stop6h 03mAmerican Airlines
Fri 12/268:00 amSDF - HHH
1 stop6h 16mAmerican Airlines
Deal found 11/1$594
This American Airlines deal was found by Cheapflights users on 10/31. 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 11/111:02 pmHHH - BNA
1 stop4h 45mAmerican Airlines
Thu 11/138:28 amBNA - HHH
1 stop4h 51mAmerican Airlines
Deal found 10/31$597

Cheap flight deals from Hilton Head Island to Kentucky

Keep the following information in mind while searching for Hilton Head Island to Kentucky flight deals. Data was last updated November 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$224
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Louisville Intl flights.
Search Deals
From Hilton Head Island to Kentucky
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Kentucky 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 2, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Kentucky that are best for you.

Fly from

Hilton Head Island

Fly to

Kentucky

Route

Depart

Return

Price

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

Thu 12/25

2:46 pm-6:21 pm

1 stop3h 35m

Louisville Intl

Fri 1/2

8:00 am-2:16 pm

1 stop6h 16m

$224

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Sat 11/15

6:48 pm-11:40 pm

1 stop5h 52m

Nashville Intl

Wed 11/19

10:15 am-2:57 pm

1 stop3h 42m

$259

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

Wed 11/12

7:07 pm-11:59 pm

1 stop4h 52m

Louisville Intl

Sun 11/16

6:25 am-11:49 am

1 stop5h 24m

$279

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

Sat 12/20

11:14 am-9:41 pm

2 stops10h 27m

Louisville Intl

Wed 12/24

5:00 am-10:44 am

1 stop5h 44m

$283

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Fri 12/12

3:27 pm-9:22 pm

1 stop5h 55m

Knoxville McGhee Tyson

Mon 12/15

12:02 pm-6:33 pm

1 stop6h 31m

$357

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Mon 11/17

3:27 pm-7:52 pm

1 stop5h 25m

Nashville Intl

Fri 11/21

8:28 am-2:19 pm

1 stop4h 51m

$411

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Mon 4/13

4:05 pm-7:01 pm

1 stop2h 56m

Knoxville McGhee Tyson

Fri 4/17

12:50 pm-5:36 pm

1 stop4h 46m

$517

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Wed 11/26

6:40 pm-10:54 pm

1 stop4h 14m

Knoxville McGhee Tyson

Sun 11/30

6:30 am-11:49 am

1 stop5h 19m

$583

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Wed 11/12

7:07 pm-10:41 pm

1 stop4h 34m

Nashville Intl

Thu 11/13

7:16 am-11:49 am

1 stop3h 33m

$597

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Mon 4/13

4:00 pm-10:00 am

2 stops18h 00m

Knoxville McGhee Tyson

Fri 4/17

2:00 pm-1:52 pm

1 stop23h 52m

$812

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 12 results
1
2

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

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

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

Currently, May is the cheapest month in which you can book a flight from Hilton Head Island to Kentucky (average of $49). Flying from Hilton Head Island to Kentucky in April is currently the most expensive (average of $225). 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.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated November 2, 2025.
Read reviews from past customers who have flown American Airlines from Hilton Head Island to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,037 reviews

Boarding

7.5

Food

6.4

Crew

8.0

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,037 reviews
American Airlines
7.2
Good
11,037 reviews

Boarding

7.5

Food

6.4

Crew

8.0

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Kentucky. 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 from for flights from Hilton Head Island to Kentucky?

    Located just 3.3 mi from the city center, Hilton Head Island (HHH) is the airport most travelers will use when flying to Kentucky from Hilton Head Island.

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

    A quick flight from Hilton Head Island to Kentucky can take about 3h 35m. American Airlines provides one of the quickest options available for as low as $224. There are 499 mi between Hilton Head Island and Kentucky.

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

    Most travelers choose Hilton Head Island - Knoxville McGhee Tyson, Hilton Head Island - Louisville Intl or Hilton Head Island - Nashville Intl when deciding on the best route from Hilton Head Island to Kentucky.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Kentucky.

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

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

    Currently, May is the cheapest month in which you can book a flight from Hilton Head Island to Kentucky (average of $49). Flying from Hilton Head Island to Kentucky in April is currently the most expensive (average of $225). 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

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Alternative routes for Hilton Head Island to Kentucky

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Top airline flying from Hilton Head Island to Kentucky

Discover the top airline that operate flights from Hilton Head Island to Kentucky. 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$307FlexibilityNo cancel feeOn-time71%

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