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Kentucky

$164+ Cheap flights from Hilton Head Island (HHH) to Kentucky

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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SDF
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$199
(American Airlines)

One-way from

$164
(American Airlines)
From Hilton Head Island to Kentucky
Search Deals
One-way flight from Hilton Head Island to Kentucky
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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 September 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.
Thu 12/252:46 pmHHH - SDF
1 stop3h 35mAmerican Airlines
Thu 1/15:00 amSDF - HHH
1 stop5h 44mAmerican Airlines
Deal found 9/14$199
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.
Wed 10/112:56 pmHHH - SDF
1 stop5h 43mAmerican Airlines
Sun 10/58:00 amSDF - HHH
1 stop3h 30mAmerican Airlines
Deal found 9/16$239
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.
Thu 12/252:46 pmHHH - SDF
1 stop3h 35mAmerican Airlines
Fri 1/28:00 amSDF - HHH
1 stop6h 16mAmerican Airlines
Deal found 9/14$244
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.
Wed 11/123:27 pmHHH - SDF
1 stop6h 12mAmerican Airlines
Sun 11/168:10 amSDF - HHH
1 stop3h 39mAmerican Airlines
Deal found 9/14$259
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.
Sat 11/86:48 pmHHH - BNA
1 stop5h 52mAmerican Airlines
Fri 11/1411:59 amBNA - HHH
1 stop5h 38mAmerican Airlines
Deal found 9/15$284
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.
Thu 9/2512:00 pmHHH - BNA
1 stop4h 06mAmerican Airlines
Sun 9/285:30 amBNA - HHH
1 stop5h 00mAmerican Airlines
Deal found 9/14$304
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.
Tue 9/233:26 pmHHH - CVG
1 stop4h 01mAmerican Airlines
Sun 9/286:07 amCVG - HHH
1 stop4h 27mAmerican Airlines
Deal found 9/14$388
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.
Mon 10/135:57 pmHHH - BNA
1 stop4h 32mAmerican Airlines
Tue 10/1410:15 amBNA - HHH
1 stop5h 36mAmerican Airlines
Deal found 9/15$434
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.
Tue 9/305:20 pmHHH - BNA
1 stop3h 39mAmerican Airlines
Sat 10/49:48 amBNA - HHH
1 stop5h 59mAmerican Airlines
Deal found 9/15$462
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.
Tue 10/145:21 pmHHH - BNA
1 stop6h 04mAmerican Airlines
Wed 10/1510:15 amBNA - HHH
1 stop5h 36mAmerican Airlines
Deal found 9/15$471
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.
Mon 10/135:57 pmHHH - SDF
1 stop4h 34mAmerican Airlines
Fri 10/246:05 amSDF - HHH
1 stop4h 41mAmerican Airlines
Deal found 9/14$499
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.
Wed 10/15:20 pmHHH - TYS
1 stop5h 43mAmerican Airlines
Sun 10/511:17 amTYS - HHH
1 stop6h 33mAmerican Airlines
Deal found 9/16$553

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 September 16, 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

Thu 1/1

5:00 am-10:44 am

1 stop5h 44m

$199

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

Wed 10/1

12:56 pm-6:39 pm

1 stop5h 43m

Louisville Intl

Sun 10/5

8:00 am-11:30 am

1 stop3h 30m

$239

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

$244

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

Wed 11/12

1:02 pm-10:55 pm

2 stops9h 53m

Louisville Intl

Sun 11/16

6:01 am-10:53 am

1 stop4h 52m

$264

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Sat 11/8

6:48 pm-11:40 pm

1 stop5h 52m

Nashville Intl

Fri 11/14

11:59 am-6:37 pm

1 stop5h 38m

$284

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Mon 10/13

5:57 pm-9:29 pm

1 stop4h 32m

Nashville Intl

Tue 10/14

10:15 am-4:51 pm

1 stop5h 36m

$434

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Tue 9/30

5:20 pm-7:59 pm

1 stop3h 39m

Nashville Intl

Sat 10/4

9:48 am-4:47 pm

1 stop5h 59m

$462

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Tue 10/14

5:21 pm-10:25 pm

1 stop6h 04m

Nashville Intl

Wed 10/15

10:15 am-4:51 pm

1 stop5h 36m

$471

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Mon 10/13

5:57 pm-11:41 pm

1 stop6h 44m

Nashville Intl

Wed 10/15

7:06 am-4:51 pm

2 stops8h 45m

$496

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Wed 10/1

5:20 pm-11:03 pm

1 stop5h 43m

Knoxville McGhee Tyson

Sun 10/5

11:17 am-5:50 pm

1 stop6h 33m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Kentucky (average of $299). Flying from Hilton Head Island to Kentucky in April is currently the most expensive (average of $369). 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 September 16, 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
10,000 reviews

Boarding

7.5

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Crew

8.0

Food

6.4

Comfort

7.2

Entertainment

6.9

Overall

7.2

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 $199. There are 499 mi between Hilton Head Island and Kentucky. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Most travelers choose Hilton Head Island - Louisville Intl, Hilton Head Island - Nashville Intl or Hilton Head Island - Cincinnati Cinci./N. Kentucky 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Kentucky (average of $299). Flying from Hilton Head Island to Kentucky in April is currently the most expensive (average of $369). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$293FlexibilityNo cancel feeOn-time71%

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