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$299+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SDF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/3111:14 amHHH - TYS
1 stop4h 53mAmerican Airlines
Sun 1/45:00 amTYS - HHH
1 stop5h 44mAmerican Airlines
Deal found 12/16$357
This American Airlines deal was found by Cheapflights users on 12/17. 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 1/25:00 amSDF - HHH
1 stop5h 44mAmerican Airlines
Deal found 12/17$357
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/232:46 pmHHH - TYS
1 stop4h 55mAmerican Airlines
Tue 12/305:00 amTYS - HHH
1 stop5h 44mAmerican Airlines
Deal found 12/14$646
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/167:08 pmHHH - BNA
1 stop4h 29mAmerican Airlines
Thu 12/189:49 amBNA - HHH
1 stop3h 27mAmerican Airlines
Deal found 12/16$723

Find 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 December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$327
(American Airlines)

One-way from

$299
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Louisville Intl flights.
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From Hilton Head Island to Kentucky
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One-way flight from Hilton Head Island to Kentucky
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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 December 18, 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 IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Thu 2/12

6:22 pm-11:54 pm

1 stop5h 32m

Knoxville McGhee Tyson

Sun 2/15

8:04 am-2:27 pm

1 stop6h 23m

$327

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Wed 12/31

11:14 am-4:07 pm

1 stop4h 53m

Knoxville McGhee Tyson

Sun 1/4

5:00 am-10:44 am

1 stop5h 44m

$357

Hilton Head IslandCincinnati

HHH - CVG

HHHCVG

Hilton Head Island

Thu 1/1

6:13 pm-11:51 pm

1 stop5h 38m

Cincinnati Cinci./N. Kentucky

Mon 1/5

5:00 am-10:44 am

1 stop5h 44m

$391

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Fri 4/17

3:00 pm-10:04 pm

1 stop8h 04m

Nashville Intl

Mon 4/20

8:00 am-3:12 pm

1 stop6h 12m

$443

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Mon 4/13

4:05 pm-9:27 pm

1 stop5h 22m

Knoxville McGhee Tyson

Fri 4/17

12:50 pm-5:36 pm

1 stop4h 46m

$517

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Thu 1/22

12:51 pm-5:39 pm

1 stop5h 48m

Nashville Intl

Sun 1/25

10:19 am-2:59 pm

1 stop3h 40m

$617

Hilton Head IslandCincinnati

HHH - CVG

HHHCVG

Hilton Head Island

Wed 2/25

12:22 pm-6:36 pm

1 stop6h 14m

Cincinnati Cinci./N. Kentucky

Fri 2/27

2:10 pm-5:52 pm

1 stop3h 42m

$656

Hilton Head IslandKnoxville

HHH - TYS

HHHTYS

Hilton Head Island

Mon 4/13

3:00 pm-10:08 am

1 stop19h 08m

Knoxville McGhee Tyson

Fri 4/17

4:18 pm-2:01 pm

2 stops21h 43m

$746

Hilton Head IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

Tue 12/23

6:13 pm-11:38 pm

1 stop6h 25m

$299

Hilton Head IslandCincinnati

HHH - CVG

HHHCVG

Hilton Head Island

Wed 12/24

2:46 pm-12:08 pm

2 stops21h 22m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 14 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 December 18, 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
11,054 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Food

6.5

Crew

8.0

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Food

6.5

Crew

8.0

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 5h 32m. American Airlines provides one of the quickest options available for as low as $327. There are 311 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 - Knoxville McGhee Tyson, Hilton Head Island - Cincinnati Cinci./N. Kentucky or Hilton Head Island - Louisville 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$293FlexibilityNo cancel feeOn-time71%

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