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Kentucky

$119+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SDF
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
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 enero 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/293:00 pm
HHH
-
BNA
1 stop7h 39m
United Airlines
dom. 7/56:00 am
BNA
-
HHH
1 stop7h 01m
United Airlines
Deal found 1/27$284
This American Airlines deal was found by Cheapflights users on 1/27. 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. 3/66:20 pm
HHH
-
SDF
1 stop4h 23m
American Airlines
dom. 3/87:00 am
SDF
-
HHH
1 stop3h 33m
American Airlines
Deal found 1/27$327
This American Airlines deal was found by Cheapflights users on 1/27. 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.
jue. 5/71:08 pm
HHH
-
BNA
1 stop5h 07m
American Airlines
dom. 5/108:43 am
BNA
-
HHH
1 stop6h 51m
American Airlines
Deal found 1/27$367
This American Airlines deal was found by Cheapflights users on 1/27. 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. 3/34:11 pm
HHH
-
SDF
1 stop5h 28m
American Airlines
mar. 3/107:50 am
SDF
-
HHH
1 stop4h 03m
American Airlines
Deal found 1/27$387
This American Airlines deal was found by Cheapflights users on 1/27. 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. 3/33:31 pm
HHH
-
SDF
1 stop5h 40m
American Airlines
lun. 3/95:00 am
SDF
-
HHH
1 stop5h 33m
American Airlines
Deal found 1/27$397
This American Airlines deal was found by Cheapflights users on 1/27. 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. 3/33:31 pm
HHH
-
SDF
2 stops7h 45m
American Airlines
dom. 3/87:00 am
SDF
-
HHH
1 stop3h 33m
American Airlines
Deal found 1/27$402
This American Airlines deal was found by Cheapflights users on 1/27. 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.
jue. 2/122:58 pm
HHH
-
BNA
1 stop3h 35m
American Airlines
lun. 2/165:15 am
BNA
-
HHH
1 stop4h 18m
American Airlines
Deal found 1/27$407
This American Airlines deal was found by Cheapflights users on 1/27. 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.
jue. 3/56:20 pm
HHH
-
SDF
1 stop4h 23m
American Airlines
sáb. 3/77:09 am
SDF
-
HHH
2 stops10h 35m
American Airlines
Deal found 1/27$412
This American Airlines deal was found by Cheapflights users on 1/27. 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. 3/412:23 pm
HHH
-
SDF
2 stops8h 50m
American Airlines
sáb. 3/77:09 am
SDF
-
HHH
2 stops10h 35m
American Airlines
Deal found 1/27$417
This American Airlines deal was found by Cheapflights users on 1/27. 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.
lun. 3/96:15 pm
HHH
-
SDF
1 stop4h 25m
American Airlines
mié. 3/115:00 am
SDF
-
HHH
1 stop5h 33m
American Airlines
Deal found 1/27$419
This American Airlines deal was found by Cheapflights users on 1/27. 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.
lun. 3/96:15 pm
HHH
-
SDF
1 stop6h 12m
American Airlines
mar. 3/106:00 am
SDF
-
HHH
2 stops10h 44m
American Airlines
Deal found 1/27$424
This American Airlines deal was found by Cheapflights users on 1/28. 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. 3/256:15 pm
HHH
-
CVG
1 stop5h 44m
American Airlines
jue. 4/25:00 am
CVG
-
HHH
2 stops9h 22m
American Airlines
Deal found 1/28$433

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 enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(United Airlines)

One-way from

$119
(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
One-way flight 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 enero 29, 2026.
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 IslandNashville

HHH - BNA

HHHBNA

Hilton Head Island

lun. 6/29

3:00 pm-9:39 pm

1 stop7h 39m

Nashville Intl

dom. 7/5

6:00 am-2:01 pm

1 stop7h 01m

$284

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

vie. 3/6

6:20 pm-10:43 pm

1 stop4h 23m

Louisville Intl

dom. 3/8

7:30 am-5:44 pm

2 stops10h 14m

$332

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

mar. 3/3

5:19 pm-11:03 pm

1 stop5h 44m

Louisville Intl

mié. 3/11

5:00 am-10:33 am

1 stop5h 33m

$387

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

mié. 3/4

5:19 pm-9:11 pm

1 stop3h 52m

Louisville Intl

mar. 3/10

7:50 am-11:53 am

1 stop4h 03m

$387

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

mié. 3/4

3:31 pm-9:11 pm

1 stop5h 40m

Louisville Intl

mié. 3/11

6:33 am-2:22 pm

2 stops7h 49m

$392

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

mié. 3/4

3:31 pm-9:11 pm

1 stop5h 40m

Louisville Intl

sáb. 3/7

5:00 am-10:33 am

1 stop5h 33m

$397

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

sáb. 3/7

2:58 pm-9:24 pm

1 stop6h 26m

Louisville Intl

mar. 3/10

10:31 am-3:01 pm

1 stop4h 30m

$397

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

jue. 3/5

2:58 pm-7:05 pm

1 stop4h 07m

Louisville Intl

mié. 3/11

5:00 am-10:33 am

1 stop5h 33m

$397

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

jue. 3/5

6:20 pm-10:43 pm

1 stop4h 23m

Louisville Intl

mar. 3/10

10:31 am-4:44 pm

1 stop6h 13m

$397

Hilton Head IslandLouisville

HHH - SDF

HHHSDF

Hilton Head Island

mar. 3/3

12:23 pm-9:26 pm

2 stops9h 03m

Louisville Intl

mar. 3/10

6:33 am-3:01 pm

2 stops8h 28m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 39 results
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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 December is currently the most expensive (average of $267). 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 enero 29, 2026.
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
11,205 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 4h 23m. United Airlines provides one of the quickest options available for as low as $327. 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 - Knoxville McGhee Tyson, 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, 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 December is currently the most expensive (average of $267). 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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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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$293FlexibilityNo cancel feeOn-time71%

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