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Hilton Head Island

$169+ Cheap flights from Florida Keys 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — HHH
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap flight deals from Florida Keys to Hilton Head Island

Cheapest flights from Florida Keys to Hilton Head Island
Explore the most affordable flight options available from Florida Keys to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.

This American Airlines deal was found by Cheapflights users on 2/16. 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 5/279:55 am
MIA
-
HHH
1 stop6h 37m
American Airlines
Tue 6/22:48 pm
HHH
-
MIA
1 stop5h 15m
American Airlines
Deal found 2/16$227
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/177:10 am
MIA
-
HHH
1 stop4h 43m
American Airlines
Tue 3/243:31 pm
HHH
-
MIA
1 stop7h 14m
American Airlines
Deal found 2/15$230
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Thu 5/286:20 am
MIA
-
HHH
1 stop4h 50m
American Airlines
Tue 6/22:48 pm
HHH
-
MIA
1 stop5h 15m
American Airlines
Deal found 2/16$272
This American Airlines deal was found by Cheapflights users on 2/14. 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 5/47:45 am
MIA
-
HHH
1 stop6h 41m
American Airlines
Fri 5/85:04 pm
HHH
-
MIA
1 stop5h 47m
American Airlines
Deal found 2/14$317
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Mon 4/67:50 am
MIA
-
HHH
1 stop6h 32m
American Airlines
Wed 4/85:04 pm
HHH
-
MIA
1 stop5h 47m
American Airlines
Deal found 2/17$323
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/297:40 am
MIA
-
HHH
1 stop6h 38m
American Airlines
Sun 5/312:48 pm
HHH
-
MIA
1 stop5h 15m
American Airlines
Deal found 2/18$343
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Sat 8/86:16 am
MIA
-
HHH
1 stop5h 14m
American Airlines
Sat 8/156:15 pm
HHH
-
MIA
1 stop5h 02m
American Airlines
Deal found 2/17$358
This American Airlines deal was found by Cheapflights users on 2/17. 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 6/46:20 am
MIA
-
HHH
1 stop4h 50m
American Airlines
Sun 6/75:21 pm
HHH
-
MIA
1 stop4h 44m
American Airlines
Deal found 2/17$388
This American Airlines deal was found by Cheapflights users on 2/16. 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 3/37:10 am
MIA
-
HHH
1 stop4h 43m
American Airlines
Sat 3/76:20 pm
HHH
-
MIA
1 stop5h 23m
American Airlines
Deal found 2/16$422
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Mon 4/137:45 am
MIA
-
HHH
1 stop4h 52m
American Airlines
Mon 4/206:39 pm
HHH
-
MIA
1 stop4h 12m
American Airlines
Deal found 2/17$452
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Mon 3/99:30 am
MIA
-
HHH
1 stop4h 52m
American Airlines
Mon 3/166:15 pm
HHH
-
MIA
2 stops15h 00m
American Airlines
Deal found 2/16$457
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Fri 5/229:55 am
MIA
-
HHH
1 stop6h 37m
American Airlines
Mon 5/255:21 pm
HHH
-
MIA
1 stop7h 26m
American Airlines
Deal found 2/16$459

Find flight deals from Florida Keys to Hilton Head Island

Keep the following information in mind while searching for Florida Keys to Hilton Head Island flight deals. Data was last updated February 18, 2026.

Round-trip from

$227
(American Airlines)

One-way from

$169
(American Airlines)
From Florida Keys to Hilton Head Island
Search Deals
One-way flight from Florida Keys to Hilton Head Island
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys 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 February 18, 2026.
Use the filters below to find and compare flights from Florida Keys to Hilton Head Island that are best for you.

Fly from

Florida Keys

Fly to

Hilton Head Island

Route

Depart

Return

Price

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Wed 5/27

9:55 am-4:32 pm

1 stop6h 37m

Hilton Head Island

Tue 6/2

2:48 pm-8:03 pm

1 stop5h 15m

$227

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Tue 3/17

7:10 am-11:53 am

1 stop4h 43m

Hilton Head Island

Tue 3/24

3:31 pm-10:45 pm

1 stop7h 14m

$230

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Thu 5/28

6:20 am-11:10 am

1 stop4h 50m

Hilton Head Island

Tue 6/2

2:48 pm-8:03 pm

1 stop5h 15m

$272

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Mon 5/4

7:45 am-2:26 pm

1 stop6h 41m

Hilton Head Island

Fri 5/8

5:04 pm-10:51 pm

1 stop5h 47m

$317

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 5/29

7:40 am-2:18 pm

1 stop6h 38m

Hilton Head Island

Sun 5/31

2:48 pm-8:03 pm

1 stop5h 15m

$343

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Sat 8/8

6:16 am-11:30 am

1 stop5h 14m

Hilton Head Island

Sat 8/15

6:15 pm-11:17 pm

1 stop5h 02m

$358

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Thu 6/4

6:20 am-11:10 am

1 stop4h 50m

Hilton Head Island

Sun 6/7

5:21 pm-10:05 pm

1 stop4h 44m

$388

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Tue 3/3

7:10 am-11:53 am

1 stop4h 43m

Hilton Head Island

Sat 3/7

6:20 pm-11:43 pm

1 stop5h 23m

$422

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Wed 3/18

7:00 am-2:22 pm

1 stop7h 22m

Hilton Head Island

Thu 3/19

6:15 pm-11:43 pm

1 stop5h 28m

$422

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 5/1

6:54 am-2:26 pm

1 stop7h 32m

Hilton Head Island

Sun 5/3

6:39 pm-10:51 pm

1 stop4h 12m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

Showing 1-10 of 20 results
1
2

Best time to book a flight from Florida Keys to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Florida Keys 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 Florida Keys to Hilton Head Island
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated February 18, 2026.
See what other customers who have flown with American Airlines from Florida Keys to Hilton Head Island have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,304 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,304 reviews
American Airlines
7.2
Good
11,304 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys 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 Florida Keys?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly into when you book flights from Florida Keys to Hilton Head Island.

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

    There are many flights that can get you from Florida Keys to Hilton Head Island in 6h 37m. Fly via American Airlines to get the fastest option. Florida Keys and Hilton Head Island are separated by a distance of 444 mi.

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

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

  • How can I find direct flights from Florida Keys 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 Florida Keys to Hilton Head Island.

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

    Yes. Cheapflights offers flight deals from Florida Keys 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.

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

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