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

Currently, January is the cheapest month in which you can book a flight from Florida Keys to Hilton Head Island (average of $275). Flying from Florida Keys to Hilton Head Island in March is currently the most expensive (average of $480). 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.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

What is the cheapest month to fly from Florida Keys to Hilton Head Island?

November is one of the best times of the year to fly to Hilton Head Island from Florida Keys. Prices for November average $498 per person but you can even find prices for as low as $173. The most expensive prices can be found in the month of March. Opting for a November flight can save you 130% on your journey compared to booking in March

What is the cheapest time of day to fly from EOA to HHH?

When flying from Florida Keys to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 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.

$129+ Cheap Flights from Florida Keys to Hilton Head Island

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Cheap flight deals from Florida Keys to Hilton Head Island

Round-trip from	$300 (American Airlines)
One-way from	$129 (American Airlines)

From Florida Keys to Hilton Head Island

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One-way flight from Florida Keys to Hilton Head Island

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Find 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 August 14, 2025.

Wed 11/125:45 amMIA - HHH

1 stop6h 01mAmerican Airlines

Sat 11/156:48 pmHHH - MIA

1 stop6h 00mAmerican Airlines

Deal found 8/11

$300

Fri 10/318:23 amMIA - HHH

1 stop6h 39mAmerican Airlines

Sun 11/26:40 pmHHH - MIA

1 stop6h 08mAmerican Airlines

Deal found 8/11

$423

Wed 8/1310:28 amMIA - HHH

1 stop4h 54mDelta

Tue 8/1912:11 pmHHH - MIA

1 stop6h 14mDelta

Deal found 8/12

$467

Thu 8/148:38 amMIA - HHH

1 stop5h 34mAmerican Airlines

Sat 8/166:15 pmHHH - MIA

1 stop5h 02mAmerican Airlines

Deal found 8/12

$487

Thu 9/47:05 amMIA - HHH

1 stop5h 15mAmerican Airlines

Sun 9/76:20 pmHHH - MIA

1 stop4h 50mAmerican Airlines

Deal found 8/12

$507

Tue 8/128:46 pmMIA - HHH

2 stops15h 13mAmerican Airlines

Mon 8/185:28 pmHHH - MIA

1 stop6h 20mAmerican Airlines

Deal found 8/12

$648

Wed 8/133:36 pmMIA - HHH

2 stops19h 54mAmerican Airlines

Wed 8/203:35 pmHHH - MIA

1 stop6h 33mAmerican Airlines

Deal found 8/12

$655

Best flights from Florida Keys to Hilton Head Island
Discover carefully curated flight deals from Florida Keys to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Wed 11/125:45 amMIA - HHH

1 stop6h 01mAmerican Airlines

Sat 11/156:48 pmHHH - MIA

1 stop6h 00mAmerican Airlines

Deal found 8/11

$300

Fri 8/291:43 pmMIA - HHH

1 stop4h 00mAmerican Airlines

Tue 9/25:28 pmHHH - MIA

1 stop6h 21mAmerican Airlines

Deal found 8/14

$367

Fri 10/318:23 amMIA - HHH

1 stop6h 39mAmerican Airlines

Sun 11/26:40 pmHHH - MIA

1 stop6h 08mAmerican Airlines

Deal found 8/11

$423

Thu 9/47:05 amMIA - HHH

1 stop5h 15mAmerican Airlines

Sun 9/76:20 pmHHH - MIA

1 stop4h 50mAmerican Airlines

Deal found 8/12

$507

Last-minute flights from Florida Keys to Hilton Head Island
Discover last-minute flight deals from Florida Keys to Hilton Head Island. Data last updated August 14, 2025 and is based on user searches.

Thu 8/148:38 amMIA - HHH

1 stop5h 34mAmerican Airlines

Sat 8/166:15 pmHHH - MIA

1 stop5h 02mAmerican Airlines

Deal found 8/12

$487

Thu 8/148:38 amMIA - HHH

1 stop5h 34mAmerican Airlines

Sun 8/176:15 pmHHH - MIA

2 stops13h 05mAmerican Airlines

Deal found 8/12

$655

Thu 8/146:16 amMIA - HHH

1 stop5h 14mAmerican Airlines

Thu 8/142:42 pmHHH - MIA

1 stop6h 17mAmerican Airlines

Deal found 8/12

$661

Thu 8/1410:28 amMIA - HHH

1 stop4h 54mDelta

Fri 8/1512:11 pmHHH - MIA

1 stop6h 14mDelta

Deal found 8/12

$667

Thu 8/145:18 amMIA - HHH

1 stop6h 12mAmerican Airlines

Wed 8/203:35 pmHHH - MIA

2 stops6h 23mAmerican Airlines

Deal found 8/12

$684

Thu 8/146:40 pmMIA - HHH

2 stops20h 42mDelta

Tue 8/1912:11 pmHHH - MIA

1 stop6h 14mDelta

Deal found 8/12

$721

Fri 8/1510:28 amMIA - HHH

1 stop4h 54mDelta

Tue 8/1912:11 pmHHH - MIA

1 stop6h 14mDelta

Deal found 8/12

$467

Fri 8/291:43 pmMIA - HHH

1 stop4h 00mAmerican Airlines

Tue 9/25:28 pmHHH - MIA

1 stop6h 21mAmerican Airlines

Deal found 8/14

$367

Thu 9/47:05 amMIA - HHH

1 stop5h 15mAmerican Airlines

Sun 9/76:20 pmHHH - MIA

1 stop4h 50mAmerican Airlines

Deal found 8/12

$507

One-way flights from Florida Keys to Hilton Head Island
Search for one-way flight options from Florida Keys to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Mon 9/155:18 amMIA - HHH

1 stop7h 02mAmerican Airlines

Deal found 8/12

$129

Fri 10/1010:40 amMIA - HHH

1 stop4h 50mDelta

Deal found 8/13

$200

Wed 10/110:28 amMIA - HHH

1 stop4h 57mDelta

Deal found 8/14

$260

Fri 10/310:28 amMIA - HHH

1 stop4h 57mDelta

Deal found 8/14

$330

Sun 8/175:18 amMIA - HHH

1 stop6h 12mAmerican Airlines

Deal found 8/13

$334

Wed 10/18:05 amMIA - HHH

2 stops27h 11mUnited Airlines

Deal found 8/14

$337

Thu 9/2510:28 amMIA - HHH

1 stop4h 57mDelta

Deal found 8/14

$379

Thu 9/258:05 amMIA - HHH

2 stops27h 11mUnited Airlines

Deal found 8/14

$419

Sun 8/2410:28 amMIA - HHH

1 stop4h 54mDelta

Deal found 8/14

$450

Sun 8/1710:28 amMIA - HHH

1 stop4h 54mDelta

Deal found 8/14

$460

Cheapflights Fare Finder

Use the filters below to find and compare flights from Florida Keys to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Wed 11/12

5:45 am-11:46 am

1 stop6h 01m

Hilton Head Island

Sat 11/15

6:48 pm-12:48 am

1 stop6h 00m

$300

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 8/29

1:43 pm-5:43 pm

1 stop4h 00m

Hilton Head Island

Tue 9/2

5:28 pm-11:49 pm

1 stop6h 21m

$367

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 10/31

8:23 am-3:02 pm

1 stop6h 39m

Hilton Head Island

Sun 11/2

6:40 pm-12:48 am

1 stop6h 08m

$423

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Thu 9/4

7:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Sun 9/7

6:20 pm-11:10 pm

1 stop4h 50m

$507

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Mon 9/15

5:18 am-12:20 pm

1 stop7h 02m

$129

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 10/10

10:40 am-3:30 pm

1 stop4h 50m

$200

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Wed 10/1

10:28 am-3:25 pm

1 stop4h 57m

$260

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Fri 10/3

10:28 am-3:25 pm

1 stop4h 57m

$330

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Mon 9/8

10:28 am-3:22 pm

1 stop4h 54m

$330

MiamiHilton Head Island

MIA - HHH

MIAHHH

Miami

Thu 10/2

10:28 am-3:25 pm

1 stop4h 57m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 14 results

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

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

10,000 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

American Airlines

7.2

Good

10,000 reviews

American Airlines

7.2

Good

10,000 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Related info for your journey

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.
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.
What is the cheapest month to book a flight from Florida Keys to Hilton Head Island?
Currently, January is the cheapest month in which you can book a flight from Florida Keys to Hilton Head Island (average of $275). Flying from Florida Keys to Hilton Head Island in March is currently the most expensive (average of $480). 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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$129+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Florida Keys to Hilton Head Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap 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 August 14, 2025.

Round-trip from

One-way from

Find flight deals from Florida Keys to Hilton Head Island

Cheapest flights from Florida Keys to Hilton Head IslandExplore 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 August 14, 2025.

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 August 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Florida Keys to Hilton Head Island that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Hilton Head Island

Reviews of airlines servicing Hilton Head Island

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.

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?

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

How can I 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?

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

Traveling to a place near Hilton Head Island?

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Alternative routes for Florida Keys to Hilton Head Island

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Travel Smart

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 August 14, 2025.