How long is the flight from Madison to Hilton Head Island?

Airlines like American Airlines fly from Madison to Hilton Head Island in about 5h 52m. The time it takes to get you to your destination can typically vary by up to . There are 888 mi between Madison and Hilton Head Island.

What is the cheapest airline to fly from Madison to Hilton Head Island round-trip?

According to our current data, American Airlines ($253), offers the cheapest pricing from Madison to Hilton Head Island. This flight start at 44% lower than the current average price 3 months from now.

What is the cheapest day to fly from Madison to Hilton Head Island?

Travelers seeking maximum savings on their Madison to Hilton Head Island flight should consider departing on Friday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 day to fly round-trip from Madison to Hilton Head Island?

Wednesday flights are generally found to be more expensive for flights from Madison to Hilton Head Island. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Hilton Head Island.

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

September is one of the best times of the year to fly to Hilton Head Island from Madison. Prices for September average $460 per person but you can even find prices for as low as $163. The most expensive prices can be found in the month of October. Opting for a September flight can save you 33% on your journey compared to booking in October

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

When flying from Madison 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.

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

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

How can I find direct flights from Madison 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 Madison to Hilton Head Island.

Can I find deals for business class flights from Madison to Hilton Head Island?

Yes. Cheapflights offers flight deals from Madison 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.

$249+ Cheap Flights from Madison to Hilton Head Island

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Cheap flight deals from Madison to Hilton Head Island

Round-trip from	$249 (American Airlines)
Popular in	October
Cheapest in	September
Average price	$196

From Madison Truax Field to Hilton Head Island

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High demand for flights, 7% potential price rise

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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Find flight deals from Madison to Hilton Head Island

Cheapest flights from Madison to Hilton Head Island
Explore the most affordable flight options available from Madison to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Wed 12/108:05 amMSN - HHH

1 stop5h 52mAmerican Airlines

Sat 12/136:48 pmHHH - MSN

1 stop6h 02mAmerican Airlines

Deal found 9/10

$249

Thu 11/2011:10 amMSN - HHH

1 stop5h 59mAmerican Airlines

Sun 11/236:40 pmHHH - MSN

1 stop6h 11mAmerican Airlines

Deal found 9/11

$279

Wed 10/158:09 amMSN - HHH

1 stop5h 53mAmerican Airlines

Mon 10/205:57 pmHHH - MSN

1 stop6h 54mAmerican Airlines

Deal found 9/9

$413

Mon 9/159:00 amMSN - HHH

2 stops25h 25mUnited Airlines

Mon 9/2212:06 pmHHH - MSN

1 stop7h 17mUnited Airlines

Deal found 9/9

$1,197

Best flights from Madison to Hilton Head Island
Discover carefully curated flight deals from Madison to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2025.

Wed 12/108:05 amMSN - HHH

1 stop5h 52mAmerican Airlines

Sat 12/136:48 pmHHH - MSN

1 stop6h 02mAmerican Airlines

Deal found 9/10

$249

Thu 11/2011:10 amMSN - HHH

1 stop5h 59mAmerican Airlines

Sun 11/236:40 pmHHH - MSN

1 stop6h 11mAmerican Airlines

Deal found 9/11

$279

Wed 10/156:29 amMSN - HHH

2 stops7h 33mAmerican Airlines

Mon 10/205:57 pmHHH - MSN

1 stop6h 54mAmerican Airlines

Deal found 9/9

$451

Mon 3/97:20 amMSN - HHH

1 stop5h 59mAmerican Airlines

Mon 3/234:10 pmHHH - MSN

1 stop6h 17mAmerican Airlines

Deal found 9/9

$458

Last-minute flights from Madison to Hilton Head Island
Discover last-minute flight deals from Madison to Hilton Head Island. Data last updated September 11, 2025 and is based on user searches.

Mon 9/159:00 amMSN - HHH

2 stops25h 25mUnited Airlines

Mon 9/2212:06 pmHHH - MSN

1 stop7h 17mUnited Airlines

Deal found 9/9

$1,197

Wed 10/158:09 amMSN - HHH

1 stop5h 53mAmerican Airlines

Mon 10/205:57 pmHHH - MSN

1 stop6h 54mAmerican Airlines

Deal found 9/9

$413

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 12/10

8:05 am-2:57 pm

1 stop5h 52m

Hilton Head Island

Sat 12/13

6:48 pm-11:50 pm

1 stop6h 02m

$249

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 11/20

11:10 am-6:09 pm

1 stop5h 59m

Hilton Head Island

Sun 11/23

6:40 pm-11:51 pm

1 stop6h 11m

$279

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 10/15

6:29 am-3:02 pm

2 stops7h 33m

Hilton Head Island

Mon 10/20

5:57 pm-11:51 pm

1 stop6h 54m

$451

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Mon 3/9

7:20 am-2:19 pm

1 stop5h 59m

Hilton Head Island

Mon 3/23

4:10 pm-9:27 pm

1 stop6h 17m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Best time to book a flight from Madison to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Madison 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 Madison to Hilton Head Island

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

Currently, January is the cheapest month in which you can book a flight from Madison to Hilton Head Island (average of $275). Flying from Madison 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.

Reviews of airlines servicing Hilton Head Island

Read through reviews of airlines operating flights from Madison to Hilton Head Island, such as American Airlines. 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

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

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

How long is the flight from Madison to Hilton Head Island?
Airlines like American Airlines fly from Madison to Hilton Head Island in about 5h 52m. The time it takes to get you to your destination can typically vary by up to . There are 888 mi between Madison and Hilton Head Island.
What is the cheapest airline to fly from Madison to Hilton Head Island round-trip?
According to our current data, American Airlines ($253), offers the cheapest pricing from Madison to Hilton Head Island. This flight start at 44% lower than the current average price 3 months from now.
Can I find deals for flights from Madison to Hilton Head Island that include hotel bookings?
Yes. In addition to deals on Madison to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Madison 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 Madison to Hilton Head Island.
Can I find deals for business class flights from Madison to Hilton Head Island?
Yes. Cheapflights offers flight deals from Madison 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 Madison to Hilton Head Island?
Currently, January is the cheapest month in which you can book a flight from Madison to Hilton Head Island (average of $275). Flying from Madison 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

Beaufort

Bluffton

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Top airline flying from Madison to Hilton Head Island

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$253	Average$472	FlexibilityNo cancel fee	On-time71%

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$249+ Cheap flights from Madison to Hilton Head Island (MSN - HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Madison to Hilton Head Island with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Madison to Hilton Head Island

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Madison to Hilton Head Island

Cheapest flights from Madison to Hilton Head IslandExplore the most affordable flight options available from Madison to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Explore the most affordable flight options available from Madison to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Madison to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Madison with our price prediction graph.

Cheapflights Insights

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

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

Reviews of airlines servicing Hilton Head Island

Read through reviews of airlines operating flights from Madison to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Madison 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.

How long is the flight from Madison to Hilton Head Island?

What is the cheapest airline to fly from Madison to Hilton Head Island round-trip?

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

How can I find direct flights from Madison to Hilton Head Island?

Can I find deals for business class flights from Madison to Hilton Head Island?

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

Traveling to a place near Hilton Head Island?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Madison to Hilton Head Island

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Book with Flexibility

Travel Smart

Cheapest flights from Madison to Hilton Head Island
Explore the most affordable flight options available from Madison to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.