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

According to our current data, American Airlines ($344), offers the cheapest pricing from Madison to Hilton Head Island. This flight start at 26% 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 $470 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 30% 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.

$234+ Flights from Madison to Hilton Head Island

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Cheap flight deals from Madison to Hilton Head Island

Round-trip from	$344 (American Airlines)
One-way from	$234 (American Airlines)
Popular in	October
Cheapest in	September
Average price	$423

From Madison Truax Field to Hilton Head Island

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One-way flight from Madison Truax Field to Hilton Head Island

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High demand for flights, 11% 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 July 2025

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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 July 29, 2025.

Mon 10/137:20 amMSN - HHH

1 stop6h 12mAmerican Airlines

Wed 10/225:21 pmHHH - MSN

1 stop6h 35mAmerican Airlines

Deal found 7/27

$344

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 July 29, 2025.

Mon 10/137:20 amMSN - HHH

1 stop6h 12mAmerican Airlines

Wed 10/225:21 pmHHH - MSN

1 stop6h 35mAmerican Airlines

Deal found 7/27

$344

Last-minute flights from Madison to Hilton Head Island
Discover last-minute flight deals from Madison to Hilton Head Island. Data last updated July 29, 2025 and is based on user searches.

Tue 8/127:56 amMSN - HHH

1 stop6h 09mAmerican Airlines

Sat 8/166:15 pmHHH - MSN

1 stop6h 44mAmerican Airlines

Deal found 7/28

$692

One-way flights from Madison to Hilton Head Island
Search for one-way flight options from Madison to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Mon 9/157:30 amMSN - HHH

1 stop6h 26mAmerican Airlines

Deal found 7/29

$234

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

Mon 10/13

7:20 am-2:32 pm

1 stop6h 12m

Hilton Head Island

Wed 10/22

5:21 pm-10:56 pm

1 stop6h 35m

$344

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Mon 9/15

7:30 am-2:56 pm

1 stop6h 26m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 $479). 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

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break

American Airlines

7.2

Good

10,000 reviews

American Airlines

7.2

Good

10,000 reviews

Reviews

1 / 20

2.0

Mediocre

Andrew,May 2025

LAX - MIA

Related info for your journey

What is the cheapest airline to fly from Madison to Hilton Head Island round-trip?
According to our current data, American Airlines ($344), offers the cheapest pricing from Madison to Hilton Head Island. This flight start at 26% 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 $479). 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$486	FlexibilityNo cancel fee	On-time71%

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$234+ Cheap flights from Madison to Hilton Head Island (MSN - 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 Madison 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 Madison to Hilton Head Island

Round-trip from

One-way from

Popular in

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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 July 29, 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 July 29, 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.

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?

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Alternative routes for Madison to Hilton Head Island

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Top airline flying from Madison to Hilton Head Island

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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 July 29, 2025.