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Cheap flights from Madison to Hilton Head Island from $249

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Hilton Head Island departing on 3/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:10 am - 2:59 pm
MSN
-
HHH
5h 49m1 stop
American Airlines Logo
4:08 pm - 9:44 pm
HHH
-
MSN
6h 36m1 stop
$456American Airlines
Sun, Feb 8 - Thu, Feb 26
American Airlines Logo
5:37 am - 2:59 pm
MSN
-
HHH
8h 22m2 stops
American Airlines Logo
6:22 pm - 11:59 pm
HHH
-
MSN
6h 37m1 stop
$461American Airlines
Sun, Feb 8 - Thu, Feb 26
American Airlines Logo
5:37 am - 2:59 pm
MSN
-
HHH
8h 22m2 stops
American Airlines Logo
11:02 am - 11:03 pm
HHH
-
MSN
13h 01m2 stops
$466American Airlines
Sun, Feb 8 - Thu, Feb 26
American Airlines Logo
10:50 am - 5:52 pm
MSN
-
HHH
6h 02m1 stop
American Airlines Logo
11:02 am - 4:46 pm
HHH
-
MSN
6h 44m1 stop
$487American Airlines
Sun, Feb 15 - Fri, Feb 20
American Airlines Logo
7:00 am - 2:27 pm
MSN
-
HHH
6h 27m1 stop
American Airlines Logo
2:58 pm - 11:28 pm
HHH
-
MSN
9h 30m2 stops
$492American Airlines
Sun, Feb 15 - Fri, Feb 20
American Airlines Logo
6:00 am - 2:27 pm
MSN
-
HHH
7h 27m2 stops
American Airlines Logo
11:02 am - 11:03 pm
HHH
-
MSN
13h 01m2 stops
$497American Airlines
Sun, Feb 15 - Fri, Feb 20
American Airlines Logo
7:00 am - 2:16 pm
MSN
-
HHH
6h 16m1 stop
American Airlines Logo
6:13 pm - 11:59 pm
HHH
-
MSN
6h 46m1 stop
$523American Airlines
Thu, Jan 1 - Mon, Jan 5
American Airlines Logo
7:00 am - 2:16 pm
MSN
-
HHH
6h 16m1 stop
American Airlines Logo
2:46 pm - 11:28 pm
HHH
-
MSN
9h 42m2 stops
$528American Airlines
Thu, Jan 1 - Mon, Jan 5
American Airlines Logo
8:09 am - 5:46 pm
MSN
-
HHH
8h 37m2 stops
American Airlines Logo
4:11 pm - 9:58 pm
HHH
-
MSN
6h 47m1 stop
$532American Airlines
Sun, Mar 29 - Thu, Apr 2
American Airlines Logo
6:00 am - 5:43 pm
MSN
-
HHH
10h 43m2 stops
American Airlines Logo
2:46 pm - 10:24 pm
HHH
-
MSN
8h 38m2 stops
$533American Airlines
Thu, Jan 1 - Mon, Jan 5

American Airlines flights from Madison to Hilton Head Island

Our best American Airlines deals on Madison to Hilton Head Island flight tickets
American Airlines
Feb 8
MSN8:10 amMadison Truax Field
5h 49m
1 stop
HHH2:59 pmHilton Head Island
Feb 26
HHH4:08 pmHilton Head Island
6h 36m
1 stop
MSN9:44 pmMadison Truax Field
$456
Find similar
American Airlines
Feb 8
MSN5:37 amMadison Truax Field
8h 22m
2 stops
HHH2:59 pmHilton Head Island
Feb 26
HHH6:22 pmHilton Head Island
6h 37m
1 stop
MSN11:59 pmMadison Truax Field
$461
Find similar
American Airlines
Feb 8
MSN5:37 amMadison Truax Field
8h 22m
2 stops
HHH2:59 pmHilton Head Island
Feb 26
HHH11:02 amHilton Head Island
13h 01m
2 stops
MSN11:03 pmMadison Truax Field
$466
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
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

Sun 2/8

8:10 am-2:59 pm

1 stop5h 49m

Hilton Head Island

Thu 2/26

4:08 pm-9:44 pm

1 stop6h 36m

$456

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/8

5:37 am-2:59 pm

2 stops8h 22m

Hilton Head Island

Thu 2/26

6:22 pm-11:59 pm

1 stop6h 37m

$461

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/8

5:37 am-2:59 pm

2 stops8h 22m

Hilton Head Island

Thu 2/26

11:02 am-11:03 pm

2 stops13h 01m

$466

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/15

10:50 am-5:52 pm

1 stop6h 02m

Hilton Head Island

Fri 2/20

11:02 am-4:46 pm

1 stop6h 44m

$487

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/15

7:00 am-2:27 pm

1 stop6h 27m

Hilton Head Island

Fri 2/20

2:58 pm-11:28 pm

2 stops9h 30m

$492

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/15

6:00 am-2:27 pm

2 stops7h 27m

Hilton Head Island

Fri 2/20

11:02 am-11:03 pm

2 stops13h 01m

$497

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 1/1

7:00 am-2:16 pm

1 stop6h 16m

Hilton Head Island

Mon 1/5

6:13 pm-11:59 pm

1 stop6h 46m

$523

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 1/1

7:00 am-2:16 pm

1 stop6h 16m

Hilton Head Island

Mon 1/5

2:46 pm-11:28 pm

2 stops9h 42m

$528

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 3/29

8:09 am-5:46 pm

2 stops8h 37m

Hilton Head Island

Thu 4/2

4:11 pm-9:58 pm

1 stop6h 47m

$532

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 1/1

6:00 am-5:43 pm

2 stops10h 43m

Hilton Head Island

Mon 1/5

2:46 pm-10:24 pm

2 stops8h 38m

$533

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Madison to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Madison to Hilton Head Island is on a Friday. Travelers who choose to depart for Hilton Head Island on a Friday will often find tickets for as low as $312. On the other hand, Thursday is the most expensive day to depart from Madison because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $625.

When to book flights from Madison to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to Hilton Head Island (MSN to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Hilton Head Island

Fastest flight time

5h 49m

Direct flights

None
The fastest flight from Madison to Hilton Head Island takes 5h 49m
There are no direct flights from Madison to Hilton Head Island. There are no popular flight routes from Madison to Hilton Head Island.
Search flight deals

  • How far is Madison Truax Field to Hilton Head Island by plane?

    Madison Truax Field and Hilton Head Island are 885.1 mi apart from one another. In terms of flight time, this usually takes a little over 5h 49m.

  • When did momondo last update prices for flights from Madison Truax Field Airport to Hilton Head Island Airport?

    Prices for flights from Madison Truax Field Airport to Hilton Head Island Airport are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Hilton Head Island Airport?

  • How old do you have to be to fly from Madison Truax Field Airport to Hilton Head Island Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The required travel and health documents for your Hilton Head Island Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Hilton Head Island Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Madison to Hilton Head Island?

Best airlines flying from Madison to Hilton Head Island

Compare and see reviews for airlines that fly from Madison to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $233Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Hilton Head Island?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Madison to Hilton Head Island. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Madison to Hilton Head Island with flexible booking policies on momondo?

All flight searches from Madison to Hilton Head Island on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Madison to Hilton Head Island?

momondo helps you find the best flight between Madison and Hilton Head Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to Hilton Head Island right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Hilton Head Island from Madison. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Hilton Head Island trip

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