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Cheap flights from Madison to Hilton Head Island from $279

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 11/4. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
11:33 am - 4:38 pmMSN  Madison Truax Field-HHH Hilton Head Island
4h 05m1 stop Charlotte Douglas
American Airlines Logo
5:46 pm - 11:49 pmHHH  Hilton Head Island-MSN Madison Truax Field
7h 03m1 stop Charlotte Douglas
$394American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
7:14 am - 2:26 pmMSN  Madison Truax Field-HHH Hilton Head Island
6h 12m1 stop Charlotte Douglas
American Airlines Logo
1:53 pm - 8:01 pmHHH  Hilton Head Island-MSN Madison Truax Field
7h 08m1 stop Chicago O'Hare Intl
$397American Airlines
Wed, Oct 21 - Sat, Nov 7
American Airlines Logo
8:05 am - 3:44 pmMSN  Madison Truax Field-HHH Hilton Head Island
6h 39m1 stop Charlotte Douglas
American Airlines Logo
5:54 pm - 11:59 pmHHH  Hilton Head Island-MSN Madison Truax Field
7h 05m1 stop Charlotte Douglas
$419American Airlines
Wed, Nov 4 - Sun, Nov 8
American Airlines Logo
5:00 am - 2:26 pmMSN  Madison Truax Field-HHH Hilton Head Island
8h 26m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
1:53 pm - 6:28 pmHHH  Hilton Head Island-MSN Madison Truax Field
5h 35m1 stop Chicago O'Hare Intl
$428American Airlines
Wed, Oct 21 - Sat, Nov 7
American Airlines Logo
8:15 am - 1:45 pmMSN  Madison Truax Field-HHH Hilton Head Island
4h 30m1 stop Charlotte Douglas
American Airlines Logo
5:15 pm - 8:50 pmHHH  Hilton Head Island-MSN Madison Truax Field
4h 35m1 stop Charlotte Douglas
$442American Airlines
Thu, Sep 17 - Thu, Sep 24
United Airlines Logo
6:06 am - 12:35 pmMSN  Madison Truax Field-HHH Hilton Head Island
5h 29m1 stop Newark
United Airlines Logo
3:00 pm - 7:27 pmHHH  Hilton Head Island-MSN Madison Truax Field
5h 27m1 stop Chicago O'Hare Intl
$447United Airlines
Wed, Oct 7 - Sat, Oct 10
United Airlines Logo
8:10 am - 2:03 pmMSN  Madison Truax Field-HHH Hilton Head Island
4h 53m1 stop Chicago O'Hare Intl
United Airlines Logo
2:58 pm - 8:53 pmHHH  Hilton Head Island-MSN Madison Truax Field
6h 55m1 stop Chicago O'Hare Intl
$459United Airlines
Mon, Aug 17 - Tue, Aug 25
United Airlines Logo
6:30 am - 2:03 pmMSN  Madison Truax Field-HHH Hilton Head Island
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
2:58 pm - 8:53 pmHHH  Hilton Head Island-MSN Madison Truax Field
6h 55m1 stop Chicago O'Hare Intl
$459United Airlines
Sun, Aug 16 - Mon, Aug 24
United Airlines Logo
8:10 am - 2:03 pmMSN  Madison Truax Field-HHH Hilton Head Island
4h 53m1 stop Chicago O'Hare Intl
United Airlines Logo
2:58 pm - 8:53 pmHHH  Hilton Head Island-MSN Madison Truax Field
6h 55m1 stop Chicago O'Hare Intl
$459United Airlines
Mon, Aug 17 - Mon, Aug 24
United Airlines Logo
6:30 am - 2:03 pmMSN  Madison Truax Field-HHH Hilton Head Island
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
2:58 pm - 8:53 pmHHH  Hilton Head Island-MSN Madison Truax Field
6h 55m1 stop Chicago O'Hare Intl
$459United Airlines
Sun, Aug 16 - Tue, Aug 25

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American Airlines flights from Madison to Hilton Head Island

Our best American Airlines deals on Madison to Hilton Head Island flight tickets
American Airlines
Aug 19
MSN11:33 amMadison Truax Field
4h 05m
1 stop
HHH4:38 pmHilton Head Island
Aug 23
HHH5:46 pmHilton Head Island
7h 03m
1 stop
MSN11:49 pmMadison Truax Field
$394
American Airlines
Oct 21
MSN7:14 amMadison Truax Field
6h 12m
1 stop
HHH2:26 pmHilton Head Island
Nov 7
HHH1:53 pmHilton Head Island
7h 08m
1 stop
MSN8:01 pmMadison Truax Field
$397
American Airlines
Nov 2
MSN8:05 amMadison Truax Field
6h 39m
1 stop
HHH3:44 pmHilton Head Island
Nov 12
HHH5:54 pmHilton Head Island
7h 05m
1 stop
MSN11:59 pmMadison Truax Field
$409

United Airlines flights from Madison to Hilton Head Island

Our best United Airlines deals on Madison to Hilton Head Island flight tickets
United Airlines
Oct 7
MSN6:06 amMadison Truax Field
5h 29m
1 stop
HHH12:35 pmHilton Head Island
Oct 10
HHH3:00 pmHilton Head Island
5h 27m
1 stop
MSN7:27 pmMadison Truax Field
$447
United Airlines
Aug 16
MSN6:30 amMadison Truax Field
6h 33m
1 stop
HHH2:03 pmHilton Head Island
Aug 24
HHH2:58 pmHilton Head Island
6h 55m
1 stop
MSN8:53 pmMadison Truax Field
$459
United Airlines
Aug 11
MSN8:10 amMadison Truax Field
4h 53m
1 stop
HHH2:03 pmHilton Head Island
Aug 21
HHH2:58 pmHilton Head Island
6h 58m
1 stop
MSN8:56 pmMadison Truax Field
$474

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 August 6, 2026.
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

Cheapest round-trip

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Wed 8/19

11:33 am-4:38 pm

1 stop4h 05m

Hilton Head Island

Sun 8/23

5:46 pm-11:49 pm

1 stop7h 03m

$394

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Wed 10/21

7:14 am-2:26 pm

1 stop6h 12m

Hilton Head Island

Sat 11/7

1:53 pm-8:01 pm

1 stop7h 08m

$397

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Wed 11/4

8:05 am-3:44 pm

1 stop6h 39m

Hilton Head Island

Sun 11/8

5:54 pm-11:59 pm

1 stop7h 05m

$419

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Wed 10/21

5:00 am-2:26 pm

2 stops8h 26m

Hilton Head Island

Sat 11/7

1:53 pm-6:28 pm

1 stop5h 35m

$428
Quickest round-trip

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Thu 9/17

8:15 am-1:45 pm

1 stop4h 30m

Hilton Head Island

Thu 9/24

5:15 pm-8:50 pm

1 stop4h 35m

$442

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Wed 10/7

6:06 am-12:35 pm

1 stop5h 29m

Hilton Head Island

Sat 10/10

3:00 pm-7:27 pm

1 stop5h 27m

$447

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Mon 8/17

8:10 am-2:03 pm

1 stop4h 53m

Hilton Head Island

Tue 8/25

2:58 pm-8:53 pm

1 stop6h 55m

$459

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Sun 8/16

6:30 am-2:03 pm

1 stop6h 33m

Hilton Head Island

Mon 8/24

2:58 pm-8:53 pm

1 stop6h 55m

$459

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Mon 8/17

8:10 am-2:03 pm

1 stop4h 53m

Hilton Head Island

Mon 8/24

2:58 pm-8:53 pm

1 stop6h 55m

$459

MadisonHilton Head Island

MSN Madison Truax Field - HHH Hilton Head Island

MSNHHH

Madison Truax Field

Sun 8/16

6:30 am-2:03 pm

1 stop6h 33m

Hilton Head Island

Tue 8/25

2:58 pm-8:53 pm

1 stop6h 55m

$459

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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 month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in January, then you should wait until June to fly from Madison, when ticket prices are also cheap, with an average price of $273.

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

4h 53m

Direct flights

None
The fastest flight from Madison to Hilton Head Island takes 4h 53m
There are no direct flights from Madison to Hilton Head Island. There are no popular flight routes from Madison to Hilton Head Island.
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Frequently asked questions about flying from Madison to Hilton Head Island

  • 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 4h 53m.

  • 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 $273Free CancellationRating
7.1
11,867 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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