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Cheap flights from Madison to Hilton Head Island from $254

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
7:15 am - 3:01 pm
MSN
-
HHH
6h 46m
1 stop
American Airlines Logo
6:20 pm - 11:40 pm
HHH
-
MSN
6h 20m
1 stop
$279American Airlines
Tue, Feb 17 - Sat, Feb 21
American Airlines Logo
6:00 am - 3:01 pm
MSN
-
HHH
8h 01m
2 stops
American Airlines Logo
6:20 pm - 11:40 pm
HHH
-
MSN
6h 20m
1 stop
$284American Airlines
Tue, Feb 17 - Sat, Feb 21
American Airlines Logo
6:00 am - 4:44 pm
MSN
-
HHH
9h 44m
2 stops
American Airlines Logo
2:58 pm - 9:58 pm
HHH
-
MSN
8h 00m
2 stops
$289American Airlines
Tue, Feb 17 - Sat, Feb 21
United Airlines Logo
6:00 am - 2:06 pm
MSN
-
HHH
7h 06m
1 stop
United Airlines Logo
3:08 pm - 7:34 pm
HHH
-
MSN
5h 26m
1 stop
$339United Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
11:35 am - 6:09 pm
MSN
-
HHH
5h 34m
1 stop
American Airlines Logo
5:51 pm - 11:01 pm
HHH
-
MSN
6h 10m
1 stop
$359American Airlines
Wed, Apr 8 - Tue, Apr 14
American Airlines Logo
10:54 am - 5:44 pm
MSN
-
HHH
5h 50m
1 stop
American Airlines Logo
6:15 pm - 11:35 pm
HHH
-
MSN
6h 20m
1 stop
$362American Airlines
Sat, Mar 14 - Wed, Mar 18
American Airlines Logo
11:35 am - 6:20 pm
MSN
-
HHH
5h 45m
1 stop
American Airlines Logo
12:57 pm - 5:14 pm
HHH
-
MSN
5h 17m
1 stop
$364American Airlines
Sat, May 16 - Sat, May 23
American Airlines Logo
10:54 am - 5:44 pm
MSN
-
HHH
5h 50m
1 stop
American Airlines Logo
2:58 pm - 9:39 pm
HHH
-
MSN
7h 41m
2 stops
$367American Airlines
Sat, Mar 14 - Wed, Mar 18
American Airlines Logo
7:00 am - 2:22 pm
MSN
-
HHH
6h 22m
1 stop
American Airlines Logo
5:51 pm - 11:01 pm
HHH
-
MSN
6h 10m
1 stop
$389American Airlines
Mon, Apr 6 - Tue, Apr 14
American Airlines Logo
8:00 am - 6:09 pm
MSN
-
HHH
9h 09m
2 stops
American Airlines Logo
3:44 pm - 10:08 pm
HHH
-
MSN
7h 24m
1 stop
$394American Airlines
Wed, Apr 29 - Wed, May 6

Delta flights from Madison to Hilton Head Island

Our best Delta deals on Madison to Hilton Head Island flight tickets
Delta
Jun 20
MSN7:00 amMadison Truax Field
27h 23m
1 stop
HHH11:23 amHilton Head Island
Jun 23
HHH12:00 pmHilton Head Island
5h 35m
1 stop
MSN4:35 pmMadison Truax Field
$505
Delta
Jun 20
MSN2:40 pmMadison Truax Field
19h 43m
2 stops
HHH11:23 amHilton Head Island
Jun 23
HHH12:00 pmHilton Head Island
5h 35m
1 stop
MSN4:35 pmMadison Truax Field
$510

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 17
MSN7:15 amMadison Truax Field
6h 46m
1 stop
HHH3:01 pmHilton Head Island
Feb 21
HHH6:20 pmHilton Head Island
6h 20m
1 stop
MSN11:40 pmMadison Truax Field
$279
American Airlines
Feb 17
MSN6:00 amMadison Truax Field
8h 01m
2 stops
HHH3:01 pmHilton Head Island
Feb 21
HHH6:20 pmHilton Head Island
6h 20m
1 stop
MSN11:40 pmMadison Truax Field
$284
American Airlines
Feb 17
MSN6:00 amMadison Truax Field
9h 44m
2 stops
HHH4:44 pmHilton Head Island
Feb 21
HHH2:58 pmHilton Head Island
8h 00m
2 stops
MSN9:58 pmMadison Truax Field
$289

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 February 3, 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

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 2/17

7:15 am-3:01 pm

1 stop6h 46m

Hilton Head Island

Sat 2/21

6:20 pm-11:40 pm

1 stop6h 20m

$279

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 2/17

6:00 am-3:01 pm

2 stops8h 01m

Hilton Head Island

Sat 2/21

6:20 pm-11:40 pm

1 stop6h 20m

$284

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 2/17

6:00 am-4:44 pm

2 stops9h 44m

Hilton Head Island

Sat 2/21

2:58 pm-9:58 pm

2 stops8h 00m

$289

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 4/29

6:00 am-2:06 pm

1 stop7h 06m

Hilton Head Island

Wed 5/6

3:08 pm-7:34 pm

1 stop5h 26m

$339

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 4/8

11:35 am-6:09 pm

1 stop5h 34m

Hilton Head Island

Tue 4/14

5:51 pm-11:01 pm

1 stop6h 10m

$359

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sat 3/14

10:54 am-5:44 pm

1 stop5h 50m

Hilton Head Island

Wed 3/18

6:15 pm-11:35 pm

1 stop6h 20m

$362

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sat 5/16

11:35 am-6:20 pm

1 stop5h 45m

Hilton Head Island

Sat 5/23

12:57 pm-5:14 pm

1 stop5h 17m

$364

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sat 3/14

10:54 am-5:44 pm

1 stop5h 50m

Hilton Head Island

Wed 3/18

2:58 pm-9:39 pm

2 stops7h 41m

$367

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Mon 4/6

7:00 am-2:22 pm

1 stop6h 22m

Hilton Head Island

Tue 4/14

5:51 pm-11:01 pm

1 stop6h 10m

$389

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 4/29

8:00 am-6:09 pm

2 stops9h 09m

Hilton Head Island

Wed 5/6

3:44 pm-10:08 pm

1 stop7h 24m

$394

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 airline that flies from Madison Truax Field to Hilton Head Island?

American Airlines and United Airlines are the most popular carriers operating from Madison Truax Field to Hilton Head Island

What airlines fly to Hilton Head Island?

Allegiant Air, American Airlines and Delta are the top three most popular airlines that fly to Hilton Head Island from Madison according to our data. Allegiant Air is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 5 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.

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 22m

Direct flights

None
The fastest flight from Madison to Hilton Head Island takes 5h 22m
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 22m.

  • 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
11,216 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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