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Cheap flights from Madison to Hilton Head Island from $265

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 9/22. 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
11:33 am - 4:38 pm
MSN
-
HHH
4h 05m
1 stop
American Airlines Logo
6:07 pm - 12:21 am
HHH
-
MSN
7h 14m
1 stop
$309American Airlines
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
5:00 am - 1:22 pm
MSN
-
HHH
7h 22m
1 stop
American Airlines Logo
6:07 pm - 11:04 pm
HHH
-
MSN
5h 57m
2 stops
$314American Airlines
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
7:55 am - 4:38 pm
MSN
-
HHH
7h 43m
2 stops
American Airlines Logo
12:37 pm - 6:49 pm
HHH
-
MSN
7h 12m
2 stops
$319American Airlines
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
6:00 am - 3:14 pm
MSN
-
HHH
8h 14m
1 stop
American Airlines Logo
3:44 pm - 9:52 pm
HHH
-
MSN
7h 08m
1 stop
$369American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
6:45 am - 2:26 pm
MSN
-
HHH
6h 41m
1 stop
American Airlines Logo
1:08 pm - 10:11 pm
HHH
-
MSN
10h 03m
2 stops
$374American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
7:49 am - 1:22 pm
MSN
-
HHH
4h 33m
1 stop
American Airlines Logo
3:27 pm - 11:59 pm
HHH
-
MSN
9h 32m
2 stops
$379American Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
5:33 am - 2:26 pm
MSN
-
HHH
7h 53m
2 stops
American Airlines Logo
1:08 pm - 10:11 pm
HHH
-
MSN
10h 03m
2 stops
$380American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
7:00 am - 12:26 pm
MSN
-
HHH
4h 26m
1 stop
American Airlines Logo
2:43 pm - 11:19 pm
HHH
-
MSN
9h 36m
2 stops
$383American Airlines
Fri, Jun 26 - Tue, Jun 30
American Airlines Logo
5:00 am - 4:32 pm
MSN
-
HHH
10h 32m
2 stops
American Airlines Logo
5:21 pm - 12:40 am
HHH
-
MSN
8h 19m
2 stops
$385American Airlines
Fri, Jun 26 - Tue, Jun 30
American Airlines Logo
5:00 am - 4:32 pm
MSN
-
HHH
10h 32m
2 stops
American Airlines Logo
2:43 pm - 11:19 pm
HHH
-
MSN
9h 36m
2 stops
$388American Airlines
Fri, Jun 26 - Tue, Jun 30

American Airlines flights from Madison to Hilton Head Island

Our best American Airlines deals on Madison to Hilton Head Island flight tickets
American Airlines
Sep 8
MSN11:33 amMadison Truax Field
4h 05m
1 stop
HHH4:38 pmHilton Head Island
Sep 15
HHH6:07 pmHilton Head Island
7h 14m
1 stop
MSN12:21 amMadison Truax Field
$309
American Airlines
Sep 8
MSN5:00 amMadison Truax Field
7h 22m
1 stop
HHH1:22 pmHilton Head Island
Sep 15
HHH6:07 pmHilton Head Island
5h 57m
2 stops
MSN11:04 pmMadison Truax Field
$314
American Airlines
Sep 8
MSN7:55 amMadison Truax Field
7h 43m
2 stops
HHH4:38 pmHilton Head Island
Sep 15
HHH12:37 pmHilton Head Island
7h 12m
2 stops
MSN6:49 pmMadison Truax Field
$319

United Airlines flights from Madison to Hilton Head Island

Our best United Airlines deals on Madison to Hilton Head Island flight tickets
United Airlines
May 19
MSN6:30 amMadison Truax Field
6h 41m
1 stop
HHH2:11 pmHilton Head Island
May 23
HHH1:45 pmHilton Head Island
9h 57m
2 stops
MSN10:42 pmMadison Truax Field
$518
United Airlines
Sep 19
MSN6:30 amMadison Truax Field
6h 31m
1 stop
HHH2:01 pmHilton Head Island
Sep 26
HHH3:00 pmHilton Head Island
6h 54m
1 stop
MSN8:54 pmMadison Truax Field
$538
United Airlines
May 19
MSN6:30 amMadison Truax Field
6h 41m
1 stop
HHH2:11 pmHilton Head Island
May 23
HHH1:45 pmHilton Head Island
7h 54m
1 stop
MSN8:39 pmMadison Truax Field
$569

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 May 4, 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
Quickest round-trip

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 9/8

11:33 am-4:38 pm

1 stop4h 05m

Hilton Head Island

Tue 9/15

6:07 pm-12:21 am

1 stop7h 14m

$309

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 9/8

5:00 am-1:22 pm

1 stop7h 22m

Hilton Head Island

Tue 9/15

6:07 pm-11:04 pm

2 stops5h 57m

$314

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 9/8

7:55 am-4:38 pm

2 stops7h 43m

Hilton Head Island

Tue 9/15

12:37 pm-6:49 pm

2 stops7h 12m

$319

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 5/14

6:00 am-3:14 pm

1 stop8h 14m

Hilton Head Island

Mon 5/18

3:44 pm-9:52 pm

1 stop7h 08m

$369

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 5/14

6:45 am-2:26 pm

1 stop6h 41m

Hilton Head Island

Mon 5/18

1:08 pm-10:11 pm

2 stops10h 03m

$374

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 8/20

7:49 am-1:22 pm

1 stop4h 33m

Hilton Head Island

Mon 8/24

3:27 pm-11:59 pm

2 stops9h 32m

$379

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 5/14

5:33 am-2:26 pm

2 stops7h 53m

Hilton Head Island

Mon 5/18

1:08 pm-10:11 pm

2 stops10h 03m

$380

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Fri 6/26

7:00 am-12:26 pm

1 stop4h 26m

Hilton Head Island

Tue 6/30

2:43 pm-11:19 pm

2 stops9h 36m

$383

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Fri 6/26

5:00 am-4:32 pm

2 stops10h 32m

Hilton Head Island

Tue 6/30

5:21 pm-12:40 am

2 stops8h 19m

$385

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Fri 6/26

5:00 am-4:32 pm

2 stops10h 32m

Hilton Head Island

Tue 6/30

2:43 pm-11:19 pm

2 stops9h 36m

$388

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 typical price of a round-trip flight between Madison and Hilton Head Island?

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 September to fly from Madison, when ticket prices are also cheap, with an average price of $233.

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 01m

Direct flights

None
The fastest flight from Madison to Hilton Head Island takes 5h 01m
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

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 5h 01m.

  • 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 $265Free CancellationRating
7.1
11,670 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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