MSN - HHH

$309 Find Cheap Flights from Madison to Hilton Head Island

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Hilton Head Island departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hilton Head Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Hilton Head Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Hilton Head Island, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$309
American Airlines
Thu 8/6Mon 8/10
MSN - HHH • 1 stop
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Madison and Hilton Head Island. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $511 (round-trip)
Shortest trip • 5h 13m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hilton Head Island!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to Hilton Head Island (MSN-HHH)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Hilton Head Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Hilton Head Island

Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
7:47 am - 1:17 pm
MSN
-
HHH
4h 30m
1 stop
American Airlines Logo
5:16 pm - 11:09 pm
HHH
-
MSN
6h 53m
1 stop
$309American Airlines
Wed, Aug 5 - Tue, Aug 11
United Airlines Logo
6:29 am - 12:58 pm
MSN
-
HHH
5h 29m
1 stop
United Airlines Logo
2:48 pm - 6:56 pm
HHH
-
MSN
5h 08m
1 stop
$389United Airlines
Wed, Aug 5 - Mon, Aug 10
American Airlines Logo
7:47 am - 1:24 pm
MSN
-
HHH
4h 37m
1 stop
American Airlines Logo
5:16 pm - 11:09 pm
HHH
-
MSN
6h 53m
1 stop
$399American Airlines
Sun, Sep 13 - Sat, Sep 19
American Airlines Logo
7:19 am - 12:33 pm
MSN
-
HHH
4h 14m
1 stop
American Airlines Logo
5:15 pm - 8:50 pm
HHH
-
MSN
4h 35m
1 stop
$402American Airlines
Sat, Aug 29 - Tue, Sep 1
United Airlines Logo
6:30 am - 2:03 pm
MSN
-
HHH
6h 33m
1 stop
United Airlines Logo
2:58 pm - 8:53 pm
HHH
-
MSN
6h 55m
1 stop
$413United Airlines
Mon, Dec 21 - Tue, Dec 29
American Airlines Logo
10:45 am - 5:43 pm
MSN
-
HHH
5h 58m
1 stop
American Airlines Logo
6:13 pm - 11:59 pm
HHH
-
MSN
6h 46m
1 stop
$414American Airlines
Thu, Aug 6 - Tue, Aug 11
American Airlines Logo
7:47 am - 1:17 pm
MSN
-
HHH
4h 30m
1 stop
American Airlines Logo
3:27 pm - 10:18 pm
HHH
-
MSN
7h 51m
2 stops
$418American Airlines
Tue, Dec 22 - Tue, Dec 29
American Airlines Logo
10:45 am - 5:43 pm
MSN
-
HHH
5h 58m
1 stop
American Airlines Logo
6:13 pm - 11:59 pm
HHH
-
MSN
6h 46m
1 stop
$429American Airlines
Fri, Aug 7 - Thu, Aug 13
United Airlines Logo
8:10 am - 2:21 pm
MSN
-
HHH
5h 11m
1 stop
United Airlines Logo
2:58 pm - 8:56 pm
HHH
-
MSN
6h 58m
1 stop
$449United Airlines
Sat, Aug 29 - Tue, Sep 1
United Airlines Logo
6:30 am - 2:03 pm
MSN
-
HHH
6h 33m
1 stop
United Airlines Logo
2:48 pm - 6:56 pm
HHH
-
MSN
5h 08m
1 stop
$472United Airlines
Booking Insights

KAYAK's insights & trends for Madison to Hilton Head Island flights

Get data-powered insights and trends into flights from Madison to Hilton Head Island to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Madison to Hilton Head Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Hilton Head Island is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $973 and $590 respectively.

Good to know

Low seasonFebruary
Cheapest flight$309
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Madison to Hilton Head Island

When to book flights from Madison to Hilton Head Island

Are your dates flexible? Find out the best times to travel from Madison to Hilton Head Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Hilton Head Island

  • What is the cheapest flight from Madison to Hilton Head Island?

    In the last 5 days, the lowest price for a flight from Madison to Hilton Head Island was $309 for a round-trip ticket.

  • Do I need a passport to fly between Madison and Hilton Head Island?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Madison to Hilton Head Island?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Madison to Hilton Head Island?

    oneworld is the only airline alliance operating flights between Madison and Hilton Head Island.

  • How does KAYAK find such low prices on flights from Madison to Hilton Head Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Hilton Head Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Hilton Head Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hilton Head Island from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Hilton Head Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Hilton Head Island with an airline and back to Madison with another airline. Booking your flights between Madison and HHH can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Hilton Head Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Hilton Head Island from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Madison to Hilton Head Island

 
See real verified KAYAK customer reviews for airlines flying from Madison to Hilton Head Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Hilton Head Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11766 reviews
7.2Comfort
6.8Entertainment
7.5Boarding
7.9Crew
6.4Food
Airline reviews

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

4.0 OkayCaleb, Jun 2026
ORD - GSP
Read more American Airlines reviews

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Multiple gate changes and significant delay leaving DFW. Made for a late arrival

For the price of the ticket you get nothing. The plane had 1 bathroom in the back and when the flight attendant did service no one could use it. No announcement just was told to go back to my seat. Ridiculous and rude.

Our flight was changed from Madison to DC to Madison to Charlotte.

In-flight Wi-Fi didn’t work and the flight was 25 minutes late. The Embraer plane I was on was pretty old and the tray table was broken.

American Airlines no longer has Bischoff biscuits. This is intolerable.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Madison to Hilton Head Island

Information on your arrival and departure airports