$284 Cheap Flights from Madison (MSN) to Hilton Head Island (HHH)
Popular airlines from Dane County Regional Airport (MSN) to Hilton Head Island Airport (HHH)
American AirlinesAmerican Airlines
DeltaDelta
Be in the knowGet alerts if flight prices drop or rise*
Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from Madison to Hilton Head Island (MSN-HHH)
Alternative airports near Hilton Head Island
Prices were available within the past 7 days. Prices and availability are subject to change.
Find the cheapest month to fly from Madison (MSN) to Hilton Head Island (HHH)
April is typically the cheapest month to flyApril is typically the cheapest month to fly
Book with confidence
Madison (MSN) to Hilton Head Island (HHH) at a glance
Experience a range of airlines offering flights from Madison (MSN) to Hilton Head Island (HHH) on this domestic short-haul route. Evaluate options from various full-service carriers to discover the itinerary that best aligns with your budget, schedule, and travel preferences while you explore the renowned attractions and neighborhoods of Hilton Head Island. Here, you’ll find essential details for flights departing from Dane County Regional Airport (MSN) to Hilton Head Island Airport (HHH).
- Fastest flight duration: around 3h 30m in-flight, plus roughly 2 hours layover with one stop
- Route distance: roughly 900 miles (1,450 km)
- Flights per week: around 7 departures on average
- Typical fares (one-way): economy tickets often range from $180–$390, depending on seasonality and how far ahead you book
Flights from Dane County Regional Airport (MSN) to Hilton Head Island Airport (HHH)
Based on the latest traveler preferences, here are the top airlines flying from Madison to Hilton Head Island, often selected for their one-stop services. Popular layover options include Charlotte-Douglas International Airport (CLT) with a typical 2-hour layover, and Philadelphia International Airport (PHL) with around a 50-minute layover. These choices allow you to balance price, overall travel time, and cabin class to create the ideal travel itinerary.
- American Airlines: This major airline provides comprehensive service with one-stop options. One-way ticket prices generally fall between $180 and $390. It dominates the route, handling around 96% of departures, with a flight duration of 3 hours and 30 minutes, and an overall travel time of about 5 hours and 30 minutes, including layover time.
Alternative routes from Madison (MSN) to Hilton Head Island (HHH)
- Madison to Savannah (MSN-SAV): Savannah - Hilton Head International Airport (SAV) is located approximately 31 miles from Hilton Head Island Airport (HHH). One-way economy prices on this route generally fall between $125 and $410, influenced by the time of year and when you book. This route is primarily served by one-stop flights with common layover points at O'Hare International Airport (ORD) and Charlotte-Douglas International Airport (CLT). Major airlines operating on this route include American Airlines and United, with first-class service also available.
- Madison to Charleston (MSN-CHS): Charleston International Airport (CHS) is about 60 miles distant from Hilton Head Island Airport (HHH). One-way economy fares for this journey typically range from $115 to $440, varying based on the season and how early you make your reservations. Flights on this route usually involve one-stop options, with popular connections at Charlotte-Douglas International Airport (CLT) and O'Hare International Airport (ORD). Leading carriers on this route include American Airlines and Delta, and first-class seating is offered as well.
How to find the best prices for flights from Madison (MSN) to Hilton Head Island (HHH)
Getting some of the best deals on flights from Madison to Hilton Head Island is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are typically available when booking 2 to 8 weeks in advance, which coincides with when most travelers make their reservations. Morning departures between 5 am and 12 pm tend to be more affordable and are also the most popular. Additionally, flying on Saturday not only offers lower prices but is also the most favored travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Hilton Head Island hotel and flight deals.
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at Hilton Head Island Airport from Dane County Regional Airport
Hilton Head Island welcomes travelers from Madison with a range of transport options based on price, convenience, and proximity. Here's how to reach Hilton Head Island efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Hilton Head Island, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
- Car rental: Renting a car from Hilton Head Island Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hilton Head Island Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
- Public transportation: From Hilton Head Island Airport, St Phillips Island Seaport, a seaport, is located about 6.4 miles from the airport, making it easily accessible for travelers.
Madison to Hilton Head Island Flights
The cheapest times to fly from Madison to Hilton Head Island
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Madison to Hilton Head Island are during the month of May. You can find some of the cheapest flights from Madison to Hilton Head Island with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Madison to Hilton Head Island
Sunday is one of the best days to book for cheap flights from Madison to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Madison to Hilton Head Island
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Madison to Hilton Head Island in 2026. You can also book with separate airlines for your outbound and return journeys, from $284 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Madison to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Madison to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Frequently Asked Questions
How much does a flight from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) cost?
You can find cheap one-way flights from $284 and cheap return flights $359 Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) with Expedia. One-way flights generally range between $196 and $638, and roundtrip flights usually range from $337 to $1256. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) ticket fares go up or down.
*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
The cheapest month to fly from MSN to HHH is May when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
Enter MSN to HHH and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
United is one of the cheapest airlines offering connecting flights from Dane County Regional (MSN) to Hilton Head Island, SC (HHH), with round-trip tickets starting from around $248 with a layover in O'Hare Intl. (ORD). This gives you a convenient way to reach your sunny destination. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
To find a cheap flight from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from MSN to HHH. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
A flight from MSN to HHH with a layover takes around 6 hours 30 minutes, with the route covering approximately 889 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
First class is available on flights from MSN to HHH. First class cabins are available on:
- American Airlines
- Delta Air Lines
- United Airlines
How do I earn miles on a Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) flight with Expedia?
It's easy to earn miles on a Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.
*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) at the last minute?
Typically, booking a last minute flight from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) flight and hotel package?
Securing a Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) Hilton Head Island Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH)?
If you booked your Madison, WI (MSN-Dane County Regional) to Hilton Head Island, SC (HHH) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.
Travel information
Origin airport | Dane County Regional Airport |
|---|---|
Destination airport | Hilton Head Island Airport |
Distance | 888 miles away |
Airlines serving | American Airlines, Delta |
Popular airline | American Airlines |
Roundtrip price | $359 |