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Hilton Head Island

$254+ Cheap flights from Madison to Hilton Head Island (MSN - HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HHH
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Madison to Hilton Head Island

Cheapest flights from Madison to Hilton Head Island
Explore the most affordable flight options available from Madison to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/108:10 am
MSN
-
HHH
1 stop5h 49m
American Airlines
Sat 2/144:31 pm
HHH
-
MSN
1 stop6h 27m
American Airlines
Deal found 1/26$279
This American Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MSN
-
HHH
2 stops10h 09m
American Airlines
Tue 6/95:54 pm
HHH
-
MSN
1 stop7h 04m
American Airlines
Deal found 1/26$304
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MSN
-
HHH
2 stops10h 09m
American Airlines
Sun 7/55:54 pm
HHH
-
MSN
1 stop7h 04m
American Airlines
Deal found 1/27$473
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:00 am
MSN
-
HHH
1 stop6h 22m
American Airlines
Fri 2/2011:03 am
HHH
-
MSN
1 stop6h 44m
American Airlines
Deal found 1/25$497
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:35 am
MSN
-
HHH
1 stop5h 34m
American Airlines
Mon 4/206:39 pm
HHH
-
MSN
1 stop6h 16m
American Airlines
Deal found 1/27$507

Find flight deals from Madison to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(American Airlines)

One-way from

$254
(American Airlines)

Popular in

December

Cheapest in

September
Provider with most accurate pricing for Madison Truax Field-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Hilton Head Island flights.
Search Deals
From Madison Truax Field to Hilton Head Island
Search Deals
One-way flight from Madison Truax Field to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($279 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($54 potential savings vs. average RT price).
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Madison to Hilton Head Island that are best for you.

Fly from

Madison

Fly to

Hilton Head Island

Route

Depart

Return

Price

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 2/10

8:10 am-2:59 pm

1 stop5h 49m

Hilton Head Island

Sat 2/14

4:31 pm-9:58 pm

1 stop6h 27m

$279

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Tue 6/2

6:00 am-5:09 pm

2 stops10h 09m

Hilton Head Island

Tue 6/9

11:40 am-7:38 pm

2 stops8h 58m

$310

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Sun 2/15

7:00 am-2:22 pm

1 stop6h 22m

Hilton Head Island

Fri 2/20

11:03 am-4:47 pm

1 stop6h 44m

$497

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 7/1

7:00 am-2:18 pm

1 stop6h 18m

Hilton Head Island

Sun 7/5

5:54 pm-11:58 pm

1 stop7h 04m

$498

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Thu 4/16

11:35 am-6:09 pm

1 stop5h 34m

Hilton Head Island

Mon 4/20

6:39 pm-11:55 pm

1 stop6h 16m

$507

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Wed 4/15

6:00 am-3:30 pm

2 stops8h 30m

Hilton Head Island

Tue 4/21

3:00 pm-9:16 pm

1 stop7h 16m

$535

MadisonHilton Head Island

MSN - HHH

MSNHHH

Madison Truax Field

Mon 3/23

7:00 am-2:22 pm

1 stop6h 22m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Compare providers for flights from Madison to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Hilton Head Island in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Madison to Hilton Head Island?

Currently, February is the cheapest month in which you can book a flight from Madison to Hilton Head Island (average of $84). Flying from Madison to Hilton Head Island in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated January 27, 2026.
Read through reviews of airlines operating flights from Madison to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,197 reviews

Entertainment

6.9

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Entertainment

6.9

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Madison to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Madison to Hilton Head Island?

    Airlines like American Airlines fly from Madison to Hilton Head Island in about 5h 49m. The time it takes to get you to your destination can typically vary by up to . There are 888 mi between Madison and Hilton Head Island.

  • What is the cheapest airline to fly from Madison to Hilton Head Island round-trip?

    According to our current data, American Airlines ($233), offers the cheapest pricing from Madison to Hilton Head Island. This flight start at 52% lower than the current average price 3 months from now.

  • Can I find deals for flights from Madison to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Madison to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Hilton Head Island.

  • Can I find deals for business class flights from Madison to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Madison to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, February is the cheapest month in which you can book a flight from Madison to Hilton Head Island (average of $84). Flying from Madison to Hilton Head Island in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Top airline flying from Madison to Hilton Head Island

Discover the top airline that operate flights from Madison to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$233Average$457FlexibilityNo cancel feeOn-time71%

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