Cheap flights from MSN to HHH (Dane County Regional to Hilton Head Island)

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Cheap Flights from MSN to HHH starting at $334 One Way, $437 Round Trip

Prices starting at $437 for return flights and $334 for one-way flights to Hilton Head Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 10 - Sat, Apr 17
MSN
Madison
HHH
Hilton Head Island
$437 Roundtrip, found 2 days ago
$437
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 10 from Madison to Hilton Head Island, returning Sat, Apr 17, priced at $437 found 2 days ago
Sat, Apr 10 - Sat, Apr 17
MSN
Madison
HHH
Hilton Head Island
$515 Roundtrip, found 2 days ago
$515
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 10 from Madison to Hilton Head Island, returning Sat, Apr 17, priced at $515 found 2 days ago
Sat, Apr 10 - Sat, Apr 17
MSN
Madison
HHH
Hilton Head Island
$527 Roundtrip, found 2 days ago
$527
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 10 from Madison to Hilton Head Island, returning Sat, Apr 17, priced at $527 found 2 days ago
Sat, Apr 10 - Sat, Apr 17
MSN
Madison
HHH
Hilton Head Island
$541 Roundtrip, found 2 days ago
$541
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 10 from Madison to Hilton Head Island, returning Sat, Apr 17, priced at $541 found 2 days ago
Sat, Apr 10 - Sat, Apr 17
MSN
Madison
HHH
Hilton Head Island
$547 Roundtrip, found 2 days ago
$547
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 10 from Madison to Hilton Head Island, returning Sat, Apr 17, priced at $547 found 2 days ago

Hotel Ideas near Hilton Head Island

Airport Hotels near Hilton Head Island

Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road Hilton Head Island SC
$100 nightly
The price is $110 total per night from Nov 29 to Nov 30
$110 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this golf hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hampton Inn Hilton Head
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
Get rates
The Westin Hilton Head Island Resort & Spa
Island Links Resort by Palmera

Island Links Resort by Palmera

3 out of 5
1 Coggins Point Road Hilton Head Island SC
Book a stay at this golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (389 reviews)
"This was one of the best places we have gone to for vacation. We will be back again!"

Reviewed on Oct 25, 2026

Get rates
Island Links Resort by Palmera
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

4.5 out of 5
1 Hotel Circle Hilton Head Island SC
$185 nightly
The price is $203 total per night from Nov 17 to Nov 18
$203 total
Nov 17 - Nov 18
Total with taxes and fees
Book a stay at this luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
Hilton Beachfront Resort & Spa Hilton Head Island
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$194 nightly
The price is $213 total per night from Nov 29 to Nov 30
$213 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
Sonesta Resort Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln Hilton Head Island SC
$112 nightly
The price is $121 total per night from Dec 1 to Dec 2
$121 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,524 reviews)
"Very clean rooms and excellent staff been staying there three years and great every time"

Reviewed on Oct 31, 2026

Palmera Inn and Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Head Island Hotels With Airport Transportation

Hilton Head Health - Weight Loss Resort and Health Spa

Hilton Head Health - Weight Loss Resort and Health Spa

4 out of 5
14 Valencia Road Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Plaza and Coligny Beach ...
Get rates
Hilton Head Health - Weight Loss Resort and Health Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Hilton Head Island Hotels

Red Roof Inn Hilton Head Island

Red Roof Inn Hilton Head Island

2 out of 5
5 Regency Pkwy Hilton Head Island SC
$71 nightly
The price is $78 total per night from Nov 3 to Nov 4
$78 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular ...
Red Roof Inn Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln Hilton Head Island SC
$112 nightly
The price is $121 total per night from Dec 1 to Dec 2
$121 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,524 reviews)
"Very clean rooms and excellent staff been staying there three years and great every time"

Reviewed on Oct 31, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$80 nightly
The price is $88 total per night from Nov 2 to Nov 3
$88 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (208 reviews)
"The property was still under renovations. It will probably be nice when complete."

Reviewed on Oct 29, 2026

Hotel Carolina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Hilton Head Island

Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane Hilton Head Island SC
$247 nightly
The price is $267 total per night from Nov 29 to Nov 30
$267 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
Omni Hilton Head Oceanfront Resort
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$194 nightly
The price is $213 total per night from Nov 29 to Nov 30
$213 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
Sonesta Resort Hilton Head Island
Hilton Head Island Beach & Tennis Resort

Hilton Head Island Beach & Tennis Resort

3.5 out of 5
40 Folly Field Rd Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Coligny Plaza and Coligny Beach ...
7.8/10 Good! (1,000 reviews)

Families like: Outdoor pools, kitchen, playground, on the beach

Travelers say...
"Not a place we would stay again. We stayed in a room that claimed it was a ocean view. That's a joke! The ocean was 3 blocks away and could only see it if we hung our heads over the balcony. We had to pay more for that view. I wouldn't suggest you stay there."

Reviewed on Oct 10, 2026

Get rates
Hilton Head Island Beach & Tennis Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MSN to HHH Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MSN Address & GPS
Address:
4000 International Lane
Madison WI, 53704-3120
United States
IATA Code:
MSN
Longitude:
-89.346497
Latitude:
43.136377
Time Zone:
America/Chicago
HHH Address & GPS
Address:
120 Beach City Road
Hilton Head SC, 29926
United States
IATA Code:
HHH
Longitude:
-80.697013
Latitude:
32.22263
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from MSN to Hilton Head Airport?
While you can't fly nonstop from Dane County Regional Airport (MSN) to Hilton Head Island Airport (HHH) at the moment, there are plenty of air carriers that operate on this route with just one stop. Why not see if the dates and times offered by American Airlines or United Airlines work with your travel plans? If they don't, take a look at Delta Air Lines.
What is the shortest flight from Dane County Regional Airport (MSN) to HHH?
The shortest flight time from Madison to Hilton Head Island is around 3 hours and 33 minutes. Order your favorite wine from the cabin crew, get stuck into your travel journal or get to know your neighbors — you'll have enough time on this medium-haul trip.
How many hours flight from Truax Field to Hilton Head Airport?
On average, flying from Truax Field to HHH takes 3 hours and 34 minutes. If your aim is to be as comfy as possible, contemplate upgrading your seat using miles or cash.
What airlines have the most flights from Truax Field to HHH?
Watch the planes take off and land, grab a quick meal, chat with a stranger ... Airport stopovers aren't all that bad! If you're traveling between Madison and Hilton Head Island, you won't find any direct flights. Get ready to make a stop somewhere.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.