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 $390 One Way, $645 Round Trip

Prices starting at $645 for return flights and $390 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.

Wed, Mar 17 - Sat, Mar 20
MSN
Madison
HHH
Hilton Head Island
$645 Roundtrip, found 2 days ago
$645
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 17 from Madison to Hilton Head Island, returning Sat, Mar 20, priced at $645 found 2 days ago
Wed, Mar 17 - Sat, Mar 20
MSN
Madison
HHH
Hilton Head Island
$665 Roundtrip, found 2 days ago
$665
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 17 from Madison to Hilton Head Island, returning Sat, Mar 20, priced at $665 found 2 days ago
Wed, Mar 17 - Sat, Mar 20
MSN
Madison
HHH
Hilton Head Island
$734 Roundtrip, found 2 days ago
$734
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 17 from Madison to Hilton Head Island, returning Sat, Mar 20, priced at $734 found 2 days ago
Wed, Mar 17 - Sat, Mar 20
MSN
Madison
HHH
Hilton Head Island
$763 Roundtrip, found 2 days ago
$763
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 17 from Madison to Hilton Head Island, returning Sat, Mar 20, priced at $763 found 2 days ago
Wed, Mar 17 - Sat, Mar 20
MSN
Madison
HHH
Hilton Head Island
$787 Roundtrip, found 2 days ago
$787
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 17 from Madison to Hilton Head Island, returning Sat, Mar 20, priced at $787 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
$97 nightly
The price is $107 total per night from Dec 5 to Dec 6
$107 total
Dec 5 - Dec 6
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. ...
8.4/10 Very Good! (1,002 reviews)
"Hotel was clean and staff was friendly. Rooms were comfortable but bathrooms were small especially the bathtub. Great proximity to the beaches. Folly Field beach being the closest. Just a couple blocks away. Pool area looks inviting as well as the breakfast area. I only had a short stay so I wasn't ..."

Reviewed on Nov 13, 2026

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
$160 nightly
The price is $176 total per night from Nov 24 to Nov 25
$176 total
Nov 24 - Nov 25
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 ...
8.8/10 Excellent! (1,576 reviews)
"Rooms were nice, views were nice, noise was such that I moved rooms. Still paper thin walls and loud, screaming people outside. Not the place to rest and relax. Could hear every sound and conversation in the next room and from above. Staff in lobby coffee shop very rude."

Reviewed on Nov 11, 2026

Sonesta Resort Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln Hilton Head Island SC
$102 nightly
The price is $110 total per night from Dec 1 to Dec 2
$110 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 ...
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 17 to Nov 18
$78 total
Nov 17 - Nov 18
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
$102 nightly
The price is $110 total per night from Dec 1 to Dec 2
$110 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 ...
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 15 to Nov 16
$88 total
Nov 15 - Nov 16
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 ...
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
$256 nightly
The price is $276 total per night from Nov 15 to Nov 16
$276 total
Nov 15 - Nov 16
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. ...
9/10 Wonderful! (1,001 reviews)

Families like: Outdoor pools, kids club, kitchenette, playground

Travelers say...
"Great access to beach, easy self parking, very comfortable bed and room. Excellent restaurant. Great pools and amenities. Spa was small. Beautiful well upkept grounds. Kind staff"

Reviewed on Nov 11, 2026

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 ...
8.8/10 Excellent! (1,576 reviews)

Families like: Outdoor pools, kids club, on the beach, bicycle rentals

Travelers say...
"Rooms were nice, views were nice, noise was such that I moved rooms. Still paper thin walls and loud, screaming people outside. Not the place to rest and relax. Could hear every sound and conversation in the next room and from above. Staff in lobby coffee shop very rude."

Reviewed on Nov 11, 2026

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

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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.