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 $285 One Way, $323 Round Trip

Prices starting at $323 for return flights and $285 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.

Tue, Oct 6 - Fri, Oct 16
MSN
Madison
HHH
Hilton Head Island
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 6 from Madison to Hilton Head Island, returning Fri, Oct 16, priced at $323 found 3 days ago
Tue, Oct 6 - Fri, Oct 16
MSN
Madison
HHH
Hilton Head Island
$348 Roundtrip, found 3 days ago
$348
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 6 from Madison to Hilton Head Island, returning Fri, Oct 16, priced at $348 found 3 days ago
Tue, Oct 6 - Fri, Oct 16
MSN
Madison
HHH
Hilton Head Island
$402 Roundtrip, found 3 days ago
$402
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 6 from Madison to Hilton Head Island, returning Fri, Oct 16, priced at $402 found 3 days ago
Tue, Oct 6 - Fri, Oct 16
MSN
Madison
HHH
Hilton Head Island
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 6 from Madison to Hilton Head Island, returning Fri, Oct 16, priced at $415 found 3 days ago
Tue, Oct 6 - Fri, Oct 16
MSN
Madison
HHH
Hilton Head Island
$438 Roundtrip, found 3 days ago
$438
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 6 from Madison to Hilton Head Island, returning Fri, Oct 16, priced at $438 found 3 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
$120 nightly
The price is $132 total per night from Sep 27 to Sep 28
$132 total
Sep 27 - Sep 28
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
$257 nightly
The price is $282 total per night from Sep 28 to Sep 29
$282 total
Sep 28 - Sep 29
Total with taxes and fees
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 ...
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! (373 reviews)
"I absolutely did not like that this was a time share property and we were roped into sitting through a time share presentation. Also, the property charges a $53 resort fee upon arrival. I must have missed that somewhere, not sure. The resort is getting old, the fridge did not close all the way so ..."

Reviewed on Aug 31, 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
$250 nightly
The price is $275 total per night from Sep 9 to Sep 10
$275 total
Sep 9 - Sep 10
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
$288 nightly
The price is $317 total per night from Sep 14 to Sep 15
$317 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,474 reviews)
"This trip was one of the best vacations I have ever had! The resort was clean, well maintained, safe, relaxing. Do not skimp on the spa either!-the massage was so worth it! Beyond all of that your staff was some of the friendliest staff I have ever encountered! The food at the resort restaurants ..."

Reviewed on Sep 2, 2026

Sonesta Resort Hilton Head Island
Beach House Resort Hilton Head

Beach House Resort Hilton Head

4 out of 5
1 South Forest Beach Drive Hilton Head Island SC
$202 nightly
The price is $222 total per night from Sep 9 to Sep 10
$222 total
Sep 9 - Sep 10
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,474 reviews)
"Love the location very convenient, great restaurant the beach view was great the only problem was that our room was vacuum very well we could feel the sand on the floor ohter then that everything was good."

Reviewed on Sep 2, 2026

Beach House Resort Hilton Head
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 Beach and Shipyard 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 Sep 7 to Sep 8
$78 total
Sep 7 - Sep 8
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
$114 nightly
The price is $124 total per night from Oct 1 to Oct 2
$124 total
Oct 1 - Oct 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! (1,447 reviews)
"Very clean great location"

Reviewed on Sep 3, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$68 nightly
The price is $75 total per night from Sep 6 to Sep 7
$75 total
Sep 6 - Sep 7
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! (154 reviews)
"Great Stay! Very accommodating and clean, the staff was very nice and helpful with all my questions. I will definitely like to come again!"

Reviewed on Aug 30, 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
The price is $381 total per night from Oct 4 to Oct 5
$381 total
per night
Oct 4 - Oct 5
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
The price is $317 total per night from Sep 14 to Sep 15
$317 total
per night
Sep 14 - Sep 15
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,474 reviews)

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

Travelers say...
"This trip was one of the best vacations I have ever had! The resort was clean, well maintained, safe, relaxing. Do not skimp on the spa either!-the massage was so worth it! Beyond all of that your staff was some of the friendliest staff I have ever encountered! The food at the resort restaurants ..."

Reviewed on Sep 2, 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 Beach and Folly Field ...
7.8/10 Good! (1,000 reviews)

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

Travelers say...
"This is our second time staying at Hilton Head Island Beach & Tennis Resort. We love the proximity to the beach. An easy, few minute walk and you’re on the sand! The beach was perfect. Not too crowded and seceral lifeguards present. Multiple pools is a great option. The smaller pool was next to our ..."

Reviewed on Aug 9, 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

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.