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 $264 One Way, $309 Round Trip

Prices starting at $309 for return flights and $264 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, Sep 26 - Tue, Oct 6
MSN
Madison
HHH
Hilton Head Island
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Madison to Hilton Head Island, returning Tue, Oct 6, priced at $309 found 2 days ago
Sat, Sep 26 - Tue, Oct 6
MSN
Madison
HHH
Hilton Head Island
$324 Roundtrip, found 2 days ago
$324
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Madison to Hilton Head Island, returning Tue, Oct 6, priced at $324 found 2 days ago
Sat, Sep 26 - Tue, Oct 6
MSN
Madison
HHH
Hilton Head Island
$387 Roundtrip, found 2 days ago
$387
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Madison to Hilton Head Island, returning Tue, Oct 6, priced at $387 found 2 days ago
Thu, Sep 24 - Sat, Oct 3
MSN
Madison
HHH
Hilton Head Island
$398 Roundtrip, found 5 days ago
$398
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Sep 24 from Madison to Hilton Head Island, returning Sat, Oct 3, priced at $398 found 5 days ago
Sat, Sep 26 - Tue, Oct 6
MSN
Madison
HHH
Hilton Head Island
$399 Roundtrip, found 2 days ago
$399
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Madison to Hilton Head Island, returning Tue, Oct 6, priced at $399 found 2 days ago

Hotel Ideas near Hilton Head Island

Airport Hotels near Hilton Head Island

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
$330 nightly
The price is $363 total per night from Jul 5 to Jul 6
$363 total
Jul 5 - Jul 6
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 ...
8.4/10 Very Good! (1,020 reviews)
"Rooms were comfy and housekeeping made sure we had everything. The room could use a little updating . We also had trouble controlling the room temperature. It was 2-3 degrees colder that we prefer."

Reviewed on Jun 12, 2026

The Westin Hilton Head Island Resort & Spa
Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road Hilton Head Island SC
$141 nightly
The price is $155 total per night from Jun 21 to Jun 22
$155 total
Jun 21 - Jun 22
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! (1,006 reviews)
"I had to wipe down everything with Clorox wipes, the refrigerator was not working, I called the desk Downstairs the Friday, we got there. maintenance check the refrigerator and it was not working, he called us and said they are no more refrigerators, so my all my food that I cooked and bought dome ..."

Reviewed on Jun 12, 2026

Hampton Inn Hilton Head
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! (341 reviews)
"Very nice property. Room was clean and friendly staff."

Reviewed on Jun 12, 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
$332 nightly
The price is $366 total per night from Jul 7 to Jul 8
$366 total
Jul 7 - Jul 8
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 ...
8.4/10 Very Good! (1,545 reviews)
"Very friendly staff."

Reviewed on Jun 10, 2026

Hilton Beachfront Resort & Spa 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
$297 nightly
The price is $326 total per night from Jul 1 to Jul 2
$326 total
Jul 1 - Jul 2
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 ...
8.8/10 Excellent! (1,274 reviews)
"The staff was EXCELLENT very friendly, very helpful. The hallway and elevators smelled strongly of mildew. It gave me a cough and detracted from my experience. The food was mostly deep fried and not to my liking. My room was clean. The main areas were clean. Housekeeping was good. The main desk staff ..."

Reviewed on Jun 12, 2026

Beach House Resort Hilton Head
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$341 nightly
The price is $375 total per night from Jun 21 to Jun 22
$375 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this beach hotel 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! (1,384 reviews)
"We had such a wonderful stay at Sonesta Resort Hilton Head Island! We’ve been coming to Hilton Head for over 20 years. We’ve stayed all over the island but really love Sonesta.The property itself is absolutely beautiful and so well maintained. From the gorgeous grounds to the spa-like adult pool ..."

Reviewed on Jun 12, 2026

Sonesta Resort Hilton Head Island
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 Coligny Plaza ...
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
$89 nightly
The price is $98 total per night from Jun 16 to Jun 17
$98 total
Jun 16 - Jun 17
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,005 reviews)
"Clean the room"

Reviewed on Jun 7, 2026

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
$195 nightly
The price is $212 total per night from Jun 14 to Jun 15
$212 total
Jun 14 - Jun 15
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! (1,372 reviews)
"Nice convenient property. Lovely room."

Reviewed on Jun 12, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$123 nightly
The price is $135 total per night from Jun 16 to Jun 17
$135 total
Jun 16 - Jun 17
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! (71 reviews)
"Had an awesome stay! The room was clean and the bed was nice and comfy. You could tell the sheets were softer than average hotel sheets. The pool was clean and they had towels by the pool. Loved the contactless check in, made it quick and easy especially since we got there late."

Reviewed on Jun 9, 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
$482 nightly
The price is $524 total per night from Jul 6 to Jul 7
$524 total
Jul 6 - Jul 7
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! (1,003 reviews)

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

Travelers say...
"It was nice but you can do better"

Reviewed on Jun 10, 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
$341 nightly
The price is $375 total per night from Jun 21 to Jun 22
$375 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this beach hotel 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! (1,384 reviews)

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

Travelers say...
"We had such a wonderful stay at Sonesta Resort Hilton Head Island! We’ve been coming to Hilton Head for over 20 years. We’ve stayed all over the island but really love Sonesta.The property itself is absolutely beautiful and so well maintained. From the gorgeous grounds to the spa-like adult pool ..."

Reviewed on Jun 12, 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 Singleton Beach and Shelter Cove ...
7.8/10 Good! (1,002 reviews)

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

Travelers say...
"everything was nice. only negative was the front desk lady seemed annoyed that I was asking questions about things on the resort, like renting pickleball paddles or bike rentals."

Reviewed on Jun 6, 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

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.