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 $281 One Way, $487 Round Trip

Prices starting at $487 for return flights and $281 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, Jul 14 - Sat, Jul 18
MSN
Madison
HHH
Hilton Head Island
$487 Roundtrip, found 2 days ago
$487
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 14 from Madison to Hilton Head Island, returning Sat, Jul 18, priced at $487 found 2 days ago
Sun, Jul 12 - Thu, Jul 16
MSN
Madison
HHH
Hilton Head Island
$549 Roundtrip, found 6 days ago
$549
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Jul 12 from Madison to Hilton Head Island, returning Thu, Jul 16, priced at $549 found 6 days ago
Sun, Jul 12 - Thu, Jul 16
MSN
Madison
HHH
Hilton Head Island
$565 Roundtrip, found 6 days ago
$565
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Jul 12 from Madison to Hilton Head Island, returning Thu, Jul 16, priced at $565 found 6 days ago
Wed, Jul 15 - Sat, Jul 18
MSN
Madison
HHH
Hilton Head Island
$578 Roundtrip, found 2 days ago
$578
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jul 15 from Madison to Hilton Head Island, returning Sat, Jul 18, priced at $578 found 2 days ago
Sun, Jul 12 - Thu, Jul 16
MSN
Madison
HHH
Hilton Head Island
$580 Roundtrip, found 6 days ago
$580
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Jul 12 from Madison to Hilton Head Island, returning Thu, Jul 16, priced at $580 found 6 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
$360 nightly
The price is $396 total per night from May 26 to May 27
$396 total
May 26 - May 27
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! (1,003 reviews)
"Room and all facilities were clean! Made vacation great!"

Reviewed on May 21, 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
$139 nightly
The price is $152 total per night from May 31 to Jun 1
$152 total
May 31 - Jun 1
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! (1,003 reviews)
"Great place to stay on the island."

Reviewed on May 21, 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! (338 reviews)
"Property was dirty. Bottles and trash on roads. Tub had a broken drain plug that didn’t stop the water so had to leave water running while bathing kiddo. Downstairs people smoked cigs and weed multiple times called 3 times and all they did was give them a curtesy call. This continued over the 3 days ..."

Reviewed on May 16, 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
$297 nightly
The price is $327 total per night from May 28 to May 29
$327 total
May 28 - May 29
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! (1,502 reviews)
"The staff members were exceptional, the food was good and the room was clean. Beach access was a huge plus and I had everything I needed."

Reviewed on May 19, 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
$298 nightly
The price is $328 total per night from May 28 to May 29
$328 total
May 28 - May 29
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! (1,238 reviews)
"Great place to spend time. Beach right there all kinds of great food at your request. Bike rentals near. Everything you need to enjoy your time is close. Staff was always so pleasant and helpful. I will return"

Reviewed on May 21, 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
$392 nightly
The price is $431 total per night from May 25 to May 26
$431 total
May 25 - May 26
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! (1,338 reviews)
"Got double charge on rooms and restaurant and had to go through the time to get that fixed bit other then that it was great"

Reviewed on May 20, 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 Palmetto Dunes ...
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
$85 nightly
The price is $93 total per night from May 25 to May 26
$93 total
May 25 - May 26
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 (1,001 reviews)
"No laundry's service, parking okay, room little smelly"

Reviewed on May 17, 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
$160 nightly
The price is $174 total per night from Jun 1 to Jun 2
$174 total
Jun 1 - Jun 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! (1,326 reviews)
"Hot tub was broken. No room service and no extra pillows. Breakfast was good. Room was nice. Great location to Coligny beach."

Reviewed on May 21, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$110 nightly
The price is $121 total per night from May 25 to May 26
$121 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and ...
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
$472 nightly
The price is $513 total per night from May 25 to May 26
$513 total
May 25 - May 26
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! (1,002 reviews)

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

Travelers say...
"Wonderful property and staff. Will return!"

Reviewed on May 21, 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
$392 nightly
The price is $431 total per night from May 25 to May 26
$431 total
May 25 - May 26
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! (1,338 reviews)

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

Travelers say...
"Got double charge on rooms and restaurant and had to go through the time to get that fixed bit other then that it was great"

Reviewed on May 20, 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 Shelter Cove Harbour and Palmetto ...
7.8/10 Good! (1,000 reviews)

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

Travelers say...
"Everything was great just wifi wasn't good."

Reviewed on May 5, 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.