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 $325 One Way, $378 Round Trip

Prices starting at $378 for return flights and $325 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.

Thu, Jun 11 - Mon, Jun 15
MSN
Madison
HHH
Hilton Head Island
$378 Roundtrip, found 2 hours ago
$378
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Madison to Hilton Head Island, returning Mon, Jun 15, priced at $378 found 2 hours ago
Sat, Jul 11 - Wed, Jul 15
MSN
Madison
HHH
Hilton Head Island
$392 Roundtrip, found 3 days ago
$392
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 11 from Madison to Hilton Head Island, returning Wed, Jul 15, priced at $392 found 3 days ago
Sat, Jul 11 - Wed, Jul 15
MSN
Madison
HHH
Hilton Head Island
$413 Roundtrip, found 3 days ago
$413
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 11 from Madison to Hilton Head Island, returning Wed, Jul 15, priced at $413 found 3 days ago
Sat, Jul 11 - Wed, Jul 15
MSN
Madison
HHH
Hilton Head Island
$416 Roundtrip, found 3 days ago
$416
Roundtrip
found 3 days ago
Select United flight, departing Sat, Jul 11 from Madison to Hilton Head Island, returning Wed, Jul 15, priced at $416 found 3 days ago
Thu, Jun 11 - Mon, Jun 15
MSN
Madison
HHH
Hilton Head Island
$431 Roundtrip, found 2 hours ago
$431
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Madison to Hilton Head Island, returning Mon, Jun 15, priced at $431 found 2 hours 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
$347 nightly
The price is $381 total per night from Jun 11 to Jun 12
$381 total
Jun 11 - Jun 12
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)
"The resort was beautiful but there were a ton of extra fees (Hilton Head Tourism fees) that added up!"

Reviewed on May 28, 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
$147 nightly
The price is $161 total per night from Jun 14 to Jun 15
$161 total
Jun 14 - Jun 15
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)
"I was very disappointed to hear that my husband‘s room did not have any hot water for his shower. He contacted somebody right away and was told that somebody would come in to fix it. He it was not. He should’ve been moved to a different room."

Reviewed on May 29, 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! (339 reviews)
"Perfect for families with young kids. They don’t provide cribs or pack and plays but the pool and splash pad was great for young kids."

Reviewed on May 24, 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
$323 nightly
The price is $355 total per night from Jun 7 to Jun 8
$355 total
Jun 7 - Jun 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! (1,515 reviews)
"Beachfront hotel… yes! As many amenities and updates as I expected from a Hilton… not quite. The bed was comfy, the majority of the staff was helpful and friendly, and the pool area was well stocked with towels and chairs. The bathroom was a little in need of updating and I really wanted that bathrobe ..."

Reviewed on May 29, 2026

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
$442 nightly
The price is $486 total per night from Jun 1 to Jun 2
$486 total
Jun 1 - Jun 2
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! (1,354 reviews)
"We travelled to HHI for the first time with 2 very young kids. We loved the hospitality of Sonesta- location, serene surroundings, access to beach, views, kids amenities and buffet breakfast, really good. We got a room upgrade and we just loved the view. We will return next time!"

Reviewed on May 29, 2026

Sonesta Resort Hilton Head Island
Holiday Inn Express Hilton Head Island by IHG

Holiday Inn Express Hilton Head Island by IHG

2.5 out of 5
10 Tanglewood Drive Hilton Head Island SC
$203 nightly
The price is $223 total per night from Jun 29 to Jun 30
$223 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and ...
8.4/10 Very Good! (552 reviews)
"Nice facility in a great location. Walking distance to beach and shops at Coligny. Staff was excellent, especially Sonia , who was extremely helpful and quite the character herself. I would definitely recommend."

Reviewed on May 30, 2026

Holiday Inn Express Hilton Head Island by IHG
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
$94 nightly
The price is $103 total per night from Jun 2 to Jun 3
$103 total
Jun 2 - Jun 3
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)
"I wish I can add pictures, room was disgusting dirty . Rolled flack hair is everywhere, old socks, previously left in a room… we couldn’t walk in the floors, was soooo dirty , I think outside was cleaner then inside. I would never recommend to stay there. I made a comment on google , property management ..."

Reviewed on May 27, 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
$174 nightly
The price is $189 total per night from May 31 to Jun 1
$189 total
May 31 - Jun 1
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! (1,343 reviews)
"Clean and the staff was great!"

Reviewed on May 29, 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 Jun 3 to Jun 4
$121 total
Jun 3 - Jun 4
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 ...
7.8/10 Good! (62 reviews)
"Clean room however the shower had a small clog so it wouldn’t drain"

Reviewed on May 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
$477 nightly
The price is $520 total per night from Jun 3 to Jun 4
$520 total
Jun 3 - Jun 4
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...
"Amazing relaxing stay with beautiful beach and pool ! Highly recommend! Great for families.."

Reviewed on May 27, 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
$442 nightly
The price is $486 total per night from Jun 1 to Jun 2
$486 total
Jun 1 - Jun 2
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! (1,354 reviews)

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

Travelers say...
"We travelled to HHI for the first time with 2 very young kids. We loved the hospitality of Sonesta- location, serene surroundings, access to beach, views, kids amenities and buffet breakfast, really good. We got a room upgrade and we just loved the view. We will return next time!"

Reviewed on May 29, 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.