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, $605 Round Trip

Prices starting at $605 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.

Fri, Oct 30 - Mon, Nov 2
MSN
Madison
HHH
Hilton Head Island
$605 Roundtrip, found 1 day ago
$605
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 30 from Madison to Hilton Head Island, returning Mon, Nov 2, priced at $605 found 1 day ago
Fri, Oct 30 - Mon, Nov 2
MSN
Madison
HHH
Hilton Head Island
$608 Roundtrip, found 1 day ago
$608
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 30 from Madison to Hilton Head Island, returning Mon, Nov 2, priced at $608 found 1 day ago
Fri, Oct 30 - Mon, Nov 2
MSN
Madison
HHH
Hilton Head Island
$667 Roundtrip, found 1 day ago
$667
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 30 from Madison to Hilton Head Island, returning Mon, Nov 2, priced at $667 found 1 day ago
Fri, Oct 30 - Mon, Nov 2
MSN
Madison
HHH
Hilton Head Island
$687 Roundtrip, found 1 day ago
$687
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 30 from Madison to Hilton Head Island, returning Mon, Nov 2, priced at $687 found 1 day ago
Fri, Oct 30 - Mon, Nov 2
MSN
Madison
HHH
Hilton Head Island
$694 Roundtrip, found 1 day ago
$694
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 30 from Madison to Hilton Head Island, returning Mon, Nov 2, priced at $694 found 1 day 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
$104 nightly
The price is $114 total per night from Nov 15 to Nov 16
$114 total
Nov 15 - Nov 16
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! (1,000 reviews)
"This Property is old and run down. Not up to Hampton standards."

Reviewed on Oct 15, 2026

Hampton Inn Hilton Head
Backyard pickleball. Private Pool. Large family home! Custom Outdoor kitchen.

Backyard pickleball. Private Pool. Large family home! Custom Outdoor kitchen.

Hilton Head Island SC
Stay at this vacation home in Hilton Head Island. Enjoy private pools, laundry facilities, and patios. Popular attractions Mitchelville Freedom Park and Fort ...
10/10 Exceptional! (3 reviews)
"Back yard was great hit of the party, love the house"

Reviewed on Aug 28, 2026

Get rates
Backyard pickleball. Private Pool. Large family home! Custom Outdoor kitchen.
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
$213 nightly
The price is $234 total per night from Nov 1 to Nov 2
$234 total
Nov 1 - Nov 2
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 ...
8.6/10 Excellent! (1,000 reviews)
"I like the guest services and the friendliness of the staff. Everyone was really courteous and helpful."

Reviewed on Oct 13, 2026

The Westin Hilton Head Island Resort & 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.

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
$209 nightly
The price is $230 total per night from Oct 30 to Oct 31
$230 total
Oct 30 - Oct 31
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! (1,676 reviews)
"We arrived at night during the rain. When we woke up we realized we had the worst resort view at the hotel. The balcony was over roof of the building next door that had a constant loud ventalation system running that you could hear in the room. They moved us four flights up right above the first ..."

Reviewed on Oct 15, 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
$210 nightly
The price is $231 total per night from Nov 1 to Nov 2
$231 total
Nov 1 - Nov 2
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 ...
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
$123 nightly
The price is $135 total per night from Nov 15 to Nov 16
$135 total
Nov 15 - Nov 16
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 ...
8.2/10 Very Good! (849 reviews)
"Clean room. Gorgeous property and beautifully landscaped. A very clean park is next door. We were able to see 2 alligators in the water(very cool experience). Short walk to beaches and Coligny Park are with shopping and resturants."

Reviewed on Oct 14, 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 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 Oct 18 to Oct 19
$78 total
Oct 18 - Oct 19
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
$124 nightly
The price is $134 total per night from Nov 1 to Nov 2
$134 total
Nov 1 - Nov 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! (1,511 reviews)
"Well worth staying at this hotel."

Reviewed on Oct 15, 2026

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 Oct 18 to Oct 19
$88 total
Oct 18 - Oct 19
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. ...
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
$210 nightly
The price is $231 total per night from Nov 1 to Nov 2
$231 total
Nov 1 - Nov 2
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 ...
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...
"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

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.