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 $538 One Way, $756 Round Trip

Prices starting at $756 for return flights and $538 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, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$756 Roundtrip, found 5 days ago
$756
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $756 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$871 Roundtrip, found 5 days ago
$871
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $871 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$898 Roundtrip, found 5 days ago
$898
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $898 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$923 Roundtrip, found 5 days ago
$923
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $923 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$945 Roundtrip, found 5 days ago
$945
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $945 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$950 Roundtrip, found 5 days ago
$950
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $950 found 5 days ago
Sat, Dec 26 - Wed, Jan 6
MSN
Madison
HHH
Hilton Head Island
$994 Roundtrip, found 5 days ago
$994
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 26 from Madison to Hilton Head Island, returning Wed, Jan 6, priced at $994 found 5 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
$111 nightly
The price is $122 total per night from Nov 9 to Nov 10
$122 total
Nov 9 - Nov 10
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
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 ...
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! (1,663 reviews)
"Staff very professional and very willing to address any issue. Location perfect"

Reviewed on Oct 10, 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
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 ...
Palmera Inn and Suites
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 14 to Oct 15
$78 total
Oct 14 - Oct 15
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 ...
6.2/10 (1,000 reviews)
"No towels in the room and the sink was clogged"

Reviewed on Oct 5, 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
$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 ...
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 11 to Oct 12
$88 total
Oct 11 - Oct 12
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! (191 reviews)
"Nice location Fair price Great for solo travelers"

Reviewed on Oct 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
$264 nightly
The price is $285 total per night from Nov 1 to Nov 2
$285 total
Nov 1 - Nov 2
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...
"."

Reviewed on Oct 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
$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! (1,001 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.