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 $242 One Way, $477 Round Trip

Prices starting at $477 for return flights and $242 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, Apr 11 - Fri, Apr 17
MSN
Madison
HHH
Hilton Head Island
$477 Roundtrip, found 3 days ago
$477
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 11 from Madison to Hilton Head Island, returning Fri, Apr 17, priced at $477 found 3 days ago
Sat, Apr 11 - Sat, Apr 18
MSN
Madison
HHH
Hilton Head Island
$490 Roundtrip, found 3 days ago
$490
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 11 from Madison to Hilton Head Island, returning Sat, Apr 18, priced at $490 found 3 days ago
Sat, Apr 11 - Sat, Apr 18
MSN
Madison
HHH
Hilton Head Island
$526 Roundtrip, found 3 days ago
$526
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 11 from Madison to Hilton Head Island, returning Sat, Apr 18, priced at $526 found 3 days ago
Sat, Apr 11 - Fri, Apr 17
MSN
Madison
HHH
Hilton Head Island
$547 Roundtrip, found 3 days ago
$547
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 11 from Madison to Hilton Head Island, returning Fri, Apr 17, priced at $547 found 3 days ago
Sat, Apr 11 - Fri, Apr 17
MSN
Madison
HHH
Hilton Head Island
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 11 from Madison to Hilton Head Island, returning Fri, Apr 17, priced at $555 found 3 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
$100 nightly
The price is $110 total per night from Oct 19 to Oct 20
$110 total
Oct 19 - Oct 20
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! (1,007 reviews)
"Decent hotel"

Reviewed on Sep 15, 2025

Hampton Inn Hilton Head
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
$230 nightly
The price is $252 total per night from Oct 19 to Oct 20
$252 total
Oct 19 - Oct 20
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! (1,006 reviews)
"It was nice and quiet, but felt a little isolated."

Reviewed on Sep 10, 2025

The Westin Hilton Head Island Resort & Spa
Island Links Resort by Palmera

Island Links Resort by Palmera

3 out of 5
1 Coggins Point Road, Hilton Head Island, SC
Stay at this 3-star golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (319 reviews)
"Other than requiring 45 min of time share harassment, this place is nice and great option when traveling w children"

Reviewed on Aug 27, 2025

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
$187 nightly
The price is $206 total per night from Oct 6 to Oct 7
$206 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this 4.5-star luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in ...
8.4/10 Very Good! (1,306 reviews)
Great time on the beach
"The staff was very nice. My grandson said "They are taking such good care of us" ."

Reviewed on Sep 15, 2025

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
$204 nightly
The price is $224 total per night from Sep 28 to Sep 29
$224 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this 4-star 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 ...
8.4/10 Very Good! (1,052 reviews)
"My favorite place to stay when visiting Hilton Head Island?"

Reviewed on Sep 14, 2025

Sonesta Resort 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
$186 nightly
The price is $205 total per night from Oct 8 to Oct 9
$205 total
Oct 8 - Oct 9
Total with taxes and fees
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the bar in our ...
8.6/10 Excellent! (858 reviews)
"The staff"

Reviewed on Sep 16, 2025

Beach House Resort Hilton Head
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
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Coligny Theater ...
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, Us 278, 30 Miles From I-95, Hilton Head Island, SC
$66 nightly
The price is $72 total per night from Oct 19 to Oct 20
$72 total
Oct 19 - Oct 20
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 ...
6.2/10 (1,004 reviews)
"Little humid."

Reviewed on Sep 10, 2025

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
$144 nightly
The price is $159 total per night from Oct 1 to Oct 2
$159 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this 3-star hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,142 reviews)
"Really nice mid range hotel, very convenient location in the middle of the Island, we had two queen size beds, a kitchenette and a bathroom. Breakfast is included, clean place, again, the room is was really nice. I would for sure stay there again!"

Reviewed on Sep 16, 2025

Palmera Inn and Suites
Hotel Carolina, a Days Inn by Wyndham

Hotel Carolina, a Days Inn by Wyndham

2 out of 5
9 Marina Side Drive, Hilton Head Island, SC
$76 nightly
The price is $83 total per night from Sep 21 to Sep 22
$83 total
Sep 21 - Sep 22
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 ...
6.6/10 (1,004 reviews)
"This hotel was great! Breakfast was fantastic, and the employees were very friendly. The downside was that there’s no parking lot, but there is a parking deck about a block away that costs around 20+ euros per day. Other than that, everything was good. It would be even better if they provided more ..."

Reviewed on Sep 6, 2025

Hotel Carolina, a Days Inn by Wyndham
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
$304 nightly
The price is $330 total per night from Oct 19 to Oct 20
$330 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this 4-star 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. ...
8.8/10 Excellent! (1,012 reviews)

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

Travelers say...
"Excellent food"

Reviewed on Sep 15, 2025

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
$204 nightly
The price is $224 total per night from Sep 28 to Sep 29
$224 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this 4-star 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 ...
8.4/10 Very Good! (1,052 reviews)

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

Travelers say...
"My favorite place to stay when visiting Hilton Head Island?"

Reviewed on Sep 14, 2025

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
Stay at this 3.5-star beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Coligny Beach and Folly Field ...
7.6/10 Good! (1,000 reviews)

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

Travelers say...
"We had a grest place to stay for our first time to hilton head. The pool was great and the distance to ocean was awesome. I would go back."

Reviewed on Aug 10, 2025

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.