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 $274 One Way, $319 Round Trip

Prices starting at $319 for return flights and $274 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, Nov 10 - Thu, Nov 19
MSN
Madison
HHH
Hilton Head Island
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 10 from Madison to Hilton Head Island, returning Thu, Nov 19, priced at $319 found 1 day ago
Sat, Oct 10 - Sat, Oct 24
MSN
Madison
HHH
Hilton Head Island
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select United flight, departing Sat, Oct 10 from Madison to Hilton Head Island, returning Sat, Oct 24, priced at $340 found 1 day ago
Wed, Nov 11 - Sat, Nov 21
MSN
Madison
HHH
Hilton Head Island
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 11 from Madison to Hilton Head Island, returning Sat, Nov 21, priced at $379 found 1 day ago
Tue, Nov 10 - Fri, Nov 20
MSN
Madison
HHH
Hilton Head Island
$399 Roundtrip, found 1 day ago
$399
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 10 from Madison to Hilton Head Island, returning Fri, Nov 20, priced at $399 found 1 day ago
Tue, Nov 10 - Thu, Nov 19
MSN
Madison
HHH
Hilton Head Island
$409 Roundtrip, found 1 day ago
$409
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 10 from Madison to Hilton Head Island, returning Thu, Nov 19, priced at $409 found 1 day 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
$257 nightly
The price is $282 total per night from Sep 7 to Sep 8
$282 total
Sep 7 - Sep 8
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
Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road Hilton Head Island SC
$126 nightly
The price is $139 total per night from Aug 23 to Aug 24
$139 total
Aug 23 - Aug 24
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)
"The bed spreads are scratchy, the room was musty and damp. The lobby is tiny, so there’s no refuge. I will not stay here again."

Reviewed on Aug 11, 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. ...
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

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$264 nightly
The price is $290 total per night from Sep 1 to Sep 2
$290 total
Sep 1 - Sep 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! (1,453 reviews)
"We came with our 1 year old and it was a perfect vacation! We wanted a hotel where we didn’t have to leave for everything and this was the perfect spot! Delicious and varied food options, amazing staff, great beach access and family friendly pool. They came everyday and refreshed our room and we ..."

Reviewed on Aug 14, 2026

Sonesta Resort 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
$250 nightly
The price is $275 total per night from Aug 23 to Aug 24
$275 total
Aug 23 - Aug 24
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! (1,559 reviews)
"The water area to wash your feet after the beach never worked."

Reviewed on Aug 14, 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
$220 nightly
The price is $242 total per night from Aug 23 to Aug 24
$242 total
Aug 23 - Aug 24
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 ...
8.6/10 Excellent! (1,429 reviews)
"The fact that there was no hot water for the three days we were there And we had to request multiple times for them to clean our room! Also, the TV didn’t work"

Reviewed on Aug 14, 2026

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
Book a stay at this beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Coligny Plaza ...
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
$76 nightly
The price is $83 total per night from Sep 6 to Sep 7
$83 total
Sep 6 - Sep 7
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 (1,000 reviews)
"Pool closed despite listed as an amenity. AC unit covered with what appeared to be black mold."

Reviewed on Aug 11, 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
$120 nightly
The price is $129 total per night from Sep 1 to Sep 2
$129 total
Sep 1 - Sep 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! (1,421 reviews)
"Room and breakfast area were clean and the staff is nice."

Reviewed on Aug 13, 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 Aug 18 to Aug 19
$121 total
Aug 18 - Aug 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
$352 nightly
The price is $381 total per night from Sep 7 to Sep 8
$381 total
Sep 7 - Sep 8
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
$264 nightly
The price is $290 total per night from Sep 1 to Sep 2
$290 total
Sep 1 - Sep 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! (1,453 reviews)

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

Travelers say...
"We came with our 1 year old and it was a perfect vacation! We wanted a hotel where we didn’t have to leave for everything and this was the perfect spot! Delicious and varied food options, amazing staff, great beach access and family friendly pool. They came everyday and refreshed our room and we ..."

Reviewed on Aug 14, 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...
"This is our second time staying at Hilton Head Island Beach & Tennis Resort. We love the proximity to the beach. An easy, few minute walk and you’re on the sand! The beach was perfect. Not too crowded and seceral lifeguards present. Multiple pools is a great option. The smaller pool was next to our ..."

Reviewed on Aug 9, 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.