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 $269 One Way, $339 Round Trip

Prices starting at $339 for return flights and $269 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, Jul 31 - Thu, Aug 6
MSN
Madison
HHH
Hilton Head Island
$339 Roundtrip, found 7 hours ago
$339
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Madison to Hilton Head Island, returning Thu, Aug 6, priced at $339 found 7 hours ago
Fri, Jul 31 - Thu, Aug 6
MSN
Madison
HHH
Hilton Head Island
$399 Roundtrip, found 7 hours ago
$399
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Madison to Hilton Head Island, returning Thu, Aug 6, priced at $399 found 7 hours ago
Fri, Jul 31 - Thu, Aug 6
MSN
Madison
HHH
Hilton Head Island
$429 Roundtrip, found 7 hours ago
$429
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Madison to Hilton Head Island, returning Thu, Aug 6, priced at $429 found 7 hours ago
Fri, Jul 31 - Thu, Aug 6
MSN
Madison
HHH
Hilton Head Island
$459 Roundtrip, found 7 hours ago
$459
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Madison to Hilton Head Island, returning Thu, Aug 6, priced at $459 found 7 hours ago
Fri, Jul 31 - Thu, Aug 6
MSN
Madison
HHH
Hilton Head Island
$489 Roundtrip, found 7 hours ago
$489
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Madison to Hilton Head Island, returning Thu, Aug 6, priced at $489 found 7 hours 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
$139 nightly
The price is $152 total per night from Jul 12 to Jul 13
$152 total
Jul 12 - Jul 13
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)
"Great breakfast"

Reviewed on Jun 26, 2026

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
$287 nightly
The price is $316 total per night from Jul 5 to Jul 6
$316 total
Jul 5 - Jul 6
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! (1,002 reviews)
"Our oceanfront room and poolside rental chairs"

Reviewed on Jun 26, 2026

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
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! (346 reviews)
"Pretty comfy beds with TV in all rooms. Kitchen well equipped for short stay. Overall great value for money with large multiple pools that kid’s thoroughly enjoyed."

Reviewed on Jun 23, 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

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$388 nightly
The price is $427 total per night from Jul 7 to Jul 8
$427 total
Jul 7 - Jul 8
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! (1,374 reviews)
"This is the second time staying at Sonesta and I strongly recomand the resort."

Reviewed on Jun 26, 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
$316 nightly
The price is $347 total per night from Jul 6 to Jul 7
$347 total
Jul 6 - Jul 7
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! (1,563 reviews)
"Rooms were spacious and clean. They helped to accommodate my handicapped father, provided extra equipment which helped make his stay more comfortable."

Reviewed on Jun 26, 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
$258 nightly
The price is $284 total per night from Jul 6 to Jul 7
$284 total
Jul 6 - Jul 7
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 ...
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 ...
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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
$89 nightly
The price is $98 total per night from Jun 30 to Jul 1
$98 total
Jun 30 - Jul 1
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)
"We were here for business. The property was in a great central location. We would stay here again."

Reviewed on Jun 25, 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
$206 nightly
The price is $224 total per night from Jul 12 to Jul 13
$224 total
Jul 12 - Jul 13
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! (1,378 reviews)
"Cleanliness and nice breakfast. Easy to check in and fast to check out. Love the big ref with dishwasher, stove and needed Utensils and pots for cooking"

Reviewed on Jun 26, 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 Jul 13 to Jul 14
$121 total
Jul 13 - Jul 14
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! (76 reviews)
"The cashier lady was very kind and helpful. The TV wasn't working, and she went to the room and fixed it. The room was very clean. The smoke detector was detached from the wall. The pool floor looked dirty or stained."

Reviewed on Jun 25, 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
$497 nightly
The price is $541 total per night from Jul 6 to Jul 7
$541 total
Jul 6 - Jul 7
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...
"Property was nice and food was just okay. The only problem we had during our stay was the noise level. The walls felt like they were made out of paper - could hear our neighbors all night especially doors opening and shutting. The worst part was there was water and mold damage staff on site repairing ..."

Reviewed on Jun 26, 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
$388 nightly
The price is $427 total per night from Jul 7 to Jul 8
$427 total
Jul 7 - Jul 8
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! (1,374 reviews)

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

Travelers say...
"This is the second time staying at Sonesta and I strongly recomand the resort."

Reviewed on Jun 26, 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! (1,001 reviews)

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

Travelers say...
"We loved everything about our stay the view was Amazing!! From our room to the beach was less than 1/4 of a mile walk! Our room was spotlessly clean & comfortable!! Our second year here & we were still in love!!"

Reviewed on Jun 26, 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.