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, $459 Round Trip

Prices starting at $459 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.

Fri, Aug 28 - Sun, Aug 30
MSN
Madison
HHH
Hilton Head Island
$459 Roundtrip, found 3 days ago
$459
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 28 from Madison to Hilton Head Island, returning Sun, Aug 30, priced at $459 found 3 days ago
Sun, May 24 - Fri, May 29
MSN
Madison
HHH
Hilton Head Island
$547 Roundtrip, found 11 hours ago
$547
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sun, May 24 from Madison to Hilton Head Island, returning Fri, May 29, priced at $547 found 11 hours ago
Fri, Aug 28 - Sun, Aug 30
MSN
Madison
HHH
Hilton Head Island
$549 Roundtrip, found 3 days ago
$549
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 28 from Madison to Hilton Head Island, returning Sun, Aug 30, priced at $549 found 3 days ago
Sun, May 24 - Thu, May 28
MSN
Madison
HHH
Hilton Head Island
$551 Roundtrip, found 5 days ago
$551
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, May 24 from Madison to Hilton Head Island, returning Thu, May 28, priced at $551 found 5 days ago
Sun, May 24 - Fri, May 29
MSN
Madison
HHH
Hilton Head Island
$552 Roundtrip, found 11 hours ago
$552
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sun, May 24 from Madison to Hilton Head Island, returning Fri, May 29, priced at $552 found 11 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
$134 nightly
The price is $148 total per night from Apr 20 to Apr 21
$148 total
Apr 20 - Apr 21
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! (1,010 reviews)
Breakfast was adequate typical Hampton Inn fare. Staff was neither good nor bad in the dining area. Parking was good. The reason this day did not write higher is because of excessive pot smoking in neighboring rooms. Stunk to high heaven no pun intended.

Reviewed on Apr 11, 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
$248 nightly
The price is $272 total per night from Apr 26 to Apr 27
$272 total
Apr 26 - Apr 27
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! (1,002 reviews)
Too many hidden charges.which was not informed at the time of booking

Reviewed on Apr 8, 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! (335 reviews)
So this is actually a vacation club that they try to get you to sit through a 45 minute sales. The room was good and it is a nice and quiet property. There is a couple things I did not like. First, check in starts at 4 pm and at 4:42 we received a call asking when we plan to check in, we were stuck ...

Reviewed on Apr 8, 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
$337 nightly
The price is $371 total per night from May 11 to May 12
$371 total
May 11 - May 12
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 ...
8.6/10 Excellent! (1,282 reviews)
Overall a good experience. Surprised to see service fee added to restaurant bills and no indication from server. Had I not thoroughly looked over the bill I would have excessively tipped.The staff should tell guests that there is 25% gratuity automatically added. Movie night cancelled due to lack ...

Reviewed on Apr 11, 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
$206 nightly
The price is $227 total per night from Apr 20 to Apr 21
$227 total
Apr 20 - Apr 21
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! (1,453 reviews)
Big full service hotel with lots of amenities and a great staff. Recently became a Hilton, was a Marriott property for many years. Shows its age in a few way, but renovations are underway…with some more investments to update the property it could be fantastic. Overall, solid value. Indoor pool and ...

Reviewed on Apr 12, 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
$244 nightly
The price is $268 total per night from Apr 20 to Apr 21
$268 total
Apr 20 - Apr 21
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 ...
8.8/10 Excellent! (1,145 reviews)
The room had a view but no actual balcony. The staff were amazing. The tiki bar had great food

Reviewed on Apr 10, 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 Palmetto Dunes ...
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
$94 nightly
The price is $103 total per night from Apr 20 to Apr 21
$103 total
Apr 20 - Apr 21
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 (1,002 reviews)
Ya'll over booked them and every reservation had to wait HOURS to get rooms.

Reviewed on Apr 10, 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 Apr 13 to Apr 14
$224 total
Apr 13 - Apr 14
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! (1,259 reviews)
this was my second time staying and it was better than the first time

Reviewed on Apr 12, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$140 nightly
The price is $154 total per night from May 10 to May 11
$154 total
May 10 - May 11
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 ...
8.2/10 Very Good! (26 reviews)
Really dislike the whole contactless thing

Reviewed on Apr 10, 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
$370 nightly
The price is $402 total per night from May 12 to May 13
$402 total
May 12 - May 13
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! (1,000 reviews)

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

Travelers say...
Internet reception very poor inside building. Fee for premium WiFi needed if you need internet inside your room. Grounds are natural and beautiful. Staff consistently friendly and helpful.

Reviewed on Apr 6, 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
$337 nightly
The price is $371 total per night from May 11 to May 12
$371 total
May 11 - May 12
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 ...
8.6/10 Excellent! (1,282 reviews)

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

Travelers say...
Overall a good experience. Surprised to see service fee added to restaurant bills and no indication from server. Had I not thoroughly looked over the bill I would have excessively tipped.The staff should tell guests that there is 25% gratuity automatically added. Movie night cancelled due to lack ...

Reviewed on Apr 11, 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 Palmetto Dunes Club and Coligny ...

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

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.