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 $254 One Way, $289 Round Trip

Prices starting at $289 for return flights and $254 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 25 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Hilton Head Island, returning Sat, May 9, priced at $289 found 1 day ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$296 Roundtrip, found 12 hours ago
$296
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $296 found 12 hours ago
Sun, Apr 12 - Sat, Apr 18
MSN
Madison
HHH
Hilton Head Island
$301 Roundtrip, found 1 hour ago
$301
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Apr 12 from Madison to Hilton Head Island, returning Sat, Apr 18, priced at $301 found 1 hour ago
Sat, Apr 25 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Hilton Head Island, returning Sat, May 9, priced at $349 found 1 day ago
Sat, Apr 25 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$354 Roundtrip, found 1 day ago
$354
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Hilton Head Island, returning Sat, May 9, priced at $354 found 1 day 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
$110 nightly
The price is $121 total per night from Mar 22 to Mar 23
$121 total
Mar 22 - Mar 23
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! (1,011 reviews)
Pool was enjoyable and the parking was safe

Reviewed on Mar 9, 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
$230 nightly
The price is $252 total per night from Apr 5 to Apr 6
$252 total
Apr 5 - Apr 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 ...
8.4/10 Very Good! (1,006 reviews)
The staff had such positive energy and they were so helpful. The only thing that I would mention to other travelers is that there is a lot of walking, there are very long, narrow halls between rooms, so if you have issues walking, I would request a room on the first floor closest to the exits.

Reviewed on Mar 9, 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! (328 reviews)
Clean room and responsive customer services. I was not able to use my included 1 hr tennis court reservation because it wasn’t clearly mention that you have to pay equipment rental fee unless you bring your own. I was bit disappointed. It was overall good experience.

Reviewed on Jan 2, 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
$269 nightly
The price is $296 total per night from Mar 22 to Mar 23
$296 total
Mar 22 - Mar 23
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! (1,246 reviews)
Nice size rooms. Workout room was nicely equipped.

Reviewed on Mar 10, 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
$247 nightly
The price is $272 total per night from Mar 16 to Mar 17
$272 total
Mar 16 - Mar 17
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! (1,429 reviews)
Very nice property close to the beach.

Reviewed on Mar 9, 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
$215 nightly
The price is $236 total per night from Mar 22 to Mar 23
$236 total
Mar 22 - Mar 23
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! (1,076 reviews)
Beautiful

Reviewed on Mar 8, 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
$85 nightly
The price is $93 total per night from Mar 15 to Mar 16
$93 total
Mar 15 - Mar 16
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 ...
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
$132 nightly
The price is $142 total per night from Mar 12 to Mar 13
$142 total
Mar 12 - Mar 13
Total with taxes and fees
Stay at this 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 staff ...
9/10 Wonderful! (1,223 reviews)
Spotless Room, Excellent Breakfast

Reviewed on Mar 9, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$98 nightly
The price is $108 total per night from Mar 11 to Mar 12
$108 total
Mar 11 - Mar 12
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 ...
8/10 Very Good! (6 reviews)
Clean room. Great value!

Reviewed on Feb 27, 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
$395 nightly
The price is $429 total per night from Mar 22 to Mar 23
$429 total
Mar 22 - Mar 23
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...
Excellent, we had shower problems and they fix it immediately

Reviewed on Feb 23, 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
$269 nightly
The price is $296 total per night from Mar 22 to Mar 23
$296 total
Mar 22 - Mar 23
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! (1,246 reviews)

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

Travelers say...
Nice size rooms. Workout room was nicely equipped.

Reviewed on Mar 10, 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 ...
7.8/10 Good! (1,000 reviews)

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

Travelers say...
Dirty floor and bedding’s

Reviewed on Dec 8, 2025

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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.