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 $263 One Way, $329 Round Trip

Prices starting at $329 for return flights and $263 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.

Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$329 Roundtrip, found 1 hour ago
$329
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $329 found 1 hour ago
Sat, Jun 13 - Wed, Jun 17
MSN
Madison
HHH
Hilton Head Island
$374 Roundtrip, found 6 days ago
$374
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jun 13 from Madison to Hilton Head Island, returning Wed, Jun 17, priced at $374 found 6 days ago
Sat, Apr 25 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$374 Roundtrip, found 12 hours ago
$374
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Hilton Head Island, returning Sat, May 9, priced at $374 found 12 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$393 Roundtrip, found 1 hour ago
$393
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $393 found 1 hour ago
Sat, May 2 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$399 Roundtrip, found 16 hours ago
$399
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, May 2 from Madison to Hilton Head Island, returning Sat, May 9, priced at $399 found 16 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
$106 nightly
The price is $116 total per night from Mar 19 to Mar 20
$116 total
Mar 19 - Mar 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! (1,004 reviews)
It was nice

Reviewed on Mar 13, 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! (1,003 reviews)
Clean room, dirty balcony, loud air conditioner

Reviewed on Mar 13, 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
$258 nightly
The price is $284 total per night from Mar 23 to Mar 24
$284 total
Mar 23 - Mar 24
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! (1,239 reviews)
Staff was very helpful. Great view!

Reviewed on Mar 12, 2026

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
$215 nightly
The price is $236 total per night from Mar 23 to Mar 24
$236 total
Mar 23 - Mar 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 ...
8.8/10 Excellent! (1,080 reviews)
We had a side view of the beach and water. It was not exactly a full ocean view. The windows do not open and there is no balcony to enjoy ocean sounds and smells.

Reviewed on Mar 12, 2026

Beach House Resort Hilton Head
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 19 to Mar 20
$272 total
Mar 19 - Mar 20
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! (1,416 reviews)
Great vacation spot!

Reviewed on Mar 10, 2026

Hilton Beachfront Resort & Spa Hilton Head Island
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 16 to Mar 17
$93 total
Mar 16 - Mar 17
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
$142 nightly
The price is $154 total per night from Mar 23 to Mar 24
$154 total
Mar 23 - Mar 24
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! (1,219 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
$106 nightly
The price is $117 total per night from Mar 15 to Mar 16
$117 total
Mar 15 - Mar 16
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 ...
8.4/10 Very Good! (7 reviews)
I had a great stay at Hotel Carolina. The room was recently renovated, very clean, and extremely comfortable. You can tell a lot of care has gone into updating the property. The mid-island location is excellent—very convenient for getting around Hilton Head and close to everything you need. I did ...

Reviewed on Mar 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
$352 nightly
The price is $383 total per night from Apr 13 to Apr 14
$383 total
Apr 13 - Apr 14
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! (1,001 reviews)

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

Travelers say...
It was a wonderful weekend stay

Reviewed on Mar 13, 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
$258 nightly
The price is $284 total per night from Mar 23 to Mar 24
$284 total
Mar 23 - Mar 24
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! (1,239 reviews)

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

Travelers say...
Staff was very helpful. Great view!

Reviewed on Mar 12, 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.