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 $298 One Way, $348 Round Trip

Prices starting at $348 for return flights and $298 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
$348 Roundtrip, found 4 hours ago
$348
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $348 found 4 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$353 Roundtrip, found 4 hours ago
$353
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $353 found 4 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$395 Roundtrip, found 4 hours ago
$395
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $395 found 4 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$400 Roundtrip, found 4 hours ago
$400
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $400 found 4 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$430 Roundtrip, found 4 hours ago
$430
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $430 found 4 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
$123 nightly
The price is $135 total per night from Mar 30 to Mar 31
$135 total
Mar 30 - Mar 31
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)
goid break fast , clean room .

Reviewed on Mar 23, 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 12 to Apr 13
$252 total
Apr 12 - Apr 13
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! (1,005 reviews)
The rooms were OK but the bed was not comfortable. The Carolina Room restaurant food was average and the service was terrible, very slow and not attentive. Very pricy. Menu needs to be reworked.

Reviewed on Mar 23, 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
$283 nightly
The price is $311 total per night from Mar 30 to Mar 31
$311 total
Mar 30 - Mar 31
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! (1,247 reviews)
The restaurant is not open and there is no place nearby. So the bar food is only option. Super over priced

Reviewed on Mar 23, 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
$206 nightly
The price is $227 total per night from Mar 29 to Mar 30
$227 total
Mar 29 - Mar 30
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! (1,098 reviews)
All great!! Stay here every year

Reviewed on Mar 23, 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
$231 nightly
The price is $254 total per night from Mar 30 to Mar 31
$254 total
Mar 30 - Mar 31
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! (1,426 reviews)
Great experience from check in to checkout. Staff was friendly and helpful. Loved this resort and will definitely stay there again.

Reviewed on Mar 20, 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 29 to Mar 30
$93 total
Mar 29 - Mar 30
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 (1,003 reviews)
NOT POORLY MAINTAINED, BUT POORLY RENOVATED. COULD BE MUCH BETTER WITH A LITTLE ELBOW GREASE

Reviewed on Mar 23, 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
$163 nightly
The price is $177 total per night from Mar 25 to Mar 26
$177 total
Mar 25 - Mar 26
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! (1,231 reviews)
We enjoyed our stay at Palmera Inn. It was very clean and comfortable. The location was good with reasonable rates.

Reviewed on Mar 22, 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 Mar 25 to Mar 26
$121 total
Mar 25 - Mar 26
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! (18 reviews)
The staff was amazing it is no contact so we only saw one lady who was incredibly helpful! The bathroom door didn’t shut or lock in our room and the bathtub was clogged so the water wouldn’t drain very fast. They had towels and 2 little soap bars in the room but that’s it. Honestly though would stay ...

Reviewed on Mar 23, 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
$365 nightly
The price is $397 total per night from Apr 21 to Apr 22
$397 total
Apr 21 - Apr 22
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! (1,007 reviews)

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

Travelers say...
Very nice resort. Helpful staff and comfortable beds. Great opportunities for eating and snacks.

Reviewed on Mar 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
$283 nightly
The price is $311 total per night from Mar 30 to Mar 31
$311 total
Mar 30 - Mar 31
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! (1,247 reviews)

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

Travelers say...
The restaurant is not open and there is no place nearby. So the bar food is only option. Super over priced

Reviewed on Mar 23, 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

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.