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, $296 Round Trip

Prices starting at $296 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.

Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$296 Roundtrip, found 10 hours ago
$296
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $296 found 10 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$301 Roundtrip, found 10 hours ago
$301
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $301 found 10 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$357 Roundtrip, found 10 hours ago
$357
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $357 found 10 hours ago
Sat, May 2 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$361 Roundtrip, found 22 hours ago
$361
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, May 2 from Madison to Hilton Head Island, returning Sat, May 9, priced at $361 found 22 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$363 Roundtrip, found 10 hours ago
$363
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Apr 8 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $363 found 10 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
$115 nightly
The price is $126 total per night from Mar 22 to Mar 23
$126 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! (1,008 reviews)
The room wasn't clean my whole stay friday- Monday. My room smelled like wet dog room 163. The bed was horrible 😫 i was in so much pain.

Reviewed on Mar 6, 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
$240 nightly
The price is $264 total per night from Mar 8 to Mar 9
$264 total
Mar 8 - Mar 9
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)
Room was great staff was excellent

Reviewed on Mar 2, 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 19 to Mar 20
$296 total
Mar 19 - Mar 20
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! (1,240 reviews)
Great place to stay at the beach with your dog

Reviewed on Mar 5, 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 15 to Mar 16
$272 total
Mar 15 - Mar 16
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! (1,427 reviews)
From the moment we stepped through the door everything was great! The free upgrade to ocean view. The pool area was so nice. When you go there see the bartenders and Dianne for breakfast! Highly recommend and will stay there again. Whats nice is they have a shuttle to go across the street for shopping ...

Reviewed on Mar 6, 2026

Hilton Beachfront Resort & Spa Hilton Head Island
Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane Hilton Head Island SC
$402 nightly
The price is $438 total per night from Mar 11 to Mar 12
$438 total
Mar 11 - Mar 12
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)
Excellent, we had shower problems and they fix it immediately

Reviewed on Feb 23, 2026

Omni Hilton Head Oceanfront 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.

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 10 to Mar 11
$93 total
Mar 10 - Mar 11
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 (1,000 reviews)
We had a generally pleasant stay at this property and wouldn't hesitate to stay there again, although the lack of a breakfast was a disappointment (I think the coffee bar photo duped me into thinking they provided it). The only things keeping it from getting 5 stars were how loud we could hear guests ...

Reviewed on Feb 17, 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
$132 nightly
The price is $142 total per night from Mar 8 to Mar 9
$142 total
Mar 8 - Mar 9
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! (1,220 reviews)
This is our go to stay over from our drive from Ct to Florida each March. Great staff, spacious room and great location with short drives to beaches, restaurants and nature walks. This is our 4 year staying here

Reviewed on Mar 6, 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 8 to Mar 9
$108 total
Mar 8 - Mar 9
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
$402 nightly
The price is $438 total per night from Mar 11 to Mar 12
$438 total
Mar 11 - Mar 12
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...
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 19 to Mar 20
$296 total
Mar 19 - Mar 20
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! (1,240 reviews)

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

Travelers say...
Great place to stay at the beach with your dog

Reviewed on Mar 5, 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 Coligny Beach and Folly Field ...
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.