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 $239 One Way, $275 Round Trip

Prices starting at $275 for return flights and $239 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
$275 Roundtrip, found 12 hours ago
$275
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 $275 found 12 hours ago
Wed, Apr 8 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$282 Roundtrip, found 12 hours ago
$282
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 $282 found 12 hours ago
Thu, Apr 9 - Wed, Apr 15
MSN
Madison
HHH
Hilton Head Island
$314 Roundtrip, found 12 hours ago
$314
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Apr 9 from Madison to Hilton Head Island, returning Wed, Apr 15, priced at $314 found 12 hours ago
Thu, Apr 9 - Wed, Apr 15
MSN
Madison
HHH
Hilton Head Island
$319 Roundtrip, found 12 hours ago
$319
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Apr 9 from Madison to Hilton Head Island, returning Wed, Apr 15, priced at $319 found 12 hours ago
Sat, May 2 - Sat, May 9
MSN
Madison
HHH
Hilton Head Island
$331 Roundtrip, found 1 day ago
$331
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 2 from Madison to Hilton Head Island, returning Sat, May 9, priced at $331 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
$102 nightly
The price is $112 total per night from Mar 5 to Mar 6
$112 total
Mar 5 - Mar 6
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! (1,001 reviews)
Everything was wonderful. Our only hesitation for not clicking the top rating was that our toilet wouldn’t flush and we were given another room. There wasn’t someone on duty to help with the issue. Otherwise, all good!

Reviewed on Feb 16, 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
$200 nightly
The price is $220 total per night from Mar 1 to Mar 2
$220 total
Mar 1 - Mar 2
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! (1,004 reviews)
Hotel was great! Spa was disappointing due to low quality products

Reviewed on Feb 22, 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. ...
9.2/10 Wonderful! (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
$245 nightly
The price is $270 total per night from Mar 23 to Mar 24
$270 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! (1,233 reviews)
Excellent stay. Room was spotless and the staff is amazing.

Reviewed on Feb 17, 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
$209 nightly
The price is $230 total per night from Feb 26 to Feb 27
$230 total
Feb 26 - Feb 27
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)
Yes

Reviewed on Feb 18, 2026

Hilton Beachfront Resort & Spa Hilton Head Island
Holiday Inn Express Hilton Head Island by IHG

Holiday Inn Express Hilton Head Island by IHG

2.5 out of 5
10 Tanglewood Drive Hilton Head Island SC
$104 nightly
The price is $114 total per night from Feb 25 to Feb 26
$114 total
Feb 25 - Feb 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and ...
8.4/10 Very Good! (419 reviews)
The room was clean , the stall was good and so was the free breakfast.

Reviewed on Feb 18, 2026

Holiday Inn Express Hilton Head Island by IHG
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 Coligny Theater ...
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
$75 nightly
The price is $83 total per night from Mar 1 to Mar 2
$83 total
Mar 1 - Mar 2
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 ...
6.2/10 (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
$128 nightly
The price is $141 total per night from Feb 24 to Feb 25
$141 total
Feb 24 - Feb 25
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 ...
8.8/10 Excellent! (1,215 reviews)
Yes very clean and spotless room

Reviewed on Feb 20, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$69 nightly
The price is $76 total per night from Feb 24 to Feb 25
$76 total
Feb 24 - Feb 25
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! (3 reviews)
The staff were very friendly and helpful. My room had nice new floors and new furniture. The bed was very comfortable. The Roku TV worked well. The bathroom and sink area were clean and very nice. I was pleased that the shower had plenty of hot water. Overall, I enjoyed my stay at the Hotel Carolina! ...

Reviewed on Feb 16, 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
$326 nightly
The price is $354 total per night from Feb 25 to Feb 26
$354 total
Feb 25 - Feb 26
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...
Beautiful property. Beautiful room. Although charging $40 a day for room coffee etc is ridiculous on top of a higher price for the hotel room. Also the hot tub was very cloudy and foamy. It needed to be cleaned and chemicals balanced and added.

Reviewed on Feb 19, 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
$245 nightly
The price is $270 total per night from Mar 23 to Mar 24
$270 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! (1,233 reviews)

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

Travelers say...
Excellent stay. Room was spotless and the staff is amazing.

Reviewed on Feb 17, 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 ...
7.6/10 Good! (1,000 reviews)

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

Travelers say...
This was a great kid friendly place to stay for our quick weekend get away with the grandkids. Once we got our groceries, there was no need to leave again. The play ground and kiddie pool were the biggest hits after playing on the beach!

Reviewed on Oct 6, 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.