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 $241 One Way, $271 Round Trip

Prices starting at $271 for return flights and $241 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.

Tue, Apr 7 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$271 Roundtrip, found 11 hours ago
$271
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Apr 7 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $271 found 11 hours ago
Tue, Apr 7 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$319 Roundtrip, found 11 hours ago
$319
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Apr 7 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $319 found 11 hours ago
Tue, Apr 7 - Tue, Apr 14
MSN
Madison
HHH
Hilton Head Island
$324 Roundtrip, found 11 hours ago
$324
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Apr 7 from Madison to Hilton Head Island, returning Tue, Apr 14, priced at $324 found 11 hours ago
Fri, Nov 14 - Wed, Nov 19
MSN
Madison
HHH
Hilton Head Island
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 14 from Madison to Hilton Head Island, returning Wed, Nov 19, priced at $334 found 4 days ago
Wed, Nov 12 - Wed, Nov 19
MSN
Madison
HHH
Hilton Head Island
$338 Roundtrip, found 4 days ago
$338
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Nov 12 from Madison to Hilton Head Island, returning Wed, Nov 19, priced at $338 found 4 days 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
$90 nightly
The price is $99 total per night from Dec 2 to Dec 3
$99 total
Dec 2 - Dec 3
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! (1,014 reviews)
Nice and Comfortable
Our room was clean and well appointed. The bed was comfortable. I think there should be a towel rack in the bathroom because there was no place to hang up a towel. That's my only complaint. The omelet they served was light and fluffy.

Reviewed on Oct 27, 2025

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
$194 nightly
The price is $213 total per night from Nov 23 to Nov 24
$213 total
Nov 23 - Nov 24
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 ...
8.2/10 Very Good! (1,003 reviews)
We had to vacate he hotel at 5 in the morning for a potential fire. There was no fire. He alarm was sounded but no one came on an intercom to report what was happening or what we were to do. We saw one staff member !

Reviewed on Oct 20, 2025

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
Stay at this 3-star 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! (322 reviews)
Great size apartment really friendly staff and lovely pool although too cold

Reviewed on Oct 14, 2025

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

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
$182 nightly
The price is $200 total per night from Nov 9 to Nov 10
$200 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this 4.5-star luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in ...
8.4/10 Very Good! (1,365 reviews)
Bathroom dirty. Hair on the floor. Property needs to be updated.

Reviewed on Oct 27, 2025

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
$93 nightly
The price is $102 total per night from Nov 30 to Dec 1
$102 total
Nov 30 - Dec 1
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 ...
8/10 Very Good! (271 reviews)
We like everything about the hotel. No problem at all. Thank you for ur services.

Reviewed on Oct 26, 2025

Holiday Inn Express Hilton Head Island by IHG
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive, Hilton Head Island, SC
$212 nightly
The price is $233 total per night from Nov 9 to Nov 10
$233 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this 4-star 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 ...
8.4/10 Very Good! (1,121 reviews)
Gorgeous property - we enjoyed every aspect of our visit!

Reviewed on Oct 28, 2025

Sonesta Resort 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
Stay at this 4-star 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, Us 278, 30 Miles From I-95, Hilton Head Island, SC
$70 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
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)
Room was great for a couple of nights great location on Hilton Head island

Reviewed on Oct 24, 2025

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
$126 nightly
The price is $139 total per night from Nov 4 to Nov 5
$139 total
Nov 4 - Nov 5
Total with taxes and fees
Stay at this 3-star 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 ...
8.8/10 Excellent! (1,168 reviews)
*My Loft Room was clean, comfortable and spacious. *Staff was friendly, especially the breakfast staff. *The grounds were pretty, surrounded by beautiful, fragrant trees, and the neighborhood allowed for quiet, safe and invigorating walks.

Reviewed on Oct 30, 2025

Palmera Inn and Suites
Hotel Carolina, a Days Inn by Wyndham

Hotel Carolina, a Days Inn by Wyndham

2 out of 5
9 Marina Side Drive, Hilton Head Island, SC
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 ...
6.6/10 (1,000 reviews)
Liked that they had a microwave but no microwaveble plates ): And no complimentary toothpaste.

Reviewed on Oct 25, 2025

Get rates
Hotel Carolina, a Days Inn by Wyndham
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
$238 nightly
The price is $257 total per night from Nov 30 to Dec 1
$257 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this 4-star 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. ...
8.8/10 Excellent! (1,001 reviews)

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

Travelers say...
The resort was amazing!

Reviewed on Oct 21, 2025

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
$212 nightly
The price is $233 total per night from Nov 9 to Nov 10
$233 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this 4-star 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 ...
8.4/10 Very Good! (1,121 reviews)

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

Travelers say...
Gorgeous property - we enjoyed every aspect of our visit!

Reviewed on Oct 28, 2025

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
Stay at this 3.5-star 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.