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 $285 One Way, $429 Round Trip

Prices starting at $429 for return flights and $285 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.

Sat, Oct 31 - Sat, Nov 7
MSN
Madison
HHH
Hilton Head Island
$429 Roundtrip, found 3 days ago
$429
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 31 from Madison to Hilton Head Island, returning Sat, Nov 7, priced at $429 found 3 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$429 Roundtrip, found 3 hours ago
$429
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $429 found 3 hours ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$444 Roundtrip, found 3 hours ago
$444
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $444 found 3 hours ago
Sat, Oct 31 - Sat, Nov 7
MSN
Madison
HHH
Hilton Head Island
$504 Roundtrip, found 3 days ago
$504
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 31 from Madison to Hilton Head Island, returning Sat, Nov 7, priced at $504 found 3 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$509 Roundtrip, found 3 hours ago
$509
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $509 found 3 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
$114 nightly
The price is $125 total per night from Sep 29 to Sep 30
$125 total
Sep 29 - Sep 30
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. ...
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
$266 nightly
The price is $292 total per night from Oct 5 to Oct 6
$292 total
Oct 5 - Oct 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 ...
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! (377 reviews)
"The accommodation were great and the amenities were wonderful. The pool and the walk up pool bar were super. The condition of the townhouse itself was not so good. There were roaches and fruit flies and the carpet was filthy disgusting."

Reviewed on Sep 7, 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

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
$250 nightly
The price is $275 total per night from Sep 15 to Sep 16
$275 total
Sep 15 - Sep 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! (1,612 reviews)
"Room is clean, quiet, staffs are friendly and helpful, Anggun Wulandari is very nice, friendly and helpful, she answered a lot of questions from me because it was my first time here, I love this place so much so I will come back by Christmas time 👍👍"

Reviewed on Sep 8, 2026

Hilton Beachfront Resort & Spa Hilton Head Island
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$288 nightly
The price is $317 total per night from Sep 14 to Sep 15
$317 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,496 reviews)
"Our family had a wonderful stay for 5 nights! The service was great and the food at the restaurants were wonderful. The staff were all so kind, friendly and so helpful with everything. The pool was great and it was such an easy and quick stroll to the beach. The beach was never crowded and was so ..."

Reviewed on Sep 8, 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
$202 nightly
The price is $222 total per night from Sep 15 to Sep 16
$222 total
Sep 15 - Sep 16
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 ...
8.6/10 Excellent! (1,482 reviews)
"Great stay! Really like the location"

Reviewed on Sep 7, 2026

Beach House Resort Hilton Head
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 Shipyard Beach ...
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
$71 nightly
The price is $78 total per night from Sep 13 to Sep 14
$78 total
Sep 13 - Sep 14
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular ...
6.2/10 (1,002 reviews)
"Roaches roaches roaches my 11 month old had a roach crawling by his foot roaches all under the desk the room smelt like dirt yeah it’s not worth the trouble"

Reviewed on Sep 7, 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
$124 nightly
The price is $134 total per night from Sep 9 to Sep 10
$134 total
Sep 9 - Sep 10
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff ...
Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$68 nightly
The price is $75 total per night from Sep 9 to Sep 10
$75 total
Sep 9 - Sep 10
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (161 reviews)
"Todo en orden"

Reviewed on Sep 8, 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
$372 nightly
The price is $404 total per night from Sep 16 to Sep 17
$404 total
Sep 16 - Sep 17
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! (1,006 reviews)

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

Travelers say...
"All good at the Omni!"

Reviewed on Sep 8, 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
$288 nightly
The price is $317 total per night from Sep 14 to Sep 15
$317 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,496 reviews)

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

Travelers say...
"Our family had a wonderful stay for 5 nights! The service was great and the food at the restaurants were wonderful. The staff were all so kind, friendly and so helpful with everything. The pool was great and it was such an easy and quick stroll to the beach. The beach was never crowded and was so ..."

Reviewed on Sep 8, 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...
"This is our second time staying at Hilton Head Island Beach & Tennis Resort. We love the proximity to the beach. An easy, few minute walk and you’re on the sand! The beach was perfect. Not too crowded and seceral lifeguards present. Multiple pools is a great option. The smaller pool was next to our ..."

Reviewed on Aug 9, 2026

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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.