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 $279 One Way, $429 Round Trip

Prices starting at $429 for return flights and $279 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, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$429 Roundtrip, found 4 days ago
$429
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $429 found 4 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$444 Roundtrip, found 4 days ago
$444
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $444 found 4 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$509 Roundtrip, found 4 days ago
$509
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $509 found 4 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$524 Roundtrip, found 4 days ago
$524
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $524 found 4 days ago
Sat, Sep 19 - Sun, Sep 20
MSN
Madison
HHH
Hilton Head Island
$579 Roundtrip, found 4 days ago
$579
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 19 from Madison to Hilton Head Island, returning Sun, Sep 20, priced at $579 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
$111 nightly
The price is $122 total per night from Sep 23 to Sep 24
$122 total
Sep 23 - Sep 24
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! (1,004 reviews)
"Property is highly used as it’s near the beach. Food court could use a facelift as could the carpets. Room bathrooms are super small with sink outside of bathroom. Floor plan a bit cramped. Staff was quick with check in and very friendly."

Reviewed on Sep 12, 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
$250 nightly
The price is $274 total per night from Oct 11 to Oct 12
$274 total
Oct 11 - Oct 12
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. ...
9.4/10 Exceptional! (379 reviews)
"Room was clean, nice and cozy. Great stay."

Reviewed on Sep 12, 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 20 to Sep 21
$275 total
Sep 20 - Sep 21
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 ...
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 Oct 4 to Oct 5
$317 total
Oct 4 - Oct 5
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 ...
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
$239 nightly
The price is $263 total per night from Sep 13 to Sep 14
$263 total
Sep 13 - Sep 14
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! (1,488 reviews)
"The staff was great Very helpful."

Reviewed on Sep 10, 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 15 to Sep 16
$78 total
Sep 15 - Sep 16
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 ...
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 27 to Sep 28
$134 total
Sep 27 - Sep 28
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 ...
9/10 Wonderful! (1,461 reviews)
"Very clean room and super friendly front desk ladies!"

Reviewed on Sep 12, 2026

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 13 to Sep 14
$75 total
Sep 13 - Sep 14
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! (166 reviews)
"Was pleasantly surprised with this stay! The room was very clean and the pool was great."

Reviewed on Sep 11, 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
$332 nightly
The price is $360 total per night from Sep 28 to Sep 29
$360 total
Sep 28 - Sep 29
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! (1,003 reviews)

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

Travelers say...
"!"

Reviewed on Sep 11, 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 Oct 4 to Oct 5
$317 total
Oct 4 - Oct 5
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 ...
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

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.