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 $278 One Way, $419 Round Trip

Prices starting at $419 for return flights and $278 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.

Thu, Aug 13 - Tue, Aug 18
MSN
Madison
HHH
Hilton Head Island
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 13 from Madison to Hilton Head Island, returning Tue, Aug 18, priced at $419 found 2 days ago
Thu, Aug 13 - Tue, Aug 18
MSN
Madison
HHH
Hilton Head Island
$459 Roundtrip, found 2 days ago
$459
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 13 from Madison to Hilton Head Island, returning Tue, Aug 18, priced at $459 found 2 days ago
Thu, Aug 13 - Tue, Aug 18
MSN
Madison
HHH
Hilton Head Island
$488 Roundtrip, found 2 days ago
$488
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 13 from Madison to Hilton Head Island, returning Tue, Aug 18, priced at $488 found 2 days ago
Thu, Aug 13 - Tue, Aug 18
MSN
Madison
HHH
Hilton Head Island
$490 Roundtrip, found 2 days ago
$490
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 13 from Madison to Hilton Head Island, returning Tue, Aug 18, priced at $490 found 2 days ago
Thu, Aug 13 - Tue, Aug 18
MSN
Madison
HHH
Hilton Head Island
$496 Roundtrip, found 2 days ago
$496
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 13 from Madison to Hilton Head Island, returning Tue, Aug 18, priced at $496 found 2 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
$130 nightly
The price is $143 total per night from May 17 to May 18
$143 total
May 17 - May 18
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)
Everyone was very helpful and operated with great customer service. Room was clean, breakfast was a huge plus. Short distance to the beach. This was the 3rd time I have used Hampton Inn on 1 Dillon Rd and as usual we were very pleased. Will be back on our next trip to Hilton Head.

Reviewed on Apr 21, 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
$270 nightly
The price is $297 total per night from Apr 26 to Apr 27
$297 total
Apr 26 - Apr 27
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)
Great resort

Reviewed on Apr 17, 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! (336 reviews)
Everything was perfect for our stay at Island Links.

Reviewed on Apr 15, 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
$372 nightly
The price is $409 total per night from May 3 to May 4
$409 total
May 3 - May 4
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 ...
8.8/10 Excellent! (1,291 reviews)
If you're a couple shaking off a long winter, the Sonesta Resort in Hilton Head really delivers. Our room was spacious and thoughtfully laid out — king bed, bistro table, balcony overlooking the pool with a glimpse of the ocean beyond. We loved stepping out there in the morning to take in the salt ...

Reviewed on Apr 20, 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
$264 nightly
The price is $290 total per night from Apr 26 to Apr 27
$290 total
Apr 26 - Apr 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! (1,470 reviews)
The pool was comfortable, but the water was still a little cold.

Reviewed on Apr 21, 2026

Hilton Beachfront Resort & Spa 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
$249 nightly
The price is $274 total per night from Apr 27 to Apr 28
$274 total
Apr 27 - Apr 28
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 ...
8.8/10 Excellent! (1,167 reviews)
The staff was great. Our room was dated and had cockroaches in the bathroom. They did move us but hard to forget. Restaurant and pool are very nice. Great to be so close to the beach and the Tiki Hut was fun with great music.

Reviewed on Apr 20, 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 Plaza and Coligny 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
$94 nightly
The price is $103 total per night from Apr 26 to Apr 27
$103 total
Apr 26 - Apr 27
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 (1,001 reviews)
Staff was helpful and friendly

Reviewed on Apr 19, 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
$182 nightly
The price is $198 total per night from Apr 22 to Apr 23
$198 total
Apr 22 - Apr 23
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! (1,274 reviews)
The staff was friendly and professional. The room was quiet, clean and spacious. Breakfast had very good grits, eggs and hot coffee. Other items were well stocked.

Reviewed on Apr 20, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$119 nightly
The price is $131 total per night from May 10 to May 11
$131 total
May 10 - May 11
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 ...
7.8/10 Good! (30 reviews)
Literally Sucked... wouldn't stay again... the No Staff is one thing but renting the parking lot to 7 plus Tour Busses 4 of which parked outside our door ... a light outside our room lit up the rom like a football stadium... Tour Busses opening cargo doors and starting diesel engines... it was clean ...

Reviewed on Apr 20, 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
$443 nightly
The price is $482 total per night from Apr 26 to Apr 27
$482 total
Apr 26 - Apr 27
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! (1,010 reviews)

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

Travelers say...
The Omni was such a pleasant surprise. Their renovations are so lovely and the staff is amazing. The gathering spots and restaurants were wonderful.

Reviewed on Apr 20, 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
$372 nightly
The price is $409 total per night from May 3 to May 4
$409 total
May 3 - May 4
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 ...
8.8/10 Excellent! (1,291 reviews)

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

Travelers say...
If you're a couple shaking off a long winter, the Sonesta Resort in Hilton Head really delivers. Our room was spacious and thoughtfully laid out — king bed, bistro table, balcony overlooking the pool with a glimpse of the ocean beyond. We loved stepping out there in the morning to take in the salt ...

Reviewed on Apr 20, 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 Palmetto Dunes Club and Coligny ...
7.8/10 Good! (1,002 reviews)

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

Travelers say...
Beach view was beautiful!

Reviewed on Apr 20, 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.