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 $269 One Way, $396 Round Trip

Prices starting at $396 for return flights and $269 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.

Sun, Jun 7 - Sat, Jun 13
MSN
Madison
HHH
Hilton Head Island
$396 Roundtrip, found 3 days ago
$396
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Jun 7 from Madison to Hilton Head Island, returning Sat, Jun 13, priced at $396 found 3 days ago
Sat, Oct 10 - Sat, Oct 24
MSN
Madison
HHH
Hilton Head Island
$402 Roundtrip, found 23 hours ago
$402
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sat, Oct 10 from Madison to Hilton Head Island, returning Sat, Oct 24, priced at $402 found 23 hours ago
Sun, Jun 7 - Sat, Jun 13
MSN
Madison
HHH
Hilton Head Island
$422 Roundtrip, found 3 days ago
$422
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Jun 7 from Madison to Hilton Head Island, returning Sat, Jun 13, priced at $422 found 3 days ago
Mon, Jun 8 - Sun, Jun 14
MSN
Madison
HHH
Hilton Head Island
$432 Roundtrip, found 3 days ago
$432
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jun 8 from Madison to Hilton Head Island, returning Sun, Jun 14, priced at $432 found 3 days ago
Sat, Oct 10 - Sat, Oct 24
MSN
Madison
HHH
Hilton Head Island
$437 Roundtrip, found 23 hours ago
$437
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sat, Oct 10 from Madison to Hilton Head Island, returning Sat, Oct 24, priced at $437 found 23 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
$130 nightly
The price is $143 total per night from May 11 to May 12
$143 total
May 11 - May 12
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)
Good place for overnight stay

Reviewed on May 3, 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
$340 nightly
The price is $374 total per night from May 10 to May 11
$374 total
May 10 - May 11
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! (1,010 reviews)
The property is beautiful and the pool is great. View 32 is a great pace to eat there.

Reviewed on May 4, 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! (337 reviews)
Really enjoyed!!!!

Reviewed on Apr 26, 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 7 to May 8
$409 total
May 7 - May 8
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! (1,316 reviews)
Patrick is amazing and he deserves a raise!! Had a great trip!!

Reviewed on May 4, 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
$288 nightly
The price is $317 total per night from May 11 to May 12
$317 total
May 11 - May 12
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! (1,488 reviews)
Very nice and clean resort

Reviewed on May 3, 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
$276 nightly
The price is $304 total per night from May 19 to May 20
$304 total
May 19 - May 20
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! (1,202 reviews)
Weather was bad but not their fault

Reviewed on May 4, 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 ...
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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
$85 nightly
The price is $93 total per night from May 10 to May 11
$93 total
May 10 - May 11
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)
Great stay for low price!

Reviewed on May 3, 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
$160 nightly
The price is $174 total per night from May 6 to May 7
$174 total
May 6 - May 7
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! (1,304 reviews)
Great location to get around the island. Easy on and off the main highway to get to the Inn. Clean rooms and a good breakfast bar to get your day started.

Reviewed on May 4, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$90 nightly
The price is $99 total per night from May 10 to May 11
$99 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! (39 reviews)
Overall the hotel was nice, clean and spacious. Our toilet did not flush and the hotel did not seemed staffed to accommodate any guests requests. They dropped a plunger off at our door and walked away. It was a good thing we were only there for one night.

Reviewed on Apr 29, 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
$412 nightly
The price is $447 total per night from May 12 to May 13
$447 total
May 12 - May 13
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! (1,005 reviews)

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

Travelers say...
The property at the Omni resort in Hilton head is beautiful and well maintained. We had a little hiccup upon check in with our room. But the hotel staff quickly intervened and found us a comparable alternative. I’d say the best part of our stay was the staff. Everyone was lovely, accommodating, and ...

Reviewed on Apr 30, 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 7 to May 8
$409 total
May 7 - May 8
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! (1,316 reviews)

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

Travelers say...
Patrick is amazing and he deserves a raise!! Had a great trip!!

Reviewed on May 4, 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 Shelter Cove ...
7.8/10 Good! (1,001 reviews)

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

Travelers say...
This was our first time staying at HHBT and we were very satisfied. The staff at check was very friendly and the process was quick. Our unit was very conveniently located just steps from the pool and beach. While the bedroom was a bit cozy, the rest of the unit fully met our needs and made for a ...

Reviewed on Apr 30, 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.