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, $339 Round Trip

Prices starting at $339 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.

Sat, Nov 7 - Sat, Nov 14
MSN
Madison
HHH
Hilton Head Island
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 7 from Madison to Hilton Head Island, returning Sat, Nov 14, priced at $339 found 4 days ago
Sat, Nov 7 - Sat, Nov 14
MSN
Madison
HHH
Hilton Head Island
$402 Roundtrip, found 4 days ago
$402
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 7 from Madison to Hilton Head Island, returning Sat, Nov 14, priced at $402 found 4 days ago
Sat, Nov 7 - Sat, Nov 14
MSN
Madison
HHH
Hilton Head Island
$429 Roundtrip, found 4 days ago
$429
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 7 from Madison to Hilton Head Island, returning Sat, Nov 14, priced at $429 found 4 days ago
Sat, Nov 7 - Sat, Nov 14
MSN
Madison
HHH
Hilton Head Island
$492 Roundtrip, found 4 days ago
$492
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 7 from Madison to Hilton Head Island, returning Sat, Nov 14, priced at $492 found 4 days ago
Sat, Nov 7 - Sat, Nov 14
MSN
Madison
HHH
Hilton Head Island
$493 Roundtrip, found 4 days ago
$493
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 7 from Madison to Hilton Head Island, returning Sat, Nov 14, priced at $493 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
$136 nightly
The price is $149 total per night from Aug 5 to Aug 6
$149 total
Aug 5 - Aug 6
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! (1,002 reviews)
"There was an unpleasant smell in the room, a musty smell. The air conditioner is entirely inside the room, both the indoor and outdoor units, and it hums very loudly. During our 5-night stay, the room was only cleaned once. Although we were told that housekeeping would be every other day. It's really ..."

Reviewed on Jul 17, 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
$287 nightly
The price is $316 total per night from Aug 9 to Aug 10
$316 total
Aug 9 - Aug 10
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 ...
8.6/10 Excellent! (1,005 reviews)
"Amazing ocean front room, helpful and kind staff and amazing on property amenities! Will return soon."

Reviewed on Jul 15, 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! (356 reviews)
"It was nice and chill the shuttle was great. Kids loved the pool"

Reviewed on Jul 17, 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

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
$145 nightly
The price is $159 total per night from Aug 3 to Aug 4
$159 total
Aug 3 - Aug 4
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 ...
8.4/10 Very Good! (656 reviews)
"Not as expected"

Reviewed on Jul 17, 2026

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
$289 nightly
The price is $318 total per night from Aug 18 to Aug 19
$318 total
Aug 18 - Aug 19
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! (1,403 reviews)
"This was our second stay with Sonesta Hilton Head. We love this property and the calmness it inspires. The majority of our interaction with staff is excellent and helpful. Amenities are set up well. Our only suggestions are related to pets and beach rules. We are dog people so we give a little grace. ..."

Reviewed on Jul 17, 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
$250 nightly
The price is $275 total per night from Aug 16 to Aug 17
$275 total
Aug 16 - Aug 17
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! (1,568 reviews)
"👍"

Reviewed on Jul 17, 2026

Hilton Beachfront Resort & Spa 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
Book a stay at this beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Coligny Plaza ...
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
$85 nightly
The price is $93 total per night from Jul 21 to Jul 22
$93 total
Jul 21 - Jul 22
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 (1,004 reviews)
"The room had a bad smell"

Reviewed on Jul 17, 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
$185 nightly
The price is $201 total per night from Aug 2 to Aug 3
$201 total
Aug 2 - Aug 3
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
$119 nightly
The price is $131 total per night from Aug 3 to Aug 4
$131 total
Aug 3 - Aug 4
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 ...
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
$497 nightly
The price is $541 total per night from Aug 16 to Aug 17
$541 total
Aug 16 - Aug 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. ...
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
$289 nightly
The price is $318 total per night from Aug 18 to Aug 19
$318 total
Aug 18 - Aug 19
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! (1,403 reviews)

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

Travelers say...
"This was our second stay with Sonesta Hilton Head. We love this property and the calmness it inspires. The majority of our interaction with staff is excellent and helpful. Amenities are set up well. Our only suggestions are related to pets and beach rules. We are dog people so we give a little grace. ..."

Reviewed on Jul 17, 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! (1,000 reviews)

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

Travelers say...
"Perfect for a getaway weekend."

Reviewed on Jul 10, 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.