Cheap flights from MDW to HHH (Midway Intl. to Hilton Head Island)
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Hotel Ideas near Hilton Head Island
Airport Hotels near Hilton Head Island
Hampton Inn Hilton Head
1 Dillon Road Hilton Head Island SC
$91 nightly
The price is $100 total per night from Dec 21 to Dec 22
$100 total
Dec 21 - Dec 22
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)
Nice staff, clean room, tasty food
Reviewed on Dec 1, 2025
The Westin Hilton Head Island Resort & Spa
2 Grasslawn Ave Hilton Head Island SC
$168 nightly
The price is $185 total per night from Dec 28 to Dec 29
$185 total
Dec 28 - Dec 29
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! (1,002 reviews)
great staff
Reviewed on Dec 1, 2025
Island Links Resort by Palmera
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! (326 reviews)
Very clean and good location. T.V.'s need to be updated but other than that it was a great place to stay.
Reviewed on Dec 4, 2025
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
130 Shipyard Drive Hilton Head Island SC
$212 nightly
The price is $233 total per night from Dec 23 to Dec 24
$233 total
Dec 23 - Dec 24
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 ...
8.6/10 Excellent! (1,176 reviews)
Beautiful area and the hotel staff were so friendly. Would love to stay for several days!
Reviewed on Dec 3, 2025
Omni Hilton Head Oceanfront Resort
23 Ocean Lane Hilton Head Island SC
$202 nightly
The price is $218 total per night from Jan 4 to Jan 5
$218 total
Jan 4 - Jan 5, 2026
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. ...
8.8/10 Excellent! (1,003 reviews)
The room was great. The staff was friendly. Paulette made sure we had a great stay
Reviewed on Dec 7, 2025
Palmera Inn and Suites
12 Park Ln Hilton Head Island SC
$99 nightly
The price is $109 total per night from Jan 1 to Jan 2
$109 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,161 reviews)
Very nice staff
Reviewed on Dec 12, 2025
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
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 Theater ...
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
5 Regency Pkwy Hilton Head Island SC
$75 nightly
The price is $83 total per night from Dec 18 to Dec 19
$83 total
Dec 18 - Dec 19
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 (1,000 reviews)
Friendly staff. Accommodated my request to be far from the smoking area. Clean room. Quiet neighborhood. Comfortable bed. Thanks for a great stay and good value!
Reviewed on Nov 5, 2025
Palmera Inn and Suites
12 Park Ln Hilton Head Island SC
$99 nightly
The price is $109 total per night from Jan 1 to Jan 2
$109 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,161 reviews)
Very nice staff
Reviewed on Dec 12, 2025
Hotel Carolina
9 Marina Side Drive Hilton Head Island SC
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 ...
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
23 Ocean Lane Hilton Head Island SC
$202 nightly
The price is $218 total per night from Jan 4 to Jan 5
$218 total
Jan 4 - Jan 5, 2026
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. ...
8.8/10 Excellent! (1,003 reviews)
Families like: Outdoor pools, kids club, kitchenette, playground
Travelers say...
The room was great. The staff was friendly. Paulette made sure we had a great stay
Reviewed on Dec 7, 2025
Sonesta Resort Hilton Head Island
130 Shipyard Drive Hilton Head Island SC
$212 nightly
The price is $233 total per night from Dec 23 to Dec 24
$233 total
Dec 23 - Dec 24
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 ...
8.6/10 Excellent! (1,176 reviews)
Families like: Outdoor pools, kids club, on the beach, bicycle rentals
Travelers say...
Beautiful area and the hotel staff were so friendly. Would love to stay for several days!
Reviewed on Dec 3, 2025
Hilton Head Island Beach & Tennis Resort
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 ...
7.6/10 Good! (1,001 reviews)
Families like: Outdoor pools, kitchen, playground, on the beach
Travelers say...
This was a great kid friendly place to stay for our quick weekend get away with the grandkids. Once we got our groceries, there was no need to leave again. The play ground and kiddie pool were the biggest hits after playing on the beach!
Reviewed on Oct 6, 2025
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.
MDW to HHH Route Info
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MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
HHH Address & GPS
Address:
120 Beach City Road
Hilton Head SC, 29926
United States
IATA Code:
HHH
Longitude:
-80.697013
Latitude:
32.22263
Time Zone:
America/New_York
Other Flights from Midway Intl. Airport (MDW)
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
Frequently asked questions
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.