Cheap flights from Chicago (CHI) to Hilton Head Island (SAV)

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Lowest round trip fares by airline from Chicago and Hilton Head Island

Cheapest prices ($138 One Way, $234 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Hilton Head Island

Red Roof Inn Hilton Head Island

Red Roof Inn Hilton Head Island

2 out of 5
5 Regency Pkwy, Us 278, 30 Miles From I-95, Hilton Head Island, SC
The price is $75 per night from Dec 1 to Dec 2
$75
per night
Dec 1 - Dec 2
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)
Good
"It was fine for the reason we were there to sleep smelled clean. Everything was good."

Reviewed on Oct 20, 2024

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
The price is $160 per night from Nov 25 to Nov 26
$160
per night
Nov 25 - Nov 26
Stay at this 3-star 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 ...
8.8/10 Excellent! (1,008 reviews)
"It was late when we arrive around midnight. The get at the front desk was extremely nice. Beautiful place inside and out"

Reviewed on Nov 23, 2024

Palmera Inn and Suites
Hotel Carolina, a Days Inn by Wyndham

Hotel Carolina, a Days Inn by Wyndham

2 out of 5
9 Marina Side Drive, Hilton Head Island, SC
The price is $75 per night from Nov 26 to Nov 27
$75
per night
Nov 26 - Nov 27
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 ...
6.4/10 (1,002 reviews)
"Nice pool. Little stair access. Ckeckin person not very welcoming . Fellow at the desk in the a.m. was pleasant."

Reviewed on Nov 20, 2024

Hotel Carolina, a Days Inn by Wyndham
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.

Fly From Chicago to Hilton Head Island

Origin
Chicago
Destination
Hilton Head Island
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Chicago to Hilton Head Island

Are you ready to book your flight, but feeling nervous about paying too much if the price drops? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus a $50 CheapCash bonus, which you can use to save on your hotel reservation.

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Save Even More Time and Money With a Hilton Head Island Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Hilton Head Island vacation that you can't get when you book flights and hotel separately.

Relax in Hilton Head Island With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.