US$228️ Cheap Flights from Chicago to Hilton Head Island (2024)

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Chicago to Hilton Head Island - Flights Starting at US$228

Book one-way or return flights from Chicago to Hilton Head Island from as little as US$228. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

We've found these cheap flights for you. You may book a one-way or round trip as per your needs.

We monitor flight fares to help you seize the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Cheapest airlines flights from Chicago to Hilton Head Island

View airlines operating flights from Chicago to Hilton Head Island. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines

From US$228

United Airlines

From US$253

Delta Air Lines

From US$254

ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Hilton Head Island

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Hilton Head Island.

Cheapest
ORD
05:30
3h 53m
1 transfer
HHH
10:23
O'Hare International Airport - Hilton Head International Airport
Thu, May 2American Airlines
US$228
MDW
08:45
6h 20m
1 transfer
HHH
16:05
Midway International Airport - Hilton Head International Airport
Mon, May 20Delta Air Lines
US$255
MDW
08:45
6h 20m
1 transfer
HHH
16:05
Midway International Airport - Hilton Head International Airport
Mon, May 20Delta Air Lines
US$255
Find More Flights

Frequently Asked Questions

When are flight tickets from Chicago (CHI) to Hilton Head Island (HHH) the cheapest?
Airlines adjust prices for flights from Chicago to Hilton Head Island based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Chicago (CHI) to Hilton Head Island (HHH) cost?
According to Trip.com's data, the lowest price is around $544.
How long does it take to fly from Chicago (CHI) to Hilton Head Island (HHH) and what is the distance?
It takes around 2 hours 20 minutes to fly from Chicago (CHI) to Hilton Head Island (HHH).
What are the most popular airlines that fly from Chicago (CHI) to Hilton Head Island (HHH)?
Airlines with flights from Chicago (CHI) to Hilton Head Island (HHH): United Airlines and American Airlines.

How to find a cheap flight from Chicago to Hilton Head Island

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Hilton Head Island. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

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Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

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Save up to £10 per person when booking your flights on Trip.com

Chicago to Hilton Head Island Flight Information

Cheapest nonstop flight price	$227
Cheapest round-trip ticket price	$362
Off-season for travel	March
Peak season for travel	November
Flight distance	1,236.42km
Average flight time	2 hours 20 minutes
Popular airline	American Airlines