$157 Cheap Flights from Chicago (ORD) to Hilton Head Island (HHH)

Bundle Your Flight + Hotel & Save!

Featured airlines

Top nine airline logos for desktop

Cheap Flights from Chicago to Hilton Head Island (ORD-HHH)

Prices were available within the past 7 days and start at $157 for one-way flights and $183 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Flights from Chicago (ORD) to Hilton Head Island (HHH)
Origin airport
O'Hare Intl.
Destination airport
Hilton Head Island
Airlines serving
American Airlines, Delta, United
Roundtrip price
$183
Distance
781 mi

Chicago to Hilton Head Island Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Hilton Head Island offer the perfect respite. Not only does exploring Hilton Head Island provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Hilton Head Island may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from ORD to HHH today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Hilton Head Island are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Hilton Head Island more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Hilton Head Island is $157 now!

Frequently asked questions

How much is a flight from ORD to Hilton Head Island Airport (HHH)?
Pack your bags, because round-trip journeys from O’Hare Airport to Hilton Head Airport start from $183. That’s based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book today to get the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to Hilton Head Airport?
Most flights can be canceled online, but every airline has its own set of terms and conditions. If you do decide to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to HHH that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for O’Hare Airport to Hilton Head Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from O'Hare Airport to Hilton Head Airport?
You won’t have time for a movie marathon on this flight — it’s just 777 mi from Chicago to Hilton Head Island. Sit down, buckle up and you’ll be there in no time.
Which airlines fly direct from ORD to Hilton Head Airport?
If you want to fly straight from O’Hare Intl. Airport (ORD) to Hilton Head Airport, you’ll have to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH) flight tickets cheaper when they're purchased at the last minute?
It is possible to get a fantastic last-minute deal from O’Hare Airport to Hilton Head Island Airport (HHH), but it can also be hit-or-miss. As many airlines release prices up to 12 months in advance, it’s worthwhile keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares carrier prices and updates flight deals all the time, so you can be certain you’re always seeing the latest offers.
Hilton Head Island nearby Airports
Chicago nearby Airports
*Available to One Key members.