$141 Cheap Flights from Chicago (ORD) to Hilton Head Island (HHH)

View $141 flight on Thu, Jul 3, 2025Opens in a new window

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $141 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jun 11 - Tue, Jul 1
ORD
Chicago
HHH
Hilton Head Island
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Delta flight, departing Wed, Jun 11 from Chicago to Hilton Head Island, returning Tue, Jul 1, priced at $229 just found
Delta
Sun, Jun 15 - Tue, Jul 1
ORD
Chicago
HHH
Hilton Head Island
$234 Roundtrip, just found
$234
Roundtrip
just found
Select Delta flight, departing Sun, Jun 15 from Chicago to Hilton Head Island, returning Tue, Jul 1, priced at $234 just found
Delta
Wed, Jun 11 - Wed, Jun 18
ORD
Chicago
HHH
Hilton Head Island
$239 Roundtrip, just found
$239
Roundtrip
just found
Select Delta flight, departing Wed, Jun 11 from Chicago to Hilton Head Island, returning Wed, Jun 18, priced at $239 just found
Delta
Wed, Jun 25 - Tue, Jul 1
ORD
Chicago
HHH
Hilton Head Island
$239 Roundtrip, found 1 hour ago
$239
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Jun 25 from Chicago to Hilton Head Island, returning Tue, Jul 1, priced at $239 found 1 hour ago
Delta
Tue, Jun 10 - Wed, Jun 18
ORD
Chicago
HHH
Hilton Head Island
$244 Roundtrip, just found
$244
Roundtrip
just found
Select Delta flight, departing Tue, Jun 10 from Chicago to Hilton Head Island, returning Wed, Jun 18, priced at $244 just found
Delta
Wed, May 7 - Tue, May 13
ORD
Chicago
HHH
Hilton Head Island
$249 Roundtrip, found 7 hours ago
$249
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, May 7 from Chicago to Hilton Head Island, returning Tue, May 13, priced at $249 found 7 hours ago
Delta
Mon, Jul 28 - Mon, Aug 4
ORD
Chicago
HHH
Hilton Head Island
$269 Roundtrip, found 5 hours ago
$269
Roundtrip
found 5 hours ago
Select Delta flight, departing Mon, Jul 28 from Chicago to Hilton Head Island, returning Mon, Aug 4, priced at $269 found 5 hours ago
Delta
Wed, Sep 24 - Tue, Sep 30
ORD
Chicago
HHH
Hilton Head Island
$274 Roundtrip, found 2 hours ago
$274
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Hilton Head Island, returning Tue, Sep 30, priced at $274 found 2 hours ago
American Airlines
Thu, May 29 - Mon, Jun 2
ORD
Chicago
HHH
Hilton Head Island
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 29 from Chicago to Hilton Head Island, returning Mon, Jun 2, priced at $279 found 1 day ago
United
Wed, May 7 - Mon, May 12
ORD
Chicago
HHH
Hilton Head Island
$282 Roundtrip, found 1 day ago
$282
Roundtrip
found 1 day ago
Select United flight, departing Wed, May 7 from Chicago to Hilton Head Island, returning Mon, May 12, priced at $282 found 1 day ago
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
$228
Distance
781 mi

Chicago to Hilton Head Island Flights

The cheapest times to fly from Chicago to Hilton Head Island

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Hilton Head Island are during the month of June. You can find some of the cheapest flights from Chicago to Hilton Head Island with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Hilton Head Island

Sunday is one of the best days to book for cheap flights from Chicago to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Hilton Head Island

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Hilton Head Island in 2025. You can also book with separate airlines for your outbound and return journeys, from $141 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH) cost?
You can pick up cheap return fares starting from $328 from O’Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on April 26 2025 and touching down at HHH. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from ORD to HHH?
The cheapest flights from ORD to HHH are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to HHH?
With prices starting from $224 for a one-way journey from ORD to HHH, United is currently the cheapest airline operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on May 10 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH)?
There aren’t any daily direct flights departing from O’Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you’ll be soaring above the clouds before you know it.
What day of the week has the most flights from ORD to HHH?
Usually you’ll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH) route, fly before 3 PM. Later departures have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Hilton Head Island from O'Hare Intl. Airport (ORD)?
If you’re taking a direct flight from O’Hare Intl. Airport (ORD) to Hilton Head Island, Savannah - Hilton Head Intl. Airport (SAV) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH) last-minute?
Last-minute fares from ORD to HHH are typically more expensive. To lock in the best prices, start looking for flights ahead of time. That said, if you can play around with your travel dates, you may land a cheap fare right before you leave.
Is it cheaper to book an ORD to HHH flight and hotel package?
You’ll typically save money by securing an ORD to HHH flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one place. After selecting your preferred accommodations and flights, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Hilton Head Island Airport (HHH)?
Typically, you’re able to cancel or reschedule your ORD to HHH flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline’s fees and guidelines on flight changes, or if you’d like more information, visit our Customer Service portal.

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*Available to One Key members.