$182 Cheap Flights from Hilton Head Island (HHH) to Chicago (ORD)

View $182 flight on Tue, Dec 23, 2025Opens in a new window

Popular airlines from Hilton Head Island Airport (HHH) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $182 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 25 - Mon, Aug 31
HHH
Hilton Head Island
ORD
Chicago
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 25 from Hilton Head Island to Chicago, returning Mon, Aug 31, priced at $249 found 5 days ago
American Airlines
Sat, Dec 13 - Mon, Dec 15
HHH
Hilton Head Island
ORD
Chicago
$288 Roundtrip, found 3 days ago
$288
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Chicago, returning Mon, Dec 15, priced at $288 found 3 days ago
American Airlines
Sat, Dec 13 - Mon, Dec 15
HHH
Hilton Head Island
ORD
Chicago
$296 Roundtrip, found 3 days ago
$296
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Chicago, returning Mon, Dec 15, priced at $296 found 3 days ago
American Airlines
Wed, Dec 3 - Fri, Dec 5
HHH
Hilton Head Island
ORD
Chicago
$298 Roundtrip, found 6 days ago
$298
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Dec 3 from Hilton Head Island to Chicago, returning Fri, Dec 5, priced at $298 found 6 days ago
American Airlines
Sat, Dec 13 - Mon, Dec 15
HHH
Hilton Head Island
ORD
Chicago
$298 Roundtrip, found 3 days ago
$298
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Chicago, returning Mon, Dec 15, priced at $298 found 3 days ago
American Airlines
Sat, Dec 13 - Mon, Dec 15
HHH
Hilton Head Island
ORD
Chicago
$303 Roundtrip, found 3 days ago
$303
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Chicago, returning Mon, Dec 15, priced at $303 found 3 days ago
American Airlines
Thu, Dec 4 - Sun, Dec 7
HHH
Hilton Head Island
ORD
Chicago
$306 Roundtrip, found 20 hours ago
$306
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Dec 4 from Hilton Head Island to Chicago, returning Sun, Dec 7, priced at $306 found 20 hours ago
American Airlines
Sat, Dec 13 - Mon, Dec 15
HHH
Hilton Head Island
ORD
Chicago
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Chicago, returning Mon, Dec 15, priced at $307 found 3 days ago
American Airlines
Wed, Jun 24 - Sat, Jun 27
HHH
Hilton Head Island
ORD
Chicago
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 24 from Hilton Head Island to Chicago, returning Sat, Jun 27, priced at $309 found 1 day ago
United
Sat, Mar 28 - Tue, Mar 31
HHH
Hilton Head Island
ORD
Chicago
$594 Roundtrip, found 1 day ago
$594
Roundtrip
found 1 day ago
Select United flight, departing Sat, Mar 28 from Hilton Head Island to Chicago, returning Tue, Mar 31, priced at $594 found 1 day ago

Find the cheapest month to fly from Hilton Head Island (HHH) to Chicago (ORD)

November is typically the cheapest month to fly

From $223 - $916 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $325
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $325

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $182 or cheap return flight from $249 from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
Planning your trip for August may help you find better deals, as it's the cheapest month for flights between HHH and ORD. You'll typically find the lowest fares during off-peak months.
Which airlines fly direct from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
There aren't any direct flights from Hilton Head Island, SC (HHH) to O'Hare Intl. Airport (ORD). However, you'll find other airports offering nonstop flights. Board your plane at Charleston Intl. Airport (CHS) and travel straight to Chicago without a layover.
What is the cheapest airline that flies from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from HHH to ORD. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
There aren't any daily direct flights from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from HHH to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) without delays, opt for a flight that takes off from Hilton Head Island Airport (HHH) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
Is it cheaper to buy a plane ticket from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from HHH to ORD often results in higher prices. While you may find some last-minute deals, there's no guarantee. Keep your travel schedule open for the best chance of scoring a bargain.
Is it cheaper to book a HHH to ORD flight and hotel package?
You can save money by booking a HHH to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've selected your preferred accommodations and flights, consider adding extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD)?
If you booked your HHH to ORD flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Origin airport
Hilton Head Island
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$248
Distance
781 mi

Book with confidence

Hilton Head Island to Chicago Flights

The cheapest times to fly from Hilton Head Island to Chicago

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 Hilton Head Island to Chicago are during the month of August. You can find some of the cheapest flights from Hilton Head Island to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Hilton Head Island to Chicago: 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 Hilton Head Island to Chicago

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 Hilton Head Island to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $182 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 Hilton Head Island to Chicago 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 Hilton Head Island to Chicago 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.

 

Hilton Head Island to Chicago Flights

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