$143 Cheap Flights from Hilton Head Island (HHH) to Chicago (ORD)

View $143 flight on Tue, Aug 5, 2025Opens in a new window
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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 $143 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 4 - Mon, Jun 9
HHH
Hilton Head Island
ORD
Chicago
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 4 from Hilton Head Island to Chicago, returning Mon, Jun 9, priced at $229 found 1 day ago
Delta
Wed, Jun 4 - Mon, Jun 9
HHH
Hilton Head Island
ORD
Chicago
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 4 from Hilton Head Island to Chicago, returning Mon, Jun 9, priced at $234 found 1 day ago
Delta
Tue, Aug 12 - Tue, Sep 2
HHH
Hilton Head Island
ORD
Chicago
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 12 from Hilton Head Island to Chicago, returning Tue, Sep 2, priced at $239 found 6 days ago
Delta
Tue, Jun 24 - Sat, Jul 5
HHH
Hilton Head Island
ORD
Chicago
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 24 from Hilton Head Island to Chicago, returning Sat, Jul 5, priced at $244 found 1 day ago
Delta
Wed, May 14 - Sun, Jun 1
HHH
Hilton Head Island
ORD
Chicago
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 14 from Hilton Head Island to Chicago, returning Sun, Jun 1, priced at $269 found 1 day ago
Delta
Thu, May 8 - Mon, May 26
HHH
Hilton Head Island
ORD
Chicago
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 8 from Hilton Head Island to Chicago, returning Mon, May 26, priced at $274 found 1 day ago
Delta
Fri, May 2 - Wed, May 7
HHH
Hilton Head Island
ORD
Chicago
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, May 2 from Hilton Head Island to Chicago, returning Wed, May 7, priced at $279 found 5 days ago
Delta
Mon, Jun 9 - Mon, Jun 16
HHH
Hilton Head Island
ORD
Chicago
$281 Roundtrip, found 4 days ago
$281
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jun 9 from Hilton Head Island to Chicago, returning Mon, Jun 16, priced at $281 found 4 days ago
American Airlines
Wed, Jun 4 - Mon, Jun 9
HHH
Hilton Head Island
ORD
Chicago
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 4 from Hilton Head Island to Chicago, returning Mon, Jun 9, priced at $288 found 1 day ago
United
Tue, May 6 - Sat, May 10
HHH
Hilton Head Island
ORD
Chicago
$309 Roundtrip, found 5 days ago
$309
Roundtrip
found 5 days ago
Select United flight, departing Tue, May 6 from Hilton Head Island to Chicago, returning Sat, May 10, priced at $309 found 5 days ago
Flights from Hilton Head Island (HHH) to Chicago (ORD)
Origin airport
Hilton Head Island
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$228
Distance
781 mi

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 June. 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 $143 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.

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to O'Hare Intl. Airport (ORD) cost?
You can book cheap return flights starting from $761 from Hilton Head Island Airport (HHH) to O’Hare Intl. Airport (ORD). 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 HHH on May 17 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from HHH to ORD?
The cheapest flights from HHH to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 HHH to ORD?
Take off from HHH to ORD with United. This carrier currently has the cheapest one-way fare on this route, starting from $224. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from HHH on June 7 2025. Prices were last updated on April 23 2025 and have not changed since.
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.

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*Available to One Key members.