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$189 Cheap Flights from Chicago (ORD) to Hilton Head Island (HHH)

View $189 flight on Fri, Jan 1, 2027Opens in a new window

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

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

Prices were available within the past 7 days and start at $189 for one-way flights and $279 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Sep 9 - Wed, Sep 23
ORD
Chicago
HHH
Hilton Head Island
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 9 from Chicago to Hilton Head Island, returning Wed, Sep 23, priced at $279 found 1 day ago
American Airlines
Sat, Oct 31 - Thu, Nov 5
ORD
Chicago
HHH
Hilton Head Island
$289 Roundtrip, found 6 hours ago
$289
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Oct 31 from Chicago to Hilton Head Island, returning Thu, Nov 5, priced at $289 found 6 hours ago
Delta
Wed, Sep 30 - Tue, Oct 6
ORD
Chicago
HHH
Hilton Head Island
$299 Roundtrip, found 20 hours ago
$299
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Sep 30 from Chicago to Hilton Head Island, returning Tue, Oct 6, priced at $299 found 20 hours ago
American Airlines
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
HHH
Hilton Head Island
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 4 from Chicago to Hilton Head Island, returning Sun, Sep 6, priced at $299 found 1 day ago
Delta
Wed, Sep 30 - Wed, Oct 7
ORD
Chicago
HHH
Hilton Head Island
$304 Roundtrip, found 20 hours ago
$304
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Sep 30 from Chicago to Hilton Head Island, returning Wed, Oct 7, priced at $304 found 20 hours ago
American Airlines
Sat, Oct 31 - Thu, Nov 5
ORD
Chicago
HHH
Hilton Head Island
$309 Roundtrip, found 6 hours ago
$309
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Oct 31 from Chicago to Hilton Head Island, returning Thu, Nov 5, priced at $309 found 6 hours ago
Delta
Wed, Sep 30 - Mon, Oct 5
ORD
Chicago
HHH
Hilton Head Island
$319 Roundtrip, found 20 hours ago
$319
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Sep 30 from Chicago to Hilton Head Island, returning Mon, Oct 5, priced at $319 found 20 hours ago
American Airlines
Sat, Sep 19 - Sat, Sep 26
ORD
Chicago
HHH
Hilton Head Island
$319 Roundtrip, found 18 hours ago
$319
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Sat, Sep 19 from Chicago to Hilton Head Island, returning Sat, Sep 26, priced at $319 found 18 hours ago
Delta
Sat, Oct 3 - Wed, Oct 7
ORD
Chicago
HHH
Hilton Head Island
$324 Roundtrip, found 20 hours ago
$324
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Oct 3 from Chicago to Hilton Head Island, returning Wed, Oct 7, priced at $324 found 20 hours ago
American Airlines
Sat, Sep 19 - Sat, Sep 26
ORD
Chicago
HHH
Hilton Head Island
$329 Roundtrip, found 18 hours ago
$329
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Sat, Sep 19 from Chicago to Hilton Head Island, returning Sat, Sep 26, priced at $329 found 18 hours ago

Alternative airports near Hilton Head Island

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

Select flight to Savannah - Hilton Head Intl. SAV. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $534
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $534

What you need to know for your flight from O'Hare Intl. to Hilton Head Island

Chicago (ORD) to Hilton Head Island (HHH) at a glance

Explore a range of airlines providing flights from Chicago (ORD) to Hilton Head Island (HHH) on this domestic short-haul route. Compare various options, from full-service carriers to budget-friendly alternatives, to discover the itinerary that aligns with your budget and travel plans. Whether you’re looking for the quickest flight time or the most convenient next flight, you'll find essential details for your journey from O'Hare International Airport to Hilton Head Island Airport as you prepare to experience the island's renowned attractions.

  • Fastest flight duration: around 2h 30m non-stop
  • Route distance: roughly 800 miles (1,290 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $130–$385, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Hilton Head Island Airport (HHH)

According to the latest traveler bookings, the most popular airlines flying from Chicago to Hilton Head Island often offer both one-stop and non-stop options. Common layover points include Charlotte-Douglas International Airport (CLT) with a layover of about 1 hour and 30 minutes, Hartsfield-Jackson Atlanta International Airport (ATL) with around a 1 hour and 15 minutes layover, and Newark Liberty International Airport (EWR) also with a 1 hour and 15 minutes layover. This variety allows you to customize your travel plans based on price, total travel time, and cabin class for the ideal itinerary.

  • American Airlines: As a major full-service airline, American Airlines provides both non-stop and one-stop options, with one-way prices generally falling between $135 and $430. It dominates this route, representing about 75% of departures, typically offering a 1-stop flight time of 3h 15m and an overall travel duration of around 4h 45m.
  • United: Another full-service option, United offers non-stop and one-stop flights, with one-way fares usually ranging from $130 to $300. This airline makes up roughly 19% of the departures on this route, featuring non-stop flight times of about 2h 30m.
  • Delta: Delta operates as a full-service carrier providing one-stop flights, with one-way fares often between $135 and $375. It accounts for approximately 5% of the departures on this route, with an in-flight duration of 3h 15m, leading to a total travel time of about 4h 45m, including layover time.

Travelers have the option to upgrade their flight from Chicago to Hilton Head Island, with American Airlines providing first-class service on this route for an enhanced travel experience.

Alternative routes from Chicago (ORD) to Hilton Head Island (HHH)

  • Chicago to Savannah (ORD-SAV): Savannah - Hilton Head International Airport (SAV) is located approximately 31 miles from Hilton Head Island Airport (HHH). One-way economy fares on this route generally vary between $80 and $420, influenced by the season and timing of the booking. Travelers can choose from both non-stop and one-stop flights on this route. Major airlines serving this route include United and American Airlines, with first-class service also available.
  • Chicago to Savannah (MDW-SAV): Midway International Airport (MDW) is situated about 16 miles from O'Hare International Airport (ORD), while Savannah - Hilton Head International Airport (SAV) is approximately 31 miles from Hilton Head Island Airport (HHH). One-way economy tickets for this journey typically range from $110 to $430, depending on the time of year and when tickets are purchased. This route features both non-stop and one-stop flight options. Leading airlines on this route include low-cost carrier Southwest Airlines and Delta.

How to find the best prices for flights from Chicago (ORD) to Hilton Head Island (HHH)

Getting some of the best deals on flights from Chicago to Hilton Head Island is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which coincides with when most travelers make their reservations. Morning departures between 5 a.m. and 12 p.m. tend to offer lower prices and are the most popular flight times. Additionally, flying on Tuesday generally results in cheaper prices, although Saturday remains the most popular travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Hilton Head Island hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Hilton Head Island Airport from O'Hare International Airport

Hilton Head Island welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Hilton Head Island efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Hilton Head Island, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Hilton Head Island Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hilton Head Island Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Hilton Head Island Airport, St Phillips Island Seaport, a seaport, is located about 6.4 miles from the airport.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) cost?
You can find cheap one-way flights from $189 and cheap return flights from $279 Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) with Expedia. One-way flights typically cost between $114 and $799, and return flights often range between $402 and $1319. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
The cheapest month to fly from ORD to HHH is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
There are 2 airlines offering direct flights from ORD to HHH:

  • United operates around 7 direct flights from ORD to HHH every week
  • American Airlines operates around 8 direct flights from ORD to HHH every week

What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
United is one of the cheapest airlines offering nonstop flights from Chicago, IL (ORD) to Hilton Head Island, SC (HHH), with round-trip tickets starting from around $551. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
On average, there are around 1 nonstop flights per day from O'Hare Intl. (ORD) to (HHH). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from ORD to HHH. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
The most popular departure times for flights from Chicago (ORD) to Hilton Head Island (HHH) are in the early morning, from 6am to 9am. About 28% of passengers prefer this time window. Many major carriers, including American Airlines and Delta Airlines, offer flights during this window. This timing is popular because it allows travelers to arrive at their destination early in the day.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
Direct flights from ORD to HHH usually take about 2 hours 30 minutes, traveling roughly 781 miles. If you opt for a connecting flight, expect to add around 2 hours to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
You can fly first class between ORD and HHH. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines

How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) Hilton Head Island Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Hilton Head Island, SC (HHH) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Hilton Head Island
Airlines serving
American Airlines, Delta, United
Roundtrip price
$279
Distance
781 mi
Average flight time
3 hours 30 mins

Book with confidence

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 September. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $189 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.

 

Chicago to Hilton Head Island Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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