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Hilton Head Island

$202+ Cheap flights from O'Hare Intl (ORD) to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Hilton Head Island are usually found in September or November, booked 81 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$309
(American Airlines)

One-way from

$202
(Delta)

Popular in

August

Cheapest in

September

Average price

$334
From Chicago O'Hare Intl to Hilton Head Island
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One-way flight from Chicago O'Hare Intl to Hilton Head Island
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Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from O'Hare Intl to Hilton Head Island

Cheapest flights from O'Hare Intl to Hilton Head Island
Explore the most affordable flight options available from O'Hare Intl to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:15 amORD - HHH
1 stop7h 12mAmerican Airlines
Tue 10/283:32 pmHHH - ORD
1 stop4h 38mAmerican Airlines
Deal found 9/10$309
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:00 amORD - HHH
2 stops7h 02mAmerican Airlines
Tue 10/285:21 pmHHH - ORD
2 stops7h 29mAmerican Airlines
Deal found 9/10$319
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Mon 11/37:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Deal found 9/9$327
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2710:00 amORD - HHH
Nonstop2h 27mAmerican Airlines
Sat 10/411:17 amHHH - ORD
1 stop7h 06mAmerican Airlines
Deal found 9/11$329
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:20 amORD - HHH
1 stop5h 12mAmerican Airlines
Thu 10/2311:16 amHHH - ORD
1 stop5h 32mAmerican Airlines
Deal found 9/9$351
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:04 amORD - HHH
1 stop5h 03mAmerican Airlines
Sun 12/1412:21 pmHHH - ORD
1 stop6h 37mAmerican Airlines
Deal found 9/10$352

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Hilton Head Island that are best for you.

Fly from

O'Hare Intl

Fly to

Hilton Head Island

Route

Depart

Return

Price

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

7:10 am-2:32 pm

1 stop6h 22m

Hilton Head Island

Tue 10/28

3:32 pm-7:10 pm

1 stop4h 38m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 10/22

9:20 am-4:51 pm

1 stop6h 31m

Hilton Head Island

Tue 10/28

3:32 pm-9:10 pm

1 stop6h 38m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

5:20 am-11:32 am

1 stop5h 12m

Hilton Head Island

Sat 10/25

11:16 am-3:48 pm

1 stop5h 32m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 11/5

6:46 am-12:29 pm

1 stop4h 43m

Hilton Head Island

Wed 11/12

11:28 am-4:53 pm

1 stop6h 25m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/11

10:35 am-11:37 am

1 stop24h 02m

$202

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 10/7

6:00 am-11:37 am

1 stop28h 37m

$202

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 11/12

6:25 am-6:37 pm

2 stops11h 12m

$218

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 11/11

8:36 pm-12:29 pm

2 stops14h 53m

$218

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 10/7

6:05 pm-10:46 am

2 stops15h 41m

$218

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 11/10

6:45 pm-12:29 pm

2 stops16h 44m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Best time to book a flight from O'Hare Intl to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Hilton Head Island

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Hilton Head Island. Price data was last updated on August 29, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Hilton Head Island, you should look to book at least 81 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $275). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in March is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to HHH?

Find hourly flight availability from O'Hare Intl to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Hilton Head Island as you normally would.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated September 11, 2025.
See what other customers who have flown with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Hilton Head Island have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Chicago O'Hare Intl?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Chicago O'Hare Intl; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Hilton Head Island airport from Chicago O'Hare Intl. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

  • How long is the flight from Chicago O'Hare Intl Airport to Hilton Head Island?

    Departing from Chicago O'Hare Intl Airport to Hilton Head Island will take you 6h 22m. The distance from Chicago O'Hare Intl Airport to Hilton Head Island is about 781 mi.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Hilton Head Island round-trip?

    Currently priced at $263, American Airlines will fly you from Chicago O'Hare Intl Airport to Hilton Head Island and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $273. American Airlines is priced at 40% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Hilton Head Island?

    No one likes to see their flight delayed. When booking a flight from Chicago O'Hare Intl Airport to Hilton Head Island consider choosing United Airlines (86%), Republic Airways (86%) or American Airlines (40%) as they are the most reliable in getting you off to your destination on time.

  • Can I find deals for flights from O'Hare Intl to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Hilton Head Island.

  • Can I find deals for business class flights from O'Hare Intl to Hilton Head Island?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $275). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in March is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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Top 2 airlines flying from O'Hare Intl to Hilton Head Island

Discover the top 2 airlines that operate flights from O'Hare Intl to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$263Average$440FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$498FlexibilityNo cancel feeOn-time69%

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