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Hilton Head Island

$153+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
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 November or January, booked 27 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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$153
(American Airlines)

Popular in

August

Cheapest in

November

Average price

$413
Provider with most accurate pricing for Chicago O'Hare Intl-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Hilton Head Island flights.
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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. 7% potential increase in price ($37 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 October 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 October 13, 2025.

This American Airlines deal was found by Cheapflights users on 10/12. 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 11/126:46 amORD - HHH
1 stop7h 11mAmerican Airlines
Sat 11/1511:46 amHHH - ORD
1 stop5h 19mAmerican Airlines
Deal found 10/12$309
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/2510:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Sat 11/11:55 pmHHH - ORD
Nonstop2h 40mAmerican Airlines
Deal found 10/12$319
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/85:00 amORD - HHH
1 stop5h 16mAmerican Airlines
Tue 11/117:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Deal found 10/12$324
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/2510:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Tue 10/283:32 pmHHH - ORD
1 stop6h 38mAmerican Airlines
Deal found 10/12$329
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/810:15 amORD - HHH
2 stops7h 02mAmerican Airlines
Wed 11/123:27 pmHHH - ORD
2 stops8h 06mAmerican Airlines
Deal found 10/12$334
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Sun 11/237:11 amORD - HHH
1 stop6h 08mAmerican Airlines
Tue 12/211:32 amHHH - ORD
1 stop6h 21mAmerican Airlines
Deal found 10/10$336
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 11/105:00 amORD - HHH
1 stop6h 29mAmerican Airlines
Mon 11/171:02 pmHHH - ORD
1 stop7h 37mAmerican Airlines
Deal found 10/11$363

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 October 13, 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

Wed 11/12

8:20 am-2:57 pm

1 stop5h 37m

Hilton Head Island

Sat 11/15

2:51 pm-7:50 pm

1 stop5h 59m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 11/8

5:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Tue 11/11

7:07 pm-11:37 pm

1 stop5h 30m

$324

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Tue 10/28

5:21 pm-10:54 pm

1 stop6h 33m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 11/8

10:15 am-6:17 pm

2 stops7h 02m

Hilton Head Island

Wed 11/12

3:27 pm-10:33 pm

2 stops8h 06m

$334

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 11/22

6:06 am-12:06 pm

1 stop5h 00m

Hilton Head Island

Thu 11/27

11:32 am-3:49 pm

1 stop5h 17m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 11/23

7:11 am-2:19 pm

1 stop6h 08m

Hilton Head Island

Tue 12/2

11:32 am-4:53 pm

1 stop6h 21m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

8:15 am-2:32 pm

1 stop5h 17m

Hilton Head Island

Sat 11/1

11:16 am-5:13 pm

1 stop6h 57m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/10

8:50 pm-12:20 pm

2 stops14h 30m

$153

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 12/9

6:45 pm-12:22 pm

2 stops16h 37m

$219

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 12/14

6:45 pm-12:22 pm

2 stops16h 37m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 12 results
1
2

Compare providers for flights from O'Hare Intl to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 10, 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 26 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, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $139). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in December is currently the most expensive (average of $277). 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 October 13, 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 October 13, 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
8,974 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,974 reviews
United Airlines
7.4
Good
8,974 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,045 reviews
United Airlines
7.4
Good
8,974 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 5h 37m. 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 $273, 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 $379. American Airlines is priced at 37% 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 (67%), Republic Airways (67%) or American Airlines (38%) 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, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $139). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in December is currently the most expensive (average of $277). 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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$273Average$457FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$379Average$498FlexibilityNo cancel feeOn-time69%

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