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Hilton Head Island

$158+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 57 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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$158
(American Airlines)

Popular in

August

Cheapest in

November

Average price

$346

Good round-trip deal

$299 or less
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 ($36 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 November 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Hilton Head Island.
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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 November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/24. 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.
Tue 12/96:45 amORD - HHH
1 stop4h 37mAmerican Airlines
Sat 12/1311:47 amHHH - ORD
1 stop7h 11mAmerican Airlines
Deal found 11/24$369
This American Airlines deal was found by Cheapflights users on 11/26. 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 12/297:11 amORD - HHH
1 stop6h 05mAmerican Airlines
Mon 1/52:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Deal found 11/26$394
This American Airlines deal was found by Cheapflights users on 11/26. 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 12/15:00 amORD - HHH
1 stop5h 49mAmerican Airlines
Wed 12/1012:52 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Deal found 11/26$397
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Thu 12/1110:29 amORD - HHH
1 stop6h 52mAmerican Airlines
Mon 12/1512:52 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Deal found 11/25$425
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Thu 12/257:11 amORD - HHH
1 stop6h 05mAmerican Airlines
Thu 1/111:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 11/25$464
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Tue 12/307:11 amORD - HHH
1 stop6h 05mAmerican Airlines
Thu 1/12:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Deal found 11/25$523

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 November 26, 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 5/23

8:49 am-3:41 pm

1 stop5h 52m

Hilton Head Island

Sat 5/30

3:55 pm-10:49 pm

1 stop7h 54m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 2/11

6:39 am-2:59 pm

2 stops7h 20m

Hilton Head Island

Wed 2/18

3:35 pm-10:20 pm

2 stops7h 45m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 1/6

5:05 am-2:59 pm

2 stops8h 54m

Hilton Head Island

Sat 1/10

12:54 pm-10:16 pm

2 stops10h 22m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Fri 2/13

11:02 am-2:15 pm

1 stop4h 13m

$333

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/12

10:28 am-5:52 pm

1 stop6h 24m

Hilton Head Island

Tue 2/17

12:22 pm-4:39 pm

1 stop5h 17m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

10:10 am-2:59 pm

1 stop3h 49m

Hilton Head Island

Sat 1/31

12:54 pm-6:01 pm

1 stop6h 07m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 1/2

5:00 am-10:44 am

1 stop4h 44m

Hilton Head Island

Tue 1/6

12:51 pm-6:01 pm

1 stop6h 10m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 4/25

12:07 pm-5:36 pm

1 stop4h 29m

Hilton Head Island

Sat 5/2

6:07 pm-11:50 pm

1 stop6h 43m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 5/2

5:10 am-10:14 am

1 stop4h 04m

Hilton Head Island

Sat 5/9

4:05 pm-9:22 pm

1 stop6h 17m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/24

10:35 am-2:01 pm

Nonstop2h 26m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 18 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Hilton Head Island flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 21, 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 37 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 May is currently the most expensive (average of $271). 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.

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 November 26, 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
9,050 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,050 reviews
United Airlines
7.4
Good
9,050 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,038 reviews
United Airlines
7.4
Good
9,050 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 52m. 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 $278, 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 $299. American Airlines is priced at 36% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Hilton Head Island?

    The cheapest flight price from Chicago O'Hare Intl Airport to Hilton Head Island is $209. On average you can expect to pay $379. The most popular route, (Chicago O'Hare Intl - Hilton Head Island), can usually be booked for $309.

  • 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 May is currently the most expensive (average of $271). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$278Average$455FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$299Average$498FlexibilityNo cancel feeOn-time69%

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