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Hilton Head Island

$164+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
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 January or November, booked 57 days in advance, depart on a Monday or Tuesday and return on a Monday

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 enero 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$164
(American Airlines)

Popular in

August

Cheapest in

January

Average price

$316

Good round-trip deal

$279 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. 8% potential increase in price ($40 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 January 2026
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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 enero 8, 2026.

This United Airlines deal was found by Cheapflights users on 1/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/1910:35 amORD - HHH
Nonstop2h 26mUnited Airlines
sáb. 9/263:00 pmHHH - ORD
Nonstop2h 45mUnited Airlines
Deal found 1/7$220
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/287:10 amORD - HHH
1 stop7h 10mDelta
mar. 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$229
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/297:10 amORD - HHH
1 stop7h 10mDelta
mar. 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$269
This United Airlines deal was found by Cheapflights users on 1/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/2710:35 amORD - HHH
Nonstop2h 26mUnited Airlines
mié. 8/53:00 pmHHH - ORD
Nonstop2h 45mUnited Airlines
Deal found 1/6$279
This American Airlines deal was found by Cheapflights users on 1/7. 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.
sáb. 9/1910:07 amORD - HHH
Nonstop2h 24mAmerican Airlines
sáb. 9/264:03 pmHHH - ORD
1 stop6h 18mAmerican Airlines
Deal found 1/7$299
This American Airlines deal was found by Cheapflights users on 1/7. 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.
sáb. 8/158:35 amORD - HHH
1 stop4h 37mAmerican Airlines
sáb. 8/226:15 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Deal found 1/7$309
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/279:30 amORD - HHH
1 stop4h 50mDelta
mar. 8/44:00 pmHHH - ORD
1 stop7h 43mDelta
Deal found 1/6$334
This American Airlines deal was found by Cheapflights users on 1/7. 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.
lun. 3/168:10 amORD - HHH
1 stop5h 12mAmerican Airlines
sáb. 3/214:31 pmHHH - ORD
1 stop5h 44mAmerican Airlines
Deal found 1/7$336
This American Airlines deal was found by Cheapflights users on 1/7. 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.
sáb. 1/318:50 pmORD - HHH
2 stops14h 30mAmerican Airlines
lun. 2/212:51 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Deal found 1/7$337

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 enero 8, 2026.
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

vie. 3/13

7:12 am-2:22 pm

1 stop6h 10m

Hilton Head Island

sáb. 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

lun. 3/16

8:10 am-2:22 pm

1 stop5h 12m

Hilton Head Island

sáb. 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

sáb. 1/31

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

lun. 2/2

12:51 pm-6:01 pm

1 stop6h 10m

$337

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

mié. 2/4

8:12 am-2:59 pm

1 stop5h 47m

Hilton Head Island

mié. 2/11

12:51 pm-6:01 pm

1 stop6h 10m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

vie. 3/13

9:48 am-3:41 pm

1 stop4h 53m

Hilton Head Island

lun. 3/16

6:15 pm-12:06 am

1 stop6h 51m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

jue. 2/5

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

jue. 2/12

6:20 pm-12:16 am

1 stop6h 56m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

vie. 2/13

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

dom. 2/15

11:03 am-6:04 pm

2 stops8h 01m

$368

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

mar. 2/3

8:50 pm-2:59 pm

2 stops17h 09m

Hilton Head Island

mié. 2/11

3:29 pm-7:50 pm

1 stop5h 21m

$384

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

mar. 2/3

7:21 pm-12:20 pm

2 stops15h 59m

Hilton Head Island

mar. 2/10

3:29 pm-7:50 pm

1 stop5h 21m

$384

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

mar. 3/3

8:49 pm-11:53 am

2 stops14h 04m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 20 results
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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 January.
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 January 2, 2026.

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 $269). 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 enero 8, 2026.
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
9,139 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,139 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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 10m. 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 $279, United Airlines will fly you from Chicago O'Hare Intl Airport to Hilton Head Island and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $288. United Airlines is priced at 35% 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 $279. The most popular route, (Chicago O'Hare Intl - Hilton Head Island), can usually be booked for $249.

  • 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 $269). 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.

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Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
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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 enero 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$279Average$498FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$456FlexibilityNo cancel feeOn-time71%

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