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Hilton Head Island

$174+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
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 April or October, booked 50 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap 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 July 23, 2026.

This American Airlines deal was found by Cheapflights users on 7/18. 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 8/158:51 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Mon 8/171:52 pm
HHH
-
ORD
Nonstop2h 38m
American Airlines
Deal found 7/18$269
This American Airlines deal was found by Cheapflights users on 7/19. 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 10/245:18 am
ORD
-
HHH
1 stop4h 47m
American Airlines
Sat 10/311:50 pm
HHH
-
ORD
Nonstop2h 44m
American Airlines
Deal found 7/19$279
This Delta deal was found by Cheapflights users on 7/19. 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.
Mon 9/217:05 am
ORD
-
HHH
2 stops7h 22m
Delta
Tue 9/294:17 pm
HHH
-
ORD
1 stop7h 01m
Delta
Deal found 7/19$294
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 8/79:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Fri 8/1410:57 am
HHH
-
ORD
1 stop7h 17m
American Airlines
Deal found 7/22$299
This Delta deal was found by Cheapflights users on 7/19. 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.
Mon 9/217:05 am
ORD
-
HHH
2 stops7h 22m
Delta
Wed 9/3012:17 pm
HHH
-
ORD
2 stops11h 01m
Delta
Deal found 7/19$300
This Delta deal was found by Cheapflights users on 7/21. 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.
Tue 9/16:59 am
ORD
-
HHH
2 stops7h 33m
Delta
Wed 9/912:17 pm
HHH
-
ORD
1 stop5h 20m
Delta
Deal found 7/21$304
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Fri 8/79:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Mon 8/101:52 pm
HHH
-
ORD
Nonstop2h 38m
American Airlines
Deal found 7/19$309
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Sat 9/510:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Mon 9/142:48 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Deal found 7/20$315
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 8/318:05 am
ORD
-
HHH
1 stop6h 27m
Delta
Tue 9/812:17 pm
HHH
-
ORD
2 stops9h 13m
Delta
Deal found 7/21$324

Find 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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$174
(United Airlines)

Popular in

March

Cheapest in

April

Average price

$469

Good round-trip deal

$324 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
Search Deals
One-way flight from Chicago O'Hare Intl to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Hilton Head Island.
Search Deals

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 July 23, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 10/7

8:05 am-3:26 pm

1 stop6h 21m

Hilton Head Island

Mon 10/12

12:15 pm-4:57 pm

1 stop5h 42m

$339
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 7/29

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Sat 8/1

3:05 pm-4:51 pm

Nonstop2h 46m

$389

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 7/30

7:05 am-3:29 pm

2 stops7h 24m

Hilton Head Island

Tue 8/4

4:18 pm-10:24 pm

1 stop7h 06m

$414

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 8/15

6:00 am-3:32 pm

2 stops8h 32m

Hilton Head Island

Tue 8/18

12:15 pm-4:51 pm

1 stop5h 36m

$419

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 9/13

5:00 am-12:59 pm

1 stop6h 59m

Hilton Head Island

Thu 9/17

2:48 pm-5:05 pm

Nonstop3h 17m

$432

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 8/15

6:00 am-3:32 pm

2 stops8h 32m

Hilton Head Island

Wed 8/19

12:15 pm-8:30 pm

2 stops9h 15m

$459

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 9/11

7:05 am-3:27 pm

2 stops7h 22m

Hilton Head Island

Mon 9/14

12:17 pm-8:30 pm

2 stops9h 13m

$461

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 8/28

6:59 am-3:32 pm

2 stops7h 33m

Hilton Head Island

Sun 8/30

12:15 pm-6:49 pm

1 stop7h 34m

$469

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 8/5

6:59 am-3:32 pm

2 stops7h 33m

Hilton Head Island

Tue 8/11

12:15 pm-8:49 pm

2 stops9h 34m

$484
Cheapest one-way
Quickest one-way

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/24

10:35 am-2:13 pm

Nonstop2h 38m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 20 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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?

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 49 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, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $369). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in March is currently the most expensive (average of $633). 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 July 23, 2026.

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.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Hilton Head Island?

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 July 23, 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
10,024 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
10,024 reviews
United Airlines
7.4
Good
10,024 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,832 reviews
United Airlines
7.4
Good
10,024 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

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 1 inbound flight 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 2h 36m. The distance from Chicago O'Hare Intl Airport to Hilton Head Island is about 781 mi. This flight may include one or multiple stops.

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

    Currently priced at $209, 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 $289. United Airlines is priced at 54% 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 Envoy Air (89%), United Airlines (87%) or American Airlines (69%) as they are the most reliable in getting you off to your destination on time.

  • 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 $269. On average you can expect to pay $359. The most popular route, (Chicago O'Hare Intl - Hilton Head Island), can usually be booked for $269.

  • 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, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Hilton Head Island (average of $369). Flying from Chicago O'Hare Intl Airport to Hilton Head Island in March is currently the most expensive (average of $633). 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

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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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$429FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$472FlexibilityNo cancel feeOn-time71%

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