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O'Hare Intl

$215+ Cheap flights from Hilton Head Island (HHH) to O'Hare Intl (ORD)

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Hilton Head Island to O'Hare Intl

Cheapest flights from Hilton Head Island to O'Hare Intl
Explore the most affordable flight options available from Hilton Head Island to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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 12/302:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Sat 1/35:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/14$526
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/2111:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Tue 12/235:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/16$742
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/212:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Sat 12/275:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/16$785
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/196:13 pmHHH - ORD
1 stop5h 21mAmerican Airlines
Fri 12/265:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/15$839

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

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to O'Hare Intl (ORD). 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 December 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$215
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Chicago O'Hare Intl flights.
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From Hilton Head Island to Chicago O'Hare Intl
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One-way flight from Hilton Head Island to Chicago O'Hare Intl
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to O'Hare Intl 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 December 16, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Chicago O'Hare Intl Airport that are best for you.

Fly from

Hilton Head Island

Fly to

O'Hare Intl

Route

Depart

Return

Price

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/22

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/29

10:35 am-2:01 pm

Nonstop2h 26m

$249

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/22

12:00 pm-4:44 pm

1 stop5h 44m

Chicago O'Hare Intl

Wed 4/29

9:30 am-3:18 pm

1 stop4h 48m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

4:00 pm-9:48 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 4/22

7:10 am-3:18 pm

1 stop7h 08m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/22

10:35 am-2:01 pm

Nonstop2h 26m

$297

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/1

4:11 pm-9:22 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 4/8

8:25 am-2:20 pm

1 stop4h 55m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/17

12:22 pm-4:39 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 2/24

9:45 am-3:05 pm

1 stop4h 20m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

2:58 pm-7:48 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 2/17

6:40 am-3:05 pm

2 stops7h 25m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:02 am-4:06 pm

1 stop6h 04m

Chicago O'Hare Intl

Sat 2/21

5:35 am-2:27 pm

2 stops7h 52m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 1/17

3:29 pm-10:50 am

2 stops20h 21m

$215

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 3/7

2:50 pm-4:25 pm

Nonstop2h 35m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 16 results
1
2

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

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 Hilton Head Island to O'Hare Intl in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Hilton Head Island-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Chicago O'Hare Intl Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Hilton Head Island-Chicago O'Hare Intl Airport 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 Hilton Head Island to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Hilton Head Island 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 Hilton Head Island to Chicago O'Hare Intl Airport

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

Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Chicago O'Hare Intl Airport (average of $113). Flying from Hilton Head Island to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $307). 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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated December 16, 2025.
Peruse reviews from past customers who have flown with American Airlines from Hilton Head Island to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,049 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Overall

7.2

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,049 reviews
American Airlines
7.2
Good
11,049 reviews

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Overall

7.2

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to O'Hare Intl. 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 from for flights from Hilton Head Island to Chicago O'Hare Intl?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly out of when you book flights from Hilton Head Island to Chicago O'Hare Intl. 1 airline have flights from Hilton Head to Chicago O'Hare Intl on a regular basis. Booking flights from Hilton Head Island to Chicago O'Hare Intl should not be difficult; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day.

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

    Departing from Hilton Head Island to Chicago O'Hare Intl Airport will take you 2h 45m. Hilton Head Island and Chicago O'Hare Intl Airport are separated by a distance of 781 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Hilton Head Island to Chicago O'Hare Intl Airport round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $228.

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

    Consider American Airlines (67%), Qatar Airways (67%) or Envoy Air (67%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago O'Hare Intl Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to O'Hare Intl 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 Hilton Head Island to Chicago O'Hare Intl Airport?

    Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Chicago O'Hare Intl Airport (average of $113). Flying from Hilton Head Island to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $307). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Top airline flying from Hilton Head Island to O'Hare Intl

Discover the top airline that operate flights from Hilton Head Island to O'Hare Intl. 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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