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Hilton Head Island

$203+ Cheap flights from Chicago (CHI) 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to Hilton Head Island with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Hilton Head Island are usually found in January or September, booked 71 days in advance, depart on a Monday or Tuesday and return on a Monday

Find flight deals from Chicago to Hilton Head Island

Cheapest flights from Chicago to Hilton Head Island
Explore the most affordable flight options available from Chicago to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 10/299:20 amORD - HHH
1 stop4h 42mAmerican Airlines
Sat 11/11:55 pmHHH - ORD
Nonstop2h 40mAmerican Airlines
Deal found 10/28$359
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/110:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Mon 11/311:28 amHHH - ORD
1 stop4h 50mAmerican Airlines
Deal found 10/28$367
This American Airlines deal was found by Cheapflights users on 10/30. 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 10/30$379
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/2310:09 pmORD - HHH
2 stops11h 35mAmerican Airlines
Wed 12/3111:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 10/29$402
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/258:03 amORD - HHH
1 stop5h 13mAmerican Airlines
Mon 12/292:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Deal found 10/28$403

Cheap flight deals from Chicago to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$307
(American Airlines)

One-way from

$203
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$617
Provider with most accurate pricing for Chicago (CHI)-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Hilton Head Island flights.
Search Deals
From Chicago (CHI) to Hilton Head Island
Search Deals
One-way flight from Chicago (CHI) to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 30, 2025.
Use the filters below to find and compare flights from Chicago to Hilton Head Island that are best for you.

Fly from

Chicago

Fly to

Hilton Head Island

Route

Depart

Return

Price

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

8:49 pm-12:20 pm

2 stops14h 31m

Hilton Head Island

Sat 1/31

12:54 pm-6:01 pm

1 stop6h 07m

$307

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 1/23

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Tue 1/27

3:29 pm-10:34 pm

2 stops8h 05m

$341

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 1/16

10:10 am-2:59 pm

1 stop3h 49m

Hilton Head Island

Mon 1/19

3:29 pm-7:50 pm

1 stop5h 21m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 1/9

10:10 am-2:59 pm

1 stop3h 49m

Hilton Head Island

Fri 1/16

12:51 pm-10:34 pm

2 stops10h 43m

$368

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 11/8

9:53 am-6:17 pm

2 stops7h 24m

Hilton Head Island

Wed 11/12

1:02 pm-5:52 pm

1 stop5h 50m

$374

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 12/23

10:09 pm-10:44 am

2 stops11h 35m

Hilton Head Island

Wed 12/31

11:14 am-4:05 pm

1 stop5h 51m

$402

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 12/25

8:03 am-2:16 pm

1 stop5h 13m

Hilton Head Island

Mon 12/29

2:46 pm-7:22 pm

1 stop5h 36m

$403

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/24

8:50 pm-12:20 pm

2 stops14h 30m

$223

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 1/27

8:50 pm-2:59 pm

2 stops17h 09m

$223

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/26

8:50 pm-12:20 pm

2 stops14h 30m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 14 results
1
2

Compare providers for flights from Chicago 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 Chicago to Hilton Head Island in October.
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-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-Hilton Head Island flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Chicago 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 to Hilton Head Island

How far ahead should I book a flight from Chicago to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Hilton Head Island. Price data was last updated on October 24, 2025.

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Hilton Head Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Hilton Head Island?

Currently, May is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $46). Flying from Chicago to Hilton Head Island in December is currently the most expensive (average of $256). 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 CHI to HHH?

Find hourly flight availability from Chicago 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 30, 2025.

It’s typically best to fly out from Chicago to Hilton Head Island in the evening. Doing so could potentially save you 76% on the flight price compared to flying in the morning, which is usually more expensive.

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 30, 2025.
Read through reviews of airlines operating flights from Chicago to Hilton Head Island, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Chicago to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Chicago; the airport handles an average of 0 inbound flights from Chicago 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. 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 to Hilton Head Island?

    Airlines like American Airlines fly from Chicago to Hilton Head Island in about 14h 31m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago and Hilton Head Island is about 781 mi.

  • What are the cheapest airlines flying from Chicago to Hilton Head Island round-trip?

    American Airlines, at $273, was found to be the cheapest airline from Chicago to Hilton Head Island. An alternate airline flying to your destination would be United Airlines. American Airlines is currently priced 38% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Chicago to Hilton Head Island?

    Consider American Airlines (83%), Envoy Air (83%) or United Airlines (0%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Hilton Head Island.

  • Can I find deals for flights from Chicago to Hilton Head Island that include hotel bookings?

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

  • How can I find direct flights from Chicago 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 Chicago to Hilton Head Island.

  • Can I find deals for business class flights from Chicago to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Chicago 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 to Hilton Head Island?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $46). Flying from Chicago to Hilton Head Island in December is currently the most expensive (average of $256). 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 Chicago to Hilton Head Island

Discover the top 2 airlines that operate flights from Chicago 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$273Average$449FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$379Average$498FlexibilityNo cancel feeOn-time69%

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