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Hilton Head Island

$223+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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

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 September 15, 2025.

Round-trip from

$309
(American Airlines)

One-way from

$223
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$347
From Chicago (CHI) to Hilton Head Island
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One-way flight from Chicago (CHI) to Hilton Head Island
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Highest demand for flights based on searches. 10% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:50 amORD - HHH
1 stop4h 35mDelta
Mon 9/294:05 pmHHH - ORD
1 stop7h 18mDelta
Deal found 9/14$284
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:10 amORD - HHH
2 stops7h 15mDelta
Tue 9/3012:14 pmHHH - ORD
2 stops11h 09mDelta
Deal found 9/14$294
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:20 amORD - HHH
1 stop7h 05mDelta
Tue 9/304:05 pmHHH - ORD
1 stop5h 30mDelta
Deal found 9/14$299
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:00 amORD - HHH
2 stops7h 25mDelta
Mon 9/294:05 pmHHH - ORD
1 stop5h 30mDelta
Deal found 9/14$304
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/2510:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Tue 10/2812:45 pmHHH - ORD
1 stop7h 25mAmerican Airlines
Deal found 9/14$314
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:20 amORD - HHH
1 stop7h 05mDelta
Thu 9/254:05 pmHHH - ORD
1 stop5h 30mDelta
Deal found 9/14$324
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:20 amORD - HHH
1 stop7h 05mDelta
Mon 9/294:05 pmHHH - ORD
1 stop5h 30mDelta
Deal found 9/14$327
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:00 amORD - HHH
2 stops8h 25mDelta
Tue 9/2312:14 pmHHH - ORD
1 stop5h 17mDelta
Deal found 9/14$329
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/2710:00 amORD - HHH
Nonstop2h 27mAmerican Airlines
Sat 10/41:57 pmHHH - ORD
Nonstop2h 38mAmerican Airlines
Deal found 9/14$336

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 September 15, 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 9/22

9:50 am-3:25 pm

1 stop4h 35m

Hilton Head Island

Mon 9/29

4:05 pm-10:23 pm

1 stop7h 18m

$284

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 9/22

7:20 am-3:25 pm

1 stop7h 05m

Hilton Head Island

Tue 9/30

4:05 pm-10:23 pm

1 stop7h 18m

$284

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 9/23

9:50 am-3:25 pm

1 stop4h 35m

Hilton Head Island

Tue 9/30

12:14 pm-7:17 pm

2 stops8h 03m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 9/23

6:00 am-3:25 pm

2 stops8h 25m

Hilton Head Island

Mon 9/29

4:05 pm-8:35 pm

1 stop5h 30m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

8:15 am-2:32 pm

1 stop5h 17m

Hilton Head Island

Tue 10/28

3:32 pm-7:10 pm

1 stop4h 38m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 11/12

6:45 pm-11:49 am

2 stops16h 04m

$223

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 10/14

8:20 pm-10:46 am

2 stops13h 26m

$223

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 11/11

8:25 pm-12:29 pm

2 stops15h 04m

$223

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 12/9

6:45 pm-12:22 pm

2 stops16h 37m

$228

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 12/10

6:45 pm-11:51 am

2 stops16h 06m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 12 results
1
2

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 September 12, 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, January is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $275). Flying from Chicago to Hilton Head Island in March is currently the most expensive (average of $480). 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 September 15, 2025.

When flying from Chicago to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 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
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Delta fly from Chicago to Hilton Head Island in about 4h 35m. 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 $263, 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 41% below the average price you’ll pay for this route.

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

    Consider United Airlines (86%), Republic Airways (86%) or American Airlines (40%) 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, January is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $275). Flying from Chicago to Hilton Head Island in March is currently the most expensive (average of $480). 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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Alternative routes for Chicago to Hilton Head Island

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$263Average$440FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$498FlexibilityNo cancel feeOn-time69%

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