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Hilton Head Island

$167+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
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 September or November, booked 55 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap 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 January 31, 2026.

This United Airlines deal was found by Cheapflights users on 1/31. 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.
Tue 5/2610:35 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Tue 6/23:00 pm
HHH
-
ORD
Nonstop2h 45m
United Airlines
Deal found 1/31$209
This United Airlines deal was found by Cheapflights users on 1/31. 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 4/410:40 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Wed 4/83:00 pm
HHH
-
ORD
Nonstop2h 44m
United Airlines
Deal found 1/31$224
This Delta deal was found by Cheapflights users on 1/31. 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 5/58:15 am
ORD
-
HHH
1 stop6h 05m
Delta
Tue 5/124:00 pm
HHH
-
ORD
1 stop5h 45m
Delta
Deal found 1/31$229
This Delta deal was found by Cheapflights users on 1/31. 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 5/139:30 am
ORD
-
HHH
1 stop4h 48m
Delta
Tue 5/194:00 pm
HHH
-
ORD
1 stop5h 45m
Delta
Deal found 1/31$249
This United Airlines deal was found by Cheapflights users on 1/31. 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 4/410:40 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Thu 4/93:00 pm
HHH
-
ORD
Nonstop2h 44m
United Airlines
Deal found 1/31$278
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Tue 4/710:40 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Tue 4/143:00 pm
HHH
-
ORD
Nonstop2h 44m
United Airlines
Deal found 1/31$284
This Delta deal was found by Cheapflights users on 1/31. 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.
Fri 5/18:15 am
ORD
-
HHH
1 stop6h 05m
Delta
Tue 5/54:00 pm
HHH
-
ORD
1 stop7h 15m
Delta
Deal found 1/31$304
This American Airlines deal was found by Cheapflights users on 1/31. 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 5/197:25 am
ORD
-
HHH
1 stop5h 59m
American Airlines
Tue 5/262:01 pm
HHH
-
ORD
Nonstop2h 37m
American Airlines
Deal found 1/31$319
This American Airlines deal was found by Cheapflights users on 1/30. 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 5/28:38 am
ORD
-
HHH
1 stop4h 46m
American Airlines
Tue 5/53:44 pm
HHH
-
ORD
1 stop6h 36m
American Airlines
Deal found 1/30$329
This American Airlines deal was found by Cheapflights users on 1/31. 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 5/26:40 am
ORD
-
HHH
2 stops6h 44m
American Airlines
Wed 5/611:03 am
HHH
-
ORD
1 stop6h 19m
American Airlines
Deal found 1/31$334

Find 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 January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(United Airlines)

One-way from

$167
(Delta)

Popular in

July

Cheapest in

September

Average price

$358

Good round-trip deal

$283 or less
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. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Hilton Head Island.
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 January 31, 2026.
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

Tue 4/7

10:40 am-2:06 pm

Nonstop2h 26m

Hilton Head Island

Tue 4/14

3:00 pm-4:44 pm

Nonstop2h 44m

$284

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 5/1

8:15 am-3:20 pm

1 stop6h 05m

Hilton Head Island

Tue 5/5

4:00 pm-10:15 pm

1 stop7h 15m

$304

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 3/14

7:10 am-2:22 pm

1 stop6h 12m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$359

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/7

6:08 am-2:24 pm

2 stops7h 16m

Hilton Head Island

Tue 4/14

1:08 pm-6:00 pm

1 stop5h 52m

$364

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/14

9:00 am-3:30 pm

1 stop5h 30m

Hilton Head Island

Fri 4/17

3:00 pm-4:44 pm

Nonstop2h 44m

$377

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 3/5

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Mon 3/9

4:11 pm-9:24 pm

1 stop6h 13m

$383

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 4/4

10:40 am-2:06 pm

Nonstop2h 26m

Hilton Head Island

Wed 4/8

4:11 pm-11:37 pm

1 stop8h 26m

$390

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/14

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Wed 2/18

3:31 pm-10:17 pm

2 stops7h 46m

$394

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 4/13

9:15 pm-3:30 pm

2 stops17h 15m

Hilton Head Island

Fri 4/17

3:00 pm-4:44 pm

Nonstop2h 44m

$407

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 4/27

5:55 pm-11:28 am

1 stop16h 33m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 16 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 January.
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-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-Hilton Head Island flight deals on Cheapflights vs. FlightHub >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 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-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 January 23, 2026.

Booking 49 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 March is currently the most expensive (average of $257). 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.

How much does it cost to fly round-trip from Chicago 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 January 31, 2026.
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
8,130 reviews

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,130 reviews
Delta
7.9
Good
8,130 reviews

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,219 reviews
Delta
7.9
Good
8,130 reviews

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,213 reviews
Delta
7.9
Good
8,130 reviews

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 United Airlines, Delta, and American Airlines fly from Chicago to Hilton Head Island in about 2h 26m. The time it takes to get you to your destination can typically vary by up to 3h 46m. The distance between Chicago and Hilton Head Island is about 781 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    United Airlines, at $279, was found to be the cheapest airline from Chicago to Hilton Head Island. An alternate airline flying to your destination would be American Airlines. United Airlines is currently priced 28% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago to Hilton Head Island?

    Looking at all options, your cheapest flight can be booked for $220. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $252 on average, our data indicates $405 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 March is currently the most expensive (average of $257). 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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Alternative routes for Chicago to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$279Average$444FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$461FlexibilityNo cancel feeOn-time71%

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