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Hilton Head Island

$174+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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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 July 11, 2026.

This United Airlines deal was found by Cheapflights users on 7/7. 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.
Mon 8/1710:25 am
ORD
-
HHH
Nonstop2h 38m
United Airlines
Mon 8/242:58 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Deal found 7/7$269
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Mon 8/249:53 am
ORD
-
HHH
Nonstop2h 24m
American Airlines
Mon 8/311:52 pm
HHH
-
ORD
Nonstop2h 38m
American Airlines
Deal found 7/10$270
This American Airlines deal was found by Cheapflights users on 7/10. 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 7/10$279
This Delta deal was found by Cheapflights users on 7/10. 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 7/319:45 am
ORD
-
HHH
1 stop4h 44m
Delta
Tue 8/1112:15 pm
HHH
-
ORD
2 stops9h 15m
Delta
Deal found 7/10$294
This Delta deal was found by Cheapflights users on 7/7. 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 10/206:00 am
ORD
-
HHH
2 stops8h 26m
Delta
Tue 10/2712:15 pm
HHH
-
ORD
2 stops9h 24m
Delta
Deal found 7/7$300
This Delta deal was found by Cheapflights users on 7/9. 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 10/76:00 am
ORD
-
HHH
2 stops8h 26m
Delta
Mon 10/1212:15 pm
HHH
-
ORD
1 stop5h 42m
Delta
Deal found 7/9$314
This American Airlines deal was found by Cheapflights users on 7/9. 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 7/245:07 am
ORD
-
HHH
1 stop6h 13m
American Airlines
Mon 7/272:03 pm
HHH
-
ORD
Nonstop2h 36m
American Airlines
Deal found 7/9$319
This American Airlines deal was found by Cheapflights users on 7/9. 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 10/165:18 am
ORD
-
HHH
1 stop4h 47m
American Airlines
Sat 10/171:50 pm
HHH
-
ORD
Nonstop2h 44m
American Airlines
Deal found 7/9$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 July 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$174
(United Airlines)

Popular in

January

Cheapest in

September

Average price

$356

Good round-trip deal

$279 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Chicago (CHI)-Hilton Head Island flight deals.
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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 ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 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 (CHI) to Hilton Head Island.
Search Deals
Price to beat on a one-way 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 July 11, 2026.
Use the filters below to find and compare flights from Chicago 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

$366

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/19

10:25 am-2:03 pm

Nonstop2h 38m

Hilton Head Island

Wed 9/23

2:48 pm-5:05 pm

Nonstop3h 17m

$369

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/19

7:00 am-3:27 pm

2 stops7h 27m

Hilton Head Island

Wed 9/23

12:15 pm-10:18 pm

2 stops11h 03m

$375

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 9/18

5:00 am-12:59 pm

1 stop6h 59m

Hilton Head Island

Mon 9/21

2:48 pm-5:05 pm

Nonstop3h 17m

$442

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 8/17

8:05 am-3:32 pm

1 stop6h 27m

Hilton Head Island

Mon 8/24

12:15 pm-9:47 pm

2 stops10h 32m

$459
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 7/23

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Sun 7/26

3:05 pm-4:51 pm

Nonstop2h 46m

$554

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 7/21

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Sun 7/26

3:05 pm-4:51 pm

Nonstop2h 46m

$554

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 7/22

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Sun 7/26

3:05 pm-4:51 pm

Nonstop2h 46m

$554
Cheapest one-way

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 10/5

6:00 am-11:34 am

1 stop28h 34m

$226

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 8/12

1:50 pm-3:32 pm

1 stop24h 42m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 18 resultsSorted by cheapest first
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 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-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

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $158). Flying from Chicago to Hilton Head Island in January is currently the most expensive (average of $389). 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 July 11, 2026.

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.

Weekly flight availability from Chicago to Hilton Head Island

Explore weekly flight availability from Chicago to Hilton Head Island. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 11, 2026.

The most flights from CHI to HHH are scheduled on a Monday (2 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Hilton Head Island?

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

Booking 65 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.

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 11, 2026.
Read through reviews of airlines operating flights from Chicago to Hilton Head Island, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,976 reviews

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.7

Crew

8.1

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
9,976 reviews
United Airlines
7.4
Good
9,976 reviews

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.7

Crew

8.1

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
11,806 reviews
United Airlines
7.4
Good
9,976 reviews

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.7

Crew

8.1

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 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 1 inbound flight 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 and United Airlines fly from Chicago to Hilton Head Island in about 6h 21m. The time it takes to get you to your destination can typically vary by up to 44m. 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 $209, 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 53% below the average price you’ll pay for this route.

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

    Consider Envoy Air (88%), United Airlines (84%) or American Airlines (69%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Hilton Head Island.

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

    Looking at all options, your cheapest flight can be booked for $173. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $269 on average, our data indicates $279 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, August is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $158). Flying from Chicago to Hilton Head Island in January is currently the most expensive (average of $389). 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 July 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$408FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$471FlexibilityNo cancel feeOn-time71%

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