HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilton Head Island

$173+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 10, 2026.

This United Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 7/110:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Wed 7/83:05 pm
HHH
-
ORD
Nonstop2h 46m
United Airlines
Deal found 5/5$269
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Tue 8/182:48 pm
HHH
-
ORD
Nonstop3h 17m
United Airlines
Deal found 5/9$283
This Delta deal was found by Cheapflights users on 5/6. 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 6/238:08 am
ORD
-
HHH
1 stop6h 24m
Delta
Mon 6/294:15 pm
HHH
-
ORD
1 stop7h 33m
Delta
Deal found 5/6$289
This Delta deal was found by Cheapflights users on 5/9. 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.
Sun 8/98:02 am
ORD
-
HHH
1 stop6h 28m
Delta
Tue 8/1812:11 pm
HHH
-
ORD
2 stops11h 13m
Delta
Deal found 5/9$294
This Delta deal was found by Cheapflights users on 5/6. 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 5/267:07 am
ORD
-
HHH
1 stop7h 26m
Delta
Tue 6/24:16 pm
HHH
-
ORD
1 stop7h 20m
Delta
Deal found 5/6$309
This Delta deal was found by Cheapflights users on 5/5. 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 7/208:03 am
ORD
-
HHH
1 stop6h 26m
Delta
Mon 7/2712:11 pm
HHH
-
ORD
1 stop6h 01m
Delta
Deal found 5/5$327
This Delta deal was found by Cheapflights users on 5/10. 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.
Sun 5/318:10 am
ORD
-
HHH
1 stop6h 23m
Delta
Sat 6/612:18 pm
HHH
-
ORD
1 stop7h 23m
Delta
Deal found 5/10$344

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$173
(Delta)

Popular in

January

Cheapest in

September

Average price

$481

Good round-trip deal

$436 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. 9% potential increase in price ($46 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 May 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 May 10, 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

Sun 8/9

8:02 am-3:30 pm

1 stop6h 28m

Hilton Head Island

Tue 8/18

12:11 pm-10:24 pm

2 stops11h 13m

$294

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

7:00 am-3:33 pm

2 stops7h 33m

Hilton Head Island

Tue 6/2

4:16 pm-10:36 pm

1 stop7h 20m

$334

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/31

8:10 am-3:33 pm

1 stop6h 23m

Hilton Head Island

Sat 6/6

12:18 pm-6:41 pm

1 stop7h 23m

$344

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 9/14

7:10 am-3:20 pm

1 stop7h 10m

Hilton Head Island

Mon 9/28

12:00 pm-6:41 pm

2 stops7h 41m

$349

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 7/6

8:08 am-3:32 pm

1 stop6h 24m

Hilton Head Island

Mon 7/13

12:11 pm-6:45 pm

1 stop7h 34m

$376

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 6/12

8:08 am-3:32 pm

1 stop6h 24m

Hilton Head Island

Tue 6/16

12:13 pm-10:34 pm

2 stops11h 21m

$449

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 6/5

6:24 am-3:33 pm

2 stops8h 09m

Hilton Head Island

Mon 6/8

12:13 pm-5:04 pm

1 stop5h 51m

$594

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/30

7:01 am-3:32 pm

2 stops7h 31m

Hilton Head Island

Fri 7/3

4:15 pm-10:48 pm

1 stop7h 33m

$604
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 5/28

9:49 am-3:33 pm

1 stop4h 44m

Hilton Head Island

Sun 5/31

12:18 pm-6:35 pm

1 stop7h 17m

$654

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 7/4

9:48 am-3:37 pm

1 stop4h 49m

Hilton Head Island

Sat 7/11

12:14 pm-9:52 pm

2 stops10h 38m

$734

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 19 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 May.
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?

Booking 88 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, June is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $100). 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 May 10, 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 May 10, 2026.

The most flights from CHI to HHH are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, 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?

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 May 10, 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
9,694 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,694 reviews
United Airlines
7.4
Good
9,694 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,667 reviews
United Airlines
7.4
Good
9,694 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 fly from Chicago to Hilton Head Island in about 6h 24m. 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?

    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 cheapest flights from Chicago to Hilton Head Island?

    Looking at all options, your cheapest flight can be booked for $289. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $299 on average, our data indicates $543 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, June is the cheapest month in which you can book a flight from Chicago to Hilton Head Island (average of $100). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$425FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$471FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.