HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HHH
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This United Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 7/1010:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Thu 7/163:05 pm
HHH
-
ORD
Nonstop2h 46m
United Airlines
Deal found 3/12$249
This Delta deal was found by Cheapflights users on 3/12. 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.
Sat 4/187:10 am
ORD
-
HHH
1 stop7h 10m
Delta
Wed 4/224:00 pm
HHH
-
ORD
1 stop7h 15m
Delta
Deal found 3/12$269
This United Airlines deal was found by Cheapflights users on 3/13. 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.
Thu 7/210:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Tue 7/73:05 pm
HHH
-
ORD
Nonstop2h 46m
United Airlines
Deal found 3/13$285
This Delta deal was found by Cheapflights users on 3/13. 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 15m
Delta
Tue 6/24:05 pm
HHH
-
ORD
1 stop7h 31m
Delta
Deal found 3/13$289
This United Airlines deal was found by Cheapflights users on 3/14. 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 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
Tue 7/73:05 pm
HHH
-
ORD
Nonstop2h 46m
United Airlines
Deal found 3/14$293
This Delta deal was found by Cheapflights users on 3/15. 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 4/226:00 am
ORD
-
HHH
2 stops8h 20m
Delta
Tue 4/2812:08 pm
HHH
-
ORD
2 stops11h 07m
Delta
Deal found 3/15$300
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Thu 5/2810:45 am
ORD
-
HHH
Nonstop2h 36m
United Airlines
Tue 6/23:05 pm
HHH
-
ORD
Nonstop2h 46m
United Airlines
Deal found 3/16$310
This Delta deal was found by Cheapflights users on 3/14. 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.
Sat 5/98:10 am
ORD
-
HHH
1 stop6h 23m
Delta
Sat 5/1612:18 pm
HHH
-
ORD
1 stop7h 23m
Delta
Deal found 3/14$314
This Delta deal was found by Cheapflights users on 3/16. 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 9/17:10 am
ORD
-
HHH
2 stops7h 10m
Delta
Sat 9/512:00 pm
HHH
-
ORD
1 stop5h 45m
Delta
Deal found 3/16$319

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$174
(United Airlines)

Popular in

January

Cheapest in

November

Average price

$594

Good round-trip deal

$279 or less

Good one-way deal

$233 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. 13% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 17, 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
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 4/18

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Wed 4/22

3:05 pm-4:49 pm

Nonstop2h 44m

$249

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 7/10

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Thu 7/16

3:05 pm-4:51 pm

Nonstop2h 46m

$249

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 8/2

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Sun 8/9

3:05 pm-4:51 pm

Nonstop2h 46m

$269

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 9/1

7:10 am-3:20 pm

2 stops7h 10m

Hilton Head Island

Sat 9/5

12:00 pm-4:45 pm

1 stop5h 45m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 6/12

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Thu 6/18

3:05 pm-4:51 pm

Nonstop2h 46m

$319

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

12:18 pm-8:14 pm

2 stops8h 56m

$324

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 6/18

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Mon 6/22

3:05 pm-4:51 pm

Nonstop2h 46m

$340

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 4/10

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Thu 4/16

3:05 pm-4:49 pm

Nonstop2h 44m

$345

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 4/10

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Fri 4/17

4:11 pm-11:37 pm

1 stop8h 26m

$367

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 4/12

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Sun 4/19

3:05 pm-4:49 pm

Nonstop2h 44m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 20 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 March.
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, 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 $297). 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 March 17, 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.

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 March 17, 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
9,431 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,431 reviews
United Airlines
7.4
Good
9,431 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,468 reviews
United Airlines
7.4
Good
9,431 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 and Delta 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 4h 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 51% 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 $178. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $269 on average, our data indicates $378 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 $297). 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.

Alternative routes for Chicago to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Savannah flights
O'Hare Intl to Charleston flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Myrtle Beach flights
Midway to Charlotte flights
Midway to Charleston flights
O'Hare Intl to Greenville flights
Midway to Savannah flights
O'Hare Intl to Hilton Head Island flights
O'Hare Intl to Columbia flights
Midway to Myrtle Beach flights
St. Louis to Charleston flights
St. Louis to Charlotte flights
St. Louis to Savannah flights
St. Louis to Myrtle Beach flights
Moline to Charlotte flights
Midway to Greenville flights
O'Hare Intl to Augusta flights
Peoria to Charlotte flights
Moline to Myrtle Beach flights
Midway to Columbia flights
St. Louis to Greenville flights
Midway to Augusta flights
Peoria to Charleston flights
St. Louis to Columbia flights
St. Louis to Hilton Head Island flights
Moline to Charleston flights
Moline to Savannah flights
Bloomington to Charlotte flights
Peoria to Myrtle Beach flights
Moline to Greenville flights
Peoria to Savannah flights
Peoria to Greenville flights
Bloomington to Charleston flights
Evansville to Savannah flights
Evansville to Charleston flights
Bloomington to Savannah flights
Peoria to Hilton Head Island flights
Peoria to Columbia flights
St. Louis to Augusta flights
Moline to Columbia flights
Moline to Augusta flights
Evansville to Charlotte flights
O'Hare Intl to Florence flights
Bloomington to Myrtle Beach flights
Springfield to Myrtle Beach flights

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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$457FlexibilityNo 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.