Cheap flights from Chicago to Hilton Head Island (CHI - HHH)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Chicago to Hilton Head Island are usually found in January or August, booked 25 days in advance, depart on a Monday or Thursday and return on a Wednesday

How to find the cheapest flight from
Chicago (CHI) to Hilton Head Island (HHH)

All the information you need to plan the best CHI to HHH flight in 2021: compare Chicago to Hilton Head Island flight prices with the expected peak season, weather and rainfall in Hilton Head Island.
CHI - HHH
Price
$304 - $472
HHH
Temperature
50 - 80.6 °F
HHH
Precipitation
2.4 - 7.8 inches

Popular in

December

High demand for flights, 23% potential price rise

Cheapest in

January

Best time to find cheap flights, 16% potential price drop

Round-trip from

$304

From Chicago (CHI) to Hilton Head Island

One-way from

$121

One-way flight from Chicago (CHI) to Hilton Head Island

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Chicago to Hilton Head Island?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 24 days in advance, which can save you up to 28% on flights from Chicago to Hilton Head Island compared to booking the week you need them. Waiting 24 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $377. For sooner than that we have options available in the next 3 days from $460.

When is the cheapest time to fly from Chicago to Hilton Head Island (CHI - HHH)?

It’s typically best to fly out from Chicago to Hilton Head Island in the afternoon. Doing so could potentially save you 5% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly round-trip from Chicago to Hilton Head Island?

Leaving on a Sunday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 37% on the overall cost on flights from Chicago to Hilton Head Island.

Cheap flights from Chicago to Hilton Head Island in November, December 2021

The best prices found for CHI to HHH flights for November, December
9 Dec - 11 Dec
$242pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Dec - 10 Dec
$243pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 10 Dec
$244pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Hilton Head Island 2022 flight deals

Cheap flights to Hilton Head Island from Chicago found for next year
9 Dec - 11 Dec
$242pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Dec - 10 Dec
$243pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Dec - 10 Dec
$244pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Hilton Head from Chicago

The cheapest one-way flights from Chicago to Hilton Head Island
12:25 am - 5:50 am
American Airlines
1 Stop
4h 25m
ORD - HHH
American Airlines
8:31 am - 5:50 am
American Airlines
1 Stop
20h 19m
ORD - HHH
American Airlines
8:31 am - 2:25 pm
American Airlines
1 Stop
4h 54m
ORD - HHH
American Airlines

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Hilton Head Island</span> flights.

Flight FAQs

From Chicago to Hilton Head Island

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 3 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.

Which airlines flying from Chicago to Hilton Head Island have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Hilton Head Island that may be offering flexible cancellation policies are United Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Hilton Head Island for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Hilton Head Island for under $200. The cheapest flight booked recently is on American Airlines for just $196, but on average you can expect to pay $246.

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

American Airlines, at $196, 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 45% 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 $91. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $243 on average our data indicates $327 when flying from Chicago to Hilton Head Island.

What are the most popular airlines that fly from Chicago to Hilton Head Island?

Before booking your flight from Chicago to Hilton Head Island check out the most popular airlines for this route: American Airlines, Delta or United Airlines.

COVID Restrictions

View COVID Travel Restrictions for Hilton Head Island, SC

Do I need a COVID test to fly to Hilton Head Island from Chicago?

Information is based on travel restrictions for travel to Hilton Head Island within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Hilton Head Island.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Hilton Head Island.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Hilton Head Island.

Do I need a test to fly back to Chicago from Hilton Head Island?

Returning to Chicago from Hilton Head Island

COVID-19 testing requirements
Visitors from Hilton Head Island must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Hilton Head Island are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Hilton Head Island, SC

Alternative routes for Chicago to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Hilton Head Island

Things to know before you go - useful duration and weather info for your trip from Chicago to Hilton Head Island.
Average temperature for November in Hilton Head Island
73.4 °F
Avg rainfall for November in Hilton Head Island
2.3 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Hilton Head Island

Top 3 airlines flying from Chicago to Hilton Head Island

The chart below displays the airlines Cheapflights users traveling from Chicago to Hilton Head Island choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Delta
$192 $377 No cancel fee N/A
American Airlines
$194 $372 No cancel fee 71%
United Airlines
$227 $396 No cancel fee 69%
Home North America USA South Carolina Hilton Head Island Cheap flights from Chicago to Hilton Head Island