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

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The best prices from Chicago to Hilton Head Island are usually found in October or September, booked 60 days in advance, depart on a Tuesday or Monday and return on a Friday

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 2022: compare Chicago to Hilton Head Island flight prices with the expected peak season, weather and rainfall in Hilton Head Island.
CHI - HHH
Price
$251 - $503
HHH
Temperature
50 - 80.6 °F
HHH
Rainfall
2.4 - 7.8 inches

Popular in

July

High demand for flights, 23% potential price rise

Cheapest in

October

Best time to find cheap flights, 35% potential price drop

Round-trip from

$251

From Chicago (CHI) to Hilton Head Island

One-way from

$247

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.
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 evening. Doing so could potentially save you 93% 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 Monday 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 39% on the overall cost on flights from Chicago to Hilton Head Island.

What is the cheapest month to fly from Chicago to Hilton Head Island?

Flights from Chicago to Hilton Head Island lean towards being more expensive in July. Prices are generally better when you fly from Chicago to Hilton Head Island in October, with the cheapest ticket starting at $241.

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 61 days in advance, which can save you up to 56% on flights from Chicago to Hilton Head Island compared to booking the week you need them. Waiting 61 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 $476. For sooner than that we have options available in the next 3 days from $599.

Cheap flights from Chicago to Hilton Head Island in August, September 2022

The best prices found for CHI to HHH flights for August, September
7 Sep - 13 Sep
$224pp
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 Sep - 21 Sep
$226pp
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
7 Sep - 13 Sep
$227pp
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

Chicago to Hilton Head Island 2022 flight deals

Cheap flights to Hilton Head Island from Chicago found for this year
5 Nov - 12 Nov
$223pp
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
7 Sep - 13 Sep
$224pp
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 Sep - 21 Sep
$226pp
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

Cheap Delta flights from Chicago to Hilton Head Island

2 Dec - 6 Dec
$230pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
3 Sep - 4 Sep
$272pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
3 Sep - 7 Sep
$276pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
HHH
Hilton Head Island
HHH
Hilton Head Island
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl

Cheap American Airlines flights from Chicago to Hilton Head Island

5 Nov - 12 Nov
$223pp
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
7 Sep - 13 Sep
$224pp
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 Sep - 21 Sep
$226pp
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

Non-stop flights to Hilton Head Island from Chicago

Save time with Chicago to Hilton Head Island direct flight deals
27 Aug - 3 Sep
$328pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HHH
Hilton Head Island
HHH
Hilton Head Island
American Airlines
Non-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
5:26 pm - 7:06 am
United Airlines
2 Stops
12h 40m
ORD - HHH
United Airlines
$247
United
5:40 am - 1:56 pm
Delta
2 Stops
7h 16m
ORD - HHH
Delta
$484
Delta
1:25 am - 8:15 am
American Airlines
3 Stops
29h 50m
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 4 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 American Airlines, United 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 $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Hilton Head Island for under $300. The cheapest flight booked recently is on American Airlines for just $223, but on average you can expect to pay $272.

Are there nonstop flights from Chicago to Hilton Head Island for under $400 on Cheapflights?

Cheapflights has at least 1 direct flight from Chicago to Hilton Head Island under $400. A good price for a nonstop flight from Chicago to Hilton Head Island is less than $328.

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

American Airlines, at $223, was found to be the cheapest airline from Chicago to Hilton Head Island. An alternate airline flying to your destination would be Delta. American Airlines is currently priced 42% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Chicago to Hilton Head Island one-way?

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $187. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Chicago to Hilton Head Island for a low price.

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, Alaska Airlines or Delta.

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

Looking at all options, your cheapest flight can be booked for $267. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $223 on average our data indicates $434 when flying from Chicago to Hilton Head Island.

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

Consider United Airlines (78%), Republic Airways (61%) or American Airlines (44%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Hilton Head Island.

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 are not required to present a negative COVID-19 PCR test or antigen result upon entering 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 are not required to present a negative COVID-19 PCR test or antigen result upon entering 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.

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
United Airlines
$168 $444 No cancel fee 69%
Delta
$242 $456 No cancel fee N/A
American Airlines
$242 $427 No cancel fee 71%

Hourly flight availability from Chicago to Hilton Head Island

See what time of day planes typically take off from Chicago towards Hilton Head Island.
Morning 6 AM to noon 100% of CHI to HHH departures
Early morning Midnight to 6 AM 0% of CHI to HHH departures
Afternoon Noon to 6 PM 0% of CHI to HHH departures
Evening 6 PM to midnight 0% of CHI to HHH departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Hilton Head Island
See how many times per day planes take to the skies headed from Chicago to Hilton Head Island.
Sunday
0 flights
Monday
0 flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
0 flights
Friday
0 flights
Saturday
2 daily flights