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Cheap flights from Chicago to Hilton Head Island from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hilton Head Island departing on 3/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
10:40 am - 2:06 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:44 pm
HHH
-
ORD
2h 44mnonstop
$224United Airlines
Tue, Apr 7 - Wed, Apr 15
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
$252United Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
8:10 am - 2:22 pm
ORD
-
HHH
5h 12m
1 stop
American Airlines Logo
4:11 pm - 9:24 pm
HHH
-
ORD
6h 13m
1 stop
$277American Airlines
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
8:10 am - 2:22 pm
ORD
-
HHH
5h 12m
1 stop
American Airlines Logo
11:03 am - 5:23 pm
HHH
-
ORD
7h 20m
2 stops
$282American Airlines
Mon, Mar 9 - Wed, Mar 11
Delta Logo
7:10 am - 3:18 pm
ORD
-
HHH
7h 08m
1 stop
Delta Logo
4:00 pm - 8:45 pm
HHH
-
ORD
5h 45m
1 stop
$294Delta
Sun, May 17 - Sun, May 24
Delta Logo
7:10 am - 3:18 pm
ORD
-
HHH
7h 08m
1 stop
Delta Logo
4:00 pm - 8:45 pm
HHH
-
ORD
5h 45m
1 stop
$304Delta
Sun, May 17 - Sun, May 24
American Airlines Logo
10:06 am - 1:31 pm
ORD
-
HHH
2h 25mnonstop
American Airlines Logo
2:01 pm - 3:38 pm
HHH
-
ORD
2h 37mnonstop
$309American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
10:06 am - 1:31 pm
ORD
-
HHH
2h 25mnonstop
American Airlines Logo
11:00 am - 3:55 pm
HHH
-
ORD
5h 55m
1 stop
$319American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
7:10 am - 2:22 pm
ORD
-
HHH
6h 12m
1 stop
American Airlines Logo
3:31 pm - 7:40 pm
HHH
-
ORD
5h 09m
1 stop
$320American Airlines
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
6:05 am - 12:20 pm
ORD
-
HHH
5h 15m
1 stop
American Airlines Logo
2:58 pm - 7:40 pm
HHH
-
ORD
5h 42m
1 stop
$323American Airlines
Wed, Feb 11 - Sat, Feb 14

American Airlines flights from Chicago to Hilton Head Island

Our best American Airlines deals on Chicago to Hilton Head Island flight tickets
American Airlines
Mar 9
ORD8:10 amChicago O'Hare Intl
5h 12m
1 stop
HHH2:22 pmHilton Head Island
Mar 11
HHH4:11 pmHilton Head Island
6h 13m
1 stop
ORD9:24 pmChicago O'Hare Intl
$277
American Airlines
Mar 9
ORD8:10 amChicago O'Hare Intl
5h 12m
1 stop
HHH2:22 pmHilton Head Island
Mar 11
HHH11:03 amHilton Head Island
7h 20m
2 stops
ORD5:23 pmChicago O'Hare Intl
$282
American Airlines
Jul 28
ORD10:06 amChicago O'Hare Intl
2h 25m
HHH1:31 pmHilton Head Island
Aug 4
HHH2:01 pmHilton Head Island
2h 37m
ORD3:38 pmChicago O'Hare Intl
$309

United Airlines flights from Chicago to Hilton Head Island

Our best United Airlines deals on Chicago to Hilton Head Island flight tickets
United Airlines
Apr 7
ORD10:40 amChicago O'Hare Intl
2h 26m
HHH2:06 pmHilton Head Island
Apr 15
HHH3:00 pmHilton Head Island
2h 44m
ORD4:44 pmChicago O'Hare Intl
$224
United Airlines
Jun 5
ORD10:35 amChicago O'Hare Intl
2h 26m
HHH2:01 pmHilton Head Island
Jun 8
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$252
United Airlines
Apr 7
ORD10:40 amChicago O'Hare Intl
2h 26m
HHH2:06 pmHilton Head Island
Apr 15
HHH4:11 pmHilton Head Island
8h 26m
1 stop
ORD11:37 pmChicago O'Hare Intl
$338

momondo 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, momondo users made 832,500 searches. Data last updated January 29, 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

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/7

10:40 am-2:06 pm

Nonstop2h 26m

Hilton Head Island

Wed 4/15

3:00 pm-4:44 pm

Nonstop2h 44m

$224

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 6/5

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Mon 6/8

3:00 pm-4:45 pm

Nonstop2h 45m

$252

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/9

8:10 am-2:22 pm

1 stop5h 12m

Hilton Head Island

Wed 3/11

4:11 pm-9:24 pm

1 stop6h 13m

$277

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/9

8:10 am-2:22 pm

1 stop5h 12m

Hilton Head Island

Wed 3/11

11:03 am-5:23 pm

2 stops7h 20m

$282

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/17

7:10 am-3:18 pm

1 stop7h 08m

Hilton Head Island

Sun 5/24

4:00 pm-8:45 pm

1 stop5h 45m

$294

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/17

7:10 am-3:18 pm

1 stop7h 08m

Hilton Head Island

Sun 5/24

4:00 pm-8:45 pm

1 stop5h 45m

$304

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 7/28

10:06 am-1:31 pm

Nonstop2h 25m

Hilton Head Island

Tue 8/4

2:01 pm-3:38 pm

Nonstop2h 37m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 7/28

10:06 am-1:31 pm

Nonstop2h 25m

Hilton Head Island

Tue 8/4

11:00 am-3:55 pm

1 stop5h 55m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/26

7:10 am-2:22 pm

1 stop6h 12m

Hilton Head Island

Tue 3/3

3:31 pm-7:40 pm

1 stop5h 09m

$320

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 2/11

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Sat 2/14

2:58 pm-7:40 pm

1 stop5h 42m

$323

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Chicago to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

If you don’t want to visit Hilton Head Island in September, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $351.

What is the cheapest day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Chicago to Hilton Head Island is on a Wednesday. Travelers who choose to depart for Hilton Head Island on a Wednesday will often find tickets for as low as $279. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $509.

What is the cheapest Chicago to Hilton Head Island flight route?

Fly from Chicago O'Hare Intl to Hilton Head Island for the best Chicago - Hilton Head Island flight prices

How far in advance should I book a flight to Hilton Head Island?

You are more likely to see cheaper flights to Hilton Head Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $435 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hilton Head Island from Chicago for as low as $305 on momondo.

What cabin class options are available on Chicago to Hilton Head Island flights?

There is only 1 cabin class available to choose from on Chicago to Hilton Head Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Hilton Head Island flights?

You could potentially save up to 51% on your flight if you consider stops on a Chicago to Hilton Head Island flight.

When to book flights from Chicago to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Hilton Head Island (CHI to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Hilton Head Island

Best Price Found

$281

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The best flight deal from Chicago to Hilton Head Island found on momondo in the last 72 hours is $281
The fastest flight from Chicago to Hilton Head Island takes 2h 24m
Direct flights go from Chicago to Hilton Head Island every day.
There is 1 airport in Hilton Head Island. From Chicago there are direct flights to Hilton Head Island (HHH).
Search flight deals

  • How far is Chicago to Hilton Head Island by plane?

    There are 766.4 mi between Chicago and Hilton Head Island. By plane, this route typically takes 2h 24m.

  • When did momondo last update prices for flights from Chicago to Hilton Head Island Airport?

    Prices for flights from Chicago to Hilton Head Island Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Hilton Head Island Airport?

  • How old do you have to be to fly from Chicago to Hilton Head Island Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The travel and health documents you'll need for your trip to Hilton Head Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Hilton Head Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Hilton Head Island?

  • What is the most popular airline from Chicago to Hilton Head Island?

Best airlines flying from Chicago to Hilton Head Island

Compare and see reviews for airlines that fly from Chicago to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $279Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $288Free CancellationRating
7.2
11,205 reviews
Search American Airlines flights

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hilton Head Island?

Finding the right flight to Hilton Head Island from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Hilton Head Island quick and easy, saving you time and money.

Can I find flights from Chicago to Hilton Head Island with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Hilton Head Island flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Hilton Head Island?

momondo helps you find the best flight between Chicago and Hilton Head Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Hilton Head Island right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Hilton Head Island flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Hilton Head Island trip

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