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Cheap flights from Illinois to Hilton Head Island from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Hilton Head Island departing on 4/27. 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 Illinois to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$147Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:00 am - 10:33 am
ORD
-
HHH
4h 33m
1 stop
American Airlines Logo
6:20 pm - 12:06 am
HHH
-
ORD
6h 46m
1 stop
$205American Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$208Delta
Wed, Jun 3 - Tue, Jun 9
American Airlines Logo
9:40 am - 5:44 pm
ORD
-
HHH
7h 04m
2 stops
American Airlines Logo
6:20 pm - 12:06 am
HHH
-
ORD
6h 46m
1 stop
$210American Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$229Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$233Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
6:00 am - 3:22 pm
ORD
-
HHH
8h 22m
2 stops
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$234Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
7:05 am - 3:22 pm
ORD
-
HHH
7h 17m
1 stop
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
$249Delta
Tue, May 26 - Wed, Jun 3
Delta Logo
8:10 am - 3:22 pm
ORD
-
HHH
6h 12m
1 stop
Delta Logo
4:00 pm - 10:43 pm
HHH
-
ORD
7h 43m
1 stop
$254Delta
Sun, May 31 - Tue, Jun 9
United Airlines Logo
7:45 am - 2:06 pm
STL
-
HHH
5h 21m
1 stop
United Airlines Logo
3:00 pm - 9:47 pm
HHH
-
STL
7h 47m
1 stop
$335United Airlines
Sun, Apr 19 - Thu, Apr 23

United Airlines flights from Illinois to Hilton Head Island

Our best United Airlines deals on Illinois to Hilton Head Island flight tickets
United Airlines
May 26
ORD10:35 amChicago O'Hare Intl
2h 26m
HHH2:01 pmHilton Head Island
Jun 2
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$264
United Airlines
Jul 14
ORD10:35 amChicago O'Hare Intl
2h 26m
HHH2:01 pmHilton Head Island
Jul 21
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$278
United Airlines
May 12
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
May 16
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
$284

Delta flights from Illinois to Hilton Head Island

Our best Delta deals on Illinois to Hilton Head Island flight tickets
Delta
Jun 2
ORD8:10 amChicago O'Hare Intl
6h 12m
1 stop
HHH3:22 pmHilton Head Island
Jun 9
HHH4:00 pmHilton Head Island
7h 43m
1 stop
ORD10:43 pmChicago O'Hare Intl
$147
Delta
Jun 3
ORD8:10 amChicago O'Hare Intl
6h 12m
1 stop
HHH3:22 pmHilton Head Island
Jun 9
HHH4:00 pmHilton Head Island
7h 43m
1 stop
ORD10:43 pmChicago O'Hare Intl
$208
Delta
May 27
ORD8:10 amChicago O'Hare Intl
6h 12m
1 stop
HHH3:22 pmHilton Head Island
Jun 3
HHH4:05 pmHilton Head Island
7h 31m
1 stop
ORD10:36 pmChicago O'Hare Intl
$229

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 February 6, 2026.
Use the filters below to find and compare flights from Illinois 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 6/2

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$147

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/19

5:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Mon 2/23

6:20 pm-12:06 am

1 stop6h 46m

$205

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 6/3

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$208

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/19

9:40 am-5:44 pm

2 stops7h 04m

Hilton Head Island

Mon 2/23

6:20 pm-12:06 am

1 stop6h 46m

$210

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 5/27

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Wed 6/3

4:05 pm-10:36 pm

1 stop7h 31m

$229

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/2

4:05 pm-10:36 pm

1 stop7h 31m

$233

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 5/27

6:00 am-3:22 pm

2 stops8h 22m

Hilton Head Island

Wed 6/3

4:05 pm-10:36 pm

1 stop7h 31m

$234

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

7:05 am-3:22 pm

1 stop7h 17m

Hilton Head Island

Wed 6/3

4:05 pm-10:36 pm

1 stop7h 31m

$249

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/31

8:10 am-3:22 pm

1 stop6h 12m

Hilton Head Island

Tue 6/9

4:00 pm-10:43 pm

1 stop7h 43m

$254

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Sun 4/19

7:45 am-2:06 pm

1 stop5h 21m

Hilton Head Island

Thu 4/23

3:00 pm-9:47 pm

1 stop7h 47m

$335

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 Illinois 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 Illinois, 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 Illinois 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 Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $520.

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

Fly from Chicago O'Hare Intl to Hilton Head Island for the best Illinois - 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 Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $438 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 Illinois for as low as $305 on momondo.

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

There is only 1 cabin class available to choose from on Illinois 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 Illinois to Hilton Head Island flights?

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

Cheap Illinois to Hilton Head Island flight deals and tips

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

Best Price Found

$283

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The best flight deal from Illinois to Hilton Head Island found on momondo in the last 72 hours is $283
The fastest flight from Illinois to Hilton Head Island takes 2h 24m
Direct flights go from Illinois to Hilton Head Island every day.
There is 1 airport in Hilton Head Island. From Illinois there are direct flights to Hilton Head Island (HHH).
Search flight deals

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

    Prices for flights from Illinois to Hilton Head Island Airport were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Hilton Head Island Airport.

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

    The travel and health documents required for your trip to Hilton Head Island Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hilton Head Island Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Illinois to Hilton Head Island

Compare and see reviews for airlines that fly from Illinois to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $276Free CancellationRating
7.2
11,246 reviews
Search American Airlines flights
United AirlinesPriceFrom $279Free CancellationRating
7.4
9,244 reviews
Search United 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 Illinois to Hilton Head Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Illinois to Hilton Head Island. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Hilton Head Island from Illinois which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Illinois to Hilton Head Island flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Hilton Head Island from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Hilton Head Island trip

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