What is the cheapest airline that flies from Illinois to Hilton Head Island?

American Airlines is the most popular carrier operating from Illinois to Hilton Head Island

What airlines fly to Hilton Head Island?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Hilton Head Island from Illinois according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 4 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Hilton Head Island?

On average, it takes 2h 01m to fly from Illinois to Hilton Head Island if you fly out of Chicago (the most popular airport in Illinois) and into Charleston (the most popular airport in Hilton Head Island). If you’re flying out of Moline and into Charleston, then the flight time is around 4h 19m.

How many flights depart from Illinois to Hilton Head Island on average per week?

As of November 2026, 1 flights take off from Illinois and land in Hilton Head Island each week. The most common flight departure day for this route is Sat, with 100% of weekly flights taking off on this day.

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?

The number of operators available for flights from Illinois to Hilton Head Island Airport is 2 as of November 2026.

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.

$205 Cheap Flights from Illinois to Hilton Head Island in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Hilton Head Island

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 am - 3:53 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 43m1 stop Charlotte Douglas

12:37 pm - 5:24 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 47m1 stop Charlotte Douglas

$369American Airlines

Fri, Jan 15 - Sun, Jan 17

5:14 am - 10:28 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 14m1 stop Charlotte Douglas

7:10 pm - 11:00 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 50m1 stop Charlotte Douglas

$369American Airlines

Thu, Feb 25 - Sun, Feb 28

8:10 am - 3:53 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 43m1 stop Charlotte Douglas

12:37 pm - 5:24 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 47m1 stop Charlotte Douglas

$369American Airlines

Fri, Jan 15 - Mon, Jan 18

1:06 pm - 6:18 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 12m1 stop Charlotte Douglas

6:17 pm - 11:00 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 43m1 stop Charlotte Douglas

$369American Airlines

Thu, Feb 18 - Mon, Feb 22

10:50 am - 2:16 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 26mnonstop

3:05 pm - 4:49 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 44mnonstop

$494United Airlines

Fri, May 7 - Fri, May 14

10:50 am - 2:16 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 26mnonstop

12:00 pm - 7:52 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

8h 52m1 stop Newark

$544United Airlines

Wed, Mar 31 - Tue, Apr 6

5:00 am - 11:12 amORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 12m1 stop Newark

3:05 pm - 4:49 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 44mnonstop

$589United Airlines

Fri, May 7 - Fri, May 14

6:00 am - 3:20 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

8h 20m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

12:00 pm - 8:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

9h 37m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$709Delta

Wed, May 5 - Sun, May 9

6:00 am - 3:20 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

8h 20m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

12:00 pm - 8:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

9h 37m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$829Delta

Fri, May 7 - Fri, May 14

6:00 am - 3:20 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

8h 20m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

12:00 pm - 8:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

9h 37m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$1,100Delta

Mon, Apr 19 - Mon, Apr 26

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American Airlines flights from Illinois to Hilton Head Island

Our best American Airlines deals on Illinois to Hilton Head Island flight tickets

American Airlines

Jan 15

ORD8:10 amChicago O'Hare Intl

6h 43m

1 stop

HHH3:53 pmHilton Head Island

Jan 18

HHH12:37 pmHilton Head Island

5h 47m

1 stop

ORD5:24 pmChicago O'Hare Intl

$369

American Airlines

Dec 17

ORD8:00 amChicago O'Hare Intl

5h 30m

1 stop

HHH2:30 pmHilton Head Island

Dec 22

HHH7:05 pmHilton Head Island

4h 57m

1 stop

ORD11:02 pmChicago O'Hare Intl

$371

American Airlines

Mar 6

ORD8:00 amChicago O'Hare Intl

5h 28m

1 stop

HHH2:28 pmHilton Head Island

Mar 13

HHH7:10 pmHilton Head Island

6h 04m

1 stop

ORD12:14 amChicago O'Hare Intl

$409

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 7

ORD10:50 amChicago O'Hare Intl

2h 26m

HHH2:16 pmHilton Head Island

May 14

HHH3:05 pmHilton Head Island

2h 44m

ORD4:49 pmChicago O'Hare Intl

$494

United Airlines

Mar 31

ORD10:50 amChicago O'Hare Intl

2h 26m

HHH2:16 pmHilton Head Island

Apr 6

HHH12:00 pmHilton Head Island

8h 52m

1 stop

ORD7:52 pmChicago O'Hare Intl

$544

United Airlines

May 7

ORD5:00 amChicago O'Hare Intl

5h 12m

1 stop

HHH11:12 amHilton Head Island

May 14

HHH3:05 pmHilton Head Island

2h 44m

ORD4:49 pmChicago O'Hare Intl

$589

momondo Fare Finder

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

Cheapest round-trip

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 1/15

8:10 am-3:53 pm

1 stop6h 43m

Hilton Head Island

Sun 1/17

12:37 pm-5:24 pm

1 stop5h 47m

$369

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Thu 2/25

5:14 am-10:28 am

1 stop4h 14m

Hilton Head Island

Sun 2/28

7:10 pm-11:00 pm

1 stop4h 50m

$369

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 1/15

8:10 am-3:53 pm

1 stop6h 43m

Hilton Head Island

Mon 1/18

12:37 pm-5:24 pm

1 stop5h 47m

$369

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Thu 2/18

1:06 pm-6:18 pm

1 stop4h 12m

Hilton Head Island

Mon 2/22

6:17 pm-11:00 pm

1 stop5h 43m

$369

Quickest round-trip

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 5/7

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Fri 5/14

3:05 pm-4:49 pm

Nonstop2h 44m

$494

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Wed 3/31

10:50 am-2:16 pm

Nonstop2h 26m

Hilton Head Island

Tue 4/6

12:00 pm-7:52 pm

1 stop8h 52m

$544

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 5/7

5:00 am-11:12 am

1 stop5h 12m

Hilton Head Island

Fri 5/14

3:05 pm-4:49 pm

Nonstop2h 44m

$589

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Wed 5/5

6:00 am-3:20 pm

2 stops8h 20m

Hilton Head Island

Sun 5/9

12:00 pm-8:37 pm

2 stops9h 37m

$709

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Fri 5/7

6:00 am-3:20 pm

2 stops8h 20m

Hilton Head Island

Fri 5/14

12:00 pm-8:37 pm

2 stops9h 37m

$829

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Mon 4/19

6:00 am-3:20 pm

2 stops8h 20m

Hilton Head Island

Mon 4/26

12:00 pm-8:37 pm

2 stops9h 37m

$1,100

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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

If you don’t want to visit Hilton Head Island in August, then you should wait until June to fly from Illinois, when ticket prices are also cheap, with an average price of $381.

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 Tuesday. Travelers who choose to depart for Hilton Head Island on a Tuesday will often find tickets for as low as $299. On the other hand, Sunday 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 $492.

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 from Illinois 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 $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 Illinois for as low as $209 on momondo.

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

There are 2 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Illinois to Hilton Head Island.

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	$205
Fastest flight time	2h 26m
Direct flights	Mon, Tue, Thu, Fri, Sat and Sun
Airports in Hilton Head Island	1 airport

The best one-way flight to Hilton Head Island from Illinois in the past 72 hours is $205. The best round-trip flight deal from Illinois to Hilton Head Island found on momondo in the last 72 hours is $369.

The fastest flight from Illinois to Hilton Head Island takes 2h 26m

Direct flights go from Illinois to Hilton Head Island on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There is 1 airport in Hilton Head Island. From Illinois there are direct flights to Hilton Head Island (HHH).

Search flight deals

Frequently asked questions about flying from Illinois to Hilton Head Island

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?
The number of operators available for flights from Illinois to Hilton Head Island Airport is 2 as of November 2026.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Illinois to Hilton Head Island is Embraer 175 (Enhanced Winglets) (40.86% of total bookings). The next most popular plane models are Embraer 175 (24.73%), Embraer 170 (17.20%), and Airbus A319 (5.38%).

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
United Airlines	PriceFrom $224	Free Cancellation	Rating 7.3 10,475 reviews		Search United Airlines flights
American Airlines	PriceFrom $276	Free Cancellation	Rating 7.0 12,225 reviews		Search American Airlines flights

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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Cheap flights from Illinois to Hilton Head Island from $205

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 11/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Illinois to Hilton Head Island

Our best American Airlines deals on Illinois to Hilton Head Island flight tickets

United Airlines flights from Illinois to Hilton Head Island

Our best United Airlines deals on Illinois to Hilton Head Island flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Illinois to Hilton Head Island that are best for you.

See travel insights to Hilton Head Island from

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

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

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

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

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

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

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

What is the cheapest airline that flies from Illinois to Hilton Head Island?

What airlines fly to Hilton Head Island?

How many flights depart from Illinois to Hilton Head Island on average per week?

How long does it take to fly to Hilton Head Island?

Cheap Illinois to Hilton Head Island flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Hilton Head Island

Frequently asked questions about flying 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

Traveling to a place near Hilton Head Island?

Why use momondo?

An easier way to manage your Hilton Head Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing South Carolina

Fly your favorite airline to Hilton Head Island

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Hilton Head Island

List of cabin classes available on flights landing in Hilton Head Island. Availability may vary depending on flight origin and airline.

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