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

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

What airlines fly to Hilton Head Island?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Hilton Head Island from Chicago according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 6 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.

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?

The number of operators available for flights from Chicago to Hilton Head Island Airport is 2 as of December 2025.

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.

$151 Cheap Flights from Chicago to Hilton Head Island in 2025/26

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Find the cheapest flights from Chicago to Hilton Head Island

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:50 pm - 12:20 pm

ORD

HHH

14h 30m2 stops

12:54 pm - 6:01 pm

HHH

ORD

6h 07m1 stop

$290American Airlines

Sat, Jan 17 - Sat, Jan 24

7:21 pm - 12:20 pm

ORD

HHH

15h 59m2 stops

12:54 pm - 10:18 pm

HHH

ORD

10h 24m2 stops

$295American Airlines

Sat, Jan 17 - Sat, Jan 24

8:49 pm - 12:20 pm

ORD

HHH

14h 31m2 stops

3:29 pm - 7:50 pm

HHH

ORD

5h 21m1 stop

$299American Airlines

Mon, Jan 19 - Sat, Jan 31

8:49 pm - 12:20 pm

ORD

HHH

14h 31m2 stops

12:54 pm - 9:02 pm

HHH

ORD

9h 08m2 stops

$304American Airlines

Mon, Jan 19 - Sat, Jan 31

6:05 am - 12:20 pm

ORD

HHH

5h 15m1 stop

12:54 pm - 6:01 pm

HHH

ORD

6h 07m1 stop

$309American Airlines

Sat, Jan 17 - Sat, Jan 24

8:50 pm - 12:20 pm

ORD

HHH

14h 30m2 stops

4:08 pm - 9:20 pm

HHH

ORD

6h 12m1 stop

$313American Airlines

Sat, Feb 7 - Fri, Feb 13

6:40 am - 2:27 pm

ORD

HHH

6h 47m2 stops

11:02 am - 4:06 pm

HHH

ORD

6h 04m1 stop

$314American Airlines

Sun, Feb 15 - Sat, Feb 28

8:50 pm - 12:20 pm

ORD

HHH

14h 30m2 stops

11:02 am - 5:49 pm

HHH

ORD

7h 47m2 stops

$318American Airlines

Sat, Feb 7 - Fri, Feb 13

8:12 am - 2:59 pm

ORD

HHH

5h 47m1 stop

3:29 pm - 7:50 pm

HHH

ORD

5h 21m1 stop

$336American Airlines

Mon, Jan 19 - Sat, Jan 31

5:00 am - 10:44 am

ORD

HHH

4h 44m1 stop

12:51 pm - 6:01 pm

HHH

ORD

6h 10m1 stop

$339American Airlines

Tue, Dec 30 - Tue, Jan 6

American Airlines flights from Chicago to Hilton Head Island

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

American Airlines

Jan 17

ORD8:50 pmChicago O'Hare Intl

14h 30m

2 stops

HHH12:20 pmHilton Head Island

Jan 24

HHH12:54 pmHilton Head Island

6h 07m

1 stop

ORD6:01 pmChicago O'Hare Intl

$290

Find similar

American Airlines

Jan 17

ORD7:21 pmChicago O'Hare Intl

15h 59m

2 stops

HHH12:20 pmHilton Head Island

Jan 24

HHH12:54 pmHilton Head Island

10h 24m

2 stops

ORD10:18 pmChicago O'Hare Intl

$295

Find similar

American Airlines

Jan 19

ORD8:49 pmChicago O'Hare Intl

14h 31m

2 stops

HHH12:20 pmHilton Head Island

Jan 31

HHH3:29 pmHilton Head Island

5h 21m

1 stop

ORD7:50 pmChicago O'Hare Intl

$299

Find similar

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 20

ORD10:35 amChicago O'Hare Intl

2h 26m

HHH2:01 pmHilton Head Island

Apr 25

HHH3:00 pmHilton Head Island

2h 45m

ORD4:45 pmChicago O'Hare Intl

$504

Find similar

United Airlines

Apr 20

ORD10:35 amChicago O'Hare Intl

2h 26m

HHH2:01 pmHilton Head Island

Apr 25

HHH4:00 pmHilton Head Island

8h 37m

1 stop

ORD11:37 pmChicago O'Hare Intl

$514

Find similar

United Airlines

Apr 26

ORD6:00 amChicago O'Hare Intl

8h 12m

1 stop

HHH3:12 pmHilton Head Island

Apr 30

HHH3:00 pmHilton Head Island

2h 45m

ORD4:45 pmChicago O'Hare Intl

$532

Find similar

momondo Fare Finder

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

Sat 1/17

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Sat 1/24

12:54 pm-6:01 pm

1 stop6h 07m

$290

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/17

7:21 pm-12:20 pm

2 stops15h 59m

Hilton Head Island

Sat 1/24

12:54 pm-10:18 pm

2 stops10h 24m

$295

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

8:49 pm-12:20 pm

2 stops14h 31m

Hilton Head Island

Sat 1/31

3:29 pm-7:50 pm

1 stop5h 21m

$299

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

8:49 pm-12:20 pm

2 stops14h 31m

Hilton Head Island

Sat 1/31

12:54 pm-9:02 pm

2 stops9h 08m

$304

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/17

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Sat 1/24

12:54 pm-6:01 pm

1 stop6h 07m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Fri 2/13

4:08 pm-9:20 pm

1 stop6h 12m

$313

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 2/15

6:40 am-2:27 pm

2 stops6h 47m

Hilton Head Island

Sat 2/28

11:02 am-4:06 pm

1 stop6h 04m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Fri 2/13

11:02 am-5:49 pm

2 stops7h 47m

$318

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

8:12 am-2:59 pm

1 stop5h 47m

Hilton Head Island

Sat 1/31

3:29 pm-7:50 pm

1 stop5h 21m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 12/30

5:00 am-10:44 am

1 stop4h 44m

Hilton Head Island

Tue 1/6

12:51 pm-6:01 pm

1 stop6h 10m

$339

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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

If you don’t want to visit Hilton Head Island in January, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $335.

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 Tuesday. Travelers who choose to depart for Hilton Head Island on a Tuesday will often find tickets for as low as $361. On the other hand, Friday 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 $498.

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 $439 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 80% 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	$299
Fastest flight time	2h 24m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
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 $299

The fastest flight from Chicago to Hilton Head Island takes 2h 24m

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

There is 1 airport near Hilton Head Island: 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 26m.
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?
The number of operators available for flights from Chicago to Hilton Head Island Airport is 2 as of December 2025.
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?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Hilton Head Island is Embraer 175 (Enhanced Winglets), representing 48.08% of all bookings. The subsequent popular models are Airbus A319 at 13.46%, Embraer 170 at 13.46%, and Airbus A320-100/200 at 9.62%.
What is the most popular airline from Chicago to Hilton Head Island?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Hilton Head Island is American Airlines (70% of total bookings). The next most popular airlines are United Airlines (22%) and Delta (8%).

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
American Airlines	PriceFrom $278	Free Cancellation	Rating 7.2 11,047 reviews		Search American Airlines flights
United Airlines	PriceFrom $299	Free Cancellation	Rating 7.4 9,066 reviews		Search United Airlines flights

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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

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.

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Cheap flights from Chicago to Hilton Head Island from $151

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 2/2. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Hilton Head Island

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Chicago to Hilton Head Island

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

United Airlines flights from Chicago to Hilton Head Island

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

momondo Fare Finder

Use the filters below to find and compare flights from Chicago 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 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 January, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $335.

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

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?

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 80% on your flight if you consider stops on a Chicago to Hilton Head Island flight.

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

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

What airlines fly to Hilton Head Island?

When to book flights from Chicago to Hilton Head Island

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

Fastest flight time

Direct flights

Airports in Hilton Head Island

How far is Chicago to Hilton Head Island by plane?

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

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?

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

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

Traveling to a place near Hilton Head Island?

Why use momondo?

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

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

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

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

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

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