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.

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

Delta, American Airlines, and United Airlines are the most popular carriers operating from Chicago to Hilton Head Island

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 September 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.

$195 Cheap Flights from Chicago to Hilton Head Island in 2025

Q: What is the typical price of a round-trip flight between Chicago and Hilton Head Island?

Prices are currently low for flights on this route. Typical prices usually range from $335 to $515. The lowest price recently found on this route was $309.

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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

5:20 am - 11:32 amORD-HHH

5h 12m1 stop

3:02 pm - 7:11 pmHHH-ORD

5h 09m1 stop

$309American Airlines

Find Deal

Sat, Oct 18 - Sat, Oct 25

10:05 am - 1:25 pmORD-HHH

2h 20mnonstop

11:16 am - 5:13 pmHHH-ORD

6h 57m1 stop

$314American Airlines

Find Deal

Sat, Oct 25 - Tue, Oct 28

7:00 am - 3:02 pmORD-HHH

7h 02m2 stops

5:21 pm - 11:50 pmHHH-ORD

7h 29m2 stops

$319American Airlines

Find Deal

Wed, Oct 22 - Tue, Oct 28

10:05 am - 1:25 pmORD-HHH

2h 20mnonstop

7:07 pm - 11:37 pmHHH-ORD

5h 30m1 stop

$327American Airlines

Find Deal

Sat, Nov 1 - Mon, Nov 3

10:00 am - 1:27 pmORD-HHH

2h 27mnonstop

11:17 am - 6:28 pmHHH-ORD

8h 11m1 stop

$329American Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

9:39 am - 3:30 pmORD-HHH

4h 51m1 stop

12:17 pm - 8:23 pmHHH-ORD

9h 06m2 stops

$504Delta

Find Deal

Sat, Oct 18 - Sat, Oct 25

9:37 pm - 11:16 amORD-HHH

12h 39m2 stops

12:21 pm - 6:34 pmHHH-ORD

7h 13m1 stop

$523United Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

7:25 am - 11:20 amORD-HHH

26h 55m2 stops

11:57 am - 10:35 pmHHH-ORD

11h 38m2 stops

$528United Airlines

Find Deal

Sat, Oct 18 - Thu, Oct 23

1:30 pm - 11:16 amORD-HHH

20h 46m2 stops

12:21 pm - 2:51 pmHHH-ORD

27h 30m2 stops

$534United Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

6:08 am - 3:30 pmORD-HHH

8h 22m2 stops

4:10 pm - 10:26 pmHHH-ORD

7h 16m1 stop

$549Delta

Find Deal

Sat, Oct 18 - Thu, Oct 23

American Airlines flights from Chicago to Hilton Head Island

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

American Airlines

Oct 18

ORD5:20 amChicago O'Hare Intl

5h 12m

1 stop

HHH11:32 amHilton Head Island

Oct 25

HHH3:02 pmHilton Head Island

5h 09m

1 stop

ORD7:11 pmChicago O'Hare Intl

$309

Find similar

American Airlines

Oct 25

ORD10:05 amChicago O'Hare Intl

2h 20m

HHH1:25 pmHilton Head Island

Oct 28

HHH11:16 amHilton Head Island

6h 57m

1 stop

ORD5:13 pmChicago O'Hare Intl

$314

Find similar

American Airlines

Oct 22

ORD7:00 amChicago O'Hare Intl

7h 02m

2 stops

HHH3:02 pmHilton Head Island

Oct 28

HHH5:21 pmHilton Head Island

7h 29m

2 stops

ORD11:50 pmChicago O'Hare Intl

$319

Find similar

Delta flights from Chicago to Hilton Head Island

Our best Delta deals on Chicago to Hilton Head Island flight tickets

Delta

Oct 18

ORD9:39 amChicago O'Hare Intl

4h 51m

1 stop

HHH3:30 pmHilton Head Island

Oct 25

HHH12:17 pmHilton Head Island

9h 06m

2 stops

ORD8:23 pmChicago O'Hare Intl

$504

Find similar

Delta

Oct 18

ORD6:08 amChicago O'Hare Intl

8h 22m

2 stops

HHH3:30 pmHilton Head Island

Oct 23

HHH4:10 pmHilton Head Island

7h 16m

1 stop

ORD10:26 pmChicago O'Hare Intl

$549

Find similar

Delta

Sep 13

ORD7:10 amChicago O'Hare Intl

7h 15m

2 stops

HHH3:25 pmHilton Head Island

Sep 15

HHH12:14 pmHilton Head Island

9h 21m

2 stops

ORD8:35 pmChicago O'Hare Intl

$587

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 10/18

5:20 am-11:32 am

1 stop5h 12m

Hilton Head Island

Sat 10/25

3:02 pm-7:11 pm

1 stop5h 09m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Tue 10/28

11:16 am-5:13 pm

1 stop6h 57m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 10/22

7:00 am-3:02 pm

2 stops7h 02m

Hilton Head Island

Tue 10/28

5:21 pm-11:50 pm

2 stops7h 29m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 11/1

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Mon 11/3

7:07 pm-11:37 pm

1 stop5h 30m

$327

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/27

10:00 am-1:27 pm

Nonstop2h 27m

Hilton Head Island

Sat 10/4

11:17 am-6:28 pm

1 stop8h 11m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

9:39 am-3:30 pm

1 stop4h 51m

Hilton Head Island

Sat 10/25

12:17 pm-8:23 pm

2 stops9h 06m

$504

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/27

9:37 pm-11:16 am

2 stops12h 39m

Hilton Head Island

Sat 10/4

12:21 pm-6:34 pm

1 stop7h 13m

$523

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

7:25 am-11:20 am

2 stops26h 55m

Hilton Head Island

Thu 10/23

11:57 am-10:35 pm

2 stops11h 38m

$528

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/27

1:30 pm-11:16 am

2 stops20h 46m

Hilton Head Island

Sat 10/4

12:21 pm-2:51 pm

2 stops27h 30m

$534

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

6:08 am-3:30 pm

2 stops8h 22m

Hilton Head Island

Thu 10/23

4:10 pm-10:26 pm

1 stop7h 16m

$549

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

Other information

What is the typical price of a round-trip flight between Chicago and Hilton Head Island?

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 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 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, 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 $514.

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 $441 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 $302 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 65% 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

Fastest flight time	2h 20m
Direct flights	Sun
Airports in Hilton Head Island	1 airport

The fastest flight from Chicago to Hilton Head Island takes 2h 20m

Direct flights go from Chicago to Hilton Head Island on 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 20m.
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 September 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 170, representing 39.13% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 17.39%, Airbus A319 at 13.04%, and Embraer 175 at 13.04%.
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 (78% of total bookings). The next most popular airlines are United Airlines (13%) and Delta (9%).

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 $263	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights
United Airlines	PriceFrom $273	Free Cancellation	Rating 7.4 8,937 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 $202

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 10/7. 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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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

Delta flights from Chicago to Hilton Head Island

Our best Delta 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 typical price of a round-trip flight between Chicago and Hilton Head Island?

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 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?

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 65% 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?

Delta, American Airlines, and United Airlines are the most popular carriers 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

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

Airports servicing South Carolina