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

Delta 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 January 2026.

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.

$208 Cheap Flights from Chicago to Hilton Head Island in 2026

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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.

9:45 am - 3:10 pm

ORD

HHH

4h 25m

1 stop

3:50 pm - 10:12 pm

HHH

ORD

7h 22m

1 stop

$279Delta

Tue, Apr 14 - Wed, Apr 22

7:00 am - 3:10 pm

ORD

HHH

7h 10m

2 stops

3:50 pm - 10:12 pm

HHH

ORD

7h 22m

1 stop

$284Delta

Tue, Apr 14 - Wed, Apr 22

10:28 am - 5:44 pm

ORD

HHH

6h 16m

1 stop

4:31 pm - 9:15 pm

HHH

ORD

5h 44m

1 stop

$329American Airlines

Sat, Feb 14 - Sat, Feb 21

9:45 am - 3:10 pm

ORD

HHH

4h 25m

1 stop

3:50 pm - 10:12 pm

HHH

ORD

7h 22m

1 stop

$334Delta

Wed, Apr 15 - Wed, Apr 22

10:28 am - 5:44 pm

ORD

HHH

6h 16m

1 stop

6:15 pm - 11:58 pm

HHH

ORD

6h 43m

1 stop

$356American Airlines

Mon, Mar 16 - Sat, Mar 21

10:28 am - 5:44 pm

ORD

HHH

6h 16m

1 stop

4:31 pm - 9:15 pm

HHH

ORD

5h 44m

1 stop

$359American Airlines

Wed, Mar 18 - Sat, Mar 21

6:08 am - 2:22 pm

ORD

HHH

7h 14m

2 stops

4:31 pm - 9:15 pm

HHH

ORD

5h 44m

1 stop

$361American Airlines

Mon, Mar 16 - Sat, Mar 21

6:08 am - 2:22 pm

ORD

HHH

7h 14m

2 stops

4:31 pm - 9:15 pm

HHH

ORD

5h 44m

1 stop

$364American Airlines

Wed, Mar 18 - Sat, Mar 21

9:38 am - 5:44 pm

ORD

HHH

7h 06m

2 stops

2:58 pm - 10:46 pm

HHH

ORD

8h 48m

2 stops

$370American Airlines

Sat, Feb 14 - Sat, Feb 21

7:10 am - 2:22 pm

ORD

HHH

6h 12m

1 stop

4:31 pm - 9:15 pm

HHH

ORD

5h 44m

1 stop

$376American Airlines

Sat, Mar 14 - Sat, Mar 21

Delta flights from Chicago to Hilton Head Island

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

Delta

Apr 14

ORD8:15 amChicago O'Hare Intl

5h 55m

1 stop

HHH3:10 pmHilton Head Island

Apr 21

HHH3:50 pmHilton Head Island

7h 22m

1 stop

ORD10:12 pmChicago O'Hare Intl

$279

Delta

Apr 14

ORD7:00 amChicago O'Hare Intl

7h 10m

2 stops

HHH3:10 pmHilton Head Island

Apr 21

HHH3:50 pmHilton Head Island

7h 22m

1 stop

ORD10:12 pmChicago O'Hare Intl

$284

Delta

Apr 15

ORD8:15 amChicago O'Hare Intl

5h 55m

1 stop

HHH3:10 pmHilton Head Island

Apr 21

HHH3:50 pmHilton Head Island

7h 22m

1 stop

ORD10:12 pmChicago O'Hare Intl

$334

American Airlines flights from Chicago to Hilton Head Island

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

American Airlines

Feb 14

ORD10:28 amChicago O'Hare Intl

6h 16m

1 stop

HHH5:44 pmHilton Head Island

Feb 21

HHH4:31 pmHilton Head Island

5h 44m

1 stop

ORD9:15 pmChicago O'Hare Intl

$329

American Airlines

Mar 16

ORD10:28 amChicago O'Hare Intl

6h 16m

1 stop

HHH5:44 pmHilton Head Island

Mar 21

HHH6:15 pmHilton Head Island

6h 43m

1 stop

ORD11:58 pmChicago O'Hare Intl

$356

American Airlines

Mar 18

ORD10:28 amChicago O'Hare Intl

6h 16m

1 stop

HHH5:44 pmHilton Head Island

Mar 21

HHH4:31 pmHilton Head Island

5h 44m

1 stop

ORD9:15 pmChicago O'Hare Intl

$359

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

Tue 4/14

9:45 am-3:10 pm

1 stop4h 25m

Hilton Head Island

Wed 4/22

3:50 pm-10:12 pm

1 stop7h 22m

$279

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:10 pm

2 stops7h 10m

Hilton Head Island

Wed 4/22

3:50 pm-10:12 pm

1 stop7h 22m

$284

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/14

10:28 am-5:44 pm

1 stop6h 16m

Hilton Head Island

Sat 2/21

4:31 pm-9:15 pm

1 stop5h 44m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 4/15

9:45 am-3:10 pm

1 stop4h 25m

Hilton Head Island

Wed 4/22

3:50 pm-10:12 pm

1 stop7h 22m

$334

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/16

10:28 am-5:44 pm

1 stop6h 16m

Hilton Head Island

Sat 3/21

6:15 pm-11:58 pm

1 stop6h 43m

$356

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 3/18

10:28 am-5:44 pm

1 stop6h 16m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$359

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/16

6:08 am-2:22 pm

2 stops7h 14m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$361

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 3/18

6:08 am-2:22 pm

2 stops7h 14m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$364

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 2/14

9:38 am-5:44 pm

2 stops7h 06m

Hilton Head Island

Sat 2/21

2:58 pm-10:46 pm

2 stops8h 48m

$370

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 3/14

7:10 am-2:22 pm

1 stop6h 12m

Hilton Head Island

Sat 3/21

4:31 pm-9:15 pm

1 stop5h 44m

$376

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 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 $502.

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 $428 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	$279
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 $279

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?
The number of operators available for flights from Chicago to Hilton Head Island Airport is 2 as of January 2026.
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 54.79% of all bookings. The subsequent popular models are Airbus A319 at 12.33%, Embraer 170 at 10.96%, and Airbus A320-100/200 at 9.59%.
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 (66% of total bookings). The next most popular airlines are United Airlines (25%) 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
United Airlines	PriceFrom $279	Free Cancellation	Rating 7.4 9,164 reviews		Search United Airlines flights
American Airlines	PriceFrom $288	Free Cancellation	Rating 7.2 11,136 reviews		Search American 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 7/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

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

Delta flights from Chicago to Hilton Head Island

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

American Airlines flights from Chicago to Hilton Head Island

Our best American 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

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?

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 51% 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 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

Airports servicing South Carolina