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

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

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Hilton Head Island according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

As of December 2025, there is 1 operator available to choose from for flights from Hilton Head Island Airport to Chicago.

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

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 Hilton Head Island Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$147 Cheap Flights from Hilton Head Island to Chicago in 2025/26

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Find the cheapest flights from Hilton Head Island to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:51 pm - 6:01 pm

HHH

ORD

6h 10m1 stop

8:49 pm - 12:20 pm

ORD

HHH

14h 31m2 stops

$341American Airlines

Thu, Jan 22 - Mon, Jan 26

12:51 pm - 8:46 pm

HHH

ORD

8h 55m2 stops

8:49 pm - 12:20 pm

ORD

HHH

14h 31m2 stops

$346American Airlines

Thu, Jan 22 - Mon, Jan 26

3:29 pm - 7:50 pm

HHH

ORD

5h 21m1 stop

6:05 am - 12:20 pm

ORD

HHH

5h 15m1 stop

$363American Airlines

Thu, Jan 22 - Mon, Jan 26

12:51 pm - 11:44 pm

HHH

ORD

11h 53m2 stops

8:12 am - 2:59 pm

ORD

HHH

5h 47m1 stop

$368American Airlines

Thu, Jan 22 - Sun, Jan 25

3:29 pm - 10:34 pm

HHH

ORD

8h 05m2 stops

5:05 am - 2:59 pm

ORD

HHH

8h 54m2 stops

$373American Airlines

Thu, Jan 22 - Sun, Jan 25

3:27 pm - 9:27 pm

HHH

ORD

7h 00m1 stop

5:00 am - 10:44 am

ORD

HHH

4h 44m1 stop

$397American Airlines

Wed, Dec 17 - Sun, Dec 21

12:52 pm - 8:26 pm

HHH

ORD

8h 34m2 stops

5:00 am - 10:44 am

ORD

HHH

4h 44m1 stop

$402American Airlines

Wed, Dec 17 - Sun, Dec 21

5:20 pm - 10:50 pm

HHH

ORD

6h 30m1 stop

7:11 am - 2:27 pm

ORD

HHH

6h 16m1 stop

$409American Airlines

Tue, Feb 24 - Sat, Feb 28

12:22 pm - 8:40 pm

HHH

ORD

9h 18m2 stops

5:00 am - 10:32 am

ORD

HHH

4h 32m1 stop

$414American Airlines

Tue, Feb 24 - Sat, Feb 28

6:13 pm - 11:42 pm

HHH

ORD

6h 29m1 stop

5:00 am - 10:44 am

ORD

HHH

4h 44m1 stop

$425American Airlines

Thu, Dec 18 - Mon, Dec 22

American Airlines flights from Hilton Head Island to Chicago

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

American Airlines

Jan 22

HHH12:51 pmHilton Head Island

6h 10m

1 stop

ORD6:01 pmChicago O'Hare Intl

Jan 26

ORD8:49 pmChicago O'Hare Intl

14h 31m

2 stops

HHH12:20 pmHilton Head Island

$341

Find similar

American Airlines

Jan 22

HHH12:51 pmHilton Head Island

8h 55m

2 stops

ORD8:46 pmChicago O'Hare Intl

Jan 26

ORD8:49 pmChicago O'Hare Intl

14h 31m

2 stops

HHH12:20 pmHilton Head Island

$346

Find similar

American Airlines

Jan 22

HHH3:29 pmHilton Head Island

5h 21m

1 stop

ORD7:50 pmChicago O'Hare Intl

Jan 26

ORD6:05 amChicago O'Hare Intl

5h 15m

1 stop

HHH12:20 pmHilton Head Island

$363

Find similar

United Airlines flights from Hilton Head Island to Chicago

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

United Airlines

Apr 11

HHH3:00 pmHilton Head Island

2h 45m

ORD4:45 pmChicago O'Hare Intl

Apr 18

ORD8:55 amChicago O'Hare Intl

5h 17m

1 stop

HHH3:12 pmHilton Head Island

$667

Find similar

United Airlines

Apr 4

HHH3:00 pmHilton Head Island

2h 45m

ORD4:45 pmChicago O'Hare Intl

Apr 10

ORD6:00 amChicago O'Hare Intl

8h 12m

1 stop

HHH3:12 pmHilton Head Island

$1,214

Find similar

United Airlines

Apr 11

HHH3:00 pmHilton Head Island

2h 45m

ORD4:45 pmChicago O'Hare Intl

Apr 18

ORD10:35 amChicago O'Hare Intl

2h 26m

HHH2:01 pmHilton Head Island

$1,439

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 1/22

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 1/26

8:49 pm-12:20 pm

2 stops14h 31m

$341

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 1/22

12:51 pm-8:46 pm

2 stops8h 55m

Chicago O'Hare Intl

Mon 1/26

8:49 pm-12:20 pm

2 stops14h 31m

$346

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 1/22

3:29 pm-7:50 pm

1 stop5h 21m

Chicago O'Hare Intl

Mon 1/26

6:05 am-12:20 pm

1 stop5h 15m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 1/22

12:51 pm-11:44 pm

2 stops11h 53m

Chicago O'Hare Intl

Sun 1/25

8:12 am-2:59 pm

1 stop5h 47m

$368

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 1/22

3:29 pm-10:34 pm

2 stops8h 05m

Chicago O'Hare Intl

Sun 1/25

5:05 am-2:59 pm

2 stops8h 54m

$373

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/17

3:27 pm-9:27 pm

1 stop7h 00m

Chicago O'Hare Intl

Sun 12/21

5:00 am-10:44 am

1 stop4h 44m

$397

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/17

12:52 pm-8:26 pm

2 stops8h 34m

Chicago O'Hare Intl

Sun 12/21

5:00 am-10:44 am

1 stop4h 44m

$402

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/24

5:20 pm-10:50 pm

1 stop6h 30m

Chicago O'Hare Intl

Sat 2/28

7:11 am-2:27 pm

1 stop6h 16m

$409

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/24

12:22 pm-8:40 pm

2 stops9h 18m

Chicago O'Hare Intl

Sat 2/28

5:00 am-10:32 am

1 stop4h 32m

$414

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 12/18

6:13 pm-11:42 pm

1 stop6h 29m

Chicago O'Hare Intl

Mon 12/22

5:00 am-10:44 am

1 stop4h 44m

$425

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 Hilton Head Island to Chicago

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $250. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Hilton Head Island to Chicago for around $493.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Hilton Head Island to Chicago during this time can be as low as $423. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $538.

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

Fly from Hilton Head Island to Chicago O'Hare Intl for the best Hilton Head Island - Chicago flight prices

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

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

You could potentially save up to 20% on your flight if you consider stops on a Hilton Head Island to Chicago flight.

When to book flights from Hilton Head Island to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hilton Head Island to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Hilton Head Island to Chicago (HHH to CHI) flight deals and tips

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

Fastest flight time	6h 10m
Direct flights	Mon and Sun
Airports in Chicago	1 airport

The fastest flight from Hilton Head Island to Chicago takes 6h 10m

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

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Hilton Head Island to Chicago by plane?
The distance between Hilton Head Island and Chicago is about 766.4 mi. In terms of flight time, this usually takes a little over 2h 45m.
When did momondo last update prices for flights from Hilton Head Island Airport to Chicago?
Prices for flights from Hilton Head Island Airport to Chicago were last updated today.
How many operators does momondo search for flights from Hilton Head Island Airport to Chicago?
As of December 2025, there is 1 operator available to choose from for flights from Hilton Head Island Airport to Chicago.
How old do you have to be to fly from Hilton Head Island Airport to Chicago?
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 Hilton Head Island Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Hilton Head Island to Chicago?
Based on momondo bookings for flights between Hilton Head Island and Chicago, the leading plane model is Airbus A319, making up 16.67% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 16.67%, Airbus A220-300 with 16.67%, and Embraer 175 with 16.67%.

Best airlines flying from Hilton Head Island to Chicago

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $228	Free Cancellation	Rating 7.2 11,047 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Hilton Head Island to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Hilton Head Island to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Hilton Head Island to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Hilton Head Island to Chicago 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 Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Hilton Head Island to Chicago from $195

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilton Head Island to Chicago 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.

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 Hilton Head Island to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Hilton Head Island to Chicago

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

United Airlines flights from Hilton Head Island to Chicago

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

momondo Fare Finder

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

See travel insights to Chicago from

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

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 day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Hilton Head Island to Chicago during this time can be as low as $423. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $538.

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

Fly from Hilton Head Island to Chicago O'Hare Intl for the best Hilton Head Island - Chicago flight prices

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

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

You could potentially save up to 20% on your flight if you consider stops on a Hilton Head Island to Chicago flight.

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

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

What airlines fly to Chicago?

When to book flights from Hilton Head Island to Chicago

Cheap Hilton Head Island to Chicago (HHH to CHI) flight deals and tips

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Hilton Head Island to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

Best airlines flying from Hilton Head Island to Chicago

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago