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.

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

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

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 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.

$191 Cheap Flights from Hilton Head Island to Chicago in 2026

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Find the cheapest flights from Hilton Head Island to Chicago

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One-way

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Cheap round-trip flights

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3:29 pm - 7:50 pm

HHH

ORD

5h 21m

1 stop

8:50 pm - 12:20 pm

ORD

HHH

14h 30m

2 stops

$352American Airlines

Tue, Feb 3 - Sat, Feb 7

11:03 am - 4:21 pm

HHH

ORD

6h 18m

1 stop

9:48 am - 3:41 pm

ORD

HHH

4h 53m

1 stop

$356American Airlines

Thu, Mar 5 - Tue, Mar 10

12:51 pm - 8:53 pm

HHH

ORD

9h 02m

2 stops

8:50 pm - 12:20 pm

ORD

HHH

14h 30m

2 stops

$358American Airlines

Tue, Feb 3 - Sat, Feb 7

12:51 pm - 6:01 pm

HHH

ORD

6h 10m

1 stop

8:12 am - 2:59 pm

ORD

HHH

5h 47m

1 stop

$389American Airlines

Tue, Feb 3 - Tue, Feb 10

3:29 pm - 10:34 pm

HHH

ORD

8h 05m

2 stops

8:12 am - 2:59 pm

ORD

HHH

5h 47m

1 stop

$394American Airlines

Tue, Feb 3 - Tue, Feb 10

12:51 pm - 8:53 pm

HHH

ORD

9h 02m

2 stops

6:00 am - 2:59 pm

ORD

HHH

7h 59m

2 stops

$400American Airlines

Tue, Feb 3 - Tue, Feb 10

6:20 pm - 11:58 pm

HHH

ORD

6h 38m

1 stop

8:08 am - 3:41 pm

ORD

HHH

6h 33m

1 stop

$417American Airlines

Sat, Feb 14 - Mon, Feb 16

11:03 am - 5:15 pm

HHH

ORD

7h 12m

2 stops

8:10 am - 2:22 pm

ORD

HHH

5h 12m

1 stop

$422American Airlines

Sat, Feb 14 - Mon, Feb 16

2:58 pm - 10:46 pm

HHH

ORD

8h 48m

2 stops

6:08 am - 2:22 pm

ORD

HHH

7h 14m

2 stops

$428American Airlines

Sat, Feb 14 - Mon, Feb 16

6:15 pm - 12:16 am

HHH

ORD

7h 01m

1 stop

8:10 am - 2:22 pm

ORD

HHH

5h 12m

1 stop

$534American Airlines

Thu, Mar 12 - Sun, Mar 15

American Airlines flights from Hilton Head Island to Chicago

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

American Airlines

Feb 3

HHH3:29 pmHilton Head Island

5h 21m

1 stop

ORD7:50 pmChicago O'Hare Intl

Feb 7

ORD8:50 pmChicago O'Hare Intl

14h 30m

2 stops

HHH12:20 pmHilton Head Island

$352

American Airlines

Mar 5

HHH11:03 amHilton Head Island

6h 18m

1 stop

ORD4:21 pmChicago O'Hare Intl

Mar 10

ORD9:48 amChicago O'Hare Intl

4h 53m

1 stop

HHH3:41 pmHilton Head Island

$356

American Airlines

Feb 3

HHH12:51 pmHilton Head Island

9h 02m

2 stops

ORD8:53 pmChicago O'Hare Intl

Feb 7

ORD8:50 pmChicago O'Hare Intl

14h 30m

2 stops

HHH12:20 pmHilton Head Island

$358

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

Tue 2/3

3:29 pm-7:50 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

$352

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 3/5

11:03 am-4:21 pm

1 stop6h 18m

Chicago O'Hare Intl

Tue 3/10

9:48 am-3:41 pm

1 stop4h 53m

$356

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

12:51 pm-8:53 pm

2 stops9h 02m

Chicago O'Hare Intl

Sat 2/7

8:50 pm-12:20 pm

2 stops14h 30m

$358

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 2/10

8:12 am-2:59 pm

1 stop5h 47m

$389

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

3:29 pm-10:34 pm

2 stops8h 05m

Chicago O'Hare Intl

Tue 2/10

8:12 am-2:59 pm

1 stop5h 47m

$394

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

12:51 pm-8:53 pm

2 stops9h 02m

Chicago O'Hare Intl

Tue 2/10

6:00 am-2:59 pm

2 stops7h 59m

$400

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

6:20 pm-11:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 2/16

8:08 am-3:41 pm

1 stop6h 33m

$417

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:03 am-5:15 pm

2 stops7h 12m

Chicago O'Hare Intl

Mon 2/16

8:10 am-2:22 pm

1 stop5h 12m

$422

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

2:58 pm-10:46 pm

2 stops8h 48m

Chicago O'Hare Intl

Mon 2/16

6:08 am-2:22 pm

2 stops7h 14m

$428

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 3/12

6:15 pm-12:16 am

1 stop7h 01m

Chicago O'Hare Intl

Sun 3/15

8:10 am-2:22 pm

1 stop5h 12m

$534

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 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?

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

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	2h 44m
Direct flights	Mon, Tue, Fri, Sat and Sun
Airports in Chicago	3 airports

The fastest flight from Hilton Head Island to Chicago takes 2h 44m

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

There are 3 airports in Chicago. From Hilton Head Island there are direct flights to 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 44m.
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 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%.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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 $191

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 4/16. 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

American Airlines flights from Hilton Head Island to Chicago

Our best American 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

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?

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

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

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

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