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

American Airlines and Delta are the most popular carriers 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 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 November 2026, there are 2 operators 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.

$180 Cheap Flights from Hilton Head Island to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hilton Head Island to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:08 am - 2:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 22m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Tue, Dec 22 - Fri, Dec 25

11:08 am - 2:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 22m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Sun, Dec 20 - Fri, Dec 25

7:05 pm - 12:14 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 09m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Sun, Dec 20 - Tue, Dec 22

7:05 pm - 12:14 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 09m1 stop Charlotte Douglas

12:05 pm - 6:32 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 27m1 stop Charlotte Douglas

$359American Airlines

Wed, Dec 30 - Mon, Jan 4

11:08 am - 4:19 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 11m1 stop Charlotte Douglas

6:30 am - 12:00 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 30m1 stop Charlotte Douglas

$359American Airlines

Tue, Jan 5 - Tue, Jan 12

11:08 am - 2:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 22m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Mon, Dec 21 - Tue, Dec 22

6:17 pm - 12:14 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 57m1 stop Charlotte Douglas

12:01 pm - 5:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 29m1 stop Charlotte Douglas

$359American Airlines

Tue, Feb 16 - Tue, Feb 23

3:02 pm - 7:59 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 57m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Sun, Dec 20 - Mon, Dec 21

11:08 am - 2:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 22m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Sun, Dec 20 - Thu, Dec 24

2:49 pm - 7:59 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 10m1 stop Charlotte Douglas

5:21 am - 10:38 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$359American Airlines

Sat, Dec 19 - Thu, Dec 24

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American Airlines flights from Hilton Head Island to Chicago

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

American Airlines

Dec 20

HHH3:02 pmHilton Head Island

5h 57m

1 stop

ORD7:59 pmChicago O'Hare Intl

Dec 21

ORD5:21 amChicago O'Hare Intl

4h 17m

1 stop

HHH10:38 amHilton Head Island

$359

American Airlines

Jan 13

HHH12:37 pmHilton Head Island

5h 47m

1 stop

ORD5:24 pmChicago O'Hare Intl

Jan 18

ORD5:28 amChicago O'Hare Intl

5h 32m

1 stop

HHH12:00 pmHilton Head Island

$360

American Airlines

Nov 14

HHH1:55 pmHilton Head Island

2h 42m

ORD3:37 pmChicago O'Hare Intl

Nov 18

ORD6:41 amChicago O'Hare Intl

4h 12m

1 stop

HHH11:53 amHilton Head Island

$389

momondo Fare Finder

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

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 12/22

11:08 am-2:30 pm

1 stop4h 22m

Chicago O'Hare Intl

Fri 12/25

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sun 12/20

11:08 am-2:30 pm

1 stop4h 22m

Chicago O'Hare Intl

Fri 12/25

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sun 12/20

7:05 pm-12:14 am

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/22

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 12/30

7:05 pm-12:14 am

1 stop6h 09m

Chicago O'Hare Intl

Mon 1/4

12:05 pm-6:32 pm

1 stop5h 27m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 1/5

11:08 am-4:19 pm

1 stop6h 11m

Chicago O'Hare Intl

Tue 1/12

6:30 am-12:00 pm

1 stop4h 30m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Mon 12/21

11:08 am-2:30 pm

1 stop4h 22m

Chicago O'Hare Intl

Tue 12/22

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 2/16

6:17 pm-12:14 am

1 stop6h 57m

Chicago O'Hare Intl

Tue 2/23

12:01 pm-5:30 pm

1 stop4h 29m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sun 12/20

3:02 pm-7:59 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 12/21

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sun 12/20

11:08 am-2:30 pm

1 stop4h 22m

Chicago O'Hare Intl

Thu 12/24

5:21 am-10:38 am

1 stop4h 17m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 12/19

2:49 pm-7:59 pm

1 stop6h 10m

Chicago O'Hare Intl

Thu 12/24

5:21 am-10:38 am

1 stop4h 17m

$359

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 Wednesday when prices can be found for as low as $340. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Hilton Head Island to Chicago for around $811.

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 at noon. Flights from Hilton Head Island to Chicago during this time can be as low as $386. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $438.

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 are 2 cabin classes 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

Best Price Found	$180
Fastest flight time	4h 45m
Direct flights	Mon, Tue, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hilton Head Island in the past 72 hours is $180. The best round-trip flight deal from Hilton Head Island to Chicago found on momondo in the last 72 hours is $359.

The fastest flight from Hilton Head Island to Chicago takes 4h 45m

Direct flights go from Hilton Head Island to Chicago on Monday, Tuesday, 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

Frequently asked questions about flying from Hilton Head Island to Chicago

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 4h 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 November 2026, there are 2 operators 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 Embraer 175 (Enhanced Winglets), making up 34.88% of the total bookings. Other popular models include Embraer 175 with 27.91%, Boeing 737 with 9.30%, and Boeing 737-800 with 6.98%.
What is the most popular airline from Hilton Head Island to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Hilton Head Island to Chicago is American Airlines (66% of total bookings). The next most popular airline is United Airlines (34%).

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
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.3 10,459 reviews		Search United Airlines flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.0 12,230 reviews		Search American Airlines flights

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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.

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Cheap flights from Hilton Head Island to Chicago from $180

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 11/22. 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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American Airlines flights from Hilton Head Island to Chicago

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

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

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

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?

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

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

Can stopping save me money on Hilton Head Island to Chicago flights?

What is the cheapest airline that flies 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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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