What airlines fly to Chicago O'Hare Intl Airport?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Hilton Head Island according to our data. United Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl?

American Airlines and Delta are the most popular carriers operating from Hilton Head Island to Chicago O'Hare Intl

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

Prices for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

As of October 2026, there are 2 operators available to choose from for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport.

How old do you have to be to fly from Hilton Head Island Airport to Chicago O'Hare Intl 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 Hilton Head Island Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$299 Cheap Flights from Hilton Head Island to Chicago O'Hare Intl Airport 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.

4:17 pm - 10:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 13m1 stop Charlotte Douglas

6:41 am - 2:21 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 40m1 stop Charlotte Douglas

$359American Airlines

Wed, Nov 11 - Sun, Nov 15

11:04 am - 4:12 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 08m1 stop Charlotte Douglas

8:10 am - 3:53 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 43m1 stop Charlotte Douglas

$359American Airlines

Thu, Dec 3 - Tue, Dec 8

5:54 pm - 12:01 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 07m1 stop Charlotte Douglas

9:00 am - 3:44 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 44m1 stop Charlotte Douglas

$359American Airlines

Thu, Nov 12 - Mon, Nov 16

1:55 pm - 3:37 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

2h 42mnonstop

6:41 am - 12:06 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 25m1 stop Charlotte Douglas

$369American Airlines

Sat, Nov 14 - Sat, Nov 28

12:25 pm - 5:38 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

6h 13m1 stop Charlotte Douglas

10:02 am - 1:24 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 22mnonstop

$389American Airlines

Tue, Nov 3 - Sat, Nov 7

12:25 pm - 4:10 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 45m1 stop Charlotte Douglas

8:05 am - 3:47 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 42m1 stop Charlotte Douglas

$399American Airlines

Tue, Nov 3 - Sat, Nov 7

4:17 pm - 10:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 13m1 stop Charlotte Douglas

5:19 am - 10:34 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 15m1 stop Charlotte Douglas

$399American Airlines

Wed, Nov 4 - Sun, Nov 8

12:23 pm - 8:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

9h 07m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

8:05 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 25m1 stop Atlanta Hartsfield-Jackson

$404Delta

Tue, Nov 3 - Sat, Nov 7

12:23 pm - 7:20 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 57m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

6:20 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

8h 10m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$409Delta

Tue, Nov 3 - Sat, Nov 7

4:17 pm - 11:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

8h 13m2 stops Charlotte Douglas Washington, D.C. Reagan-National

5:19 am - 10:34 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 15m1 stop Charlotte Douglas

$428American Airlines

Wed, Nov 11 - Sun, Nov 15

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Delta flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best Delta deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets

Delta

Nov 3

HHH12:23 pmHilton Head Island

9h 07m

2 stops

ORD8:30 pmChicago O'Hare Intl

Nov 7

ORD8:05 amChicago O'Hare Intl

6h 25m

1 stop

HHH3:30 pmHilton Head Island

$404

Delta

Nov 3

HHH12:23 pmHilton Head Island

7h 57m

2 stops

ORD7:20 pmChicago O'Hare Intl

Nov 7

ORD6:20 amChicago O'Hare Intl

8h 10m

2 stops

HHH3:30 pmHilton Head Island

$409

Delta

Oct 31

HHH12:23 pmHilton Head Island

9h 07m

2 stops

ORD8:30 pmChicago O'Hare Intl

Nov 7

ORD8:05 amChicago O'Hare Intl

6h 25m

1 stop

HHH3:30 pmHilton Head Island

$439

American Airlines flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best American Airlines deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets

American Airlines

Nov 12

HHH5:54 pmHilton Head Island

7h 07m

1 stop

ORD12:01 amChicago O'Hare Intl

Nov 16

ORD9:00 amChicago O'Hare Intl

5h 44m

1 stop

HHH3:44 pmHilton Head Island

$359

American Airlines

Nov 14

HHH1:55 pmHilton Head Island

2h 42m

ORD3:37 pmChicago O'Hare Intl

Nov 28

ORD6:41 amChicago O'Hare Intl

4h 25m

1 stop

HHH12:06 pmHilton Head Island

$369

American Airlines

Nov 3

HHH12:25 pmHilton Head Island

6h 13m

1 stop

ORD5:38 pmChicago O'Hare Intl

Nov 7

ORD10:02 amChicago O'Hare Intl

2h 22m

HHH1:24 pmHilton Head Island

$389

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 11/11

4:17 pm-10:30 pm

1 stop7h 13m

Chicago O'Hare Intl

Sun 11/15

6:41 am-2:21 pm

1 stop6h 40m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Thu 12/3

11:04 am-4:12 pm

1 stop6h 08m

Chicago O'Hare Intl

Tue 12/8

8:10 am-3:53 pm

1 stop6h 43m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Thu 11/12

5:54 pm-12:01 am

1 stop7h 07m

Chicago O'Hare Intl

Mon 11/16

9:00 am-3:44 pm

1 stop5h 44m

$359

Quickest round-trip

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 11/14

1:55 pm-3:37 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sat 11/28

6:41 am-12:06 pm

1 stop4h 25m

$369

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 11/3

12:25 pm-5:38 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 11/7

10:02 am-1:24 pm

Nonstop2h 22m

$389

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 11/3

12:25 pm-4:10 pm

1 stop4h 45m

Chicago O'Hare Intl

Sat 11/7

8:05 am-3:47 pm

1 stop6h 42m

$399

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 11/4

4:17 pm-10:30 pm

1 stop7h 13m

Chicago O'Hare Intl

Sun 11/8

5:19 am-10:34 am

1 stop4h 15m

$399

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 11/3

12:23 pm-8:30 pm

2 stops9h 07m

Chicago O'Hare Intl

Sat 11/7

8:05 am-3:30 pm

1 stop6h 25m

$404

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 11/3

12:23 pm-7:20 pm

2 stops7h 57m

Chicago O'Hare Intl

Sat 11/7

6:20 am-3:30 pm

2 stops8h 10m

$409

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 11/11

4:17 pm-11:30 pm

2 stops8h 13m

Chicago O'Hare Intl

Sun 11/15

5:19 am-10:34 am

1 stop4h 15m

$428

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Monday is the most expensive day to depart from Hilton Head Island because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $811.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Hilton Head Island at noon is the least expensive time of day to depart. momondo users have found prices as low as $396 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $438. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Hilton Head Island to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Hilton Head Island to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Hilton Head Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 11% on your flight if you consider stops on a Hilton Head Island to Chicago O'Hare Intl Airport flight.

When to book flights from Hilton Head Island to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Hilton Head Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (HHH to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Chicago O'Hare Intl Airport

Best Price Found	$299
Fastest flight time	4h 05m
Direct flights	None

The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $299. The best round-trip flight deal from Hilton Head Island to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $359.

The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 4h 05m

There are no direct flights from Hilton Head Island to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Hilton Head Island Airport - Chicago O'Hare Intl Airport.

Search flight deals

Frequently asked questions about flying from Hilton Head Island to Chicago O'Hare Intl Airport

How far is Hilton Head Island to Chicago O'Hare Intl by plane?
The straight-line distance from Hilton Head Island to Chicago O'Hare Intl is 780.0 mi. By plane, this route typically takes 4h 05m.
When did momondo last update prices for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport?
Prices for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport?
As of October 2026, there are 2 operators available to choose from for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Hilton Head Island Airport to Chicago O'Hare Intl 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 Hilton Head Island Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Hilton Head Island to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Hilton Head Island and Chicago O'Hare Intl Airport, the leading plane model is Embraer 175 (Enhanced Winglets), making up 36.17% of the total bookings. Other popular models include Embraer 175 with 29.79%, Boeing 737 with 8.51%, and Boeing 737-800 with 6.38%.
What is the most popular airline from Hilton Head Island to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Hilton Head Island to Chicago O'Hare Intl Airport is United Airlines (72% of total bookings). The next most popular airline is American Airlines (28%).

Best airlines flying from Hilton Head Island to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.3 10,404 reviews		Search United Airlines flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.0 12,186 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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Hilton Head Island to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Hilton Head Island to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hilton Head Island.

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

Price alerts on flights to Chicago from Hilton Head Island are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Hilton Head Island to Chicago from $299

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 11/12. 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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Delta flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best Delta deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets

American Airlines flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best American Airlines deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Hilton Head Island to Chicago O'Hare Intl Airport

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Hilton Head Island to Chicago O'Hare Intl flight route?

What cabin class options are available on Hilton Head Island to Chicago O'Hare Intl Airport flights?

Can stopping save me money on Hilton Head Island to Chicago O'Hare Intl Airport flights?

What is the cheapest airline that flies from Hilton Head Island to Chicago O'Hare Intl?

What airlines fly to Chicago O'Hare Intl Airport?

When to book flights from Hilton Head Island to Chicago O'Hare Intl Airport

Cheap Hilton Head Island to Chicago O'Hare Intl Airport (HHH to ORD) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Hilton Head Island to Chicago O'Hare Intl Airport

Best airlines flying from Hilton Head Island to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago O'Hare Intl Airport with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago O'Hare Intl Airport 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 Chicago

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

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