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

Delta is the most popular carrier operating from Hilton Head Island to Chicago O'Hare Intl

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.

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 September 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.

$209 Cheap Flights from Hilton Head Island to Chicago O'Hare Intl Airport in 2026/27

Q: How many flights depart from Hilton Head Island to Chicago O'Hare Intl Airport on average per week?

As of September 2026, there are 1 flights per week flying from Hilton Head Island to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Wed, with 100% of flights taking off on this day.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hilton Head Island to Chicago

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Enter your travel dates to find the best prices.

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

$329American Airlines

Wed, Nov 11 - Sat, Nov 14

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

7h 13m1 stop Charlotte Douglas

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

2h 22mnonstop

$331American Airlines

Wed, Nov 11 - Sat, Nov 14

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

$333American Airlines

Wed, Nov 11 - Sat, Nov 14

10:55 am - 5:17 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 22m1 stop Washington, D.C. Reagan-National

5:00 am - 11:05 amORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 05m1 stop Charlotte Douglas

$335American Airlines

Tue, Oct 20 - Sat, Oct 24

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

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

7:00 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

7h 30m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$509Delta

Fri, Oct 9 - Tue, Oct 13

4:13 pm - 10:17 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 04m1 stop New York LaGuardia

7:00 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

7h 30m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$564Delta

Tue, Oct 20 - Sat, Oct 24

12:23 pm - 10:17 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

10h 54m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

10:35 am - 3:30 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

3h 55m1 stop Atlanta Hartsfield-Jackson

$564Delta

Tue, Oct 20 - Sat, Oct 24

1:20 pm - 7:36 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

19h 16m2 stops Newark Lambert-St Louis

9:32 pm - 12:35 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

14h 03m2 stops Cincinnati Cinci./N. Kentucky Newark

$753United Airlines

Fri, Oct 16 - Sun, Oct 18

1:20 pm - 7:59 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

19h 39m2 stops Newark Boston Logan Intl

7:45 pm - 12:35 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

15h 50m2 stops Detroit Metropolitan Wayne County Newark

$1,088United Airlines

Mon, Oct 5 - Fri, Oct 9

1:20 pm - 7:42 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

19h 22m1 stop Newark

9:35 pm - 12:35 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

14h 00m1 stop Newark

$1,144United Airlines

Mon, Oct 5 - Fri, Oct 9

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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 11

HHH12:25 pmHilton Head Island

6h 13m

1 stop

ORD5:38 pmChicago O'Hare Intl

Nov 14

ORD10:02 amChicago O'Hare Intl

2h 22m

HHH1:24 pmHilton Head Island

$329

American Airlines

Nov 11

HHH4:17 pmHilton Head Island

7h 13m

1 stop

ORD10:30 pmChicago O'Hare Intl

Nov 14

ORD10:02 amChicago O'Hare Intl

2h 22m

HHH1:24 pmHilton Head Island

$331

American Airlines

Nov 11

HHH12:25 pmHilton Head Island

6h 13m

1 stop

ORD5:38 pmChicago O'Hare Intl

Nov 14

ORD10:02 amChicago O'Hare Intl

2h 22m

HHH1:24 pmHilton Head Island

$333

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

Oct 31

HHH12:23 pmHilton Head Island

6h 24m

1 stop

ORD5:47 pmChicago O'Hare Intl

Nov 5

ORD6:00 amChicago O'Hare Intl

8h 30m

2 stops

HHH3:30 pmHilton Head Island

$441

Delta

Oct 31

HHH12:23 pmHilton Head Island

9h 07m

2 stops

ORD8:30 pmChicago O'Hare Intl

Nov 5

ORD6:00 amChicago O'Hare Intl

8h 30m

2 stops

HHH3:30 pmHilton Head Island

$446

Delta

Sep 25

HHH12:17 pmHilton Head Island

7h 28m

1 stop

ORD6:45 pmChicago O'Hare Intl

Sep 28

ORD6:00 amChicago O'Hare Intl

8h 27m

2 stops

HHH3:27 pmHilton Head Island

$507

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.

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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

Wed 11/11

12:25 pm-5:38 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 11/14

10:02 am-1:24 pm

Nonstop2h 22m

$329

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

Sat 11/14

10:02 am-1:24 pm

Nonstop2h 22m

$331

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 11/11

12:25 pm-5:38 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 11/14

10:02 am-1:24 pm

Nonstop2h 22m

$333

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 10/20

10:55 am-5:17 pm

1 stop7h 22m

Chicago O'Hare Intl

Sat 10/24

5:00 am-11:05 am

1 stop5h 05m

$335

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/9

12:23 pm-8:30 pm

2 stops9h 07m

Chicago O'Hare Intl

Tue 10/13

7:00 am-3:30 pm

2 stops7h 30m

$509

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 10/20

4:13 pm-10:17 pm

1 stop7h 04m

Chicago O'Hare Intl

Sat 10/24

7:00 am-3:30 pm

2 stops7h 30m

$564

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 10/20

12:23 pm-10:17 pm

2 stops10h 54m

Chicago O'Hare Intl

Sat 10/24

10:35 am-3:30 pm

1 stop3h 55m

$564

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/16

1:20 pm-7:36 am

2 stops19h 16m

Chicago O'Hare Intl

Sun 10/18

9:32 pm-12:35 pm

2 stops14h 03m

$753

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Mon 10/5

1:20 pm-7:59 am

2 stops19h 39m

Chicago O'Hare Intl

Fri 10/9

7:45 pm-12:35 pm

2 stops15h 50m

$1,088

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Mon 10/5

1:20 pm-7:42 am

1 stop19h 22m

Chicago O'Hare Intl

Fri 10/9

9:35 pm-12:35 pm

1 stop14h 00m

$1,144

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

Other information

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, Sunday 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 $671.

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 $386 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $437. 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 3% 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	$209
Fastest flight time	2h 44m
Direct flights	Sun

The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $209. 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 $329.

The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 44m

Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.

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 2h 44m.
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 September 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 32.88% of the total bookings. Other popular models include Embraer 175 with 30.14%, Airbus A319 with 12.33%, and Boeing 737 with 5.48%.
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 (71% of total bookings). The next most popular airline is American Airlines (29%).

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 7.4 10,233 reviews		Search United Airlines flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.0 12,074 reviews		Search American Airlines flights

United Airlines Flights From Hilton Head Island to Chicago O'Hare Intl Airport
Across 1 United Airlines flight from Hilton Head Island to Chicago O'Hare Intl Airport this week, the average price was $355, with the best United Airlines deals starting from $229 round-trip. 10,233 users have rated United Airlines on momondo, with an average score of 7.4/10.

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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 $209

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 10/31. 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 O'Hare Intl Airport

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

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

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

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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?

How many flights depart from Hilton Head Island to Chicago O'Hare Intl Airport on average per week?

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

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Daily price changes in your inbox - only with Price Alerts.

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