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

Delta and American Airlines are the most popular carriers 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 62% 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 is 1 operator 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.

$229 Cheap Flights from Hilton Head Island to Chicago O'Hare Intl Airport in 2026

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 7 flights per week flying from Hilton Head Island to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

The number of flights available between Hilton Head Island and Chicago O'Hare Intl Airport is 1 per day as of September 2026. The most frequent departure time is 2:00PM, with 100% of daily flights leaving in the afternoon.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hilton Head Island to Chicago

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One-way

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Cheap round-trip flights

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

$309American Airlines

Wed, Nov 11 - Sat, Nov 14

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

7h 07m1 stop Charlotte Douglas

5:19 am - 10:36 amORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 17m1 stop Charlotte Douglas

$319American Airlines

Fri, Nov 13 - Tue, Nov 24

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

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

7:59 am - 2:26 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 27m1 stop Charlotte Douglas

$319American Airlines

Tue, Oct 20 - Sat, Oct 24

6:08 pm - 12:08 amHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 00m1 stop Charlotte Douglas

12:05 pm - 5:38 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 33m1 stop Charlotte Douglas

$319American Airlines

Wed, Oct 21 - Wed, Oct 28

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

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

9:02 am - 2:26 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 24m1 stop Charlotte Douglas

$319American Airlines

Wed, Oct 14 - Mon, Oct 19

6:08 pm - 11:00 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 52m1 stop Charlotte Douglas

8:05 am - 3:44 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 39m1 stop Charlotte Douglas

$319American Airlines

Fri, Oct 30 - Wed, Nov 4

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

4h 45m1 stop Charlotte Douglas

9:00 am - 3:47 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

5h 47m1 stop Charlotte Douglas

$319American Airlines

Wed, Nov 11 - Sat, Nov 14

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

10:35 am - 2:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 35mnonstop

$359United Airlines

Tue, Sep 22 - Sat, Sep 26

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

6:00 pm - 12:35 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

17h 35m1 stop Newark

$712United Airlines

Wed, Sep 23 - Sun, Sep 27

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

19h 16m2 stops Newark Lambert-St Louis

6:10 pm - 12:35 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

17h 25m2 stops Detroit Metropolitan Wayne County Newark

$746United Airlines

Wed, Oct 14 - Mon, Oct 19

Cheap last minute flights

Enter your travel dates to find the best prices.

12:50 pm - 5:38 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

5h 48m1 stop Charlotte Douglas

9:45 am - 1:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 25mnonstop

$419American Airlines

Tue, Sep 15 - Sat, Sep 19

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

$429United Airlines

Tue, Sep 15 - Sat, Sep 19

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

10:25 am - 2:03 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 38mnonstop

$429United Airlines

Mon, Sep 14 - Sat, Sep 19

2:48 pm - 5:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

3h 17mnonstop

6:00 am - 1:14 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 14m1 stop Newark

$479United Airlines

Mon, Sep 14 - Sat, Sep 19

11:07 am - 3:05 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

4h 58m1 stop Washington, D.C. Reagan-National

6:45 am - 12:15 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

4h 30m1 stop Charlotte Douglas

$484American Airlines

Tue, Sep 15 - Sat, Sep 19

1:50 pm - 9:00 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

8h 10m1 stop Newark

6:00 am - 1:14 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 14m1 stop Newark

$529United Airlines

Mon, Sep 14 - Sat, Sep 19

11:07 am - 5:28 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 21m1 stop Washington, D.C. Reagan-National

9:45 am - 1:10 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

2h 25mnonstop

$557American Airlines

Mon, Sep 14 - Sat, Sep 19

4:17 pm - 10:18 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 01m1 stop New York LaGuardia

8:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 22m1 stop Atlanta Hartsfield-Jackson

$574Delta

Mon, Sep 14 - Sat, Sep 19

4:17 pm - 10:18 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

7h 01m1 stop New York LaGuardia

7:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

7h 22m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$579Delta

Mon, Sep 14 - Sat, Sep 19

12:17 pm - 8:30 pmHHH Hilton Head Island-ORD Chicago O'Hare Intl

9h 13m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

8:05 am - 3:27 pmORD Chicago O'Hare Intl-HHH Hilton Head Island

6h 22m1 stop Atlanta Hartsfield-Jackson

$579Delta

Tue, Sep 15 - Sat, Sep 19

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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

Oct 30

HHH4:13 pmHilton Head Island

7h 04m

1 stop

ORD10:17 pmChicago O'Hare Intl

Nov 4

ORD6:00 amChicago O'Hare Intl

8h 30m

2 stops

HHH3:30 pmHilton Head Island

$344

Delta

Sep 18

HHH4:17 pmHilton Head Island

7h 01m

1 stop

ORD10:18 pmChicago O'Hare Intl

Sep 22

ORD6:00 amChicago O'Hare Intl

8h 27m

2 stops

HHH3:27 pmHilton Head Island

$434

Delta

Oct 21

HHH12:23 pmHilton Head Island

7h 57m

2 stops

ORD7:20 pmChicago O'Hare Intl

Oct 28

ORD6:00 amChicago O'Hare Intl

8h 30m

2 stops

HHH3:30 pmHilton Head Island

$446

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

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

United Airlines

Sep 22

HHH2:48 pmHilton Head Island

3h 17m

ORD5:05 pmChicago O'Hare Intl

Sep 26

ORD10:35 amChicago O'Hare Intl

2h 35m

HHH2:10 pmHilton Head Island

$359

United Airlines

Sep 14

HHH2:48 pmHilton Head Island

3h 17m

ORD5:05 pmChicago O'Hare Intl

Sep 19

ORD10:25 amChicago O'Hare Intl

2h 38m

HHH2:03 pmHilton Head Island

$429

United Airlines

Sep 14

HHH2:48 pmHilton Head Island

3h 17m

ORD5:05 pmChicago O'Hare Intl

Sep 19

ORD6:00 amChicago O'Hare Intl

6h 14m

1 stop

HHH1:14 pmHilton Head Island

$479

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

12:25 pm-5:38 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 11/14

10:02 am-1:24 pm

Nonstop2h 22m

$309

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 11/13

5:54 pm-12:01 am

1 stop7h 07m

Chicago O'Hare Intl

Tue 11/24

5:19 am-10:36 am

1 stop4h 17m

$319

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

7:59 am-2:26 pm

1 stop5h 27m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/21

6:08 pm-12:08 am

1 stop7h 00m

Chicago O'Hare Intl

Wed 10/28

12:05 pm-5:38 pm

1 stop4h 33m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/14

10:55 am-5:17 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 10/19

9:02 am-2:26 pm

1 stop4h 24m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/30

6:08 pm-11:00 pm

1 stop5h 52m

Chicago O'Hare Intl

Wed 11/4

8:05 am-3:44 pm

1 stop6h 39m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 11/11

12:25 pm-4:10 pm

1 stop4h 45m

Chicago O'Hare Intl

Sat 11/14

9:00 am-3:47 pm

1 stop5h 47m

$319

Quickest round-trip

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 9/22

2:48 pm-5:05 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sat 9/26

10:35 am-2:10 pm

Nonstop2h 35m

$359

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 9/23

2:48 pm-5:05 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 9/27

6:00 pm-12:35 pm

1 stop17h 35m

$712

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/14

1:20 pm-7:36 am

2 stops19h 16m

Chicago O'Hare Intl

Mon 10/19

6:10 pm-12:35 pm

2 stops17h 25m

$746

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 $339. 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 $363 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?

No. A direct flight is the cheapest option for a flight between Hilton Head Island to Chicago O'Hare Intl Airport.

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	$229
Fastest flight time	3h 17m
Direct flights	Tue, Wed, Thu and Sun

The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $229. 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 $309.

The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 3h 17m

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

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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 3h 17m.
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 is 1 operator 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 33.68% of the total bookings. Other popular models include Embraer 175 with 31.58%, Airbus A319 with 10.53%, and Boeing 737 with 5.26%.
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 (100% of total bookings).

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 10,194 reviews		Search United Airlines flights

United Airlines Flights From Hilton Head Island to Chicago O'Hare Intl Airport
Across 7 United Airlines flights 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. 10,194 users have rated United Airlines on momondo, with an average score of 7.4/10.

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Joliet

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Elgin

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Skokie

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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 $229

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 11/1. 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

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

Our best United Airlines 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.

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?

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

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

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