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Cheap flights from Hilton Head Island to Chicago from $289

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hilton Head Island to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:05 pm - 12:14 amHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 09m1 stop Charlotte Douglas
American Airlines Logo
5:21 am - 10:38 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 17m1 stop Charlotte Douglas
$359American Airlines
Tue, Dec 22 - Thu, Dec 24
American Airlines Logo
11:08 am - 2:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 22m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
11:08 am - 2:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 22m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
7:05 pm - 12:14 amHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 09m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
7:05 pm - 12:14 amHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 09m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
11:08 am - 4:19 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 11m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
6:17 pm - 12:14 amHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 57m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
11:08 am - 2:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 22m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
3:02 pm - 7:59 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
5h 57m1 stop Charlotte Douglas
American Airlines Logo
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
American Airlines Logo
11:08 am - 2:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 22m1 stop Charlotte Douglas
American Airlines Logo
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

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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
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
Dec 11
HHH5:54 pmHilton Head Island
5h 38m
1 stop
ORD10:32 pmChicago O'Hare Intl
Dec 13
ORD8:10 amChicago O'Hare Intl
5h 12m
1 stop
HHH2:22 pmHilton Head Island
$369

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

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 12/22

7:05 pm-12:14 am

1 stop6h 09m

Chicago O'Hare Intl

Thu 12/24

5:21 am-10:38 am

1 stop4h 17m

$359
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

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

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

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

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 $386 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?

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

$289

Fastest flight time

4h 57m

Direct flights

Mon, Tue, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $289. 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 57m
Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport on Monday, Tuesday, Saturday and 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 4h 57m.

  • 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?

  • 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?

  • What is the most popular airline 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
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $229Free CancellationRating
7.3
10,458 reviews
Search United Airlines flights
American AirlinesPriceFrom $269Free CancellationRating
7.0
12,231 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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