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Cheap flights from Hilton Head Island to Chicago from $201

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 2/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:58 am - 7:03 pm
HHH
-
ORD
8h 05m2 stops
Delta Logo
8:15 am - 3:10 pm
ORD
-
HHH
5h 55m1 stop
$254Delta
Thu, Apr 23 - Sun, Apr 26
Delta Logo
11:58 am - 4:41 pm
HHH
-
ORD
5h 43m1 stop
Delta Logo
8:15 am - 3:10 pm
ORD
-
HHH
5h 55m1 stop
$269Delta
Thu, Apr 23 - Sun, Apr 26
American Airlines Logo
3:29 pm - 7:50 pm
HHH
-
ORD
5h 21m1 stop
American Airlines Logo
7:10 am - 2:22 pm
ORD
-
HHH
6h 12m1 stop
$309American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
12:51 pm - 10:38 pm
HHH
-
ORD
10h 47m2 stops
American Airlines Logo
10:28 am - 5:44 pm
ORD
-
HHH
6h 16m1 stop
$314American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
12:51 pm - 11:44 pm
HHH
-
ORD
11h 53m2 stops
American Airlines Logo
9:38 am - 5:44 pm
ORD
-
HHH
7h 06m2 stops
$320American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
6:20 pm - 11:58 pm
HHH
-
ORD
6h 38m1 stop
American Airlines Logo
7:10 am - 2:22 pm
ORD
-
HHH
6h 12m1 stop
$336American Airlines
Sat, Feb 14 - Mon, Feb 16
American Airlines Logo
12:51 pm - 6:01 pm
HHH
-
ORD
6h 10m1 stop
American Airlines Logo
8:12 am - 2:59 pm
ORD
-
HHH
5h 47m1 stop
$339American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
11:03 am - 5:15 pm
HHH
-
ORD
7h 12m2 stops
American Airlines Logo
7:10 am - 2:22 pm
ORD
-
HHH
6h 12m1 stop
$341American Airlines
Sat, Feb 14 - Mon, Feb 16
American Airlines Logo
3:29 pm - 10:34 pm
HHH
-
ORD
8h 05m2 stops
American Airlines Logo
10:10 am - 2:59 pm
ORD
-
HHH
3h 49m1 stop
$344American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
2:58 pm - 10:46 pm
HHH
-
ORD
8h 48m2 stops
American Airlines Logo
6:08 am - 2:22 pm
ORD
-
HHH
7h 14m2 stops
$347American Airlines
Sat, Feb 14 - Mon, Feb 16

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
Feb 11
HHH3:29 pmHilton Head Island
5h 21m
1 stop
ORD7:50 pmChicago O'Hare Intl
Feb 14
ORD7:10 amChicago O'Hare Intl
6h 12m
1 stop
HHH2:22 pmHilton Head Island
$309
American Airlines
Feb 11
HHH12:51 pmHilton Head Island
10h 47m
2 stops
ORD10:38 pmChicago O'Hare Intl
Feb 14
ORD10:28 amChicago O'Hare Intl
6h 16m
1 stop
HHH5:44 pmHilton Head Island
$314
American Airlines
Feb 11
HHH12:51 pmHilton Head Island
11h 53m
2 stops
ORD11:44 pmChicago O'Hare Intl
Feb 14
ORD9:38 amChicago O'Hare Intl
7h 06m
2 stops
HHH5:44 pmHilton Head Island
$320

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
Apr 23
HHH11:58 amHilton Head Island
8h 05m
2 stops
ORD7:03 pmChicago O'Hare Intl
Apr 26
ORD8:15 amChicago O'Hare Intl
5h 55m
1 stop
HHH3:10 pmHilton Head Island
$254
Delta
Apr 23
HHH11:58 amHilton Head Island
5h 43m
1 stop
ORD4:41 pmChicago O'Hare Intl
Apr 26
ORD8:15 amChicago O'Hare Intl
5h 55m
1 stop
HHH3:10 pmHilton Head Island
$269
Delta
Apr 24
HHH3:50 pmHilton Head Island
7h 22m
1 stop
ORD10:12 pmChicago O'Hare Intl
Apr 26
ORD8:15 amChicago O'Hare Intl
5h 55m
1 stop
HHH3:10 pmHilton Head Island
$354

momondo Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 8, 2026.
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

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/23

11:58 am-7:03 pm

2 stops8h 05m

Chicago O'Hare Intl

Sun 4/26

8:15 am-3:10 pm

1 stop5h 55m

$254

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 4/23

11:58 am-4:41 pm

1 stop5h 43m

Chicago O'Hare Intl

Sun 4/26

8:15 am-3:10 pm

1 stop5h 55m

$269

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

3:29 pm-7:50 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 2/14

7:10 am-2:22 pm

1 stop6h 12m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

12:51 pm-10:38 pm

2 stops10h 47m

Chicago O'Hare Intl

Sat 2/14

10:28 am-5:44 pm

1 stop6h 16m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

12:51 pm-11:44 pm

2 stops11h 53m

Chicago O'Hare Intl

Sat 2/14

9:38 am-5:44 pm

2 stops7h 06m

$320

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

6:20 pm-11:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 2/16

7:10 am-2:22 pm

1 stop6h 12m

$336

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 2/10

8:12 am-2:59 pm

1 stop5h 47m

$339

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:03 am-5:15 pm

2 stops7h 12m

Chicago O'Hare Intl

Mon 2/16

7:10 am-2:22 pm

1 stop6h 12m

$341

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/3

3:29 pm-10:34 pm

2 stops8h 05m

Chicago O'Hare Intl

Tue 2/10

10:10 am-2:59 pm

1 stop3h 49m

$344

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

2:58 pm-10:46 pm

2 stops8h 48m

Chicago O'Hare Intl

Mon 2/16

6:08 am-2:22 pm

2 stops7h 14m

$347

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 flights?

There is only 1 cabin class available to choose from on Hilton Head Island to Chicago O'Hare Intl 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 42% 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

Fastest flight time

2h 44m

Direct flights

Mon, Tue, Fri, Sat and Sun
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 Monday, Tuesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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?

  • 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
American AirlinesPriceFrom $228Free CancellationRating
7.2
11,094 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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