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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 2/2. 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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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
6:13 pm - 11:42 pm
HHH
-
ORD
6h 29m1 stop
American Airlines Logo
8:12 am - 2:59 pm
ORD
-
HHH
5h 47m1 stop
$363American Airlines
Mon, Jan 5 - Mon, Jan 12
American Airlines Logo
12:51 pm - 6:01 pm
HHH
-
ORD
6h 10m1 stop
American Airlines Logo
9:11 pm - 12:20 pm
ORD
-
HHH
14h 09m2 stops
$367American Airlines
Tue, Jan 13 - Fri, Jan 16
American Airlines Logo
6:13 pm - 11:42 pm
HHH
-
ORD
6h 29m1 stop
American Airlines Logo
6:00 am - 2:59 pm
ORD
-
HHH
7h 59m2 stops
$368American Airlines
Mon, Jan 5 - Mon, Jan 12
American Airlines Logo
11:14 am - 4:05 pm
HHH
-
ORD
5h 51m1 stop
American Airlines Logo
5:00 am - 10:44 am
ORD
-
HHH
4h 44m1 stop
$369American Airlines
Sat, Dec 20 - Wed, Dec 24
American Airlines Logo
3:29 pm - 10:34 pm
HHH
-
ORD
8h 05m2 stops
American Airlines Logo
9:11 pm - 12:20 pm
ORD
-
HHH
14h 09m2 stops
$372American Airlines
Tue, Jan 13 - Fri, Jan 16
American Airlines Logo
11:02 am - 5:49 pm
HHH
-
ORD
7h 47m2 stops
American Airlines Logo
9:43 am - 5:52 pm
ORD
-
HHH
7h 09m2 stops
$373American Airlines
Fri, Feb 13 - Mon, Feb 16
American Airlines Logo
4:18 pm - 9:15 pm
HHH
-
ORD
5h 57m1 stop
American Airlines Logo
9:45 am - 4:50 pm
ORD
-
HHH
6h 05m1 stop
$379American Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
11:02 am - 9:15 pm
HHH
-
ORD
11h 13m2 stops
American Airlines Logo
8:10 am - 3:05 pm
ORD
-
HHH
5h 55m1 stop
$384American Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
6:22 pm - 12:10 am
HHH
-
ORD
6h 48m1 stop
American Airlines Logo
9:43 am - 3:36 pm
ORD
-
HHH
4h 53m1 stop
$406American Airlines
Sat, Feb 14 - Mon, Feb 16
American Airlines Logo
11:02 am - 9:15 pm
HHH
-
ORD
11h 13m2 stops
American Airlines Logo
9:43 am - 3:36 pm
ORD
-
HHH
4h 53m1 stop
$411American 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
Jan 5
HHH6:13 pmHilton Head Island
6h 29m
1 stop
ORD11:42 pmChicago O'Hare Intl
Jan 12
ORD8:12 amChicago O'Hare Intl
5h 47m
1 stop
HHH2:59 pmHilton Head Island
$363
Find similar
American Airlines
Dec 10
HHH12:52 pmHilton Head Island
6h 10m
1 stop
ORD6:02 pmChicago O'Hare Intl
Feb 16
ORD8:10 amChicago O'Hare Intl
5h 17m
1 stop
HHH2:27 pmHilton Head Island
$366
Find similar
American Airlines
Jan 13
HHH12:51 pmHilton Head Island
6h 10m
1 stop
ORD6:01 pmChicago O'Hare Intl
Jan 16
ORD9:11 pmChicago O'Hare Intl
14h 09m
2 stops
HHH12:20 pmHilton Head Island
$367
Find similar

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
Apr 11
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
Apr 18
ORD8:55 amChicago O'Hare Intl
5h 17m
1 stop
HHH3:12 pmHilton Head Island
$667
Find similar
United Airlines
Apr 14
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
Apr 19
ORD7:00 amChicago O'Hare Intl
7h 12m
1 stop
HHH3:12 pmHilton Head Island
$944
Find similar
United Airlines
Apr 14
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
Apr 19
ORD10:35 amChicago O'Hare Intl
2h 26m
HHH2:01 pmHilton Head Island
$1,004
Find similar

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 December 6, 2025.
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

Mon 1/5

6:13 pm-11:42 pm

1 stop6h 29m

Chicago O'Hare Intl

Mon 1/12

8:12 am-2:59 pm

1 stop5h 47m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 1/13

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Fri 1/16

9:11 pm-12:20 pm

2 stops14h 09m

$367

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 1/5

6:13 pm-11:42 pm

1 stop6h 29m

Chicago O'Hare Intl

Mon 1/12

6:00 am-2:59 pm

2 stops7h 59m

$368

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 12/20

11:14 am-4:05 pm

1 stop5h 51m

Chicago O'Hare Intl

Wed 12/24

5:00 am-10:44 am

1 stop4h 44m

$369

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 1/13

3:29 pm-10:34 pm

2 stops8h 05m

Chicago O'Hare Intl

Fri 1/16

9:11 pm-12:20 pm

2 stops14h 09m

$372

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 2/13

11:02 am-5:49 pm

2 stops7h 47m

Chicago O'Hare Intl

Mon 2/16

9:43 am-5:52 pm

2 stops7h 09m

$373

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

4:18 pm-9:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Tue 2/17

9:45 am-4:50 pm

1 stop6h 05m

$379

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:02 am-9:15 pm

2 stops11h 13m

Chicago O'Hare Intl

Tue 2/17

8:10 am-3:05 pm

1 stop5h 55m

$384

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

6:22 pm-12:10 am

1 stop6h 48m

Chicago O'Hare Intl

Mon 2/16

9:43 am-3:36 pm

1 stop4h 53m

$406

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

11:02 am-9:15 pm

2 stops11h 13m

Chicago O'Hare Intl

Mon 2/16

9:43 am-3:36 pm

1 stop4h 53m

$411

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 Thursday when prices can be found for as low as $258. 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 $599.

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 in the morning is the least expensive time of day to depart. momondo users have found prices as low as $469 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $538. 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 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 20% 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 45m

Direct flights

Mon, Wed, Thu, Fri and Sun
The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 45m
Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport on Monday, Wednesday, Thursday, Friday 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 45m.

  • 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
11,043 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Tinley Park
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Benton Harbor

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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