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Cheap flights from Hilton Head Island to Chicago from $216

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 1/17. 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

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American Airlines Logo
11:16 am - 3:48 pmHHH-ORD
5h 32m1 stop
American Airlines Logo
6:46 am - 12:29 pmORD-HHH
4h 43m1 stop
$324American Airlines
Find Deal
vie., oct. 31 - mar., nov. 4
American Airlines Logo
3:32 pm - 11:50 pmHHH-ORD
9h 18m2 stops
American Airlines Logo
8:20 am - 2:57 pmORD-HHH
5h 37m1 stop
$329American Airlines
Find Deal
vie., oct. 31 - mar., nov. 4
American Airlines Logo
3:32 pm - 11:50 pmHHH-ORD
9h 18m2 stops
American Airlines Logo
10:15 am - 6:37 pmORD-HHH
7h 22m2 stops
$334American Airlines
Find Deal
vie., oct. 31 - mar., nov. 4
American Airlines Logo
7:07 pm - 11:37 pmHHH-ORD
5h 30m1 stop
American Airlines Logo
6:46 am - 2:57 pmORD-HHH
7h 11m1 stop
$336American Airlines
Find Deal
vie., nov. 14 - mié., nov. 19
American Airlines Logo
11:28 am - 4:53 pmHHH-ORD
6h 25m1 stop
American Airlines Logo
10:15 am - 6:37 pmORD-HHH
7h 22m2 stops
$341American Airlines
Find Deal
vie., nov. 14 - mié., nov. 19
American Airlines Logo
12:19 pm - 4:05 pmHHH-ORD
4h 46m1 stop
American Airlines Logo
7:11 am - 2:19 pmORD-HHH
6h 08m1 stop
$363American Airlines
Find Deal
jue., nov. 13 - jue., nov. 20
American Airlines Logo
5:21 pm - 10:54 pmHHH-ORD
6h 33m1 stop
American Airlines Logo
5:00 am - 11:49 amORD-HHH
5h 49m1 stop
$367American Airlines
Find Deal
mié., oct. 29 - dom., nov. 2
American Airlines Logo
6:40 pm - 11:40 pmHHH-ORD
6h 00m1 stop
American Airlines Logo
5:00 am - 2:19 pmORD-HHH
8h 19m2 stops
$368American Airlines
Find Deal
jue., nov. 13 - jue., nov. 20
American Airlines Logo
5:21 pm - 11:50 pmHHH-ORD
7h 29m2 stops
American Airlines Logo
5:00 am - 11:49 amORD-HHH
5h 49m1 stop
$372American Airlines
Find Deal
mié., oct. 29 - dom., nov. 2
American Airlines Logo
12:38 pm - 7:29 pmHHH-ORD
7h 51m1 stop
American Airlines Logo
10:29 am - 6:09 pmORD-HHH
6h 40m1 stop
$379American Airlines
Find Deal
sáb., nov. 15 - sáb., nov. 22

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
Oct 18
HHH1:55 pmHilton Head Island
2h 40m
ORD3:35 pmChicago O'Hare Intl
Nov 15
ORD10:30 amChicago O'Hare Intl
6h 47m
1 stop
HHH6:17 pmHilton Head Island
$314
Find similar
American Airlines
Oct 18
HHH1:55 pmHilton Head Island
2h 40m
ORD3:35 pmChicago O'Hare Intl
Nov 15
ORD6:50 amChicago O'Hare Intl
6h 29m
2 stops
HHH2:19 pmHilton Head Island
$324
Find similar
American Airlines
Oct 18
HHH3:02 pmHilton Head Island
5h 09m
1 stop
ORD7:11 pmChicago O'Hare Intl
Nov 15
ORD6:50 amChicago O'Hare Intl
6h 29m
2 stops
HHH2:19 pmHilton Head Island
$329
Find similar

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 24
HHH4:10 pmHilton Head Island
5h 27m
1 stop
ORD8:37 pmChicago O'Hare Intl
Oct 26
ORD7:10 amChicago O'Hare Intl
7h 20m
2 stops
HHH3:30 pmHilton Head Island
$357
Find similar
Delta
Oct 24
HHH12:17 pmHilton Head Island
11h 09m
2 stops
ORD10:26 pmChicago O'Hare Intl
Oct 26
ORD7:10 amChicago O'Hare Intl
7h 20m
2 stops
HHH3:30 pmHilton Head Island
$362
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 octubre 16, 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

vie. 10/31

11:16 am-3:48 pm

1 stop5h 32m

Chicago O'Hare Intl

mar. 11/4

6:46 am-12:29 pm

1 stop4h 43m

$324

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

vie. 10/31

3:32 pm-11:50 pm

2 stops9h 18m

Chicago O'Hare Intl

mar. 11/4

8:20 am-2:57 pm

1 stop5h 37m

$329

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

vie. 10/31

3:32 pm-11:50 pm

2 stops9h 18m

Chicago O'Hare Intl

mar. 11/4

10:15 am-6:37 pm

2 stops7h 22m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

vie. 11/14

7:07 pm-11:37 pm

1 stop5h 30m

Chicago O'Hare Intl

mié. 11/19

6:46 am-2:57 pm

1 stop7h 11m

$336

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

vie. 11/14

11:28 am-4:53 pm

1 stop6h 25m

Chicago O'Hare Intl

mié. 11/19

10:15 am-6:37 pm

2 stops7h 22m

$341

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

jue. 11/13

12:19 pm-4:05 pm

1 stop4h 46m

Chicago O'Hare Intl

jue. 11/20

7:11 am-2:19 pm

1 stop6h 08m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

mié. 10/29

5:21 pm-10:54 pm

1 stop6h 33m

Chicago O'Hare Intl

dom. 11/2

5:00 am-11:49 am

1 stop5h 49m

$367

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

jue. 11/13

6:40 pm-11:40 pm

1 stop6h 00m

Chicago O'Hare Intl

jue. 11/20

5:00 am-2:19 pm

2 stops8h 19m

$368

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

mié. 10/29

5:21 pm-11:50 pm

2 stops7h 29m

Chicago O'Hare Intl

dom. 11/2

5:00 am-11:49 am

1 stop5h 49m

$372

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

sáb. 11/15

12:38 pm-7:29 pm

1 stop7h 51m

Chicago O'Hare Intl

sáb. 11/22

10:29 am-6:09 pm

1 stop6h 40m

$379

Flights are sorted by cheapest round-trip flights 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 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

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 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 4h 21m.

  • 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?

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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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