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Cheap flights from Hilton Head Island to Chicago from $198

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 10/3. 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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Find the cheapest flights from Hilton Head Island to Chicago (HHH-ORD)

Cheap round-trip flights

Delta Logo
4:05 pm - 10:23 pmHHH-ORD
7h 18m1 stop
Delta Logo
9:42 am - 3:30 pmORD-HHH
4h 48m1 stop
$249Delta
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Fri, Oct 3 - Mon, Oct 6
American Airlines Logo
11:28 am - 4:53 pmHHH-ORD
6h 25m1 stop
American Airlines Logo
10:30 am - 6:17 pmORD-HHH
6h 47m1 stop
$309American Airlines
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Wed, Nov 12 - Sat, Nov 15
American Airlines Logo
1:02 pm - 9:23 pmHHH-ORD
9h 21m2 stops
American Airlines Logo
8:20 am - 2:57 pmORD-HHH
5h 37m1 stop
$314American Airlines
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Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
3:27 pm - 10:33 pmHHH-ORD
8h 06m2 stops
American Airlines Logo
6:50 am - 2:19 pmORD-HHH
6h 29m2 stops
$319American Airlines
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Wed, Nov 12 - Sat, Nov 15
American Airlines Logo
12:45 pm - 7:10 pmHHH-ORD
7h 25m1 stop
American Airlines Logo
9:20 am - 4:51 pmORD-HHH
6h 31m1 stop
$324American Airlines
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Tue, Oct 7 - Tue, Oct 14
American Airlines Logo
5:20 pm - 11:12 pmHHH-ORD
6h 52m1 stop
American Airlines Logo
10:00 am - 1:27 pmORD-HHH
2h 27mnonstop
$329American Airlines
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Tue, Sep 23 - Sat, Sep 27
United Airlines Logo
12:06 pm - 8:05 amHHH-ORD
20h 59m2 stops
United Airlines Logo
9:37 pm - 11:16 amORD-HHH
12h 39m2 stops
$516United Airlines
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Tue, Sep 23 - Sat, Sep 27
United Airlines Logo
11:57 am - 7:34 amHHH-ORD
20h 37m2 stops
United Airlines Logo
1:30 pm - 11:20 amORD-HHH
20h 50m2 stops
$562United Airlines
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Thu, Oct 9 - Sat, Oct 11
Delta Logo
4:05 pm - 8:35 pmHHH-ORD
5h 30m1 stop
Delta Logo
6:00 am - 3:25 pmORD-HHH
8h 25m2 stops
$580Delta
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Mon, Sep 29 - Wed, Oct 1
United Airlines Logo
11:57 am - 6:34 pmHHH-ORD
7h 37m1 stop
United Airlines Logo
10:35 am - 11:16 amORD-HHH
23h 41m2 stops
$600United Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23

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
Nov 12
HHH11:28 amHilton Head Island
6h 25m
1 stop
ORD4:53 pmChicago O'Hare Intl
Nov 15
ORD10:30 amChicago O'Hare Intl
6h 47m
1 stop
HHH6:17 pmHilton Head Island
$309
Find similar
American Airlines
Nov 12
HHH1:02 pmHilton Head Island
9h 21m
2 stops
ORD9:23 pmChicago O'Hare Intl
Nov 19
ORD8:20 amChicago O'Hare Intl
5h 37m
1 stop
HHH2:57 pmHilton Head Island
$314
Find similar
American Airlines
Nov 12
HHH3:27 pmHilton Head Island
8h 06m
2 stops
ORD10:33 pmChicago O'Hare Intl
Nov 15
ORD6:50 amChicago O'Hare Intl
6h 29m
2 stops
HHH2:19 pmHilton Head Island
$319
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
Sep 23
HHH12:06 pmHilton Head Island
20h 59m
2 stops
ORD8:05 amChicago O'Hare Intl
Sep 27
ORD9:37 pmChicago O'Hare Intl
12h 39m
2 stops
HHH11:16 amHilton Head Island
$516
Find similar
United Airlines
Oct 9
HHH11:57 amHilton Head Island
20h 37m
2 stops
ORD7:34 amChicago O'Hare Intl
Oct 11
ORD1:30 pmChicago O'Hare Intl
20h 50m
2 stops
HHH11:20 amHilton Head Island
$562
Find similar
United Airlines
Oct 21
HHH11:57 amHilton Head Island
7h 37m
1 stop
ORD6:34 pmChicago O'Hare Intl
Oct 23
ORD10:35 amChicago O'Hare Intl
23h 41m
2 stops
HHH11:16 amHilton Head Island
$600
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 September 9, 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

Fri 10/3

4:05 pm-10:23 pm

1 stop7h 18m

Chicago O'Hare Intl

Mon 10/6

9:42 am-3:30 pm

1 stop4h 48m

$249

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 11/12

11:28 am-4:53 pm

1 stop6h 25m

Chicago O'Hare Intl

Sat 11/15

10:30 am-6:17 pm

1 stop6h 47m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 11/12

1:02 pm-9:23 pm

2 stops9h 21m

Chicago O'Hare Intl

Wed 11/19

8:20 am-2:57 pm

1 stop5h 37m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 11/12

3:27 pm-10:33 pm

2 stops8h 06m

Chicago O'Hare Intl

Sat 11/15

6:50 am-2:19 pm

2 stops6h 29m

$319

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 10/7

12:45 pm-7:10 pm

1 stop7h 25m

Chicago O'Hare Intl

Tue 10/14

9:20 am-4:51 pm

1 stop6h 31m

$324

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/23

5:20 pm-11:12 pm

1 stop6h 52m

Chicago O'Hare Intl

Sat 9/27

10:00 am-1:27 pm

Nonstop2h 27m

$329

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/23

12:06 pm-8:05 am

2 stops20h 59m

Chicago O'Hare Intl

Sat 9/27

9:37 pm-11:16 am

2 stops12h 39m

$516

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 10/9

11:57 am-7:34 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 10/11

1:30 pm-11:20 am

2 stops20h 50m

$562

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mon 9/29

4:05 pm-8:35 pm

1 stop5h 30m

Chicago O'Hare Intl

Wed 10/1

6:00 am-3:25 pm

2 stops8h 25m

$580

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 10/21

11:57 am-6:34 pm

1 stop7h 37m

Chicago O'Hare Intl

Thu 10/23

10:35 am-11:16 am

2 stops23h 41m

$600

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 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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $465 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $469. 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 27% 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 38m

Direct flights

Sun
The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 38m
Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
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  • 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 27m.

  • 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
10,000 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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Orland Park
Tinley Park
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Janesville
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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