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Cheap flights from Hilton Head Island to Chicago from $218

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 11/10. 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

American Airlines Logo
7:08 pm - 11:39 pmHHH-ORD
5h 31m1 stop
American Airlines Logo
6:45 am - 12:22 pmORD-HHH
4h 37m1 stop
$309American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
12:52 pm - 7:22 pmHHH-ORD
7h 30m1 stop
American Airlines Logo
10:15 am - 6:38 pmORD-HHH
7h 23m2 stops
$314American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
11:04 am - 3:50 pmHHH-ORD
5h 46m1 stop
American Airlines Logo
10:00 am - 1:27 pmORD-HHH
2h 27mnonstop
$329American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
5:20 pm - 8:27 pmHHH-ORD
4h 07m1 stop
American Airlines Logo
11:26 am - 6:54 pmORD-HHH
6h 28m1 stop
$339American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
5:20 pm - 11:48 pmHHH-ORD
7h 28m2 stops
American Airlines Logo
11:26 am - 6:54 pmORD-HHH
6h 28m1 stop
$344American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Delta Logo
12:17 pm - 7:25 pmHHH-ORD
8h 08m2 stops
Delta Logo
9:42 am - 3:30 pmORD-HHH
4h 48m1 stop
$754Delta
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Tue, Oct 7 - Thu, Oct 9
Delta Logo
4:10 pm - 8:37 pmHHH-ORD
5h 27m1 stop
Delta Logo
9:42 am - 3:30 pmORD-HHH
4h 48m1 stop
$769Delta
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Tue, Oct 7 - Thu, Oct 9
United Airlines Logo
11:57 am - 6:34 pmHHH-ORD
7h 37m1 stop
United Airlines Logo
9:37 pm - 11:20 amORD-HHH
12h 43m2 stops
$938United Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
United Airlines Logo
11:57 am - 8:00 amHHH-ORD
21h 03m2 stops
United Airlines Logo
10:50 am - 11:20 amORD-HHH
23h 30m2 stops
$1,273United Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
United Airlines Logo
11:57 am - 8:00 amHHH-ORD
21h 03m2 stops
United Airlines Logo
6:06 pm - 11:16 amORD-HHH
16h 10m2 stops
$1,737United Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5

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
Sep 19
HHH4:05 pmHilton Head Island
7h 18m
1 stop
ORD10:23 pmChicago O'Hare Intl
Sep 22
ORD9:50 amChicago O'Hare Intl
4h 35m
1 stop
HHH3:25 pmHilton Head Island
$324
Find similar
Delta
Sep 19
HHH4:05 pmHilton Head Island
7h 18m
1 stop
ORD10:23 pmChicago O'Hare Intl
Sep 22
ORD6:00 amChicago O'Hare Intl
8h 25m
2 stops
HHH3:25 pmHilton Head Island
$329
Find similar
Delta
Sep 18
HHH4:05 pmHilton Head Island
5h 30m
1 stop
ORD8:35 pmChicago O'Hare Intl
Sep 21
ORD7:20 amChicago O'Hare Intl
7h 05m
1 stop
HHH3:25 pmHilton Head Island
$534
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 19
HHH12:06 pmHilton Head Island
20h 59m
2 stops
ORD8:05 amChicago O'Hare Intl
Sep 21
ORD6:09 pmChicago O'Hare Intl
16h 16m
2 stops
HHH11:25 amHilton Head Island
$727
Find similar
United Airlines
Sep 18
HHH12:06 pmHilton Head Island
5h 59m
1 stop
ORD5:05 pmChicago O'Hare Intl
Sep 21
ORD9:15 pmChicago O'Hare Intl
13h 10m
2 stops
HHH11:25 amHilton Head Island
$765
Find similar
United Airlines
Sep 30
HHH11:57 amHilton Head Island
7h 37m
1 stop
ORD6:34 pmChicago O'Hare Intl
Oct 4
ORD9:37 pmChicago O'Hare Intl
12h 43m
2 stops
HHH11:20 amHilton Head Island
$938
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 15, 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

Wed 12/3

7:08 pm-11:39 pm

1 stop5h 31m

Chicago O'Hare Intl

Wed 12/10

6:45 am-12:22 pm

1 stop4h 37m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/3

12:52 pm-7:22 pm

1 stop7h 30m

Chicago O'Hare Intl

Wed 12/10

10:15 am-6:38 pm

2 stops7h 23m

$314

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

11:04 am-3:50 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/4

10:00 am-1:27 pm

Nonstop2h 27m

$329

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

5:20 pm-8:27 pm

1 stop4h 07m

Chicago O'Hare Intl

Sat 10/4

11:26 am-6:54 pm

1 stop6h 28m

$339

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

5:20 pm-11:48 pm

2 stops7h 28m

Chicago O'Hare Intl

Sat 10/4

11:26 am-6:54 pm

1 stop6h 28m

$344

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 10/7

12:17 pm-7:25 pm

2 stops8h 08m

Chicago O'Hare Intl

Thu 10/9

9:42 am-3:30 pm

1 stop4h 48m

$754

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 10/7

4:10 pm-8:37 pm

1 stop5h 27m

Chicago O'Hare Intl

Thu 10/9

9:42 am-3:30 pm

1 stop4h 48m

$769

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

11:57 am-6:34 pm

1 stop7h 37m

Chicago O'Hare Intl

Sat 10/4

9:37 pm-11:20 am

2 stops12h 43m

$938

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

11:57 am-8:00 am

2 stops21h 03m

Chicago O'Hare Intl

Sat 10/4

10:50 am-11:20 am

2 stops23h 30m

$1,273

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 10/3

11:57 am-8:00 am

2 stops21h 03m

Chicago O'Hare Intl

Sun 10/5

6:06 pm-11:16 am

2 stops16h 10m

$1,737

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 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 40m

Direct flights

Sun
The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 40m
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 07m.

  • 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

  • American Airlines Flights From Hilton Head Island to Chicago O'Hare Intl Airport

    Across 1 American Airlines flight from Hilton Head Island to Chicago O'Hare Intl Airport this week, the average price was $308, with the best American Airlines deals starting from $228 round-trip. 10,000 users have rated American Airlines on momondo, with an average score of 7.2/10.

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
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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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