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Cheap flights from Chicago O'Hare Intl Airport to Hilton Head Island from $141

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Hilton Head Island departing on 8/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Hilton Head Island

Cheap round-trip flights

American Airlines Logo
6:58 pm - 11:30 amORD-HHH
15h 32m2 stops
American Airlines Logo
5:19 pm - 8:27 pmHHH-ORD
4h 08m1 stop
$289American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
American Airlines Logo
6:58 pm - 11:30 amORD-HHH
15h 32m2 stops
American Airlines Logo
1:57 pm - 3:35 pmHHH-ORD
2h 38mnonstop
$299American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
9:39 am - 3:30 pmORD-HHH
4h 51m1 stop
Delta Logo
12:17 pm - 5:00 pmHHH-ORD
5h 43m1 stop
$306Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
American Airlines Logo
8:37 am - 4:47 pmORD-HHH
7h 10m1 stop
American Airlines Logo
5:19 pm - 8:27 pmHHH-ORD
4h 08m1 stop
$309American Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
American Airlines Logo
11:26 am - 6:54 pmORD-HHH
6h 28m1 stop
American Airlines Logo
5:20 pm - 11:48 pmHHH-ORD
7h 28m2 stops
$314American Airlines
Find Deal
Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
10:05 am - 1:25 pmORD-HHH
2h 20mnonstop
American Airlines Logo
1:55 pm - 3:35 pmHHH-ORD
2h 40mnonstop
$321American Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Delta Logo
7:10 am - 3:30 pmORD-HHH
7h 20m2 stops
Delta Logo
12:17 pm - 7:32 pmHHH-ORD
8h 15m2 stops
$476Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
United Airlines Logo
10:35 am - 11:25 amORD-HHH
23h 50m2 stops
United Airlines Logo
12:21 pm - 6:34 pmHHH-ORD
7h 13m1 stop
$531United Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
Delta Logo
7:10 am - 3:25 pmORD-HHH
7h 15m2 stops
Delta Logo
12:14 pm - 9:34 pmHHH-ORD
10h 20m2 stops
$569Delta
Find Deal
Sat, Sep 27 - Sat, Oct 4
United Airlines Logo
10:35 am - 11:25 amORD-HHH
23h 50m2 stops
United Airlines Logo
12:21 pm - 8:00 amHHH-ORD
20h 39m2 stops
$590United Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27

Delta flights from Chicago O'Hare Intl Airport to Hilton Head Island

Our best Delta deals on Chicago O'Hare Intl Airport to Hilton Head Island flight tickets
Delta
Oct 18
ORD9:39 amChicago O'Hare Intl
4h 51m
1 stop
HHH3:30 pmHilton Head Island
Oct 25
HHH12:17 pmHilton Head Island
5h 43m
1 stop
ORD5:00 pmChicago O'Hare Intl
$306
Find similar
Delta
Oct 18
ORD7:10 amChicago O'Hare Intl
7h 20m
2 stops
HHH3:30 pmHilton Head Island
Oct 25
HHH12:17 pmHilton Head Island
8h 15m
2 stops
ORD7:32 pmChicago O'Hare Intl
$476
Find similar
Delta
Sep 27
ORD7:10 amChicago O'Hare Intl
7h 15m
2 stops
HHH3:25 pmHilton Head Island
Oct 4
HHH12:14 pmHilton Head Island
10h 20m
2 stops
ORD9:34 pmChicago O'Hare Intl
$569
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to Hilton Head Island

Our best American Airlines deals on Chicago O'Hare Intl Airport to Hilton Head Island flight tickets
American Airlines
Aug 30
ORD6:58 pmChicago O'Hare Intl
15h 32m
2 stops
HHH11:30 amHilton Head Island
Sep 6
HHH5:19 pmHilton Head Island
4h 08m
1 stop
ORD8:27 pmChicago O'Hare Intl
$289
Find similar
American Airlines
Aug 30
ORD6:58 pmChicago O'Hare Intl
15h 32m
2 stops
HHH11:30 amHilton Head Island
Sep 6
HHH1:57 pmHilton Head Island
2h 38m
ORD3:35 pmChicago O'Hare Intl
$299
Find similar
American Airlines
Sep 20
ORD8:37 amChicago O'Hare Intl
7h 10m
1 stop
HHH4:47 pmHilton Head Island
Sep 27
HHH5:19 pmHilton Head Island
4h 08m
1 stop
ORD8:27 pmChicago O'Hare Intl
$309
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Hilton Head Island 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 July 31, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 8/30

6:58 pm-11:30 am

2 stops15h 32m

Hilton Head Island

Sat 9/6

5:19 pm-8:27 pm

1 stop4h 08m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 8/30

6:58 pm-11:30 am

2 stops15h 32m

Hilton Head Island

Sat 9/6

1:57 pm-3:35 pm

Nonstop2h 38m

$299

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

9:39 am-3:30 pm

1 stop4h 51m

Hilton Head Island

Sat 10/25

12:17 pm-5:00 pm

1 stop5h 43m

$306

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/20

8:37 am-4:47 pm

1 stop7h 10m

Hilton Head Island

Sat 9/27

5:19 pm-8:27 pm

1 stop4h 08m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/20

11:26 am-6:54 pm

1 stop6h 28m

Hilton Head Island

Tue 9/23

5:20 pm-11:48 pm

2 stops7h 28m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Sat 11/1

1:55 pm-3:35 pm

Nonstop2h 40m

$321

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/18

7:10 am-3:30 pm

2 stops7h 20m

Hilton Head Island

Sat 10/25

12:17 pm-7:32 pm

2 stops8h 15m

$476

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/20

10:35 am-11:25 am

2 stops23h 50m

Hilton Head Island

Sat 9/27

12:21 pm-6:34 pm

1 stop7h 13m

$531

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/27

7:10 am-3:25 pm

2 stops7h 15m

Hilton Head Island

Sat 10/4

12:14 pm-9:34 pm

2 stops10h 20m

$569

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 9/20

10:35 am-11:25 am

2 stops23h 50m

Hilton Head Island

Sat 9/27

12:21 pm-8:00 am

2 stops20h 39m

$590

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 Hilton Head Island from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Hilton Head Island

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 month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in September, then you should wait until August to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $344.

What is the cheapest day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Chicago O'Hare Intl Airport to Hilton Head Island is on a Tuesday. Travelers who choose to depart for Hilton Head Island on a Tuesday will often find tickets for as low as $361. On the other hand, Saturday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $527.

What is the cheapest Chicago O'Hare Intl to Hilton Head Island flight route?

Fly from Chicago O'Hare Intl to Hilton Head Island for the best Chicago O'Hare Intl - Hilton Head Island flight prices

How far in advance should I book a flight to Hilton Head Island?

You are more likely to see cheaper flights to Hilton Head Island from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hilton Head Island from Chicago O'Hare Intl Airport for as low as $311 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Hilton Head Island flights?

There are 1 cabin classes available to choose from on Chicago O'Hare Intl to Hilton Head Island 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 Chicago O'Hare Intl Airport to Hilton Head Island flights?

You could potentially save up to 8% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Hilton Head Island flight.

When to book flights from Chicago O'Hare Intl Airport to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Hilton Head Island (ORD to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Hilton Head Island

Best Price Found

$141

Fastest flight time

2h 20m

Direct flights

Sun

Airports in Hilton Head Island

1 airport
The best one-way flight to Hilton Head Island from Chicago O'Hare Intl Airport in the past 72 hours is $141. The best round-trip flight deal from Chicago O'Hare Intl Airport to Hilton Head Island found on momondo in the last 72 hours is $289.
The fastest flight from Chicago O'Hare Intl Airport to Hilton Head Island takes 2h 20m
Direct flights go from Chicago O'Hare Intl Airport to Hilton Head Island on Sunday. The only airline offering direct flights is American Airlines.
There is 1 airport near Hilton Head Island: Hilton Head Island (HHH)
Search flight deals

  • How far is Chicago O'Hare Intl to Hilton Head Island by plane?

    Hilton Head Island is 780.0 mi away from Chicago O'Hare Intl. In terms of flight time, this usually takes a little over 2h 20m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Hilton Head Island Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Hilton Head Island Airport were last updated today.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Hilton Head Island Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The necessary travel and health documents for your Hilton Head Island 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 Chicago O'Hare Intl Airport to Hilton Head Island?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Hilton Head Island?

Best airlines flying from Chicago O'Hare Intl Airport to Hilton Head Island

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $238Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $273Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hilton Head Island?

Finding the right flight to Hilton Head Island from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Hilton Head Island quick and easy, saving you time and money.

Can I find flights from Chicago to Hilton Head Island with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Hilton Head Island from Chicago with this policy.

How can momondo help me find flights from Chicago to Hilton Head Island?

momondo provides multiple filters to help you find the best flight to Hilton Head Island from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Hilton Head Island right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Hilton Head Island flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Hilton Head Island trip

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