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Cheap flights from Chicago O'Hare Intl Airport to Hilton Head Island from $177

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 5/24. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:08 am - 3:32 pm
ORD
-
HHH
6h 24m
1 stop
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
$289Delta
Di, Jun 23 - Mo, Jun 29
Delta Logo
8:03 am - 3:29 pm
ORD
-
HHH
6h 26m
1 stop
Delta Logo
12:11 pm - 8:31 pm
HHH
-
ORD
9h 20m
2 stops
$294Delta
Mi, Jul 22 - Di, Jul 28
Delta Logo
9:49 am - 3:33 pm
ORD
-
HHH
4h 44m
1 stop
Delta Logo
4:16 pm - 7:47 am
HHH
-
ORD
16h 31m
1 stop
$300Delta
Di, Mai 26 - Mi, Jun 3
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
Delta Logo
4:16 pm - 7:47 am
HHH
-
ORD
16h 31m
1 stop
$305Delta
Di, Mai 26 - Mi, Jun 3
Delta Logo
8:03 am - 3:29 pm
ORD
-
HHH
6h 26m
1 stop
Delta Logo
12:11 pm - 5:12 pm
HHH
-
ORD
6h 01m
1 stop
$309Delta
Fr, Jul 24 - Mo, Jul 27
Delta Logo
6:00 am - 3:29 pm
ORD
-
HHH
8h 29m
2 stops
Delta Logo
12:11 pm - 6:45 pm
HHH
-
ORD
7h 34m
1 stop
$314Delta
Mi, Jul 15 - Di, Jul 21
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
$329Delta
Fr, Mai 8 - Di, Mai 12
Delta Logo
7:00 am - 3:29 pm
ORD
-
HHH
7h 29m
2 stops
Delta Logo
12:11 pm - 6:45 pm
HHH
-
ORD
7h 34m
1 stop
$334Delta
Mi, Jul 15 - Mo, Jul 20
Delta Logo
7:05 am - 3:29 pm
ORD
-
HHH
7h 24m
2 stops
Delta Logo
12:11 pm - 9:52 pm
HHH
-
ORD
10h 41m
2 stops
$339Delta
Di, Jul 14 - Di, Jul 21
Delta Logo
8:08 am - 3:32 pm
ORD
-
HHH
6h 24m
1 stop
Delta Logo
12:13 pm - 6:42 pm
HHH
-
ORD
7h 29m
1 stop
$344Delta
Do, Jun 25 - So, Jun 28

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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
May 27
ORD10:05 amChicago O'Hare Intl
2h 28m
HHH1:33 pmHilton Head Island
Jun 2
HHH2:09 pmHilton Head Island
2h 32m
ORD3:41 pmChicago O'Hare Intl
$349
American Airlines
Jun 9
ORD10:04 amChicago O'Hare Intl
2h 30m
HHH1:34 pmHilton Head Island
Jun 16
HHH2:04 pmHilton Head Island
2h 33m
ORD3:37 pmChicago O'Hare Intl
$350
American Airlines
Jul 1
ORD10:04 amChicago O'Hare Intl
2h 30m
HHH1:34 pmHilton Head Island
Jul 7
HHH2:48 pmHilton Head Island
6h 06m
1 stop
ORD7:54 pmChicago O'Hare Intl
$359

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Hilton Head Island flight tickets
United Airlines
May 9
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
May 13
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
$309
United Airlines
May 5
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
May 12
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
$344
United Airlines
Jun 20
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jun 25
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
$367

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 April 28, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Di 6/23

8:08 am-3:32 pm

1 stop6h 24m

Hilton Head Island

Mo 6/29

12:13 pm-5:04 pm

1 stop5h 51m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mi 7/22

8:03 am-3:29 pm

1 stop6h 26m

Hilton Head Island

Di 7/28

12:11 pm-8:31 pm

2 stops9h 20m

$294

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Di 5/26

9:49 am-3:33 pm

1 stop4h 44m

Hilton Head Island

Mi 6/3

4:16 pm-7:47 am

1 stop16h 31m

$300

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Di 5/26

7:00 am-3:33 pm

2 stops7h 33m

Hilton Head Island

Mi 6/3

4:16 pm-7:47 am

1 stop16h 31m

$305

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fr 7/24

8:03 am-3:29 pm

1 stop6h 26m

Hilton Head Island

Mo 7/27

12:11 pm-5:12 pm

1 stop6h 01m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mi 7/15

6:00 am-3:29 pm

2 stops8h 29m

Hilton Head Island

Di 7/21

12:11 pm-6:45 pm

1 stop7h 34m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fr 5/8

7:07 am-3:33 pm

1 stop7h 26m

Hilton Head Island

Di 5/12

4:16 pm-10:36 pm

1 stop7h 20m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mi 7/15

7:00 am-3:29 pm

2 stops7h 29m

Hilton Head Island

Mo 7/20

12:11 pm-6:45 pm

1 stop7h 34m

$334

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Di 7/14

7:05 am-3:29 pm

2 stops7h 24m

Hilton Head Island

Di 7/21

12:11 pm-9:52 pm

2 stops10h 41m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Do 6/25

8:08 am-3:32 pm

1 stop6h 24m

Hilton Head Island

So 6/28

12:13 pm-6:42 pm

1 stop7h 29m

$344

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Hilton Head Island?

What is the cheapest month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in November, then you should wait until April to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $369.

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 Wednesday. Travelers who choose to depart for Hilton Head Island on a Wednesday will often find tickets for as low as $279. On the other hand, Sunday 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 $554.

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 from Chicago O'Hare Intl Airport 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 $440 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 $283 on momondo.

Can stopping save me money on Chicago O'Hare Intl Airport to Hilton Head Island flights?

You could potentially save up to 27% 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

$349

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The best flight deal from Chicago O'Hare Intl Airport to Hilton Head Island found on momondo in the last 72 hours is $349
The fastest flight from Chicago O'Hare Intl Airport to Hilton Head Island takes 2h 24m
Direct flights go from Chicago O'Hare Intl Airport to Hilton Head Island every day.
There is 1 airport in Hilton Head Island. From Chicago O'Hare Intl Airport there are direct flights to Hilton Head Island (HHH).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Hilton Head Island

  • 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 24m.

  • 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
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,672 reviews
Search United Airlines flights
American AirlinesPriceFrom $335Free CancellationRating
7.1
11,677 reviews
Search American Airlines flights

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

    The lowest priced United Airlines flight from Chicago O'Hare Intl Airport to Hilton Head Island from the last 72 hours was $209. Generally, United Airlines has 3 flights on this route every week with an average price of $416. United Airlines is rated 7.4/10 by our users.

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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