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Cheap flights from Chicago O'Hare Intl Airport to Hilton Head Island from $188

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 2/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
American Airlines Logo
9:45 am - 3:44 pmORD-HHH
4h 59m1 stop
American Airlines Logo
4:14 pm - 9:15 pmHHH-ORD
6h 01m1 stop
$309American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
6:05 am - 12:20 pmORD-HHH
5h 15m1 stop
American Airlines Logo
12:54 pm - 6:01 pmHHH-ORD
6h 07m1 stop
$336American Airlines
Find Deal
Mon, Jan 19 - Sat, Jan 31
American Airlines Logo
7:00 am - 2:20 pmORD-HHH
6h 20m1 stop
American Airlines Logo
6:07 pm - 9:22 pmHHH-ORD
4h 15m1 stop
$339American Airlines
Find Deal
Sat, May 2 - Sat, May 9
American Airlines Logo
10:10 am - 2:59 pmORD-HHH
3h 49m1 stop
American Airlines Logo
12:54 pm - 10:18 pmHHH-ORD
10h 24m2 stops
$341American Airlines
Find Deal
Mon, Jan 19 - Sat, Jan 31
American Airlines Logo
6:00 am - 3:09 pmORD-HHH
8h 09m2 stops
American Airlines Logo
4:14 pm - 9:15 pmHHH-ORD
6h 01m1 stop
$344American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
6:00 am - 2:59 pmORD-HHH
7h 59m2 stops
American Airlines Logo
12:54 pm - 10:18 pmHHH-ORD
10h 24m2 stops
$346American Airlines
Find Deal
Mon, Jan 19 - Sat, Jan 31
American Airlines Logo
6:45 am - 12:22 pmORD-HHH
4h 37m1 stop
American Airlines Logo
11:30 am - 4:51 pmHHH-ORD
6h 21m1 stop
$363American Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
American Airlines Logo
5:00 am - 10:44 amORD-HHH
4h 44m1 stop
American Airlines Logo
11:14 am - 4:05 pmHHH-ORD
5h 51m1 stop
$367American Airlines
Find Deal
Thu, Dec 25 - Wed, Dec 31
United Airlines Logo
7:10 am - 3:12 pmORD-HHH
7h 02m1 stop
United Airlines Logo
3:00 pm - 4:45 pmHHH-ORD
2h 45mnonstop
$457United Airlines
Find Deal
Mon, Mar 30 - Fri, Apr 3
United Airlines Logo
10:35 am - 1:52 pmORD-HHH
2h 17mnonstop
United Airlines Logo
3:00 pm - 4:45 pmHHH-ORD
2h 45mnonstop
$470United Airlines
Find Deal
Sat, Mar 21 - Sat, Mar 28

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
Mar 30
ORD7:10 amChicago O'Hare Intl
7h 02m
1 stop
HHH3:12 pmHilton Head Island
Apr 3
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$457
Find similar
United Airlines
Mar 21
ORD10:35 amChicago O'Hare Intl
2h 17m
HHH1:52 pmHilton Head Island
Mar 28
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$470
Find similar
United Airlines
Mar 21
ORD10:35 amChicago O'Hare Intl
2h 17m
HHH1:52 pmHilton Head Island
Mar 28
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$494
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
Feb 18
ORD9:45 amChicago O'Hare Intl
4h 59m
1 stop
HHH3:44 pmHilton Head Island
Feb 21
HHH4:14 pmHilton Head Island
6h 01m
1 stop
ORD9:15 pmChicago O'Hare Intl
$309
Find similar
American Airlines
Jan 19
ORD6:05 amChicago O'Hare Intl
5h 15m
1 stop
HHH12:20 pmHilton Head Island
Jan 31
HHH12:54 pmHilton Head Island
6h 07m
1 stop
ORD6:01 pmChicago O'Hare Intl
$336
Find similar
American Airlines
May 2
ORD7:00 amChicago O'Hare Intl
6h 20m
1 stop
HHH2:20 pmHilton Head Island
May 9
HHH6:07 pmHilton Head Island
4h 15m
1 stop
ORD9:22 pmChicago O'Hare Intl
$339
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 November 4, 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

Wed 2/18

9:45 am-3:44 pm

1 stop4h 59m

Hilton Head Island

Sat 2/21

4:14 pm-9:15 pm

1 stop6h 01m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

6:05 am-12:20 pm

1 stop5h 15m

Hilton Head Island

Sat 1/31

12:54 pm-6:01 pm

1 stop6h 07m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 5/2

7:00 am-2:20 pm

1 stop6h 20m

Hilton Head Island

Sat 5/9

6:07 pm-9:22 pm

1 stop4h 15m

$339

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

10:10 am-2:59 pm

1 stop3h 49m

Hilton Head Island

Sat 1/31

12:54 pm-10:18 pm

2 stops10h 24m

$341

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 2/18

6:00 am-3:09 pm

2 stops8h 09m

Hilton Head Island

Sat 2/21

4:14 pm-9:15 pm

1 stop6h 01m

$344

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

6:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Sat 1/31

12:54 pm-10:18 pm

2 stops10h 24m

$346

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 12/5

6:45 am-12:22 pm

1 stop4h 37m

Hilton Head Island

Sun 12/7

11:30 am-4:51 pm

1 stop6h 21m

$363

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 12/25

5:00 am-10:44 am

1 stop4h 44m

Hilton Head Island

Wed 12/31

11:14 am-4:05 pm

1 stop5h 51m

$367

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 3/30

7:10 am-3:12 pm

1 stop7h 02m

Hilton Head Island

Fri 4/3

3:00 pm-4:45 pm

Nonstop2h 45m

$457

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 3/21

10:35 am-1:52 pm

Nonstop2h 17m

Hilton Head Island

Sat 3/28

3:00 pm-4:45 pm

Nonstop2h 45m

$470

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 November, then you should wait until January to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $347.

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 $528.

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 $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 $305 on momondo.

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

There is only 1 cabin class 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

$319

Fastest flight time

2h 17m

Direct flights

Tue, Thu, Sat and Sun

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 $319
The fastest flight from Chicago O'Hare Intl Airport to Hilton Head Island takes 2h 17m
Direct flights go from Chicago O'Hare Intl Airport to Hilton Head Island on Tuesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
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 17m.

  • 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 $278Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
United AirlinesPriceFrom $379Free CancellationRating
7.4
9,002 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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