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Cheap flights from Chicago to Hilton Head Island from $259

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
10:35 am - 2:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 35mnonstop
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$279United Airlines
Sat, Sep 26 - Sat, Oct 3
United Airlines Logo
10:35 am - 2:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 35mnonstop
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$279United Airlines
Sat, Oct 17 - Sat, Oct 24
United Airlines Logo
10:35 am - 2:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 35mnonstop
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$279United Airlines
Sat, Oct 3 - Sat, Oct 10
United Airlines Logo
10:35 am - 2:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 35mnonstop
United Airlines Logo
2:51 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 14mnonstop
$279United Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
9:45 am - 1:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 25mnonstop
American Airlines Logo
10:55 am - 5:00 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 05m1 stop Washington, D.C. Reagan-National
$289American Airlines
Sat, Oct 3 - Sat, Oct 10
American Airlines Logo
5:00 am - 11:05 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
American Airlines Logo
10:55 am - 4:08 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 13m1 stop Washington, D.C. Reagan-National
$299American Airlines
Sat, Oct 24 - Sat, Oct 31
Delta Logo
8:05 am - 3:27 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:13 pm - 10:17 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 04m1 stop New York LaGuardia
$299Delta
Sat, Oct 3 - Tue, Oct 6
Delta Logo
8:05 am - 3:27 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:17 pm - 4:37 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
5h 20m1 stop Atlanta Hartsfield-Jackson
$299Delta
Sat, Oct 3 - Mon, Oct 5
American Airlines Logo
5:00 am - 11:05 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
American Airlines Logo
10:55 am - 5:00 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 05m1 stop Washington, D.C. Reagan-National
$299American Airlines
Sat, Oct 17 - Sat, Oct 24
Delta Logo
8:05 am - 3:27 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:13 pm - 10:17 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 04m1 stop New York LaGuardia
$299Delta
Sat, Oct 3 - Wed, Oct 7

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United Airlines flights from Chicago to Hilton Head Island

Our best United Airlines deals on Chicago to Hilton Head Island flight tickets
United Airlines
Oct 3
ORD10:35 amChicago O'Hare Intl
2h 35m
HHH2:10 pmHilton Head Island
Oct 10
HHH2:51 pmHilton Head Island
3h 14m
ORD5:05 pmChicago O'Hare Intl
$279
United Airlines
Sep 7
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
Sep 21
HHH2:48 pmHilton Head Island
3h 17m
ORD5:05 pmChicago O'Hare Intl
$299
United Airlines
Sep 17
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
Sep 22
HHH2:48 pmHilton Head Island
3h 17m
ORD5:05 pmChicago O'Hare Intl
$334

American Airlines flights from Chicago to Hilton Head Island

Our best American Airlines deals on Chicago to Hilton Head Island flight tickets
American Airlines
Oct 3
ORD9:45 amChicago O'Hare Intl
2h 25m
HHH1:10 pmHilton Head Island
Oct 10
HHH10:55 amHilton Head Island
7h 05m
1 stop
ORD5:00 pmChicago O'Hare Intl
$289
American Airlines
Sep 7
ORD9:53 amChicago O'Hare Intl
2h 24m
HHH1:17 pmHilton Head Island
Sep 21
HHH2:15 pmHilton Head Island
6h 23m
1 stop
ORD7:38 pmChicago O'Hare Intl
$309
American Airlines
Sep 7
ORD5:05 amChicago O'Hare Intl
5h 04m
1 stop
HHH11:09 amHilton Head Island
Sep 21
HHH2:15 pmHilton Head Island
4h 23m
1 stop
ORD5:38 pmChicago O'Hare Intl
$319

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Hilton Head Island that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 9/26

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/3

2:51 pm-5:05 pm

Nonstop3h 14m

$279

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/17

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/24

2:51 pm-5:05 pm

Nonstop3h 14m

$279

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/3

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/10

2:51 pm-5:05 pm

Nonstop3h 14m

$279

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/17

10:35 am-2:10 pm

Nonstop2h 35m

Hilton Head Island

Sat 10/24

2:51 pm-5:05 pm

Nonstop3h 14m

$279

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/3

9:45 am-1:10 pm

Nonstop2h 25m

Hilton Head Island

Sat 10/10

10:55 am-5:00 pm

1 stop7h 05m

$289

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/24

5:00 am-11:05 am

1 stop5h 05m

Hilton Head Island

Sat 10/31

10:55 am-4:08 pm

1 stop6h 13m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/3

8:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Tue 10/6

4:13 pm-10:17 pm

1 stop7h 04m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/3

8:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Mon 10/5

12:17 pm-4:37 pm

1 stop5h 20m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/17

5:00 am-11:05 am

1 stop5h 05m

Hilton Head Island

Sat 10/24

10:55 am-5:00 pm

1 stop7h 05m

$299

ChicagoHilton Head Island

ORD Chicago O'Hare Intl - HHH Hilton Head Island

ORDHHH

Chicago O'Hare Intl

Sat 10/3

8:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Wed 10/7

4:13 pm-10:17 pm

1 stop7h 04m

$299

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 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 and Hilton Head Island?

Prices are currently typical for flights on this route.

Typical prices usually range from $274 to $655.
The lowest price recently found on this route was $279.

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

If you don’t want to visit Hilton Head Island in August, then you should wait until June to fly from Chicago, when ticket prices are also cheap, with an average price of $377.

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

The cheapest day to depart from Chicago 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 $299. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $507.

What is the cheapest Chicago to Hilton Head Island flight route?

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

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

You are more likely to see cheaper flights to Hilton Head Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $439 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 for as low as $209 on momondo.

What cabin class options are available on Chicago to Hilton Head Island flights?

There are 2 cabin classes available to choose from on Chicago 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.

When to book flights from Chicago to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to Hilton Head Island (CHI to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Hilton Head Island

Best Price Found

$259

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The best one-way flight to Hilton Head Island from Chicago in the past 72 hours is $259. The best round-trip flight deal from Chicago to Hilton Head Island found on momondo in the last 72 hours is $279.
The fastest flight from Chicago to Hilton Head Island takes 2h 35m
Direct flights go from Chicago to Hilton Head Island every day.
There is 1 airport in Hilton Head Island. From Chicago there are direct flights to Hilton Head Island (HHH).
Search flight deals

Frequently asked questions about flying from Chicago to Hilton Head Island

  • How far is Chicago to Hilton Head Island by plane?

    There are 766.4 mi between Chicago and Hilton Head Island. By plane, this route typically takes 2h 35m.

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

    Prices for flights from Chicago to Hilton Head Island Airport are updated daily.

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

  • How old do you have to be to fly from Chicago to Hilton Head Island 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 Chicago to Hilton Head Island Airport.

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

    The travel and health documents you'll need for your trip to Hilton Head Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Hilton Head Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Hilton Head Island?

  • What is the most popular airline from Chicago to Hilton Head Island?

Best airlines flying from Chicago to Hilton Head Island

Compare and see reviews for airlines that fly from Chicago to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $220Free CancellationRating
7.4
10,121 reviews
Search United Airlines flights
American AirlinesPriceFrom $269Free CancellationRating
7.1
11,994 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Hilton Head Island

    United Airlines is one of the most popular airlines flying from Chicago to Hilton Head Island, operating 7 flights/week on average for this route. A good United Airlines flight deal for Chicago to Hilton Head Island starts from $220 round-trip, up to an average price of $443. Our users have rated United Airlines at 7.4/10.

  • American Airlines Flights From Chicago to Hilton Head Island

    Across 11,994 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Chicago to Hilton Head Island about 3 times each week, with ticket deals ranging from $269 to $452. Price data is based on momondo searches in the last 72 hours.

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 allows you to filter the results for Chicago to Hilton Head Island flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Chicago and Hilton Head Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Chicago to Hilton Head Island flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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