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Cheap flights from Chicago to Hilton Head Island from $174

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 to Hilton Head Island departing on 5/26. 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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0 bags

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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
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
$269United Airlines
Tue, Jul 7 - Wed, Jul 15
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
$280United Airlines
Mon, Jun 8 - Thu, Jul 2
Delta Logo
9:49 am - 3:33 pm
ORD
-
HHH
4h 44m
1 stop
Delta Logo
4:15 pm - 10:34 pm
HHH
-
ORD
7h 19m
1 stop
$289Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:00 am - 3:33 pm
ORD
-
HHH
8h 33m
2 stops
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
$294Delta
Tue, Jun 2 - Tue, Jun 9
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
$299United Airlines
Sat, Oct 17 - Sat, Oct 24
Delta Logo
6:00 am - 3:33 pm
ORD
-
HHH
8h 33m
2 stops
Delta Logo
12:13 pm - 10:34 pm
HHH
-
ORD
11h 21m
2 stops
$300Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
9:48 am - 3:32 pm
ORD
-
HHH
4h 44m
1 stop
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
$309Delta
Tue, Jun 23 - Mon, Jun 29
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
$314Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
6:00 am - 3:20 pm
ORD
-
HHH
8h 20m
2 stops
Delta Logo
12:00 pm - 8:24 pm
HHH
-
ORD
9h 24m
2 stops
$319Delta
Wed, Aug 19 - Tue, Aug 25
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
$324United Airlines
Fri, Jul 17 - Wed, Jul 22

United Airlines flights from Chicago to Hilton Head Island

Our best United Airlines deals on Chicago to Hilton Head Island flight tickets
United Airlines
Jul 7
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jul 15
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
$269
United Airlines
Jun 8
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
Jul 2
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
$280
United Airlines
Oct 17
ORD10:35 amChicago O'Hare Intl
2h 26m
HHH2:01 pmHilton Head Island
Oct 24
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$299

Delta flights from Chicago to Hilton Head Island

Our best Delta deals on Chicago to Hilton Head Island flight tickets
Delta
Jun 2
ORD9:49 amChicago O'Hare Intl
4h 44m
1 stop
HHH3:33 pmHilton Head Island
Jun 9
HHH4:15 pmHilton Head Island
7h 19m
1 stop
ORD10:34 pmChicago O'Hare Intl
$289
Delta
Jun 2
ORD6:00 amChicago O'Hare Intl
8h 33m
2 stops
HHH3:33 pmHilton Head Island
Jun 9
HHH12:13 pmHilton Head Island
5h 51m
1 stop
ORD5:04 pmChicago O'Hare Intl
$294
Delta
Jun 2
ORD6:00 amChicago O'Hare Intl
8h 33m
2 stops
HHH3:33 pmHilton Head Island
Jun 9
HHH12:13 pmHilton Head Island
11h 21m
2 stops
ORD10:34 pmChicago O'Hare Intl
$300

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 May 2, 2026.
Use the filters below to find and compare flights from Chicago to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 7/7

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Wed 7/15

3:05 pm-4:51 pm

Nonstop2h 46m

$269

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 6/8

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Thu 7/2

3:05 pm-4:51 pm

Nonstop2h 46m

$280

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

9:49 am-3:33 pm

1 stop4h 44m

Hilton Head Island

Tue 6/9

4:15 pm-10:34 pm

1 stop7h 19m

$289

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

6:00 am-3:33 pm

2 stops8h 33m

Hilton Head Island

Tue 6/9

12:13 pm-5:04 pm

1 stop5h 51m

$294
Quickest round-trip

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/17

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Sat 10/24

3:00 pm-4:45 pm

Nonstop2h 45m

$299

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/2

6:00 am-3:33 pm

2 stops8h 33m

Hilton Head Island

Tue 6/9

12:13 pm-10:34 pm

2 stops11h 21m

$300

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 6/23

9:48 am-3:32 pm

1 stop4h 44m

Hilton Head Island

Mon 6/29

12:13 pm-5:04 pm

1 stop5h 51m

$309

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 5/26

7:00 am-3:33 pm

2 stops7h 33m

Hilton Head Island

Tue 6/2

4:16 pm-10:36 pm

1 stop7h 20m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 8/19

6:00 am-3:20 pm

2 stops8h 20m

Hilton Head Island

Tue 8/25

12:00 pm-8:24 pm

2 stops9h 24m

$319

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 7/17

10:45 am-2:21 pm

Nonstop2h 36m

Hilton Head Island

Wed 7/22

3:05 pm-4:51 pm

Nonstop2h 46m

$324

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?

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

If you don’t want to visit Hilton Head Island in June, then you should wait until August to fly from Chicago, when ticket prices are also cheap, with an average price of $209.

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 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 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 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 $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 for as low as $283 on momondo.

Can stopping save me money on Chicago to Hilton Head Island flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago to Hilton Head Island flight.

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

$369

Fastest flight time

2h 26m

Direct flights

Every day

Airports in Hilton Head Island

1 airport
The best flight deal from Chicago to Hilton Head Island found on momondo in the last 72 hours is $369
The fastest flight from Chicago to Hilton Head Island takes 2h 26m
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 26m.

  • 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 $209Free CancellationRating
7.4
9,682 reviews
Search United Airlines flights
American AirlinesPriceFrom $328Free CancellationRating
7.1
11,674 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 $209 round-trip, up to an average price of $416. Our users have rated United Airlines at 7.4/10.

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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