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Cheap flights from Chicago to Hilton Head Island from $224

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 5/17. 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 to Hilton Head Island

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Hilton Head Island that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Hilton Head Island.

Cheap last minute flights

Planning a quick getaway from Chicago to Hilton Head Island? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Hilton Head Island, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Hilton Head Island

Find recent round-trip train or bus tickets from Chicago to Hilton Head Island.

All round-trip flight deals to Hilton Head Island

The cheapest plane tickets to Hilton Head Island found on KAYAK recently.
10:28 am - 5:35 pmORD-HHH
6h 07m1 stop
6:05 pm - 9:42 pmHHH-ORD
4h 37m1 stop
$228American Airlines
Find Deal
Sat, Jan 25 - Mon, Jan 27
8:12 am - 2:18 pmORD-HHH
5h 06m1 stop
2:46 pm - 5:55 pmHHH-ORD
4h 09m1 stop
$229American Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
6:06 am - 2:16 pmORD-HHH
7h 10m2 stops
6:01 pm - 11:52 pmHHH-ORD
6h 51m1 stop
$233American Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
6:30 am - 2:18 pmORD-HHH
6h 48m2 stops
2:46 pm - 5:55 pmHHH-ORD
4h 09m1 stop
$234American Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$410United Airlines
Find Deal
Sat, May 10 - Sat, May 17
7:10 am - 3:31 pmORD-HHH
7h 21m1 stop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$475United Airlines
Find Deal
Wed, May 7 - Sat, May 10
7:10 am - 3:37 pmORD-HHH
7h 27m1 stop
5:11 pm - 6:55 pmHHH-ORD
2h 44mnonstop
$479United Airlines
Find Deal
Tue, Apr 8 - Sat, Apr 12
8:55 am - 4:41 pmORD-HHH
6h 46m2 stops
1:15 pm - 6:40 pmHHH-ORD
6h 25m2 stops
$838Delta
Find Deal
Sat, Jun 7 - Sat, Jun 14
7:00 am - 4:42 pmORD-HHH
8h 42m2 stops
1:15 pm - 8:34 pmHHH-ORD
8h 19m2 stops
$918Delta
Find Deal
Sat, Jun 14 - Sat, Jun 21
8:55 am - 4:41 pmORD-HHH
6h 46m2 stops
1:15 pm - 6:41 pmHHH-ORD
6h 26m2 stops
$1,033Delta
Find Deal
Wed, May 14 - Sun, May 18
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
$224United Airlines
Find Deal
Sat, May 17
8:12 am - 2:18 pmORD-HHH
5h 06m1 stop
$233American Airlines
Find Deal
Fri, Jan 24
8:05 am - 5:35 pmORD-HHH
8h 30m2 stops
$238American Airlines
Find Deal
Fri, Jan 24
10:28 am - 5:29 pmORD-HHH
6h 01m1 stop
$279American Airlines
Find Deal
Mon, Mar 24
6:17 am - 2:19 pmORD-HHH
7h 02m2 stops
$284American Airlines
Find Deal
Mon, Mar 24
6:00 pm - 3:31 pmORD-HHH
20h 31m2 stops
$358United Airlines
Find Deal
Mon, Jun 23
9:30 am - 4:42 pmORD-HHH
6h 12m1 stop
$379Delta
Find Deal
Mon, Jun 23
7:00 am - 12:21 pmORD-HHH
4h 21m1 stop
$388American Airlines
Find Deal
Thu, Jan 2
8:05 am - 5:29 pmORD-HHH
8h 24m2 stops
$393American Airlines
Find Deal
Thu, Jan 2
9:30 am - 4:42 pmORD-HHH
6h 12m1 stop
$449Delta
Find Deal
Sun, Jun 22
12:15 pm - 5:29 pmORD-HHH
4h 14m1 stop
2:42 pm - 7:24 pmHHH-ORD
5h 42m1 stop
$418American Airlines
Find Deal
Thu, Dec 26 - Sun, Dec 29
9:55 am - 5:29 pmORD-HHH
6h 34m2 stops
2:42 pm - 7:24 pmHHH-ORD
5h 42m1 stop
$423American Airlines
Find Deal
Thu, Dec 26 - Sun, Dec 29
12:15 pm - 5:29 pmORD-HHH
4h 14m1 stop
12:51 pm - 3:51 pmHHH-ORD
4h 00m1 stop
$609American Airlines
Find Deal
Thu, Dec 26 - Thu, Jan 2
9:55 am - 5:29 pmORD-HHH
6h 34m2 stops
12:51 pm - 3:51 pmHHH-ORD
4h 00m1 stop
$614American Airlines
Find Deal
Thu, Dec 26 - Thu, Jan 2
9:55 am - 5:29 pmORD-HHH
6h 34m2 stops
12:51 pm - 7:50 pmHHH-ORD
7h 59m2 stops
$778American Airlines
Find Deal
Thu, Dec 26 - Thu, Jan 2
7:00 am - 2:12 pmORD-HHH
6h 12m1 stop
6:24 pm - 8:55 amHHH-ORD
15h 31m1 stop
$887American Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 4
6:05 am - 2:12 pmORD-HHH
7h 07m2 stops
6:24 pm - 8:55 amHHH-ORD
15h 31m1 stop
$892American Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 4
6:05 am - 2:12 pmORD-HHH
7h 07m2 stops
12:51 pm - 8:07 pmHHH-ORD
8h 16m2 stops
$964American Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 4
6:05 am - 2:12 pmORD-HHH
7h 07m2 stops
6:24 pm - 11:37 pmHHH-ORD
6h 13m1 stop
$1,029American Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 4
6:05 am - 2:12 pmORD-HHH
7h 07m2 stops
2:42 pm - 10:58 pmHHH-ORD
9h 16m2 stops
$1,188American Airlines
Find Deal
Sat, Dec 28 - Sat, Jan 4
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$410United Airlines
Find Deal
Sat, May 10 - Sat, May 17
9:45 am - 1:10 pmORD-HHH
2h 25mnonstop
1:55 pm - 3:29 pmHHH-ORD
2h 34mnonstop
$528American Airlines
Find Deal
Sat, Jun 7 - Sat, Jun 14
9:45 am - 1:10 pmORD-HHH
2h 25mnonstop
1:55 pm - 3:29 pmHHH-ORD
2h 34mnonstop
$539American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
9:45 am - 1:10 pmORD-HHH
2h 25mnonstop
1:55 pm - 3:29 pmHHH-ORD
2h 34mnonstop
$624American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21

American Airlines flights from Chicago to Hilton Head Island

Our best American Airlines deals on Chicago to Hilton Head Island flight tickets
American Airlines
Jan 25
ORD10:28 amChicago O'Hare Intl
6h 07m
1 stop
HHH5:35 pmHilton Head Island
Jan 27
HHH6:05 pmHilton Head Island
4h 37m
1 stop
ORD9:42 pmChicago O'Hare Intl
American Airlines
Feb 8
ORD8:12 amChicago O'Hare Intl
5h 06m
1 stop
HHH2:18 pmHilton Head Island
Feb 15
HHH2:46 pmHilton Head Island
4h 09m
1 stop
ORD5:55 pmChicago O'Hare Intl
American Airlines
Feb 18
ORD6:06 amChicago O'Hare Intl
7h 10m
2 stops
HHH2:16 pmHilton Head Island
Feb 25
HHH6:01 pmHilton Head Island
6h 51m
1 stop
ORD11:52 pmChicago O'Hare Intl

United Airlines flights from Chicago to Hilton Head Island

Our best United Airlines deals on Chicago to Hilton Head Island flight tickets
United Airlines
May 10
ORD3:15 pmChicago O'Hare Intl
2h 27m
HHH6:42 pmHilton Head Island
May 17
HHH1:11 pmHilton Head Island
2h 46m
ORD2:57 pmChicago O'Hare Intl
United Airlines
May 7
ORD7:10 amChicago O'Hare Intl
7h 21m
1 stop
HHH3:31 pmHilton Head Island
May 10
HHH1:11 pmHilton Head Island
2h 46m
ORD2:57 pmChicago O'Hare Intl
United Airlines
Apr 8
ORD7:10 amChicago O'Hare Intl
7h 27m
1 stop
HHH3:37 pmHilton Head Island
Apr 12
HHH5:11 pmHilton Head Island
2h 44m
ORD6:55 pmChicago O'Hare Intl

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 January, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $305.

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 $361. 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 $490.

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

Flying to Hilton Head Island from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $236 when looking at flights departing in the afternoon. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $418 on average. Flights to Hilton Head Island from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 to Hilton Head Island?

The best time to book a flight to Hilton Head Island from Chicago is 58 days out, which is when prices tend to be around $427. Keep in mind that you might be able to find cheaper flights to Hilton Head Island at any time. In fact, our users found flights for as low as $149 in the past 72 hours.

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

There are 1 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.

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

You could potentially save up to 4% 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

$224

Fastest flight time

2h 25m

Direct flights

Sun

Airports in Hilton Head Island

1 airport
The best one-way flight to Hilton Head Island from Chicago in the past 72 hours is $224. The best round-trip flight deal from Chicago to Hilton Head Island found on momondo in the last 72 hours is $228.
The fastest flight from Chicago to Hilton Head Island takes 2h 25m
Direct flights go from Chicago to Hilton Head Island on Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There is 1 airport near Hilton Head Island: Hilton Head Island (HHH)

  • 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 25m.

  • 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 $149Free CancellationRating
7.4
9,007 reviews
Search United Airlines flights
American AirlinesPriceFrom $223Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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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