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Cheap flights from Chicago to Hilton Head Island from $233

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 5/20. 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.
8:12 am - 2:18 pmORD-HHH
5h 06m1 stop
6:05 pm - 7:14 amHHH-ORD
14h 09m2 stops
$297American Airlines
Find Deal
Wed, Jan 29 - Sun, Feb 2
8:20 am - 5:35 pmORD-HHH
8h 15m2 stops
6:05 pm - 7:14 amHHH-ORD
14h 09m2 stops
$302American Airlines
Find Deal
Wed, Jan 29 - Sun, Feb 2
6:11 am - 2:16 pmORD-HHH
7h 05m2 stops
6:01 pm - 7:15 amHHH-ORD
14h 14m2 stops
$357American Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18
6:00 am - 1:29 pmORD-HHH
6h 29m1 stop
2:10 pm - 8:25 pmHHH-ORD
7h 15m1 stop
$359United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
12:20 pm - 5:30 pmORD-HHH
4h 10m1 stop
6:17 pm - 9:58 pmHHH-ORD
4h 41m1 stop
$364American Airlines
Find Deal
Sat, Apr 19 - Sat, Apr 26
8:16 am - 2:16 pmORD-HHH
5h 00m1 stop
6:01 pm - 10:32 amHHH-ORD
17h 31m1 stop
$373American Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$405United Airlines
Find Deal
Sat, Apr 19 - Sat, Apr 26
8:12 am - 2:18 pmORD-HHH
5h 06m1 stop
6:05 pm - 9:42 pmHHH-ORD
4h 37m1 stop
$439American Airlines
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:00 am - 2:18 pmORD-HHH
7h 18m2 stops
6:05 pm - 12:09 amHHH-ORD
7h 04m1 stop
$448American Airlines
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:00 am - 1:29 pmORD-HHH
6h 29m1 stop
2:10 pm - 9:38 amHHH-ORD
20h 28m2 stops
$478United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
11:19 am - 4:41 pmORD-HHH
4h 22m1 stop
$233Delta
Find Deal
Tue, May 20
7:00 am - 4:41 pmORD-HHH
8h 41m2 stops
$238Delta
Find Deal
Tue, May 20
7:00 am - 4:41 pmORD-HHH
8h 41m2 stops
$274Delta
Find Deal
Sat, May 17
12:25 pm - 5:35 pmORD-HHH
4h 10m1 stop
$344American Airlines
Find Deal
Sun, Feb 9
6:13 am - 2:18 pmORD-HHH
7h 05m2 stops
$349American Airlines
Find Deal
Sun, Feb 9
9:30 am - 4:41 pmORD-HHH
6h 11m1 stop
$359Delta
Find Deal
Sun, May 18
8:10 am - 5:31 pmORD-HHH
8h 21m2 stops
$364American Airlines
Find Deal
Sun, May 11
9:05 pm - 3:31 pmORD-HHH
17h 26m2 stops
$428United Airlines
Find Deal
Sun, May 18
8:35 am - 5:30 pmORD-HHH
7h 55m2 stops
$438American Airlines
Find Deal
Sun, Dec 8
8:05 am - 2:16 pmORD-HHH
5h 11m1 stop
$439American Airlines
Find Deal
Sun, Dec 8
7:00 am - 2:15 pmORD-HHH
6h 15m1 stop
6:03 pm - 12:16 amHHH-ORD
7h 13m1 stop
$854American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
6:01 am - 2:15 pmORD-HHH
7h 14m2 stops
6:03 pm - 9:38 pmHHH-ORD
4h 35m1 stop
$863American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
6:01 am - 2:15 pmORD-HHH
7h 14m2 stops
2:45 pm - 7:46 pmHHH-ORD
6h 01m2 stops
$1,057American Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
9:55 am - 5:33 pmORD-HHH
6h 38m2 stops
2:45 pm - 7:45 pmHHH-ORD
6h 00m2 stops
$1,190American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$405United Airlines
Find Deal
Sat, Apr 19 - Sat, Apr 26
3:15 pm - 6:42 pmORD-HHH
2h 27mnonstop
1:11 pm - 2:57 pmHHH-ORD
2h 46mnonstop
$415United Airlines
Find Deal
Sat, May 3 - Sat, May 10

United Airlines flights from Chicago to Hilton Head Island

Our best United Airlines deals on Chicago to Hilton Head Island flight tickets
United Airlines
Mar 15
ORD6:00 amChicago O'Hare Intl
6h 29m
1 stop
HHH1:29 pmHilton Head Island
Mar 22
HHH2:10 pmHilton Head Island
7h 15m
1 stop
ORD8:25 pmChicago O'Hare Intl
United Airlines
Apr 19
ORD3:15 pmChicago O'Hare Intl
2h 27m
HHH6:42 pmHilton Head Island
Apr 26
HHH1:11 pmHilton Head Island
2h 46m
ORD2:57 pmChicago O'Hare Intl
United Airlines
Mar 15
ORD6:00 amChicago O'Hare Intl
6h 29m
1 stop
HHH1:29 pmHilton Head Island
Mar 22
HHH2:10 pmHilton Head Island
20h 28m
2 stops
ORD9:38 amChicago O'Hare Intl

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 29
ORD8:12 amChicago O'Hare Intl
5h 06m
1 stop
HHH2:18 pmHilton Head Island
Feb 2
HHH6:05 pmHilton Head Island
14h 09m
2 stops
ORD7:14 amChicago O'Hare Intl
American Airlines
Jan 29
ORD8:20 amChicago O'Hare Intl
8h 15m
2 stops
HHH5:35 pmHilton Head Island
Feb 2
HHH6:05 pmHilton Head Island
14h 09m
2 stops
ORD7:14 amChicago O'Hare Intl
American Airlines
Feb 15
ORD6:11 amChicago O'Hare Intl
7h 05m
2 stops
HHH2:16 pmHilton Head Island
Feb 18
HHH6:01 pmHilton Head Island
14h 14m
2 stops
ORD7:15 amChicago 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 Wednesday. Travelers who choose to depart for Hilton Head Island on a Wednesday will often find tickets for as low as $350. 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 $478.

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

Flying to Hilton Head Island from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $0 when looking at flights departing at noon. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $406 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 53 days out, which is when prices tend to be around $425. 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 $223 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 2% 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

$233

Fastest flight time

2h 27m

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 $233. The best round-trip flight deal from Chicago to Hilton Head Island found on momondo in the last 72 hours is $297.
The fastest flight from Chicago to Hilton Head Island takes 2h 27m
Direct flights go from Chicago to Hilton Head Island on Sunday. The only airline offering direct flights is United 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 27m.

  • 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
9,172 reviews
Search United Airlines flights
American AirlinesPriceFrom $200Free 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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