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Cheap flights from Illinois 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 Illinois 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.
1 adult
0 bags

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Find the cheapest flights from Illinois 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
6:52 am - 12:20 pmSTL-HHH
4h 28m1 stop
American Airlines Logo
3:29 pm - 6:34 pmHHH-STL
4h 05m1 stop
$319American Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
6:14 am - 12:22 pmMLI-HHH
5h 08m1 stop
American Airlines Logo
11:47 am - 5:01 pmHHH-MLI
6h 14m1 stop
$319American Airlines
Find Deal
Wed, Dec 10 - Sat, Dec 13
American Airlines Logo
6:00 am - 2:59 pmSTL-HHH
7h 59m2 stops
American Airlines Logo
12:51 pm - 6:34 pmHHH-STL
6h 43m1 stop
$324American Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
6:14 am - 2:57 pmMLI-HHH
7h 43m1 stop
American Airlines Logo
11:47 am - 7:12 pmHHH-MLI
8h 25m2 stops
$324American Airlines
Find Deal
Wed, Dec 10 - Sat, Dec 13
American Airlines Logo
6:00 am - 2:59 pmSTL-HHH
7h 59m2 stops
American Airlines Logo
12:51 pm - 6:34 pmHHH-STL
6h 43m1 stop
$326American Airlines
Find Deal
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
6:00 am - 2:59 pmSTL-HHH
7h 59m2 stops
American Airlines Logo
12:51 pm - 9:51 pmHHH-STL
10h 00m2 stops
$329American Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
5:09 am - 6:33 pmMLI-HHH
12h 24m2 stops
American Airlines Logo
11:47 am - 7:12 pmHHH-MLI
8h 25m2 stops
$329American Airlines
Find Deal
Wed, Dec 10 - Sat, Dec 13
United Airlines Logo
10:35 am - 1:52 pmORD-HHH
2h 17mnonstop
United Airlines Logo
3:00 pm - 4:45 pmHHH-ORD
2h 45mnonstop
$413United Airlines
Find Deal
Sat, Mar 28 - 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
$428United Airlines
Find Deal
Sat, Mar 28 - Thu, Apr 2

American Airlines flights from Illinois to Hilton Head Island

Our best American Airlines deals on Illinois 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
Dec 10
MLI6:14 amMoline Quad-City
5h 08m
1 stop
HHH12:22 pmHilton Head Island
Dec 13
HHH11:47 amHilton Head Island
6h 14m
1 stop
MLI5:01 pmMoline Quad-City
$319
Find similar
American Airlines
Dec 10
MLI6:14 amMoline Quad-City
7h 43m
1 stop
HHH2:57 pmHilton Head Island
Dec 13
HHH11:47 amHilton Head Island
8h 25m
2 stops
MLI7:12 pmMoline Quad-City
$324
Find similar

United Airlines flights from Illinois to Hilton Head Island

Our best United Airlines deals on Illinois to Hilton Head Island flight tickets
United Airlines
Mar 28
ORD10:35 amChicago O'Hare Intl
2h 17m
HHH1:52 pmHilton Head Island
Apr 3
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$413
Find similar
United Airlines
Mar 28
ORD10:35 amChicago O'Hare Intl
2h 17m
HHH1:52 pmHilton Head Island
Apr 2
HHH3:00 pmHilton Head Island
2h 45m
ORD4:45 pmChicago O'Hare Intl
$428
Find similar
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
$467
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 6, 2025.
Use the filters below to find and compare flights from Illinois 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

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Fri 1/9

6:52 am-12:20 pm

1 stop4h 28m

Hilton Head Island

Mon 1/12

3:29 pm-6:34 pm

1 stop4h 05m

$319

MolineHilton Head Island

MLI - HHH

MLIHHH

Moline Quad-City

Wed 12/10

6:14 am-12:22 pm

1 stop5h 08m

Hilton Head Island

Sat 12/13

11:47 am-5:01 pm

1 stop6h 14m

$319

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Fri 1/9

6:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Mon 1/12

12:51 pm-6:34 pm

1 stop6h 43m

$324

MolineHilton Head Island

MLI - HHH

MLIHHH

Moline Quad-City

Wed 12/10

6:14 am-2:57 pm

1 stop7h 43m

Hilton Head Island

Sat 12/13

11:47 am-7:12 pm

2 stops8h 25m

$324

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Thu 1/15

6:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Mon 1/19

12:51 pm-6:34 pm

1 stop6h 43m

$326

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Fri 1/9

6:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Mon 1/12

12:51 pm-9:51 pm

2 stops10h 00m

$329

MolineHilton Head Island

MLI - HHH

MLIHHH

Moline Quad-City

Wed 12/10

5:09 am-6:33 pm

2 stops12h 24m

Hilton Head Island

Sat 12/13

11:47 am-7:12 pm

2 stops8h 25m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 3/28

10:35 am-1:52 pm

Nonstop2h 17m

Hilton Head Island

Fri 4/3

3:00 pm-4:45 pm

Nonstop2h 45m

$413

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 3/28

10:35 am-1:52 pm

Nonstop2h 17m

Hilton Head Island

Thu 4/2

3:00 pm-4:45 pm

Nonstop2h 45m

$428

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 Illinois 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 January, then you should wait until September to fly from Illinois, when ticket prices are also cheap, with an average price of $335.

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

The cheapest day to depart from Illinois 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 Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $528.

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

Fly from Chicago O'Hare Intl to Hilton Head Island for the best Illinois - 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 Illinois 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 Illinois for as low as $305 on momondo.

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

There is only 1 cabin class available to choose from on Illinois 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 Illinois to Hilton Head Island flights?

You could potentially save up to 67% on your flight if you consider stops on a Illinois to Hilton Head Island flight.

Cheap Illinois to Hilton Head Island flight deals and tips

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

Best Price Found

$319

Fastest flight time

2h 17m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Hilton Head Island

1 airport
The best flight deal from Illinois to Hilton Head Island found on momondo in the last 72 hours is $319
The fastest flight from Illinois to Hilton Head Island takes 2h 17m
Direct flights go from Illinois to Hilton Head Island on Monday, Tuesday, Wednesday, Friday, 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

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

    Prices for flights from Illinois to Hilton Head Island Airport were last updated today.

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

  • How old do you have to be to fly from Illinois to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Hilton Head Island Airport.

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

    The travel and health documents required for your trip to Hilton Head Island Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hilton Head Island Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Illinois to Hilton Head Island

Compare and see reviews for airlines that fly from Illinois to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $278Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
United AirlinesPriceFrom $379Free CancellationRating
7.4
9,003 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 Illinois to Hilton Head Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Illinois to Hilton Head Island. momondo saves you time and could save you money on your trip.

Can I find flights from Illinois to Hilton Head Island with flexible booking policies on momondo?

momondo does allow users to show only those flights to Hilton Head Island from Illinois which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Illinois to Hilton Head Island flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Hilton Head Island from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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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