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Hilton Head Island

$129+ Cheap flights from Illinois to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Illinois to Hilton Head Island

Cheapest flights from Illinois to Hilton Head Island
Explore the most affordable flight options available from Illinois to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:40 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Wed 4/153:00 pm
HHH
-
ORD
Nonstop2h 44m
United Airlines
Deal found 1/28$224
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/510:35 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Mon 6/83:00 pm
HHH
-
ORD
Nonstop2h 45m
United Airlines
Deal found 1/28$252
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:10 am
ORD
-
HHH
1 stop5h 12m
American Airlines
Wed 3/114:11 pm
HHH
-
ORD
1 stop6h 13m
American Airlines
Deal found 1/27$277
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:35 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Sat 9/123:00 pm
HHH
-
ORD
Nonstop2h 45m
United Airlines
Deal found 1/27$291
This Delta deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:10 am
ORD
-
HHH
1 stop7h 08m
Delta
Sun 5/244:00 pm
HHH
-
ORD
1 stop5h 45m
Delta
Deal found 1/28$294
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:45 am
STL
-
HHH
1 stop5h 21m
United Airlines
Wed 4/223:00 pm
HHH
-
STL
1 stop7h 08m
United Airlines
Deal found 1/28$297
This American Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:06 am
ORD
-
HHH
Nonstop2h 25m
American Airlines
Tue 8/42:01 pm
HHH
-
ORD
Nonstop2h 37m
American Airlines
Deal found 1/28$309
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:35 am
ORD
-
HHH
Nonstop2h 26m
United Airlines
Sat 9/263:00 pm
HHH
-
ORD
Nonstop2h 45m
United Airlines
Deal found 1/27$316
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:10 am
ORD
-
HHH
1 stop6h 12m
American Airlines
Tue 3/33:31 pm
HHH
-
ORD
1 stop5h 09m
American Airlines
Deal found 1/27$320
This American Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:05 am
ORD
-
HHH
1 stop5h 15m
American Airlines
Sat 2/142:58 pm
HHH
-
ORD
1 stop5h 42m
American Airlines
Deal found 1/28$323
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:15 am
MLI
-
HHH
1 stop4h 38m
American Airlines
Tue 3/245:19 pm
HHH
-
MLI
1 stop4h 40m
American Airlines
Deal found 1/27$329
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/287:05 am
STL
-
HHH
1 stop6h 17m
American Airlines
Wed 4/12:58 pm
HHH
-
STL
1 stop5h 32m
American Airlines
Deal found 1/27$369

Find flight deals from Illinois to Hilton Head Island

Keep the following information in mind while searching for Illinois to Hilton Head Island flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(United Airlines)

One-way from

$129
(American Airlines)

Popular in

July

Cheapest in

September

Average price

$358

Good round-trip deal

$281 or less
Provider with most accurate pricing for Chicago (CHI)-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Hilton Head Island flights.
Search Deals
From Illinois to Hilton Head Island
Search Deals
One-way flight from Illinois to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Hilton Head Island.
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Illinois to Hilton Head Island that are best for you.

Fly from

Illinois

Fly to

Hilton Head Island

Route

Depart

Return

Price

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/7

10:40 am-2:06 pm

Nonstop2h 26m

Hilton Head Island

Wed 4/15

3:00 pm-4:44 pm

Nonstop2h 44m

$224

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Sat 4/18

7:45 am-2:06 pm

1 stop5h 21m

Hilton Head Island

Wed 4/22

3:00 pm-9:08 pm

1 stop7h 08m

$297

MolineHilton Head Island

MLI - HHH

MLIHHH

Moline Quad-City

Tue 3/17

6:15 am-11:53 am

1 stop4h 38m

Hilton Head Island

Tue 3/24

5:19 pm-8:59 pm

1 stop4h 40m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 4/7

5:00 am-12:37 pm

1 stop6h 37m

Hilton Head Island

Wed 4/15

1:08 pm-6:00 pm

1 stop5h 52m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 4/20

7:14 am-3:20 pm

1 stop7h 06m

Hilton Head Island

Mon 4/27

4:00 pm-10:15 pm

1 stop7h 15m

$344

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 2/11

8:12 am-2:59 pm

1 stop5h 47m

Hilton Head Island

Sun 2/15

6:20 pm-12:16 am

1 stop6h 56m

$356

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/5

6:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Wed 2/11

12:51 pm-6:01 pm

1 stop6h 10m

$356

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 2/26

6:08 am-2:22 pm

2 stops7h 14m

Hilton Head Island

Tue 3/3

3:31 pm-10:17 pm

2 stops7h 46m

$361

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Sat 3/28

7:05 am-2:22 pm

1 stop6h 17m

Hilton Head Island

Wed 4/1

2:58 pm-7:30 pm

1 stop5h 32m

$369

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Sat 4/18

7:05 am-6:20 pm

2 stops10h 15m

Hilton Head Island

Wed 4/22

1:08 pm-6:04 pm

1 stop5h 56m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 36 results
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Best time to book a flight from Illinois to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Hilton Head Island

What is the cheapest month to book a flight from Illinois to Hilton Head Island?

Currently, May is the cheapest month in which you can book a flight from Illinois to Hilton Head Island (average of $46). Flying from Illinois to Hilton Head Island in March is currently the most expensive (average of $257). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Illinois?

    Most people fly into Hilton Head Island (HHH) if they book a flight to Hilton Head Island from Illinois. Hilton Head is conveniently located just 3.3 mi from Hilton Head Island’s city center.

  • How long is the flight from Illinois to Hilton Head Island?

    A quick flight from Illinois to Hilton Head Island can take about 2h 26m. United Airlines provides one of the quickest options available for as low as $224. There are 781 mi between Illinois and Hilton Head Island. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Illinois to Hilton Head Island?

    While some choose either Lambert-St Louis - Hilton Head Island or Moline Quad-City - Hilton Head Island, Chicago O'Hare Intl - Hilton Head Island is the most popular route from Illinois to Hilton Head Island.

  • What are the cheapest flights from Illinois to Hilton Head Island?

    Looking at all options, your cheapest flight can be booked for $220. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $224 on average, our data indicates $405 when flying from Illinois to Hilton Head Island.

  • Can I find deals for flights from Illinois to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Illinois to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Hilton Head Island.

  • Can I find deals for business class flights from Illinois to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Illinois to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Hilton Head Island?

    Currently, May is the cheapest month in which you can book a flight from Illinois to Hilton Head Island (average of $46). Flying from Illinois to Hilton Head Island in March is currently the most expensive (average of $257). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Alternative routes for Illinois to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Hilton Head Island

Discover the top 2 airlines that operate flights from Illinois to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$279Average$444FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$442FlexibilityNo cancel feeOn-time71%

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