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Hilton Head Island

$249+ Cheap flights from Illinois to Hilton Head Island (HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheap 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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$628
Provider with most accurate pricing for Chicago (CHI)-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Hilton Head Island flights.
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From Illinois to Hilton Head Island
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 6, 2025.

This American Airlines deal was found by Cheapflights users on 10/4. 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 11/196:52 amSTL - HHH
1 stop7h 05mAmerican Airlines
Sun 11/236:40 pmHHH - STL
1 stop6h 25mAmerican Airlines
Deal found 10/4$249
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/216:25 amSTL - HHH
1 stop4h 50mAmerican Airlines
Sat 10/253:02 pmHHH - STL
1 stop5h 28mAmerican Airlines
Deal found 10/6$284
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Fri 10/318:20 pmORD - HHH
2 stops14h 12mAmerican Airlines
Tue 11/43:27 pmHHH - ORD
1 stop4h 47mAmerican Airlines
Deal found 10/4$301
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/46:50 amORD - HHH
2 stops7h 07mAmerican Airlines
Tue 11/1111:28 amHHH - ORD
1 stop6h 25mAmerican Airlines
Deal found 10/5$314
This American Airlines deal was found by Cheapflights users on 10/5. 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 12/106:14 amMLI - HHH
1 stop5h 08mAmerican Airlines
Sat 12/1311:47 amHHH - MLI
1 stop6h 14mAmerican Airlines
Deal found 10/5$319
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Fri 10/318:20 pmORD - HHH
2 stops14h 12mAmerican Airlines
Mon 11/37:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Deal found 10/4$328
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/2510:05 amORD - HHH
Nonstop2h 20mAmerican Airlines
Tue 10/285:21 pmHHH - ORD
1 stop4h 49mAmerican Airlines
Deal found 10/6$329
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Sun 11/238:20 amORD - HHH
1 stop4h 59mAmerican Airlines
Tue 12/27:07 pmHHH - ORD
1 stop6h 05mAmerican Airlines
Deal found 10/4$336
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/226:06 amORD - HHH
1 stop5h 00mAmerican Airlines
Tue 12/27:07 pmHHH - ORD
1 stop6h 05mAmerican Airlines
Deal found 10/4$357
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/136:06 amORD - HHH
2 stops7h 13mAmerican Airlines
Mon 11/177:07 pmHHH - ORD
1 stop5h 30mAmerican Airlines
Deal found 10/6$368
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Fri 11/215:00 amSTL - HHH
1 stop5h 49mAmerican Airlines
Wed 11/266:40 pmHHH - STL
1 stop6h 25mAmerican Airlines
Deal found 10/4$387
This American Airlines deal was found by Cheapflights users on 10/5. 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 12/106:20 amPIA - HHH
1 stop5h 02mAmerican Airlines
Sat 12/1311:47 amHHH - PIA
1 stop7h 20mAmerican Airlines
Deal found 10/5$439

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 October 6, 2025.
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

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Wed 11/19

6:52 am-2:57 pm

1 stop7h 05m

Hilton Head Island

Sun 11/23

6:40 pm-12:05 am

1 stop6h 25m

$249

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Tue 10/21

6:25 am-12:15 pm

1 stop4h 50m

Hilton Head Island

Sat 10/25

3:02 pm-7:30 pm

1 stop5h 28m

$284

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 11/4

6:50 am-2:57 pm

2 stops7h 07m

Hilton Head Island

Tue 11/11

11:28 am-4:53 pm

1 stop6h 25m

$314

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 3/3

6:30 am-2:16 pm

2 stops6h 46m

Hilton Head Island

Tue 3/10

6:25 pm-12:13 am

1 stop6h 48m

$314

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

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Fri 10/31

8:20 pm-11:32 am

2 stops14h 12m

Hilton Head Island

Mon 11/3

7:07 pm-11:37 pm

1 stop5h 30m

$328

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 10/25

10:05 am-1:25 pm

Nonstop2h 20m

Hilton Head Island

Tue 10/28

11:16 am-3:48 pm

1 stop5h 32m

$329

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 11/23

8:20 am-2:19 pm

1 stop4h 59m

Hilton Head Island

Tue 12/2

7:07 pm-12:12 am

1 stop6h 05m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Tue 10/21

8:35 am-4:51 pm

1 stop7h 16m

Hilton Head Island

Sat 10/25

3:02 pm-9:29 pm

1 stop7h 27m

$339

St. LouisHilton Head Island

STL - HHH

STLHHH

Lambert-St Louis

Fri 11/21

5:00 am-11:49 am

1 stop5h 49m

Hilton Head Island

Wed 11/26

6:40 pm-12:05 am

1 stop6h 25m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 26 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 December is currently the most expensive (average of $248). 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.

What is the cheapest time of day to fly from IL to HHH?

Find hourly flight availability from Illinois to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 6, 2025.

One of the essential ways to save on airfare from Illinois to Hilton Head Island is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 79% on airfare.

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 7h 05m. American Airlines provides one of the quickest options available for as low as $249. There are 706 mi between Illinois and Hilton Head Island.

  • 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 most reliable airlines from Illinois to Hilton Head Island?

    The top 3 most reliable airlines when flying from Illinois to Hilton Head Island are United Airlines (67%), Republic Airways (67%) and American Airlines (38%).

  • 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 December is currently the most expensive (average of $248). 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
Bluffton

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Alternative routes for Illinois to Hilton Head Island

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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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$273Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$379Average$498FlexibilityNo cancel feeOn-time69%

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