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Hilton Head Island

$145+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HHH
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/205:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Mon 12/2211:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 12/16$397
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/188:25 amORD - HHH
2 stops8h 18mAmerican Airlines
Wed 12/2411:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 12/17$402
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/198:03 amORD - HHH
1 stop5h 13mAmerican Airlines
Sun 12/2111:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Deal found 12/15$425
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/245:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Mon 12/296:13 pmHHH - ORD
1 stop6h 29mAmerican Airlines
Deal found 12/17$458
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/255:10 amEVV - HHH
1 stop4h 34mAmerican Airlines
Mon 12/296:13 pmHHH - EVV
1 stop6h 11mAmerican Airlines
Deal found 12/18$520
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/256:09 amORD - HHH
2 stops7h 07mAmerican Airlines
Tue 12/302:46 pmHHH - ORD
1 stop5h 36mAmerican Airlines
Deal found 12/17$579
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/3110:29 amORD - HHH
1 stop6h 14mAmerican Airlines
Sun 1/46:13 pmHHH - ORD
1 stop5h 21mAmerican Airlines
Deal found 12/16$624
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/209:09 amSTL - HHH
1 stop4h 07mAmerican Airlines
Mon 12/2211:14 amHHH - STL
1 stop7h 10mAmerican Airlines
Deal found 12/15$764

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$145
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$418

Good round-trip deal

$279 or less
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
Search Deals
One-way flight from Illinois to Hilton Head Island
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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Illinois to Hilton Head Island.
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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 December 18, 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

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Thu 6/11

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Tue 6/16

3:00 pm-4:45 pm

Nonstop2h 45m

$279

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 6/10

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Mon 6/15

3:00 pm-4:45 pm

Nonstop2h 45m

$279

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 6/10

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Tue 6/16

3:00 pm-4:45 pm

Nonstop2h 45m

$279

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 5/24

10:35 am-2:01 pm

Nonstop2h 26m

Hilton Head Island

Sat 5/30

3:00 pm-4:45 pm

Nonstop2h 45m

$282

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 1/17

8:50 pm-12:20 pm

2 stops14h 30m

Hilton Head Island

Tue 1/20

3:29 pm-7:50 pm

1 stop5h 21m

$293

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sat 4/25

12:07 pm-5:36 pm

1 stop4h 29m

Hilton Head Island

Sat 5/2

6:07 pm-11:50 pm

1 stop6h 43m

$309

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

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Sun 3/1

8:10 am-2:27 pm

1 stop5h 17m

Hilton Head Island

Sat 3/7

6:22 pm-12:10 am

1 stop6h 48m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Mon 1/19

8:12 am-2:59 pm

1 stop5h 47m

Hilton Head Island

Sat 1/31

12:54 pm-6:01 pm

1 stop6h 07m

$336

ChicagoHilton Head Island

ORD - HHH

ORDHHH

Chicago O'Hare Intl

Wed 6/10

6:00 am-11:23 am

1 stop28h 23m

Hilton Head Island

Tue 6/16

4:00 pm-10:43 pm

1 stop7h 43m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 27 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.

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 December 18, 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 2h 26m. United Airlines provides one of the quickest options available for as low as $279. 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 Evansville Dress Regional - Hilton Head Island or Greater Peoria - 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 $209. While the most popular route (Chicago O'Hare Intl - Hilton Head Island) can be booked for $209 on average, our data indicates $361 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$278Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$299Average$498FlexibilityNo cancel feeOn-time69%

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