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$218+ Cheap flights from Hilton Head Island (HHH) to Illinois

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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Illinois

Keep the following information in mind while searching for Hilton Head Island to Illinois flight deals. Data was last updated September 15, 2025.

Round-trip from

$274
(American Airlines)

One-way from

$218
(American Airlines)
From Hilton Head Island to Illinois
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One-way flight from Hilton Head Island to Illinois
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Find flight deals from Hilton Head Island to Illinois

Cheapest flights from Hilton Head Island to Illinois
Explore the most affordable flight options available from Hilton Head Island to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 10/305:21 pmHHH - STL
1 stop6h 44mAmerican Airlines
Sun 11/25:00 amSTL - HHH
1 stop5h 49mAmerican Airlines
Deal found 9/13$274
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/312:52 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Wed 12/106:45 amORD - HHH
1 stop7h 12mAmerican Airlines
Deal found 9/14$309
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 9/194:05 pmHHH - ORD
1 stop7h 18mDelta
Mon 9/229:50 amORD - HHH
1 stop4h 35mDelta
Deal found 9/13$324
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 9/305:20 pmHHH - ORD
1 stop4h 07mAmerican Airlines
Sat 10/411:26 amORD - HHH
1 stop6h 28mAmerican Airlines
Deal found 9/15$339
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/173:02 pmHHH - ORD
1 stop7h 22mAmerican Airlines
Mon 10/207:10 amORD - HHH
1 stop6h 22mAmerican Airlines
Deal found 9/13$363
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/1911:04 amHHH - ORD
1 stop7h 19mAmerican Airlines
Sun 9/215:00 amORD - HHH
1 stop5h 30mAmerican Airlines
Deal found 9/13$395
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/195:20 pmHHH - ORD
2 stops7h 28mAmerican Airlines
Mon 9/227:00 amORD - HHH
2 stops6h 56mAmerican Airlines
Deal found 9/13$405
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/66:40 pmHHH - STL
1 stop6h 25mAmerican Airlines
Sun 11/97:00 amSTL - HHH
1 stop3h 49mAmerican Airlines
Deal found 9/14$644
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 9/2012:14 pmHHH - STL
1 stop3h 34mDelta
Sun 9/219:19 amSTL - HHH
1 stop5h 06mDelta
Deal found 9/13$1,951

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Illinois 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 September 15, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Illinois that are best for you.

Fly from

Hilton Head Island

Fly to

Illinois

Route

Depart

Return

Price

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Thu 10/30

3:32 pm-10:55 pm

2 stops8h 23m

Lambert-St Louis

Sun 11/2

7:00 am-11:49 am

1 stop3h 49m

$279

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Fri 10/31

3:32 pm-10:55 pm

2 stops8h 23m

Lambert-St Louis

Sun 11/2

5:00 am-11:49 am

1 stop5h 49m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/3

12:52 pm-6:02 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 12/10

6:45 am-2:57 pm

1 stop7h 12m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 9/30

11:04 am-3:50 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/4

10:00 am-1:27 pm

Nonstop2h 27m

$329

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 10/17

3:02 pm-9:24 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 10/20

7:10 am-2:32 pm

1 stop6h 22m

$363

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 10/17

3:02 pm-9:24 pm

1 stop7h 22m

Chicago O'Hare Intl

Sun 10/19

5:22 am-11:32 am

1 stop5h 10m

$363

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Thu 11/6

6:40 pm-12:05 am

1 stop6h 25m

Lambert-St Louis

Sun 11/9

7:00 am-11:49 am

1 stop3h 49m

$644

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 11/14

7:07 pm-10:49 am

2 stops16h 42m

$218

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 10/15

4:10 pm-9:43 am

2 stops18h 33m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 12/10

12:52 pm-7:20 am

2 stops19h 28m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 16 results
1
2

Best time to book a flight from Hilton Head Island to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Hilton Head Island 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 Hilton Head Island to Illinois

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

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Illinois (average of $245). Flying from Hilton Head Island to Illinois in March is currently the most expensive (average of $321). 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 HHH to IL?

Find hourly flight availability from Hilton Head Island to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Hilton Head Island to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown American Airlines from Hilton Head Island to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Illinois. 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 from for flights from Hilton Head Island to Illinois?

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

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

    American Airlines can get you from Hilton Head Island to Illinois in just under 8h 23m. Your travel time can differ by up to . Hilton Head Island and Illinois are separated by a distance of 706 mi.

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

    When deciding which route to take from Hilton Head Island to Illinois consider Hilton Head Island - Chicago O'Hare Intl, Hilton Head Island - Lambert-St Louis or Hilton Head Island - Moline Quad-City as they are the most popular.

  • What are the most reliable airlines from Hilton Head Island to Illinois?

    The top 3 most reliable airlines when flying from Hilton Head Island to Illinois are American Airlines (60%), Qatar Airways (60%) and Envoy Air (60%).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to Illinois 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 Hilton Head Island to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Illinois (average of $245). Flying from Hilton Head Island to Illinois in March is currently the most expensive (average of $321). 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.

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Alternative routes for Hilton Head Island to Illinois

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Top airline flying from Hilton Head Island to Illinois

Discover the top airline that operate flights from Hilton Head Island to Illinois. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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