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$215+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 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.
Wed 12/312:46 pmHHH - STL
1 stop5h 44mAmerican Airlines
Sun 1/47:05 amSTL - HHH
1 stop6h 11mAmerican Airlines
Deal found 12/16$400
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.
Sun 12/2111:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Tue 12/235:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/16$742
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.
Sun 12/216:13 pmHHH - ORD
1 stop6h 29mAmerican Airlines
Sat 12/275:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/17$785
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 12/196:13 pmHHH - ORD
1 stop5h 21mAmerican Airlines
Fri 12/265:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/15$839

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$294
(Delta)

One-way from

$215
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Chicago (CHI) flights.
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From Hilton Head Island to Illinois
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One-way flight from Hilton Head Island to Illinois
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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 December 18, 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 IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

4:00 pm-9:48 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 4/22

7:10 am-3:18 pm

1 stop7h 08m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 4/15

3:00 pm-4:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 4/22

10:35 am-2:01 pm

Nonstop2h 26m

$297

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

4:18 pm-9:15 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 2/21

7:11 am-2:27 pm

1 stop6h 16m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/10

3:29 pm-7:50 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 2/17

8:10 am-3:05 pm

1 stop5h 55m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Tue 2/17

3:35 pm-7:42 pm

1 stop5h 07m

Chicago O'Hare Intl

Tue 2/24

9:43 am-3:45 pm

1 stop5h 02m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 2/14

2:58 pm-7:48 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 2/17

6:40 am-3:05 pm

2 stops7h 25m

$314

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Wed 12/31

2:46 pm-7:30 pm

1 stop5h 44m

Lambert-St Louis

Sun 1/4

7:05 am-2:16 pm

1 stop6h 11m

$400

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Sun 4/5

3:00 pm-9:03 pm

1 stop7h 03m

Lambert-St Louis

Wed 4/8

7:45 am-2:01 pm

1 stop5h 16m

$648

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Sun 3/8

4:12 pm-9:26 pm

1 stop6h 14m

Lambert-St Louis

Fri 3/13

6:50 pm-10:33 am

2 stops14h 43m

$659

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 1/17

3:29 pm-10:50 am

2 stops20h 21m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 18 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, April is the cheapest month in which you can book a flight from Hilton Head Island to Illinois (average of $76). Flying from Hilton Head Island to Illinois in February is currently the most expensive (average of $235). 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.

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 December 18, 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
11,055 reviews

Comfort

7.2

Overall

7.2

Food

6.5

Boarding

7.5

Crew

8.0

Entertainment

6.9

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
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Comfort

7.2

Overall

7.2

Food

6.5

Boarding

7.5

Crew

8.0

Entertainment

6.9

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?

    Delta, United Airlines, and American Airlines can get you from Hilton Head Island to Illinois in just under 2h 45m. Your travel time can differ by up to 4h 03m. Hilton Head Island and Illinois are separated by a distance of 781 mi. This flight may include one or multiple stops.

  • 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 (67%), Qatar Airways (67%) and Envoy Air (67%).

  • 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, April is the cheapest month in which you can book a flight from Hilton Head Island to Illinois (average of $76). Flying from Hilton Head Island to Illinois in February is currently the most expensive (average of $235). 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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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