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$223+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$279
(American Airlines)

One-way from

$223
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Chicago (CHI) flight deals.
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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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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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 11/147:07 pmHHH - STL
1 stop5h 00mAmerican Airlines
Sun 11/165:00 amSTL - HHH
1 stop5h 49mAmerican Airlines
Deal found 10/29$279
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 10/3112:45 pmHHH - MLI
1 stop4h 45mAmerican Airlines
Mon 11/36:17 amMLI - HHH
1 stop5h 12mAmerican Airlines
Deal found 10/28$346
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 10/3112:45 pmHHH - STL
1 stop4h 46mAmerican Airlines
Sun 11/27:00 amSTL - HHH
1 stop3h 49mAmerican Airlines
Deal found 10/28$346
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 10/305:21 pmHHH - STL
1 stop6h 44mAmerican Airlines
Sun 11/25:00 amSTL - HHH
1 stop5h 49mAmerican Airlines
Deal found 10/28$369
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/156:48 pmHHH - ORD
1 stop6h 10mAmerican Airlines
Wed 11/196:46 amORD - HHH
1 stop4h 43mAmerican Airlines
Deal found 10/30$369
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/1512:38 pmHHH - ORD
1 stop5h 15mAmerican Airlines
Sun 11/167:10 amORD - HHH
1 stop6h 09mAmerican Airlines
Deal found 10/30$397
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/193:27 pmHHH - ORD
2 stops8h 06mAmerican Airlines
Sun 11/236:07 amORD - HHH
2 stops7h 12mAmerican Airlines
Deal found 10/29$407
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/132:51 pmHHH - ORD
1 stop5h 27mAmerican Airlines
Mon 11/178:20 amORD - HHH
1 stop5h 37mAmerican Airlines
Deal found 10/29$425
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/1811:14 amHHH - ORD
1 stop5h 51mAmerican Airlines
Sat 12/205:00 amORD - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/30$427
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/141:02 pmHHH - ORD
1 stop7h 24mAmerican Airlines
Sun 11/168:20 amORD - HHH
1 stop4h 59mAmerican Airlines
Deal found 10/30$495

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 October 30, 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

Fri 11/14

7:07 pm-11:07 pm

1 stop5h 00m

Lambert-St Louis

Sun 11/16

5:00 am-11:49 am

1 stop5h 49m

$279

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Fri 4/3

3:00 pm-7:25 pm

1 stop5h 25m

Lambert-St Louis

Tue 4/7

6:30 am-3:12 pm

1 stop7h 42m

$359

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 11/15

6:48 pm-11:58 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 11/19

6:46 am-12:29 pm

1 stop4h 43m

$369

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 11/19

3:27 pm-7:18 pm

1 stop4h 51m

Chicago O'Hare Intl

Sun 11/23

8:20 am-2:19 pm

1 stop4h 59m

$397

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sat 11/15

12:38 pm-4:53 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 11/16

7:10 am-2:19 pm

1 stop6h 09m

$397

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Fri 4/3

6:25 pm-11:32 pm

1 stop6h 07m

Lambert-St Louis

Tue 4/7

7:34 am-2:20 pm

1 stop5h 46m

$414

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 12/18

11:14 am-4:05 pm

1 stop5h 51m

Chicago O'Hare Intl

Sat 12/20

5:00 am-10:44 am

1 stop4h 44m

$427

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 11/13

2:51 pm-7:18 pm

1 stop5h 27m

Chicago O'Hare Intl

Mon 11/17

6:06 am-2:57 pm

2 stops7h 51m

$430

Hilton Head IslandMoline

HHH - MLI

HHHMLI

Hilton Head Island

Fri 4/3

3:00 pm-8:58 pm

1 stop6h 58m

Moline Quad-City

Tue 4/7

3:52 pm-1:52 pm

1 stop21h 00m

$438

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 11/13

11:28 am-3:18 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 11/16

7:10 am-2:19 pm

1 stop6h 09m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 20 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 $228). 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 October 30, 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 October 30, 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
11,034 reviews

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

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
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

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 and United Airlines can get you from Hilton Head Island to Illinois in just under 5h. Your travel time can differ by up to 25m. Hilton Head Island and Illinois are separated by a distance of 706 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 - Lambert-St Louis, Hilton Head Island - Chicago O'Hare Intl 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 (83%), Qatar Airways (83%) and Envoy Air (83%).

  • 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 $228). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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