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$134+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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 2/1211:03 am
HHH
-
ORD
1 stop5h 18m
American Airlines
Mon 2/165:00 am
ORD
-
HHH
1 stop4h 33m
American Airlines
Deal found 1/28$257
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:08 pm
HHH
-
STL
1 stop4h 24m
Delta
Tue 5/59:59 am
STL
-
HHH
1 stop4h 21m
Delta
Deal found 1/28$310
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/33:29 pm
HHH
-
ORD
1 stop5h 21m
American Airlines
Tue 2/106:05 am
ORD
-
HHH
1 stop5h 15m
American Airlines
Deal found 1/27$312
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:08 pm
HHH
-
STL
2 stops9h 34m
Delta
Wed 5/69:59 am
STL
-
HHH
1 stop4h 21m
Delta
Deal found 1/28$315
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:08 pm
HHH
-
STL
1 stop4h 24m
Delta
Wed 5/66:48 am
STL
-
HHH
2 stops7h 32m
Delta
Deal found 1/28$322
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/512:51 pm
HHH
-
ORD
2 stops10h 43m
American Airlines
Sun 2/810:10 am
ORD
-
HHH
1 stop3h 49m
American Airlines
Deal found 1/28$332
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/1112:51 pm
HHH
-
ORD
1 stop6h 10m
American Airlines
Sat 2/1410:28 am
ORD
-
HHH
1 stop6h 16m
American Airlines
Deal found 1/27$333
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:00 pm
HHH
-
STL
2 stops17h 30m
Delta
Tue 5/59:59 am
STL
-
HHH
1 stop4h 21m
Delta
Deal found 1/28$349
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:08 pm
HHH
-
STL
1 stop4h 24m
Delta
Mon 5/49:59 am
STL
-
HHH
1 stop4h 21m
Delta
Deal found 1/28$358
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:00 pm
HHH
-
STL
2 stops19h 34m
Delta
Wed 5/66:48 am
STL
-
HHH
2 stops7h 32m
Delta
Deal found 1/28$362
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:08 pm
HHH
-
STL
2 stops9h 34m
Delta
Mon 5/49:59 am
STL
-
HHH
1 stop4h 21m
Delta
Deal found 1/28$363
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:08 pm
HHH
-
STL
1 stop7h 00m
United Airlines
Tue 5/57:45 am
STL
-
HHH
1 stop5h 26m
United Airlines
Deal found 1/28$364

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(American Airlines)

One-way from

$134
(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.
Search Deals
From Hilton Head Island to Illinois
Search Deals
One-way flight from Hilton Head Island to Illinois
Search Deals

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 January 29, 2026.
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

Thu 2/12

11:03 am-3:21 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 2/16

5:00 am-10:33 am

1 stop4h 33m

$257

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Tue 4/28

12:08 pm-3:32 pm

1 stop4h 24m

Lambert-St Louis

Wed 5/6

9:59 am-3:20 pm

1 stop4h 21m

$310

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Tue 4/28

12:08 pm-3:32 pm

1 stop4h 24m

Lambert-St Louis

Tue 5/5

9:59 am-3:20 pm

1 stop4h 21m

$310

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Wed 4/29

12:08 pm-8:42 pm

2 stops9h 34m

Lambert-St Louis

Wed 5/6

6:48 am-3:20 pm

2 stops7h 32m

$328

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Wed 2/11

12:51 pm-6:01 pm

1 stop6h 10m

Chicago O'Hare Intl

Sat 2/14

10:28 am-5:44 pm

1 stop6h 16m

$333

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Mon 4/27

4:00 pm-8:30 am

2 stops17h 30m

Lambert-St Louis

Wed 5/6

9:59 am-3:20 pm

1 stop4h 21m

$349

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Tue 4/28

12:08 pm-3:32 pm

1 stop4h 24m

Lambert-St Louis

Sat 5/2

1:03 pm-3:20 pm

1 stop25h 17m

$370

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Fri 5/1

3:08 pm-9:08 pm

1 stop7h 00m

Lambert-St Louis

Tue 5/5

7:45 am-2:11 pm

1 stop5h 26m

$374

Hilton Head IslandSt. Louis

HHH - STL

HHHSTL

Hilton Head Island

Sat 2/14

4:31 pm-9:37 pm

1 stop6h 06m

Lambert-St Louis

Wed 2/18

10:20 am-3:01 pm

1 stop3h 41m

$389

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sun 6/14

2:01 pm-3:38 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sat 6/20

8:15 am-11:40 am

Nonstop2h 25m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 22 results
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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 January 29, 2026.
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
11,205 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Crew

8.0

Overall

7.2

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
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Crew

8.0

Overall

7.2

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 Delta can get you from Hilton Head Island to Illinois in just under 4h 24m. Your travel time can differ by up to 54m. 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 - Chicago O'Hare Intl, Hilton Head Island - Lambert-St Louis or Hilton Head Island - Moline Quad-City as they are the most popular.

  • 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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