$205 Find Cheap Flights from Hilton Head Island to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Illinois departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Illinois, as well as popular online travel agencies
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Cheap Flights from Hilton Head Island to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Moline
Moline1 stop$389
St. Louis
St. Louis1 stop$613
Moline
Moline1 stop$389
St. Louis
St. Louis1 stop$613

Book Cheap Hilton Head Island to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Illinois

Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
2:03 pm - 3:39 pm
HHH
-
ORD
2h 36mnonstop
American Airlines Logo
9:59 am - 1:32 pm
ORD
-
HHH
2h 33mnonstop
$269American Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
11:07 am - 5:30 pm
HHH
-
ORD
7h 23m
1 stop
American Airlines Logo
9:59 am - 1:32 pm
ORD
-
HHH
2h 33mnonstop
$279American Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
2:03 pm - 3:39 pm
HHH
-
ORD
2h 36mnonstop
American Airlines Logo
9:59 am - 1:32 pm
ORD
-
HHH
2h 33mnonstop
$289American Airlines
Thu, Oct 15 - Sun, Oct 18
Delta Logo
12:00 pm - 8:39 pm
HHH
-
ORD
9h 39m
2 stops
Delta Logo
8:15 am - 3:19 pm
ORD
-
HHH
6h 04m
1 stop
$294Delta
Thu, Jul 2 - Mon, Jul 6
American Airlines Logo
2:03 pm - 3:39 pm
HHH
-
ORD
2h 36mnonstop
American Airlines Logo
5:07 am - 11:17 am
ORD
-
HHH
5h 10m
1 stop
$299American Airlines
Thu, Jul 2 - Mon, Jul 6
American Airlines Logo
2:48 pm - 7:51 pm
HHH
-
ORD
6h 03m
1 stop
American Airlines Logo
5:07 am - 11:17 am
ORD
-
HHH
5h 10m
1 stop
$309American Airlines
Thu, Aug 20 - Sun, Aug 23
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$324American Airlines
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
3:05 pm - 6:56 pm
HHH
-
MLI
4h 51m
1 stop
United Airlines Logo
6:30 am - 2:21 pm
MLI
-
HHH
6h 51m
1 stop
$389United Airlines
Thu, Jul 23 - Sun, Jul 26
United Airlines Logo
3:05 pm - 9:26 pm
HHH
-
STL
7h 21m
1 stop
United Airlines Logo
7:20 am - 2:21 pm
STL
-
HHH
6h 01m
1 stop
$613United Airlines
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
3:05 pm - 6:56 pm
HHH
-
MLI
4h 51m
1 stop
United Airlines Logo
6:30 pm - 12:52 pm
MLI
-
HHH
17h 22m
2 stops
$959United Airlines
Booking Insights

KAYAK's insights & trends for Hilton Head Island to Illinois flights

Get data-powered insights and trends into flights from Hilton Head Island to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Hilton Head Island to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Hilton Head Island found in the last 5 days was to Chicago, at $255 round-trip. The most popular route is from Hilton Head Island (HHH) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $255.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Hilton Head Island to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $289 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $437.

Can I save money by flying with a layover from Hilton Head Island to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $298, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Hilton Head Island to Illinois?

The average price of all round-trip flights from Hilton Head Island to Illinois clicked on KAYAK for each day over the last 12 months.

When flying from Hilton Head Island to Illinois, you should consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Hilton Head Island, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

Good to know

Cheapest flight$205
Flight from Hilton Head Island to Chicago

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Hilton Head Island to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hilton Head Island to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Hilton Head Island to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Hilton Head Island to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Hilton Head Island to the following destinations at these prices or less: Chicago $372 one-way - $269 round-trip

Reviews of the top airlines flying from Hilton Head Island to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9845 reviews
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Everything you need to know for your flight from Hilton Head Island to Illinois

Information on your arrival and departure airports