$182 Find Cheap Flights from Hilton Head Island to Illinois

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 7/27. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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

ср., май 20 - ср., май 27
United Airlines Logo
3:08 pm - 4:49 pm
HHH
-
ORD
2h 41mnonstop
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
$269United Airlines
чт., июн 11 - вт., июн 16
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
Delta Logo
8:08 am - 3:32 pm
ORD
-
HHH
6h 24m
1 stop
$289Delta
ср., май 20 - ср., май 27
Delta Logo
12:18 pm - 6:41 pm
HHH
-
ORD
7h 23m
1 stop
Delta Logo
6:00 am - 3:33 pm
ORD
-
HHH
8h 33m
2 stops
$294Delta
ср., май 13 - вс., май 17
United Airlines Logo
3:08 pm - 4:49 pm
HHH
-
ORD
2h 41mnonstop
United Airlines Logo
10:45 am - 2:11 pm
ORD
-
HHH
2h 26mnonstop
$309United Airlines
пн., июн 8 - ср., июл 1
Delta Logo
12:13 pm - 5:04 pm
HHH
-
ORD
5h 51m
1 stop
Delta Logo
5:45 pm - 11:31 am
ORD
-
HHH
16h 46m
1 stop
$321Delta
пн., июн 8 - ср., июл 1
Delta Logo
12:13 pm - 6:29 pm
HHH
-
ORD
7h 16m
2 stops
Delta Logo
7:00 pm - 11:31 am
ORD
-
HHH
15h 31m
1 stop
$326Delta
пн., авг 10 - ср., авг 12
American Airlines Logo
3:27 pm - 6:59 pm
HHH
-
STL
4h 32m
1 stop
American Airlines Logo
8:34 am - 4:38 pm
STL
-
HHH
7h 04m
1 stop
$433American Airlines
пн., авг 10 - ср., авг 12
American Airlines Logo
5:16 pm - 10:40 pm
HHH
-
STL
6h 24m
1 stop
American Airlines Logo
6:00 am - 4:38 pm
STL
-
HHH
9h 38m
2 stops
$438American Airlines
пн., авг 10 - ср., авг 12
American Airlines Logo
11:40 am - 8:44 pm
HHH
-
STL
10h 04m
2 stops
American Airlines Logo
6:00 am - 4:38 pm
STL
-
HHH
9h 38m
2 stops
$443American Airlines
пт., май 15 - вс., май 17
United Airlines Logo
3:08 pm - 9:13 pm
HHH
-
STL
7h 05m
1 stop
United Airlines Logo
7:45 am - 2:11 pm
STL
-
HHH
5h 26m
1 stop
$564United 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 72 hours was to Chicago, at $269 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 72 hours was $269.

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 evening, when round-trip flights cost $389 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 $389.

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 $379, 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 Thursday 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 Wednesdays and the most expensive ones on Sundays.

Good to know

Cheapest flight$182
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 $213 one-way - $339 round-trip

Reviews of the top airline 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 9677 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
Airline reviews

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

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

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.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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

Information on your arrival and departure airports