$151 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 9/9. 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.
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1 adult, Economy, 0 bags

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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, Aug 20 - Mon, Aug 24
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
$279American Airlines
Fri, Aug 28 - Sat, Aug 29
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
8:51 am - 12:15 pm
ORD
-
HHH
2h 24mnonstop
$279American Airlines
Fri, Sep 4 - Mon, Sep 7
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
$279United Airlines
Thu, Aug 27 - Tue, Sep 1
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
$279United Airlines
Thu, Aug 27 - Tue, Sep 1
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
$279American Airlines
Fri, Sep 4 - Mon, Sep 7
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
$279American Airlines
Thu, Aug 27 - Tue, Sep 1
American Airlines Logo
10:57 am - 5:14 pm
HHH
-
ORD
7h 17m
1 stop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$289American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
3:27 pm - 9:57 pm
HHH
-
ORD
7h 30m
1 stop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$289American Airlines
Fri, Aug 28 - Sat, Aug 29
American Airlines Logo
5:16 pm - 9:57 pm
HHH
-
ORD
5h 41m
1 stop
American Airlines Logo
8:51 am - 12:15 pm
ORD
-
HHH
2h 24mnonstop
$289American Airlines
Fri, Aug 28 - Tue, Sep 1
Delta Logo
4:18 pm - 10:24 pm
HHH
-
ORD
7h 06m
1 stop
Delta Logo
8:05 am - 3:32 pm
ORD
-
HHH
6h 27m
1 stop
$299Delta
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 $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 5 days 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 afternoon, when round-trip flights cost $343 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 $289, 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 Wednesday 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

$151
Flight from Hilton Head Island to St. Louis

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 $280 one-way - $343 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 10061 reviews
7.1Entertainment
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
Airline reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

4.0 OkayN, Jul 2026
PHL - ORD
Read more United Airlines reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

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

Information on your arrival and departure airports