$218 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 10/15. 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

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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
St. Louis
St. Louis1 stop$274
St. Louis
St. Louis1 stop$274

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

Fri, Oct 3 - Mon, Oct 6
Delta Logo
4:05 pm - 8:35 pmHHH-ORD
5h 30m1 stop
Delta Logo
9:42 am - 3:30 pmORD-HHH
4h 48m1 stop
$259Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
5:21 pm - 11:05 pmHHH-STL
6h 44m1 stop
American Airlines Logo
5:00 am - 11:49 amSTL-HHH
5h 49m1 stop
$274American Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
3:32 pm - 10:55 pmHHH-STL
8h 23m2 stops
American Airlines Logo
5:00 am - 11:49 amSTL-HHH
5h 49m1 stop
$279American Airlines
Find Deal
Fri, Oct 3 - Mon, Oct 6
Delta Logo
4:05 pm - 8:35 pmHHH-ORD
5h 30m1 stop
Delta Logo
6:00 am - 3:30 pmORD-HHH
8h 30m2 stops
$289Delta
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
7:08 pm - 11:39 pmHHH-ORD
5h 31m1 stop
American Airlines Logo
6:45 am - 12:22 pmORD-HHH
4h 37m1 stop
$309American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
12:52 pm - 7:22 pmHHH-ORD
7h 30m1 stop
American Airlines Logo
6:04 am - 2:57 pmORD-HHH
7h 53m2 stops
$314American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
11:04 am - 3:50 pmHHH-ORD
5h 46m1 stop
American Airlines Logo
10:00 am - 1:27 pmORD-HHH
2h 27mnonstop
$329American Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23
United Airlines Logo
11:57 am - 7:56 amHHH-ORD
20h 59m2 stops
United Airlines Logo
9:20 pm - 11:16 amORD-HHH
12h 56m2 stops
$536United Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
United Airlines Logo
11:57 am - 7:56 amHHH-ORD
20h 59m2 stops
United Airlines Logo
6:25 pm - 11:16 amORD-HHH
15h 51m2 stops
$541United Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23
United Airlines Logo
11:57 am - 6:34 pmHHH-ORD
7h 37m1 stop
United Airlines Logo
9:20 pm - 11:16 amORD-HHH
12h 56m2 stops
$565United Airlines
Find Deal
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 $465 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 $465.

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 Tuesdays and the most expensive ones on Saturdays.

Good to know

Cheapest flight$218
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.

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

    The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $423 on average. Morning departures are around 9% 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 $465.

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.
7.2
American AirlinesOverall score based on 10000 reviews
6.9Entertainment
6.4Food
7.2Comfort
7.5Boarding
8.0Crew
Airline reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

6.0 GoodMitchell, Aug 2025CMH - ORD
Read more American Airlines reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

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