$215 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 1/17. 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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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

Wed, Apr 15 - Wed, Apr 22
Delta Logo
4:00 pm - 9:48 pm
HHH
-
ORD
6h 48m1 stop
Delta Logo
7:10 am - 3:18 pm
ORD
-
HHH
7h 08m1 stop
$294Delta
Wed, Apr 15 - Wed, Apr 22
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
$297United Airlines
Wed, Apr 15 - Wed, Apr 22
Delta Logo
12:00 pm - 9:48 pm
HHH
-
ORD
10h 48m2 stops
Delta Logo
9:30 am - 3:18 pm
ORD
-
HHH
4h 48m1 stop
$299Delta
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
6:22 pm - 12:10 am
HHH
-
ORD
6h 48m1 stop
American Airlines Logo
9:45 am - 3:05 pm
ORD
-
HHH
4h 20m1 stop
$309American Airlines
Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
11:02 am - 4:06 pm
HHH
-
ORD
6h 04m1 stop
American Airlines Logo
5:35 am - 2:27 pm
ORD
-
HHH
7h 52m2 stops
$314American Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
11:02 am - 5:31 pm
HHH
-
ORD
7h 29m2 stops
American Airlines Logo
5:35 am - 3:05 pm
ORD
-
HHH
8h 30m2 stops
$319American Airlines
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
4:00 pm - 11:37 pm
HHH
-
ORD
8h 37m1 stop
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
$338United Airlines
Tue, Apr 21 - Wed, Apr 29
United Airlines Logo
3:00 pm - 4:45 pm
HHH
-
ORD
2h 45mnonstop
United Airlines Logo
10:35 am - 2:01 pm
ORD
-
HHH
2h 26mnonstop
$348United Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
2:58 pm - 10:15 pm
HHH
-
ORD
8h 17m2 stops
American Airlines Logo
6:07 am - 2:20 pm
ORD
-
HHH
7h 13m2 stops
$349American Airlines
Sat, Mar 7 - Sat, Mar 14
American Airlines Logo
4:18 pm - 9:15 pm
HHH
-
ORD
5h 57m1 stop
American Airlines Logo
7:12 am - 2:22 pm
ORD
-
HHH
6h 10m1 stop
$356American 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 $1,394 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 $1,394.

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 Wednesdays 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.

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Good to know

Cheapest flight$145
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 21% 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 $538.

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 11055 reviews
6.5Food
7.5Boarding
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

2.0 MediocreJohn, Dec 2025
GSO - ORD
Read more American Airlines reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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

Information on your arrival and departure airports

Hilton Head Island (HHH)