$167 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 4/28. 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, Mar 18 - Wed, Mar 25
American Airlines Logo
4:11 pm - 9:24 pm
HHH
-
ORD
6h 13m
1 stop
American Airlines Logo
11:50 am - 5:44 pm
ORD
-
HHH
4h 54m
1 stop
$352American Airlines
Wed, Mar 18 - Wed, Mar 25
American Airlines Logo
6:15 pm - 12:06 am
HHH
-
ORD
6h 51m
1 stop
American Airlines Logo
6:08 am - 2:22 pm
ORD
-
HHH
7h 14m
2 stops
$357American Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
12:23 pm - 4:21 pm
HHH
-
ORD
4h 58m
1 stop
American Airlines Logo
7:10 am - 3:01 pm
ORD
-
HHH
6h 51m
1 stop
$359American Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
3:31 pm - 10:17 pm
HHH
-
ORD
7h 46m
2 stops
American Airlines Logo
9:40 am - 3:41 pm
ORD
-
HHH
5h 01m
1 stop
$364American Airlines
Thu, Mar 26 - Tue, Mar 31
American Airlines Logo
4:11 pm - 9:24 pm
HHH
-
ORD
6h 13m
1 stop
American Airlines Logo
7:12 am - 3:01 pm
ORD
-
HHH
6h 49m
1 stop
$387American Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
2:58 pm - 6:07 pm
HHH
-
STL
4h 09m
1 stop
American Airlines Logo
7:05 am - 3:01 pm
STL
-
HHH
6h 56m
1 stop
$389American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
3:29 pm - 7:50 pm
HHH
-
ORD
5h 21m
1 stop
American Airlines Logo
5:00 am - 10:33 am
ORD
-
HHH
4h 33m
1 stop
$389American Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
2:58 pm - 6:07 pm
HHH
-
STL
4h 09m
1 stop
American Airlines Logo
6:00 am - 4:44 pm
STL
-
HHH
9h 44m
2 stops
$394American Airlines
Sun, Jun 28 - Sat, Jul 4
United Airlines Logo
3:00 pm - 9:11 pm
HHH
-
STL
7h 11m
1 stop
United Airlines Logo
7:30 am - 2:01 pm
STL
-
HHH
5h 31m
1 stop
$493United Airlines
Sun, Jun 28 - Sat, Jul 4
Delta Logo
12:00 pm - 2:37 pm
HHH
-
STL
3h 37m
1 stop
Delta Logo
6:45 am - 3:18 pm
STL
-
HHH
7h 33m
2 stops
$597Delta
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 $283 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 $283.

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 $425, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$167
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 evening, when round-trip flights cost $465 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 $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 11211 reviews
7.2Comfort
6.9Entertainment
7.5Boarding
8.0Crew
6.4Food
Airline reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

2.0 MediocreManikandan, Jan 2026
DFW - ORD
Read more American Airlines reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

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.

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)