HHH - ORD

$182 Find Cheap Flights from Hilton Head Island to Chicago

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 Chicago departing on 6/23. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Chicago, 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 Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$269
United Airlines
Wed 5/20Wed 5/27
HHH - ORD • Non-stop
Cheapest one-way
$182
Delta
Tue 6/23
HHH - ORD • 1 stop
Top airlines
Cheapest • from $269 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 40m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hilton Head Island to Chicago (HHH-ORD)

 
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 Chicago 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 Chicago

Wed, May 20 - Wed, May 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
Thu, Jun 11 - Tue, Jun 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
Wed, May 20 - Wed, May 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
Wed, May 13 - Sun, May 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
Wed, May 13 - Sun, May 17
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$329Delta
Wed, May 13 - Sun, May 17
Delta Logo
12:18 pm - 10:36 pm
HHH
-
ORD
11h 18m
2 stops
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$334Delta
Wed, Jul 8 - Wed, Sep 2
Delta Logo
12:11 pm - 10:36 pm
HHH
-
ORD
11h 25m
2 stops
Delta Logo
6:00 am - 3:20 pm
ORD
-
HHH
8h 20m
2 stops
$340Delta
Thu, May 14 - Sun, May 17
Delta Logo
12:18 pm - 4:56 pm
HHH
-
ORD
5h 38m
1 stop
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$344Delta
Sat, May 9 - Wed, May 13
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
$349United Airlines
Sat, May 9 - Wed, May 13
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
$359United Airlines
Booking Insights

KAYAK's insights & trends for Hilton Head Island to Chicago flights

Get data-powered insights and trends into flights from Hilton Head Island to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Hilton Head Island to Chicago?

The average price of all round-trip flights from Hilton Head Island to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from Hilton Head Island to Chicago, 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.

Can I save money by flying with a layover from Hilton Head Island to Chicago O'Hare Intl Airport?

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.

Good to know

Cheapest flight$182
Flight from Hilton Head Island to Chicago

When to book flights from Hilton Head Island to Chicago

Are your dates flexible? Find out the best times to travel from Hilton Head Island to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hilton Head Island to Chicago flights

  • What is the cheapest flight from Hilton Head Island to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Hilton Head Island to Chicago O'Hare Intl Airport was $182 for a one-way ticket and $269 for a round-trip.

  • Do I need a passport to fly between Hilton Head Island and Chicago?

    A passport is not required to fly from Hilton Head Island to Chicago.

  • Which airports will I be using when flying from Hilton Head Island to Chicago?

    On your way to Chicago, you’ll fly out from Hilton Head Island. You’ll be landing at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Hilton Head Island to Chicago?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Hilton Head Island to Chicago flight route.

  • Which aircraft models fly most regularly from Hilton Head Island to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Hilton Head Island to Chicago flight route.

  • Which airline alliances offer flights from Hilton Head Island to Chicago?

    Star Alliance is the only airline alliance operating flights between Hilton Head Island and Chicago.

  • On which days can I fly direct from Hilton Head Island to Chicago?

    There are nonstop flights from Hilton Head Island to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Hilton Head Island to Chicago?

    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 Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hilton Head Island 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 Chicago?

    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 to Chicago with an airline and back to Hilton Head Island with another airline. Booking your flights between Hilton Head Island and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Chicago?

    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 to Chicago from Hilton Head Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Hilton Head Island to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $213 or less one-way and $339 or less round-trip.

Prefer to fly direct from Hilton Head Island to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Hilton Head Island to Chicago O'Hare Intl.
Find which airlines fly direct from Hilton Head Island Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Hilton Head Island to Chicago O'Hare Intl

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to Hilton Head Island

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top airline flying from Hilton Head Island to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Chicago. 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 Chicago? 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 9680 reviews
7.1Entertainment
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
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 Chicago

Information on your arrival and departure airports