ORD - HHH

$175 Find Cheap Flights from Chicago to Hilton Head Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hilton Head Island departing on 6/13. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Hilton Head Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hilton Head Island, 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 Chicago to Hilton Head Island, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to Hilton Head Island (ORD-HHH)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hilton Head Island 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.

Recent round-trip flight deals from Chicago to Hilton Head Island

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Hilton Head Island.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
7:10 am - 3:18 pmORD-HHH
7h 08m1 stop
Delta Logo
12:00 pm - 4:59 pmHHH-ORD
5h 59m1 stop
$229Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
Delta Logo
6:00 am - 3:18 pmORD-HHH
8h 18m2 stops
Delta Logo
3:58 pm - 10:21 pmHHH-ORD
7h 23m1 stop
$234Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
Delta Logo
6:00 am - 3:18 pmORD-HHH
8h 18m2 stops
Delta Logo
12:00 pm - 10:21 pmHHH-ORD
11h 21m2 stops
$239Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
American Airlines Logo
9:17 am - 5:39 pmORD-HHH
7h 22m1 stop
American Airlines Logo
11:01 am - 5:16 pmHHH-ORD
7h 15m1 stop
$309American Airlines
Find Deal
Sat, Jul 19 - Sat, Jul 26
American Airlines Logo
9:17 am - 5:39 pmORD-HHH
7h 22m1 stop
American Airlines Logo
11:56 am - 6:24 pmHHH-ORD
7h 28m2 stops
$314American Airlines
Find Deal
Sat, Jul 19 - Wed, Jul 23
American Airlines Logo
5:15 am - 11:26 amORD-HHH
5h 11m1 stop
American Airlines Logo
6:10 pm - 9:31 pmHHH-ORD
4h 21m1 stop
$331American Airlines
Find Deal
Fri, Jul 11 - Sat, Jul 19
American Airlines Logo
8:09 am - 5:45 pmORD-HHH
8h 36m2 stops
American Airlines Logo
12:37 pm - 6:42 pmHHH-ORD
7h 05m2 stops
$334American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
United Airlines Logo
10:35 am - 2:01 pmORD-HHH
2h 26mnonstop
United Airlines Logo
5:00 pm - 6:35 pmHHH-ORD
2h 35mnonstop
$369United Airlines
Find Deal
Sat, Jul 19 - Sat, Jul 26
United Airlines Logo
8:45 am - 3:29 pmORD-HHH
5h 44m1 stop
United Airlines Logo
5:00 pm - 6:35 pmHHH-ORD
2h 35mnonstop
$449United Airlines
Find Deal
Wed, May 21 - Sat, May 24
United Airlines Logo
7:10 am - 10:36 amORD-HHH
26h 26m2 stops
United Airlines Logo
5:00 pm - 6:35 pmHHH-ORD
2h 35mnonstop
$466United Airlines
Find Deal
Wed, May 21 - Sat, May 24
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KAYAK's insights & trends for Chicago to Hilton Head Island flights

Get data-powered insights and trends into flights from Chicago to Hilton Head Island 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 Chicago to Hilton Head Island?

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

If your flying dates are flexible, you should consider flying to Hilton Head Island on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Hilton Head Island. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Hilton Head Island is September, where tickets cost $333 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $608 and $491 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Hilton Head Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Hilton Head Island, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$175
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago to Hilton Head Island

When to book flights from Chicago to Hilton Head Island

Are your dates flexible? Find out the best times to travel from Chicago to Hilton Head Island 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 Chicago to Hilton Head Island flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Hilton Head Island was $175 for a one-way ticket and $229 for a round-trip.

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

    No

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

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Hilton Head Island, also known as Hilton Head Island.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Hilton Head Island flight route.

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

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

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

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Hilton Head Island, with oneworld being the most commonly used for this route.

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

    You can catch a nonstop flight from Chicago to Hilton Head Island on Saturday.

  • Which is the best airline for flights from Chicago to Hilton Head Island, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Hilton Head Island are United Airlines and American Airlines. With an average price for the route of $498 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $400 and an overall rating of 7.2.

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

    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 Chicago to Hilton Head Island.

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

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

    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 Hilton Head Island with an airline and back to Chicago with another airline. Booking your flights between Chicago and HHH 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 Chicago to Hilton Head Island?

    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 Hilton Head Island from Chicago 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 Chicago O'Hare Intl Airport to Hilton Head Island

  • Looking for a cheap flight? 25% of our users found flights on this route for $527 or less round-trip.

Prefer to fly direct from Chicago to Hilton Head Island?

Find which airlines fly direct from Chicago O'Hare Intl Airport to Hilton Head Island Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Hilton Head Island

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

See more direct flights

Direct returns

Hilton Head Island to Chicago O'Hare Intl

Saturday

United Airlines, American Airlines, Qatar Airways

United Airlines, American Airlines, +1 more

See more direct flights
See more direct flights

Top airlines flying from Chicago to Hilton Head Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hilton Head Island. 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 Chicago to Hilton Head Island? 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 8696 reviews
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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