HHH - ORD

$212 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 7/5. 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

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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Flights Deals

Cheap Flight Deals 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.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Hilton Head Island to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
3:58 pm - 10:21 pmHHH-ORD
7h 23m1 stop
Delta Logo
7:10 am - 3:18 pmORD-HHH
7h 08m1 stop
$291Delta
Find Deal
Thu, Jun 12 - Tue, Jun 17
Delta Logo
3:58 pm - 10:21 pmHHH-ORD
7h 23m1 stop
Delta Logo
6:00 am - 3:18 pmORD-HHH
8h 18m2 stops
$296Delta
Find Deal
Thu, Jun 12 - Tue, Jun 17
Delta Logo
3:58 pm - 10:21 pmHHH-ORD
7h 23m1 stop
Delta Logo
7:05 am - 3:18 pmORD-HHH
7h 13m2 stops
$306Delta
Find Deal
Thu, Jun 12 - Sun, Jun 15
American Airlines Logo
6:10 pm - 11:57 pmHHH-ORD
6h 47m1 stop
American Airlines Logo
5:15 am - 11:26 amORD-HHH
5h 11m1 stop
$309American Airlines
Find Deal
Sat, Jul 12 - Sat, Jul 19
American Airlines Logo
11:01 am - 5:16 pmHHH-ORD
7h 15m1 stop
American Airlines Logo
7:05 am - 2:15 pmORD-HHH
6h 10m1 stop
$331American Airlines
Find Deal
Fri, Jul 25 - Tue, Jul 29
American Airlines Logo
11:01 am - 5:16 pmHHH-ORD
7h 15m1 stop
American Airlines Logo
8:05 am - 4:57 pmORD-HHH
7h 52m2 stops
$336American Airlines
Find Deal
Fri, Jul 25 - Tue, Jul 29
United Airlines Logo
4:10 pm - 11:44 pmHHH-ORD
8h 34m1 stop
United Airlines Logo
6:00 am - 3:29 pmORD-HHH
8h 29m1 stop
$349United Airlines
Find Deal
Tue, May 13 - Tue, May 20
American Airlines Logo
11:03 am - 5:23 pmHHH-ORD
7h 20m1 stop
American Airlines Logo
5:29 am - 1:13 pmORD-HHH
6h 44m1 stop
$353American Airlines
Find Deal
Fri, Jun 13 - Sun, Jun 15
American Airlines Logo
6:20 pm - 12:11 amHHH-ORD
6h 51m1 stop
American Airlines Logo
5:00 am - 10:55 amORD-HHH
4h 55m1 stop
$362American Airlines
Find Deal
Wed, May 14 - Sun, May 18
United Airlines Logo
11:17 am - 8:02 amHHH-ORD
21h 45m2 stops
United Airlines Logo
10:56 am - 11:21 amORD-HHH
23h 25m2 stops
$1,339United Airlines
Find Deal
Thu, Jun 12 - Sun, Jun 15
Useful Info

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 Tuesdays and the most expensive ones on Saturdays.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $538 on average.

Good to know

Low seasonMarch
High seasonSeptember
Cheapest flight$212
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 63% increase in price.
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 $212 for a one-way ticket and $291 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 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?

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

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

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

  • 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.

Prefer to fly direct from Hilton Head Island to Chicago?

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

Saturday

United Airlines, American Airlines, Qatar Airways

United Airlines, American Airlines, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Hilton Head Island

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

See more direct flights
See more direct flights

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.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

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