CHI - HHH
Find cheap flights from Chicago to Hilton Head Island
Round-trip
1 adult
Economy
Wed 4/19
Wed 4/26
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Good to know
Low season | January |
|---|---|
High season | March |
Cheapest flight | $177 |
Average price round-trip | $448 |
Good deal round-trip | $423 |
Good deal one-way | $324 |
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago to Hilton Head Island
(avg. price over the last 2 weeks)
or less
or less
When to book flights from Chicago to Hilton Head
Estimated round-trip price
Average price per month
Flight prices as travel date approaches
Top tips for finding a cheap flight out of Chicago
- Looking for a cheap flight? 25% of our users found flights on this route for $324 or less one-way and $423 or less round-trip.
- The cheapest flight from Chicago to Hilton Head Island was found 46 days before departure, on average.
- Book at least 5 weeks before departure in order to get a below-average price.
- High season is considered to be February, March and April. The cheapest month to fly is January.
- Morning departure is around 17% more expensive than an evening flight, on average*.
FAQs for booking flights from Chicago to Hilton Head Island
Top airlines flying Chicago to Hilton Head Island
Scores according to KAYAK customer reviews7.2
American AirlinesOverall score based on 46178 reviews
7.5Boarding
7.1Comfort
7.8Crew
6.8Entertainment
6.7Food
Pros: "Nothing"
Cons: "Individual TVs, perhaps"
Cons: "Late and then mechanical issues."
Pros: "Crew was great"
Cons: "Seat was uncomfortable. Flight was much too crowded"
Pros: "Flight was cancelled after multiple delays & I changed to United."
Cons: "Stop delaying & canceling flights, especially last minute"
Pros: "Really easy boarding and flight. Great in flight entertainment options."
Pros: "All was good"
Cons: "Nothing to complain about."
Pros: "Seat assignment process was great and considerate of my preferences."
Cons: "If AA could fix its luggage handling process that would be great. BOTH (!) of my bags have been lost on this flight. Both have been eventually located, recovered and delivered to me, but experience was not pleasant this time."
Pros: "Flight attendants were friendly and thoughtful."
Cons: "Seating is too tight. Hard to believe that in 2019, major airlines still have seats without any electrical or UBS outlets for charging devices."
Pros: "Crew was great."
Cons: "Plane was about 1000 years old and I don’t think I’ve sat in a more uncomfortable seat."
Cons: "Unable to connect to the new AA so-fi"
Pros: "Comfortable seats and snack / drinks service"
Cons: "Delayed flight departure and bumpy landing"
Cons: "I was apparently "flagged" by British Airways for extra security checks. As I understood it in London, I was randomly selected for this security check. This then apparently meant that I was to be flagged for all subsequent flights. This meant that in Chicago, after going through two other security checks that day (Zurich and London) and completing customs, I had to engage in a full Homeland security check. This involved removing protective covers from my laptop and phone that were hard to get off (not meant to be taken off regularly) and a full body search that I did not have to do in London. After many hours of traveling, this was very a frustrating experience."
Cons: "I will never, ever book with Kayak again"
Pros: "Flight crew was great. The plane was half full, so the attendants allowed us to move."
Cons: "Terrible landing in Charlotte. The plane was rattling and had an annoying whistle."
Cons: "British Airways/American Airlines lost/delayed luggage again! Then send an email in the middle of night with a link to schedule home delivery of the luggage that was valid for 4 hours only. It is clearly an attempt to cheat out of their responsibility of home delivery of the luggage that was delayed the second time. Poor, poor service by American Airlines."
Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"
Cons: "Flight was delayed for more than 4 hours with little communication from staff as to why, gate was changed to a gate across the airport."
Pros: "The boarding was quick and easy as well as the crew was friendly and accommodating. Great end to a fun weekend away."
Pros: "Our plane was late getting to the gate. They kept us informed and turned it around pretty quickly. There were storms between Chicago and Rochester so we were rerouted. As a result the hour flight was an hour and a half. The pilot kept us informed and it was a very smooth flight. So even though I was over an hour late arriving I so appreciated the communications and the safer route. AA seems to be communicating more than other airlines and I appreciate that. Flying is absolutely no fun anymore so you take what you can get for the positives."
Cons: "WiFi wasn’t working so I couldn’t communicate my late arrival to family picking me up."
Cons: "On my first flight from SLC to ORD I asked 3 different American Airlines employees if I needed to pay for my carryon before I got on the plane. They all said no. I got on the plane, put my carryon under the seat in front of me and everything was great. I landed in Chicago, got to my gate, went to board and this very rude employee stopped me after I scanned my ticket and told me I couldn’t board with my bag. The EXACT bag I had boarded with in SLC. After harshly grabbing my bag and putting it in the carryon basket to check for size, she wouldn’t let me pass by her into the boarding bridge and told me I was going to have to pay. I tried explaining that I had asked I’m SLC if I needed to check it and they had all said no and that it fit under my seat. She said, “I don’t care what they said in SL, this is what I’m saying here.” And directed me to the front desk where I had to pay $50!! $50 for a carryon backpack that fit under my seat comfortably 20 minutes before!! Without saying a word (cause I didn’t want to yell at the poor girl behind the desk) I paid the $50 and proceeded to enter the bridge but before I passed through, the rude woman said, “have a nice flight ma’am” and scoffed!! An audible scoff. So I’m short, I hate American Airlines and I will do my BEST to not have to fly with them in the future."
Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."
Cons: "Flight was delayed by untold circumstances causing us to miss our connecting flight to Venice."
Pros: "On time departure and early arrival"
Cons: "Nothing"
Pros: "Nice crew Spacious plane"
Pros: "The crew was amazing, flight was very smooth, arrived early, plane clean, service was great."
Cons: "For being in first class, my seat did not recline so I couldn't sleep and audio for my entertainment center was not working"
Pros: "Good time for flight"
Cons: "Tight, hot inside plane, no refreshments"
Cons: "They left the lights on the whole flight"
Pros: "They alerted me to problems with our flight and we switched to an earlier flight. No problems with new flight. Good service."
Cons: "Great trip"
Pros: "Not turbulence"
Pros: "Was on time."
Cons: "Not eventful."
Pros: "crew was great, plane seemed newer and clean. individual screens worked better than others I've used in flights."
Cons: "newer touch screens were great except viewing angle couldn't be adjusted. standard food was horrible, esp for an international flight; not sure if specialty diets have better meals. kid movies were dubbed into many language options but Chinese was not one for ANY kid films. bathrooms with the same crappy mini sinks that you can't really wash your hands in, esp if someone pukes in it. they should all learn from Japan's ANA airliners with the motion sensor sinks with faucets raised up high enough for you to wash your hands without touching the gross basin."
Pros: "On time, good service."
Cons: "Luggage did not make the transfer on time (Chicago-Charlotte after Tokyo), although they had about 45 minutes to load it. Do not buy an international ticket with less than 1.5 hours transfer time. (It took 45 minutes to get through customs/immigration and retrieve luggage for transfer."
Cons: "Missed it."
Pros: "Nothing"
Cons: "An S80? Really? This plane was older than me! Horrible plane! The crew looked like they had been up since 4 am. Looked exhausted and unfriendly. I do want to clarify that this was an American Airlines operated plane, not etihad."
Cons: "The cramped space"
Cons: "All was excellent! Only the internet was not working good , payed for all flight access but most of the time the internet was not working. Anyway I contacted support team and they refunded me"
Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."
Pros: "on time"
Cons: "very cold"
Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."
Pros: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."
Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."
Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."
Pros: "Good flight. Arrived on time"
Cons: "Jet bridge was broken and needed repair. Delayed departure."
Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."
Pros: "Seats were really neither notably comfortable nor notably uncomfortable. I think they were slightly on the comfortable side."
Cons: "Would be nice to have more modern aircraft amenities, like power outlets for device charging, and display screens with at least some complimentary entertainment, or at least flight path tracking. Boarding counter lady was obnoxiously strict about not letting our carry-on bags to be carry-on. She made us test them in the size device and said they were too big, even though they could easy be pushed into the space, and regardless of the fact that we just flew on an American Airlines flight with them as carry-on and were only on a layover with them! Regarding the previous AA agent who let them be carry-on, she said "shame on them." Complete opposite of the positive experience we had with her counterpart in Phoenix. ಠ_ಠ"
Cons: "They cancelled the flight and put me to fly the next day"
Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"
Pros: "They were friendly. Seats are rarely comfortable..."
Cons: "I think all planes need better leg room...."
Cons: "Everything was good!"
Pros: "Flight attendants were absolutely amazing!!!!! They made the trip very enjoyable!"
Cons: "Food!"
Pros: "Great crew"
Cons: "Very uncomfortable seats"
Pros: "Nothing"
Cons: "My economy plus seat wouldn’t recline!"
Pros: "I have always loved flying Lufthansa however we didn't fly Lufthansa, we were on United for both legs of our flight. Like all American opperated airlines they skimp on comfort in order to pack more people on their flight. I hope we are on Lufthansa on our way home at least."
Cons: "I have always loved flying Lufthansa however we didn't fly Lufthansa, we were on United for both legs of our flight. Like all American opperated airlines they skimp on comfort in order to pack more people on their flight. I hope we are on Lufthansa on our way home at least."
Pros: "Nothing at all!!! That should really tell you something!"
Cons: "The staff were rude, abrasive, ignored several passengers that were trying to get her attention before take off as 2 overhead bins were wide open and full to the brim. She of course was too busy playing on her cell phone in the back of the plane and ignored/silenced the passenger call button. They were so loud when people were sleeping, yelling ‘trash please’ every 5 minutes, we are not stupid, we can see what you are doing and if we have trash, we will give it to you - so please STOP disturbing my peace and let me bloody sleep!!!! I was never offered any food or drink during the entire flight, not even when I was awake - other airline attendants are more observant and come back and ask us when we are awake if we would like anything to eat or drink. So essentially that was 7 hours with nothing after having paid a little over $700 for what was seemingly the WORST transatlantic flight I’ve ever taken. I travel back and forth often, because I’m a dual national, but I will stick to BA or Virgin Atlantic - the planes and service are far superior to this pile of turd that goes by the name of United. There were no charging facilities (power outlet or USB port) and the TVs had such horrendous resolution that you would get a headache from having to squint at the screen."
Cons: "Great"
Pros: "Entertainment."
Cons: "Nothing."
Pros: "NOTHING"
Cons: "Every thing I will never fly with United"
Cons: "The fight to flint was canceled last night beacuse they had no captian. What the heck!!! My mom is a senior citizen and the last thing she needed to be doing was schlepping all of her things to and from the airport in fridged temps. She’s battling a major cough and is now so exhausted!! This is totally unacceptable...not to have a captian?!???! Please respond as to how I will be reimbursed or what I can do to feel satisfied."
Pros: "Quick"
Cons: "You better get rid of basic economy."
Cons: "Tight seats, seat belt uncomfortable"
Pros: "No delay, friendly crew"
Cons: "Late flight. Plane 1 hour and 37 minutes late because arriving plane was late, then the arriving plane was slow to de-plane, then spent the next hour waiting on "paperwork" to approve takeoff. Very dissatisfied."
Pros: "While it was a long flight it was comfortable and surprisingly the food was good."
Cons: "We ran late as the plane needed some work on it before we could take off; when it was finally done there was a storm and could not take off again. We were behind over an hour before we could leave but we made up for in as we had good tail wind."
Pros: "Associates were nice and knowledgeable. The airplanes were comfortable. Love the onetime performance of scheduling."
Cons: "Unite Airline performance wasn't the good. Also, there was nobody in Chicago to help us with the transferring process."
Pros: "Great captain and crew."
Cons: "I prefer the entertainment on your own device."
Pros: "Chicken wrap was very tasty. Very attentive flight crew."
Pros: "I had the exit window and that made a huge difference in my trip as I am a 6ft tall woman who is all legs."
Cons: "It was slightly turbulent and TSA at O'hare airport are the rudest and laziest humans on the planet."
Pros: "Snacks and drink"
Cons: "Average"
Pros: "Flight was on time."
Cons: "Seats are uncomfortable and cramped."
Cons: "Wouldn't let me bring my bag even though there was plenty of space."
Pros: "Wasn't thrown off"
Cons: "Another delayed flight with United"
Cons: "They might as well have thrown us in a car trunk the crew was very unaccommodating they didn't really care about us and the room legroom is ridiculously smal. On the connecting flight, the last flight the plane was two thirds empty and the crew made us sit in our assigned seats, crammed together telling us that if we want to sit in a seat with more legroom we have to pay $180"
Cons: "Too many seats too close together. The entire trip was too hot and stuffy. The flight attendants showed minimal care about the uncomfortable hot and stuffy environment."
Pros: "On time, crew was friendly"
Pros: "Not much."
Cons: "Originally, there was an announcement that we would be delayed by 45 minutes because of "air traffic" issues in San Francisco, where we were landing. In spite of this, the captain decided to have passengers board the plane, and try to push our way up the line, so to speak. Well, once we were on the tarmac, the flight crew were told that the plane could not take off, and that we needed to wait there for 45 minutes, without moving, in our seats, with nothing to do. Even though it would still not have been ideal to wait 45 minutes at the gate, at least we could have walked around and could have entertained ourselves."
Pros: "Everything went smoothly"
Cons: "Good options are terrible"
Pros: "Crew was attentive."
Cons: "From Gregory at the check in being rude and anything but welcoming, to seats in first class needing replaced, this was anything BUT a first class trip. This was my second time giving United a chance as I normally fly Delta. I don't think I'll make that mistake again. I understand a late night flight doesn't have a meal service, but snacks of chips and bananas is not my idea of how you should serve Firat Class passengers. I would have a hard time recommending anyone choose United as their airline. Time for an upgrade of not just the seats, but overall customer service."
Cons: "Worst customer service of my life. I will NEVER fly United Airlines again."
Cons: "Turbulence was insane"
Pros: "We'll coordinated."
Pros: "The crew were very kind and attentive without being overbearing. They were helpful."
Cons: "I did not like how my boarding pass for a ticket I had paid for long in advance had a 'see us' note about my seating. The counter attendent waltzed in after boarding had already started and treated the issue like it was a joke. I ended up seated in between two hot messes of people which made the flight seriously uncomfortable, there were no other options supposedly for me. There weren't even options for me to pay the outrageous pick a seat option when I was doing my preflight check in 24 hours in advance."
Cons: "The seats were terribly uncomfortable (including her flight to Chicago). The cushion made me slide down the seat and could not get comfortable."
Cons: "I went on this trip as an veterinary humanitarian out reach. I was also guardian to one high school student so that she might have an experience of such to guild her future. Her flight was missed booked to leave after mine, I attempted to rebook my flight with Luthansia but they would not let me me even partial rebook. I attempted a number of times to rebook the flight but their solution was extreme financial gain for them when more reasonable alternative could have been arranged. They canceled my entire return flight and left me stranded. I had to piece together a return flight on a shoe string budget. Thankfully American Airlines was understanding for it appears Luthansia and United are not."
Pros: "Loved that it was an empty flight"
Pros: "."
Cons: "."
Cons: "2.5 hour delay. No working bathrooms. Couldn't hear the tv and headphones that they gave out were useless."
Cons: "The flight got cancelled"
Cons: "Flight was delayed due to severl technical issues. Crew at least offer free drinks or snacks for the five hour delay."
Pros: "I made it to the airport safe and sound."
Cons: "It was a complete cluster as if no one knew what was going on. Once we were finally able to board we sat on the plane for an additional 30 minutes or so because the air conditioning went out on the plan and we all had to sit there in the scalding heat while they fixed it."
Pros: "Nice clean planes and seat, on time performance"
Cons: "The flight attendant was hard to understand"
Pros: "Flight itself was fine. Major delay resulted in arriving one day later than planned, additional transportation cost, unplanned, and unplanned parking fees. No travel voucher was offered and when I asked was told it was not possible to issue a travel voucher."
Cons: "It would have been helpful if hanging a garment bag were available, which was the case on my return flights to DC on American Airlines."
Pros: "The process was good"
Cons: "Wish there were more morning flights"
Pros: "Very good"
Cons: "Comfortable"
Pros: "I was comfortable and I didn't die."
Cons: "N/A"
Cons: "There should be some free tv"
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Flights to Hilton Head Island
Destination:
Hilton Head Island (HHH)United States
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Cabin classes:
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$523
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