$286 Find Cheap Flights from Chicago to Sicily

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 Sicily departing on 8/13. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Sicily

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sicily, 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 Sicily, as well as popular online travel agencies
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Cheap Flights from Chicago to Sicily

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Palermo
Palermo1 stop$491
Palermo
Palermo1 stop$491

Book Cheap Chicago to Sicily Plane Tickets

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

Wed, Sep 10 - Wed, Sep 24
Turkish Airlines Logo
11:25 am - 8:20 amORD-PMO
13h 55m1 stop
Turkish Airlines Logo
7:15 pm - 9:40 amPMO-ORD
21h 25m1 stop
$491Turkish Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Turkish Airlines Logo
11:25 am - 8:25 amORD-CTA
14h 00m1 stop
Turkish Airlines Logo
7:10 pm - 9:40 amCTA-ORD
21h 30m1 stop
$491Turkish Airlines
Find Deal
Wed, Nov 5 - Wed, Nov 12
Turkish Airlines Logo
8:20 pm - 8:30 amORD-PMO
29h 10m1 stop
Turkish Airlines Logo
6:45 pm - 6:25 pmPMO-ORD
30h 40m1 stop
$500Turkish Airlines
Find Deal
Mon, Aug 11 - Wed, Aug 27
ITA Airways Logo
3:00 pm - 6:30 pmORD-CTA
20h 30m1 stop
ITA Airways Logo
6:00 am - 1:10 pmCTA-ORD
14h 10m1 stop
$727ITA Airways
Find Deal
Wed, Aug 27 - Wed, Sep 3
ITA Airways Logo
3:00 pm - 11:00 pmORD-SUF
25h 00m1 stop
ITA Airways Logo
6:15 am - 1:10 pmSUF-ORD
13h 55m1 stop
$751ITA Airways
Find Deal
Mon, Aug 11 - Mon, Aug 25
Delta Logo
9:31 am - 3:00 pmMDW-PMO
22h 29m2 stops
Delta Logo
3:45 pm - 5:37 pmPMO-MDW
32h 52m2 stops
$771Delta
Find Deal
Mon, Aug 11 - Fri, Aug 29
Delta Logo
1:08 pm - 3:00 pmMDW-PMO
18h 52m2 stops
Delta Logo
3:45 pm - 6:37 pmPMO-MDW
33h 52m2 stops
$831Delta
Find Deal
Tue, Oct 7 - Thu, Oct 23
Lufthansa Logo
9:40 pm - 10:55 amORD-SUF
30h 15m1 stop
Lufthansa Logo
11:40 am - 6:15 pmSUF-ORD
13h 35m1 stop
$849Lufthansa
Find Deal
Tue, Aug 26 - Thu, Sep 4
Lufthansa Logo
7:55 pm - 10:35 amORD-SUF
31h 40m2 stops
Lufthansa Logo
11:25 am - 7:55 pmSUF-ORD
15h 30m1 stop
$873Lufthansa
Find Deal
Thu, Dec 18 - Fri, Jan 9
SWISS Logo
6:50 pm - 2:00 pmORD-SUF
12h 10m1 stop
SWISS Logo
10:20 am - 4:20 pmSUF-ORD
13h 00m1 stop
$1,000SWISS
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Sicily flights

Get data-powered insights and trends into flights from Chicago to Sicily 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 Sicily?

The average price of all round-trip flights from Chicago to Sicily clicked on KAYAK for each day over the last 12 months.

For Chicago to Sicily, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Sicily back to Chicago, the best deals are generally found on Tuesday, with Friday being the most expensive.

How far in advance should I book a flight from Chicago to Sicily?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Sicily, 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 to Sicily, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$286
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago O'Hare Airport to Palermo

FAQs - booking Sicily flights

  • Can I find direct flights from Chicago to Sicily?

    There aren’t any airlines that fly direct from Chicago to Sicily. Your best option will be to track down an airline that makes just one stop between Chicago and Sicily with a short layover. SWISS, for example, has flights from Chicago O'Hare International Airport (ORD) to Falcone Borsellino Airport (PMO) that make just one stop and get to Sicily in about 15 hours.

  • Can I get free Wi-Fi on flights from Chicago to Sicily?

    You'll be able to get free Wi-Fi on Air France that you can use to send in-flight messages to family and friends. You'll also be able to get free Wi-Fi on Delta flights after you sign up for a free SkyMiles membership.

  • Where will layovers occur when flying from Chicago to Sicily?

    Since most flights from Chicago to Sicily feature numerous stops, you may have to endure layovers at any number of locations. Some airports where layovers might take place include Frankfurt Airport (FRA), Istanbul Airport (IST), Zurich Airport (ZRH), and Lamezia Terme International Airport (SUF).

  • What can I do to make a flight from Chicago to Sicily sustainable?

    Each airline that flies from Chicago to Sicily is taking steps toward building a more sustainable business. Choose the one with the sustainability plan you like most. Turkish Airlines, for instance, has a plan that calls for the airline to become carbon-neutral in the coming years by using more fuel-friendly planes and technology to come up with shorter flight plans.

  • How does KAYAK find such low prices on flights from Chicago to Sicily?

    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 Sicily.

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

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

    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 Chicago to Sicily 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 Chicago to Sicily?

    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 Chicago to Sicily 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 Sicily?

    The cheapest time of day to fly to Sicily is generally in the morning, when round-trip flights cost $759 on average. Morning departures are around 23% cheaper than evening flights, on average. The most expensive time of day to fly to Sicily is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,178.

Top tips for finding cheap flights to Sicily

  • Anyone wishing to fly from Chicago to Sicily will be able to leave from either Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), but ORD offers more options for those searching for flights. You'll also be able to fly into either Vincenzo Bellini Catania Airport (CTA) or Falcone Borsellino Airport (PMO) in Sicily. CTA is on the southeast coast of Sicily near Catania, while PMO is situated in the northwest region near Palermo.
  • Those planning to fly from Chicago to Sicily will only need to bring a valid U.S. passport. The only time you’ll need to bring a visa is if you plan to stay in Sicily for more than 90 days.
  • Flying first class is a wonderful way to keep yourself comfortable while flying from Chicago to Sicily. Air France, Delta, and SWISS all offer great first-class accommodations to those who wish to upgrade their seats. You’ll be able to get access to everything from a lie-flat seat you can utilize for sleep to more in-flight entertainment than you would ever need, so you can stay busy on long flights to Sicily.
  • If you’re lucky enough to fly first class from Chicago to Sicily, you should be able to check bags through most airlines without paying extra fees. But if you’ll be flying to Sicily in a lower cabin class, every bag you check will be subjected to fees through airlines like Lufthansa, SWISS, and others. You may be able to keep your travel costs down by flying with just a carry-on bag.
  • Chicago O'Hare International Airport and Chicago Midway International Airport offer lounges you can use to fill time after arriving for a flight to Sicily. ORD has options like the Delta Sky Club for Delta passengers, while MDW has Club MDW available to all passengers regardless of which airline they’re flying with.

Reviews of the top 5 airlines serving from Chicago to Sicily

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sicily. 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 Sicily? 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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

I can’t even the whole trip was a catastrophe

Poor. Seats uncomfortable. No leg room. Hot and humid the whole trip. Food and staffs were ok.

Delay more than hour created pressure to catch the connecting flight

The seats were so close together, when the man in front of me put his seat back, the screen in front of me was 9 inches from my face. There is no way to lean forward if I needed to pick something up. It was pretty uncomfortable for a ten hour flight. I was very surprised.

The food was good. Most the staff was pleasant. The flight would be drastically improved with WiFi on a long international flight.

The whole experience was positive. Crew very friendly and helpful. Very greedy with pre-seat allocation. Web site too complicated

When I needed to get my bag off of the plane so that I could take a train because the connection was 4 hours later, they took 2 hours to take my bag off making me take the train and miss my flight simultaneously. The seat size on the plane is too small for an average aged woman let alone a middle-aged man. It's unacceptable and I will not fly Boeing again.

They didn't give us Nothing to eat, come on..... 1 package of chips and a glass of soda won't do anything to the company

The cushion of the seats are old and very thin. The food can be more tasty or come with salt packages

The biggest let down was with booking experience through Kayak. I booked a flight with checked bags on Kayak. Right away I got a message from travel agency that the flight is not confirmed and to call them. I called them and they said the flight I have booked is no longer available with the price I have booked it for and I can book it with about $100 more. I already had other options I could book with cheaper price so I asked them to cancel my booking. Then they said I can have the ticket with the same price but a date change which was not working for me as I had to be there for a seminar. So again I said no then they said they will cover the charges and confirm my flight. When comes time for check-in I see I have no checked bag option which means the travel agency deceived me saying I can have my booking as I had booked it. And at that point I ended up paying $155 for my checked bag going back and forth. I am extremely angry and unhappy with this experience

The economy seat was so uncomfortable, had not enough leg room for 13 hours flight, front seat basket was broken and couldn’t hold anything, food quality was horrible( we got food poisoned ) we charged for logged which used to be free. We paid too much for this flight and very disappointed. Turkish air line better to make satisfy and respect people instead of find different way to scam people.

This is really the rating of two flights. JFK to IST then IST to NQZ. New York to Istanbul was good. Good crew and all positives. The flight to Astana was so bad that brought it all down. Crew was nonexistent above the minimum, seats were cramped, and it was hot on the plane. Turkish Airlines seems to be slipping down to US based carriers level.

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

Everything was very good, except that the plane was an hour and a half late

flight with heavy turbulence old boeing 777 rest wasnt clean dashboard doesn’t work

Light and recline did not work on my seat. Very uncomfortable and could not read in the dark

Bad experience; they are not good anymore. They charge too much for luggage seat are so uncomfortable, Flight delays which may miss your next flight, they don’t care if you miss the flight or not. Zero customer services for front desk representatives Istanbul's airport I’m not using this airline any more.

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

It wasn't good. I didn’t understand. They changed 320 dollars for 2 luggage. My ticket was regular and I paid almost 1200.00 dollars. Why they did charge? I want my money back.. thanks Yılmaz polat

Very punctual, the onboard staff was friendly and correct, the flight was fortunately very calm, the toilets were clean, in short, an excellent experience Thanks

Boarding and flight update was fantastic as I experienced about a 10-15 delayed for both flights. The food served onboard was great; the service of the flight attendants was excellent.

The row of seats were so cramped it was difficult to get in and out of your seat. I even upgraded. A long flight and sad accommodations 😵‍💫 the shorter flight was very comfortable and the seating was spacious

Complete mess. Our reservation was mistakenly cancelled. After almost missing the connection and walking all over the Munich airport, the Service desk got involved and we were run to our flight. Not all 4 of us in Business and not seated together as originally booked. This was the worst treatment I have ever had. And I travel a lot. 1K million miler.

I have flown with many airlines. My first time was several years ago. Now I remember why I avoided them for so long. Lufthanza is the only airline who has ever raised a size/weight issue with my modest standard size carry on. I had to repack three times to meet their carry-on weight criteria. (Apparently the rules of physics apply differently on Lufthansa flight than on other airlines.) In the meantime their staff was quite rude, repeating meaningless phrases like "Rules are Rules." And ignoring the additional fact that weight is also weight, whether it is in found in your carry on or in your suitcase. They eventually acknowledged that customer service and satisfaction is, for them, a low priority. Never choosing Lufthansa again.

They are professional. Nice crew. Still flying Boeing 747. Thank you for that. I love this airplane. Traditional.

There is more space in this economy seat. It felt like a better layout, not so cramped.

Connecting from Germany with not enough time to go thru TSA and security so many times. Kayak or whomever doesn’t leave you enough time between flights. I made it with 5 min before my zone was called. Too stressful

The seats were extremely uncomfortable. I spent €25 on internet and never gained access to it. A flight attendant told me she would file a complaint/report on my behalf but it put me in a very difficult situation.

The staff was not at pleasant as those on the first leg of our trip.

Boarding was easy and well organized, Breakfast was not very good.

Better consideration for families traveling with a disabled person. They insisted each person hold their own boarding pass on their own devices and gave us a hard time accepting eight boarding passes on a single device.

Two of my four flights had issues with toilets either NOT fully operational or completely out of order. Boarding was a joke because they have NOT established who is running the show. In the end, she did a terrible job. The seats 💺 were loose goose and the drinks and snacks were limiting in choices. Also, following Alitalia as an inspiration was strange since they went out of business.

We had a 3 hour delay and then a long taxi to take off. It would have been helpful for the pilot to have communicated more about what was going on. There was no A/C during the wait, and the cabin must have been more than 85 to 90 degrees. The crew gave water to the people in the front but by the time they go to the back of the plane they stopped giving out water. Eventually I went back and asked for some in the rear of the plane (for a second time). The food was close to inedible. I thought on an Italian flight that the pasta would be better than the chick, but honestly, a Swanson's TV dinner would have been better. I had a bite or two to keep my blood sugar up, but basically I couldn't eat it.

Boarding was chaotic. Service was poor. Attendant was slow and rude. In business class, I was not offered a drink until 1.5 hrs,after takeoff. Food was inedible.

Terrible. They canceled 2 flights and then sent everyone by BUS from Rome. They should make amends by offering some sort of compensation.

We ordered a gluten free meal and never got it!

The company tries shamelessly to squeeze every dollar)Euro out of its passengers. During the check-in the force you to go through the seat selection, you can skip it. They will assign you the worst seat available, then show you the other available seats on the map, for a fee. But they won't show you the fee until you click on it. And once you do click, there's no way to unselect it!! You will get stuck and forced to pay for that seat. Cheaters!!

Seats weren’t comfortable. Both of our seat backs were either almost straight vertical or laying back into the laps of the people behind us, which is a weird angle to try to get some sleep even on a plane. No in between. Also, neither seat would spring forward like they should.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

Flight on time, flight assistants super nice, business class very comfortable. The whole experience was very good.

Everything you need to know for your flight from Chicago to Sicily

Cabin class types available on flights to Sicily

Cabin classes available on flights to Sicily. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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