$373 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Sicily departing on 9/15. 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 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 O'Hare Intl to Sicily

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Palermo
Palermo1 stop$836
Catania
Catania1 stop$687
Palermo
Palermo1 stop$836
Catania
Catania1 stop$687

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Sicily

Thu, Oct 1 - Fri, Oct 16
Turkish Airlines Logo
8:10 pm - 8:25 am
ORD
-
CTA
29h 15m
1 stop
Turkish Airlines Logo
7:25 pm - 6:15 pm
CTA
-
ORD
29h 50m
1 stop
$687Turkish Airlines
Thu, Oct 1 - Fri, Oct 16
Turkish Airlines Logo
8:10 pm - 8:25 am
ORD
-
CTA
29h 15m
1 stop
Turkish Airlines Logo
7:25 pm - 6:15 pm
CTA
-
ORD
29h 50m
1 stop
$691Turkish Airlines
Thu, Oct 8 - Tue, Oct 13
Turkish Airlines Logo
8:10 pm - 6:25 pm
ORD
-
CTA
15h 15m
1 stop
Turkish Airlines Logo
7:25 pm - 9:40 am
CTA
-
ORD
21h 15m
1 stop
$724Turkish Airlines
Sat, Oct 3 - Thu, Oct 22
Turkish Airlines Logo
8:10 pm - 8:25 am
ORD
-
CTA
29h 15m
1 stop
Turkish Airlines Logo
7:25 pm - 9:40 am
CTA
-
ORD
21h 15m
1 stop
$729Turkish Airlines
Fri, Oct 2 - Mon, Oct 12
Turkish Airlines Logo
11:25 am - 8:25 am
ORD
-
CTA
14h 00m
1 stop
Turkish Airlines Logo
9:25 am - 6:15 pm
CTA
-
ORD
15h 50m
1 stop
$764Turkish Airlines
Sat, May 2 - Fri, May 8
Scandinavian Airlines Logo
7:15 pm - 4:45 pm
ORD
-
PMO
14h 30m
1 stop
Scandinavian Airlines Logo
6:50 pm - 4:10 pm
PMO
-
ORD
28h 20m
1 stop
$836Scandinavian Airlines
Wed, Aug 5 - Fri, Aug 21
ITA Airways Logo
3:00 pm - 6:30 pm
ORD
-
SUF
20h 30m
1 stop
ITA Airways Logo
11:15 am - 1:10 pm
SUF
-
ORD
32h 55m
1 stop
$862ITA Airways
Mon, May 11 - Mon, May 25
Lufthansa Logo
3:35 pm - 11:00 am
ORD
-
PMO
12h 25m
1 stop
Lufthansa Logo
6:10 pm - 6:15 pm
PMO
-
ORD
31h 05m
1 stop
$919Lufthansa
Wed, May 13 - Wed, May 20
SWISS Logo
7:05 pm - 9:00 am
ORD
-
PMO
30h 55m
1 stop
SWISS Logo
7:25 pm - 12:35 pm
PMO
-
ORD
24h 10m
1 stop
$932SWISS
Wed, Aug 5 - Fri, Aug 21
ITA Airways Logo
3:00 pm - 6:30 pm
ORD
-
SUF
20h 30m
1 stop
ITA Airways Logo
6:35 am - 1:10 pm
SUF
-
ORD
37h 35m
2 stops
$941ITA Airways
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Sicily flights

Get data-powered insights and trends into flights from O'Hare Intl to Sicily to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Sicily?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Sicily departing in October.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Sicily?

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 Sicily, 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 Sicily is August, when tickets cost $56 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $669 and $597 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Sicily, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$373
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago to Catania

FAQs - booking Sicily flights

  • What are some common layovers on the route from Chicago O'Hare Airport to Sicily?

    Flights from Chicago O'Hare (ORD) to Sicily usually involve at least one layover, as direct flights to the island are not typically available. Common layover points include major European hubs like Rome's Leonardo da Vinci–Fiumicino Airport (FCO), Milan Malpensa Airport (MXP), Istanbul Airport (IST), Munich International Airport (MUC), or Frankfurt Airport (FRA). From these cities, you can find connecting flights to Sicily's main airports, such as Falcone Borsellino Airport (PMO) in Palermo or Fontanarossa Airport (CTA) in Catania.

  • If I want to visit the Valley of the Temples, which airport should I fly to?

    To visit the Valley of the Temples, a renowned archaeological site in Sicily, you should fly into Falcone Borsellino Airport (PMO) in Palermo or Vincenzo Florio Airport Trapani-Birgi (TPS). Both airports offer access to this area, but Palermo is larger with more flight options. The Valley of the Temples is located near Agrigento, about a two-hour drive from Palermo and a slightly shorter drive from Trapani.

  • Which airlines offer Wi-Fi on board? Is it free or with a fee?

    On routes from Chicago O'Hare to Sicily, airlines like ITA Airways, Lufthansa, and United Airlines typically provide Wi-Fi on board. However, the Wi-Fi service – whether it's complimentary or requires payment – depends on the airline. Lufthansa, for example, often charges for Wi-Fi based on how much you use it, whereas other airlines may offer free basic Wi-Fi or messaging services. To get precise information about Wi-Fi availability and costs, it's best to contact the airline directly before your flight.

  • How can I make my flight from Chicago O'Hare to Sicily more sustainable?

    To reduce the environmental impact of your flight, consider choosing airlines that prioritize sustainability. Airlines like Lufthansa and United Airlines have been focusing on reducing their carbon footprints through initiatives such as using more fuel-efficient aircraft and offering carbon offset programs for passengers. Also, opting for flights with fewer layovers can help minimize fuel consumption.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Sicily.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to Sicily up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Sicily

  • Your journey to Sicily begins at Chicago O'Hare International Airport (ORD), a major hub for United Airlines, American Airlines, and Spirit Airlines. American Airlines, United Airlines, and many European airlines such as Lufthansa, ITA Airways, SWISS, and TAP Air Portugal operate from O'Hare International Airport, offering flights to Europe with connections to Sicily.
  • Sicily is served by three main airports: Falcone Borsellino Airport (PMO) in Palermo, Vincenzo Florio Airport Trapani-Birgi (TPS) in Trapani for the western part of the island, and Catania-Fontanarossa Airport (CTA) in Catania for the eastern part. You can choose the airport that best aligns with your final destination in Sicily.
  • While direct flights from Chicago to Sicily are not common, airlines such as United Airlines, Lufthansa, and Turkish Airlines provide routes with just one stop, typically in European hubs like Istanbul (IST) or Munich (MUC). Flights with TAP Air Portugal, Iberia, and ITA Airways typically have two stops.
  • At Chicago O'Hare International Airport, families traveling with children can take advantage of several facilities, such as play areas for kids, nursing rooms, and family restrooms, ensuring a comfortable and stress-free experience.
  • On long-haul flights like the one from Chicago to Sicily, consider upgrading your seat for added comfort. Airlines such as American and United Airlines offer premium economy or business class upgrades, which include additional legroom, priority boarding, and better in-flight service.

Reviews of the top 4 airlines serving from O'Hare Intl 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 O'Hare Intl 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.
7.5
SWISSOverall score based on 1924 reviews
7.7Boarding
7.4Comfort
8.3Crew
7.1Food
6.8Entertainment
Airline reviews

The flight itself was fine, but due to a snow delay my connection to Lisbon was delayed by six hours. Despite this, Swiss Air still managed to lose my luggage. Not acceptable. Someone else on the flight also lost their luggage.

6.0 GoodSonja, Jan 2026
BOS - ZRH
Read more SWISS reviews

The flight itself was fine, but due to a snow delay my connection to Lisbon was delayed by six hours. Despite this, Swiss Air still managed to lose my luggage. Not acceptable. Someone else on the flight also lost their luggage.

Bad experience overall. Crew did not provide food for our 2 year old (even though we specifically bought a child infant seat for her and literally bought another full price flight), which was unacceptable. And we had to pay $310 each way to carry our ski equipment even though they advertise it as something that is free. Tickets were purchased the same way as usual, but they told us we had Economy Light tickets (I never elected to have such seats). Just plain manipulation and false advertisment. Very disappointed overall about this airline.

The trip was great until my luggage was lost on transfer from United to Swiss. It took Swiss 3 days to get my luggage to me though it was located almost immediately.

It was much better than most airlines we have flown with. It remo des me Swiss Air 25 years ago.

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

Horrible!! The WiFi was not working, the food was awful

We’ve never been more uncomfortable on a flight than we have on this particular one. The seats in front of us reclined so far back that when the person reclined their seat of broccoli, it almost hit me in the face and left me with literally no room to move that said I had to recline my seed in which made the person behind me upset. It seemed like the seats also would recline without even pressing the button in the armrest and would unrecline as well for that same reason, and it also seemed that some seats reclined more than others. The bottom cushions of the seat were so thin that even after one hour of an 11 hour flight, our tailbones were so sore. It seemed like an overall old airplane. It also didn’t have individual air vents and it was extremely hot the entire flight. Several passengers were commenting on how hot it was. The breakfast was some kind of flavorless triangle, puffy egg, laying in a watery bed of steamed peppers and onions and spinach. It was not appetizing at all. The flight crew was extremely nice so that was a nice thing this flight attendant. They let us try different types of Swiss sodas, which was really nice and the dinner was actually delicious but still overall given the other considerations. It was pretty much a miserable flight without basic seat comfort.

Food used to be better and comfort was not attainable after 5 hours everything starts hurting.

horrible.. they cause such a problem and my daughter 14 years old was stranded in san francisco

I can’t even the whole trip was a catastrophe

The ground crew members at check in counter were courteous. The boarding was seamless. Flight departed as scheduled. Service on board was great

Very comfortable in business class. Excellent service. Good food. Smooth trip.

The seats seems abit small and the reclining is too much, the seat in front of me came back too much and made it uncomfortable for me.

As a first time flyer with Turkish Airlines. My experience was very good due to the factor that there were to many passengers on the my first flight compared to my connecting flight. However, I know that nothing is perfect and all companies are trying to accommodate their passengers to the best way possible. I will always say, a FEW INCHES will go LONG WAY. That's something all airliners should consider, and not only the money aspect!!! A long time commitment is better than one time service! Thank you

Flight was delayed. While standing at the gate, a note appeared on the sign saying the gate had changed to a gate far away. No member of the Turkish airlines team got on the microphone to instruct passengers to go to the other gate, to ignore the chiron, etc. Finally, the message disappeared. Eventually, the flight began to board. Very slowly. More slowly than I experience with other airlines. Though Istanbul may just be slow . . . In all other ways, great flight, great entertainment (top notch movies), great service, excellent food, comfortable lie-flat seat, dimmed lights, etc.

Staff at the airport wasn't helpful or friendly. Probably the worst airport experience I have ever had, going and coming. The staff on the plane was better. Still not super friendly or personable. However, they were not rude like airport staff. They ran out of certain menu items. Maybe could have been prepared better? Overall just ok.

It was a pleasant experience. In flight entertainment could have been better

The desk crew at the LAX crew could do better. A girl named Mahesi was very abrasive and unfriendly. She needs a better customer service uproar.

It was peaceful excited We enjoyed it always Turkish peaceful excited

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

I liked Quiet people around me. Crew could have helped people with overhead luggage so they aren't moving other peoples bags around and causing problems for people that had there bags there first

The plane was delayed by two hours in Chicago which led to us missing the next flight. Lufthansa rebooked the flight and booked us a hotel for the night in Frankfurt. The level of customer service and getting us taken care of was superb. The flight crew and the service on the ground was superb.

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.

Flight was canceled. Rebooked on Lufthansa Also Canceled. Had to pay 3000 more per person and fly Alaska to EWR and fly emirates to Athens.

Our flight was cancelled the day before our trip and we we put on a Turkish Airline flight that got us in half a day later.

Everything is smooth without canceling the flight or long delay. We're happy about it.

The flight I initially booked from Los Angeles to Florence. I made sure had a layover of about 90 minutes in Rome, so there’d be enough time to connect. A couple weeks before the flight for some reason I was updated that that flight had changed and I was only gonna have 60 minutes to connect. From LAX we were delayed by 45 minutes meaning making the connection was unlikely. The crew informed me that my connecting flight would not wait and they would rebook me on one four or five hours later. I wasn’t happy, but I accepted it. It is what it is. Except when we got closer, two separate flight attendant approached me eagerly and said they had great news that my connecting flight would in fact wait for me, but I needed to hurry through the airport so they didn’t have to wait too long. I was first off the flight. I ran about 4000 steps. And got through passport control all in under 15 minutes. When I arrived to my gate, I was greeted by a flight attendant there who was completely indifferent, said they didn’t hold the plane and they just closed the doors. Had they even held it for two minutes I would’ve made it. She simply told me that the flight attendant on my flight lied about the plane being held, and that they do it all the time. These were all employees of the same company ITA. I was absolutely livid at her indifference and having been lied to and then having to wait five hours and waste a day in Europe at an airport.

The flight was canceled and we have not received the refund

They lost my checked in bag and have not helped me.

First, ITA lost my bag and the baggage team showed no regard in trying to find it. Second, I had paid for priority boarding as part of a first class ticket and instead they disregarded boarding groups and we all boarded at the same time. Third, wasn't allowed to select my seat in advance even with a first class ticket. When I was assigned bulkhead, I was told I would need to pay to change my seat. Overall, very disappointing experience.

The seats needs to be spruced up , for a long flight very uncomfortable , cushions are worn out but everything else is very good , crew is great.

I guess that was fine with ITA but the Rome airport is so difficult to navigate with so many checkpoints getting new tickets from what was originally given to me

My seat was broken and ducted taped and my monitor did not work the entire time over 8 hrs sitting. And I had no books or anything with me

Everything you need to know for your flight from O'Hare Intl to Sicily

Information on your arrival and departure airports