$325 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 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.
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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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sicily.
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Best Sicily Flight Deals from O'Hare Intl

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Palermo
Palermo1 stop$666
Catania
Catania1 stop$670
Palermo
Palermo1 stop$666
Catania
Catania1 stop$670

Cheap Flight Deals from O'Hare Intl to Sicily (ORD-ITSI)

 
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.

Recent round-trip flight deals from O'Hare Intl to Sicily

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from O'Hare Intl to Sicily.
Discover the best prices for you by selecting your travel dates on KAYAK.
Turkish Airlines Logo
11:25 am - 8:20 amORD-PMO
13h 55m1 stop
Turkish Airlines Logo
9:20 am - 5:55 pmPMO-ORD
15h 35m1 stop
$666Turkish Airlines
Find Deal
Thu, Sep 11 - Fri, Oct 3
Turkish Airlines Logo
11:45 pm - 6:15 pmORD-PMO
35h 30m1 stop
Turkish Airlines Logo
9:20 am - 10:00 pmPMO-ORD
19h 40m1 stop
$667Turkish Airlines
Find Deal
Mon, Oct 6 - Mon, Oct 13
ITA Airways Logo
7:30 am - 10:55 amORD-CTA
20h 25m2 stops
ITA Airways Logo
7:15 pm - 1:10 pmCTA-ORD
24h 55m1 stop
$843ITA Airways
Find Deal
Wed, Sep 10 - Tue, Sep 16
ITA Airways Logo
3:00 pm - 6:10 pmORD-PMO
20h 10m2 stops
ITA Airways Logo
4:10 pm - 1:10 pmPMO-ORD
28h 00m1 stop
$846ITA Airways
Find Deal
Sun, Sep 14 - Sun, Sep 21
Delta Logo
5:10 pm - 3:00 pmORD-PMO
14h 50m1 stop
Delta Logo
9:35 am - 10:03 pmPMO-ORD
19h 28m2 stops
$1,037Delta
Find Deal
Mon, Jul 21 - Thu, Jul 31
Delta Logo
2:10 pm - 3:00 pmORD-PMO
17h 50m2 stops
Delta Logo
9:35 am - 10:03 pmPMO-ORD
19h 28m2 stops
$1,041Delta
Find Deal
Mon, Jul 21 - Thu, Jul 31
Lufthansa Logo
3:35 pm - 11:00 amORD-CTA
12h 25m1 stop
Lufthansa Logo
11:55 am - 6:15 pmCTA-ORD
13h 20m1 stop
$1,245Lufthansa
Find Deal
Wed, Oct 1 - Fri, Oct 10
SWISS Logo
7:05 pm - 11:25 pmORD-PMO
21h 20m1 stop
SWISS Logo
3:00 pm - 12:10 pmPMO-ORD
28h 10m1 stop
$1,337SWISS
Find Deal
Sun, May 18 - Mon, May 26
SWISS Logo
2:20 pm - 2:00 pmORD-PMO
16h 40m1 stop
SWISS Logo
5:50 am - 12:10 pmPMO-ORD
13h 20m1 stop
$1,345SWISS
Find Deal
Tue, Jul 29 - Tue, Aug 12
Lufthansa Logo
4:00 pm - 10:55 amORD-SUF
11h 55m1 stop
Lufthansa Logo
8:50 pm - 6:15 pmSUF-ORD
52h 25m2 stops
$1,354Lufthansa
Find Deal
Sat, Jun 28 - Sun, Jul 6
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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.

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 February, when tickets cost $759 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $1,271 and $1,183 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Sicily?

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

Your flight ticket price will generally be cheaper if you fly to Sicily on a Tuesday and more expensive on a Thursday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

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 3 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$325
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Palermo

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.

  • 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

  • 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.

Top 5 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 1588 reviews
6.7Entertainment
8.2Crew
7.6Boarding
7.4Comfort
7.0Food
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ZRH - FLR
Read more SWISS reviews

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

PLEASE DONT TAKE FORCEFULLY(SIZE APPROPRIATE) CARRY ONS FROM PASSENGERS WHO FOR SOME REASON NEED TO KEEP IT

It was great. My seat was comfortable. The bathrooms were clean . The service was superb . I travel a lot and I have been in 64 counties. I wish I could fly first class, even though I could , but I prefer to budget my yearly travelling expense on actual visiting , not on flight. Anyway, my point is that your economy was far much better than other airlines as good as Air France. The flight attendants and all crew were polite and very helpful and respectful. Thank you for making my long trip tolerable.

I slept the whole flight so I can't tell you about the food and there was no entertainment offered. Crew was very nice, seats were comfortable in business, and boarding was easy.

We are flying with Swiss for a long time but this time was terrible do to are flight cancellations we are in some bad hotel with out normal food

It is a good airlines, very professional very good food. I wish they offered free luggage is the only thing.

I like how professional, fast and good the whole experience was.

Everything was great except food . It as okay not good not bad

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

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

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.

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

Ordered Vegan meal - it was ok, but not exceptional. Seat ok row 39 middle section aisle. Nearly full flight - crew was busy but they did the best they could. There was a USB A port at the seat. I listened to my own music and only looked at flight information. One nice thing was the connection information was made available in the screen.

Very nice and friendly crew. Boarding system can be improved.

The Etickets had been changed (Why?) without notice ; Hence, that caused troubles when checking in. Not until I contacted my ticket agent and was given correct Etickets could I then check in.

Cleanliness of seats, trays, storage pockets need more attention, but everything else was good.

A great airline, no complaints at all. My experience with Cheap Tickets was very disappointing however. Two hours after purchasing the flight they called to tell me that the ticket price had gone up. I’ve never heard of such a thing. That is called false advertising; I will never use this ticketing service again and will warn all friends to never use it.

One of the worst check in process at the DIA as well as the boarding counter Changed seat at the last minute and assigned middle seat while I paid for window seat. Requested many times but to no avail . horrible customer service and very poor process Requesting refund for seat that was changed last minute

Good overall flight. Excellent crew. Food options could be improved.

Vegan food tasted good. Restroom could be kept cleaner. Seat tray table was a bit tilted so food tray kept sliding down a bit. Flight crew can be a little more friendly, caring and approachable. Their faces lacked smiles and tone was stern.

Flight was delayed then we had to redirect for medical emergency during which time we had no information on what is the plan. The connecting flight was also delayed.

We ordered a gluten free meal and never got it!

The seats are horribly uncomfortable. We were in premium economy and paid a premium price yet, the seats were the worst! You could feel every structural bar in the seat, there was no padding, no amenities kit, and the leg rests were broken. Duct tape was holding another seat together. When we arrived at our final destination, Venice, my suitcase was ripped open, and my clothes were about to fall out of the bag. I would’ve been more comfortable if I flew a paper airplane across the Atlantic.

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.

It is the worst ever airline. All employees I spoke with over the phone were pompous asses.

The gate information was never populated on the Delta app or the airport displays or the desk at the Delta lounge. We found at the last minute that we had to switch terminals and just made it to our flight. Even this we found accidentally by asking an employee at another gate. On board service was poor. Seats were very poor. All in all a poor experience. At best like a Premium Economy on other airlines

No online or self check in. Sent emails in Italian language. In general, not recommended airline company.

You idiots…ITA cancelled our flights one month out and we had to buy new tickets at a much higher price. You stiffed us by not refunding the cost of the insurance. I’ll never buy through Kayak again.

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.

Sitting in a hotel in Chicago because I was rebooked due to a missed connection. Very frustrating.

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

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