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Find cheap flights from Chicago O'Hare Airport to Sicily from $252

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 9/27. 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
0 bags
Sun 6/2
Sun 6/9

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Best Sicily Flight Deals

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

Palermo
Palermo1 stop$899
Catania
Catania1 stop$721

Good to know

Low season

February

High season

September

Cheapest flight

$252
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 2% 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 to Sicily from Chicago O'Hare Airport 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 to Sicily with an airline and back to Chicago O'Hare Airport 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 to Sicily from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Sicily

  • Morning departure is around 18% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from O'Hare Intl to Sicily

 
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.
8.3
EVA AirOverall score based on 1542 reviews
8.6Crew
8.2Comfort
8.0Entertainment
8.0Food
8.4Boarding
Airline reviews

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

10.0 ExcellentDamian, Mar 2024LAX - TPE
Read more about EVA Air reviews

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant, comfortable, and entertaining. All told, ZERO issues with it. And sadly, so far the flight was WAY more comfortable than the hellhole that is "Lambug Beach Resort" at Badian Beach!

It was a pleasant fly with Eva Air from NYC to Taipei. The crew were friendly and the food was exceeded my expectation.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Overall the flight was what might be expected for a long haul flight to Asia in economy class. The cabin crew was attentive and the food was good. Boarding was fairly fast and easy. The one thing I found frustrating was the EVA app. It is terrible. Trying to do anything on it was almost impossible.

EVA would not help with ticket issue since they were purchased through a travel agency. Even though it was EVA ticket stock. Travel agency Budget Air didn't reissue ticket after airline change which I didn’t learn until trying to checkin on Christmas Day and there was no contact number for the agency to help. I will never use Budget Air to purchase flight again and disappointed in EVA’s refusal to help. Thankfully just under 12 hrs before departure someone from the agency was available to reissue tickets. I was starting to think we would not be flying and the stress trying to resolve was completely unacceptable.

seamless check in/ friendly staff, food is good, always love flying Eva Air

Very uncomfortable and crowded seats in economy. Flight attendant refused request to move to nearby unused seat with more legroom because “It was more money for that seat”. It was also near impossible to reach airline directly by phone. Waits upwards of an hour and not very helpful customer service representatives after long wait. Cannot recommend this airline.

My experience with Eva sir was good except the long walk in LA Lex, that was inconvenient for my age,

The overall flight went well and the aircrew was pleasant.

Cathay Pacific seems to be an airline in trouble and on its way out. Lots of broken or poorly functioning things like entertainment screens, seats, and enough well trained staff to handle a full flight. Sad...

The flight crew was exceptionally good. Personal needs were well met. The food choices were very nice.

Excellent. Planes are a little older and could get some refurbishment, but besides that everything was excellent.

The boarding experience was as expected and went well. The plane's economy seating plan is not designed for a positive customer experience but rather for company profit. When the passenger in front of me reclined, the distance from the screen to my face was the span of my hand (thumb tip to pinky fingertip). There is no such thing as personal space in this setting. This results in the domino effect, for when I recline the person in back of me reclines and so it goes. This is not to say that reclining is the answer as the experience is not increased, but simply managed.

While I was in great pain, the seat was sufficiently comfortable to allow me to rest and not be in so much pain.

we were upgraded which was a blessing and tender mercy for us. I fell the day before and was in extreme pain from knee to shoulder. Sitting in a more comfortable seat during the flight was an unexpected blessing and experience.

Not impressed with check in desk staff at Vancouver airport. Not a professional mind service and not cared or tried to help. Don’t think I would fly with them again

Seats were very comfortable. Crew were excellent. Food very good.

Flight crew was especially thoughtful and attentive, made sure our seats were comfortable so we could rest on the long flight

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

Book cheap flights from Chicago to Sicily

Recent round-trip flight deals

9/16Mon
1 stopTurkish Airlines
29h 05mORD-CTA
9/23Mon
1 stopTurkish Airlines
21h 25mCTA-ORD
$721
9/20Fri
1 stopTurkish Airlines
29h 05mORD-CTA
9/26Thu
1 stopTurkish Airlines
21h 25mCTA-ORD
$760
9/17Tue
1 stopTurkish Airlines
71h 50mORD-CTA
9/26Thu
1 stopTurkish Airlines
21h 25mCTA-ORD
$775
7/28Sun
1 stopBritish Airways
14h 30mORD-PMO
8/12Mon
1 stopBritish Airways
25h 00mPMO-ORD
$965
7/13Sat
2 stopsAir France
36h 40mORD-PMO
8/24Sat
1 stopAir France
35h 25mPMO-ORD
$967
7/28Sun
2 stopsBritish Airways
17h 34mORD-PMO
8/12Mon
1 stopBritish Airways
25h 00mPMO-ORD
$969
7/30Tue
2 stopsDelta
20h 10mORD-PMO
8/13Tue
2 stopsDelta
23h 39mPMO-ORD
$994
9/17Tue
2 stopsLufthansa
18h 25mORD-CTA
9/26Thu
2 stopsLufthansa
20h 55mCTA-ORD
$1,009
9/6Fri
1 stopLufthansa
19h 30mORD-CTA
9/14Sat
1 stopLufthansa
13h 30mCTA-ORD
$1,156
7/10Wed
2 stopsDelta
20h 10mORD-PMO
7/27Sat
2 stopsDelta
24h 19mPMO-ORD
$1,188

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Recent one-way flight deals

9/27Fri
2 stops
22h 31mORD-CTA
$252
5/15Wed
2 stops
53h 30mORD-CTA
$393
6/15Sat
3 stops
59h 29mORD-PMO
$412
9/27Fri
1 stopScandinavian Airlines
30h 40mORD-CTA
$631
8/1Thu
1 stopITA Airways
12h 30mORD-PMO
$752
6/15Sat
1 stopTurkish Airlines
15h 00mORD-PMO
$874
5/24Fri
1 stopTurkish Airlines
71h 50mORD-CTA
$954
5/15Wed
1 stopEmirates
32h 15mORD-CTA
$1,023
6/1Sat
1 stopITA Airways
16h 25mORD-PMO
$1,095
8/30Fri
1 stopScandinavian Airlines
32h 55mORD-CTA
$2,091

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Last minute flights from O'Hare Intl to Sicily

Last minute flight, train and bus deals

5/4Sat
multi-stop
19h 20mORD-PMO
5/7Tue
multi-stop
36h 36mPMO-ORD
$965
5/4Sat
multi-stopITA Airways
16h 00mORD-PMO
5/7Tue
multi-stopITA Airways
14h 00mPMO-ORD
$979
5/4Sat
multi-stop
12h 20mORD-PMO
5/7Tue
multi-stop
14h 00mPMO-ORD
$986
5/4Sat
multi-stopITA Airways
32h 40mORD-CTA
5/12Sun
multi-stopITA Airways
24h 55mCTA-ORD
$987
5/7Tue
multi-stop
12h 20mORD-PMO
5/28Tue
multi-stop
43h 44mPMO-ORD
$1,087
5/6Mon
multi-stopTAP AIR PORTUGAL
37h 30mORD-PMO
5/28Tue
multi-stopTAP AIR PORTUGAL
37h 05mPMO-ORD
$1,367
5/6Mon
multi-stopTAP AIR PORTUGAL
21h 50mORD-PMO
5/27Mon
multi-stopTAP AIR PORTUGAL
55h 55mPMO-ORD
$1,403
5/4Sat
multi-stopAer Lingus
14h 05mORD-CTA
5/12Sun
multi-stopAer Lingus
26h 10mCTA-ORD
$1,535
5/4Sat
multi-stopAer Lingus
14h 05mORD-CTA
5/12Sun
multi-stopAer Lingus
26h 10mCTA-ORD
$1,638
5/7Tue
multi-stopLufthansa
12h 35mORD-PMO
5/28Tue
multi-stopLufthansa
31h 40mPMO-ORD
$2,059

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Chicago O'Hare Airport - Sicily Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Sicily - Chicago O'Hare Airport

Cabin classes: