$336 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 8/4. 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
Palermo2 stops$714
Catania
Catania1 stop$785
Palermo
Palermo2 stops$714
Catania
Catania1 stop$785

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

Sun, Nov 8 - Tue, Nov 17
Multiple Airlines Logo
8:10 pm - 9:50 pm
ORD
-
PMO
18h 40m
2 stops
Multiple Airlines Logo
10:25 pm - 3:30 pm
PMO
-
ORD
24h 05m
2 stops
$714Multiple Airlines
Wed, Aug 12 - Wed, Aug 19
SWISS Logo
2:20 pm - 2:05 pm
ORD
-
PMO
16h 45m
1 stop
SWISS Logo
7:25 pm - 12:35 pm
PMO
-
ORD
24h 10m
1 stop
$764SWISS
Sun, Aug 16 - Thu, Aug 27
SWISS Logo
7:05 pm - 2:05 pm
ORD
-
PMO
12h 00m
1 stop
SWISS Logo
9:45 am - 3:55 pm
PMO
-
ORD
13h 10m
1 stop
$765SWISS
Wed, Aug 19 - Wed, Sep 9
Turkish Airlines Logo
11:25 am - 8:25 am
ORD
-
PMO
14h 00m
1 stop
Turkish Airlines Logo
7:35 pm - 9:40 am
PMO
-
ORD
21h 05m
1 stop
$779Turkish Airlines
Tue, Aug 18 - Tue, Sep 22
Turkish Airlines Logo
11:25 am - 6:35 pm
ORD
-
PMO
24h 10m
1 stop
Turkish Airlines Logo
7:35 pm - 9:40 am
PMO
-
ORD
21h 05m
1 stop
$781Turkish Airlines
Sun, Aug 2 - Tue, Aug 18
ITA Airways Logo
3:00 pm - 1:25 pm
ORD
-
CTA
15h 25m
1 stop
ITA Airways Logo
9:30 pm - 1:10 pm
CTA
-
ORD
22h 40m
1 stop
$785ITA Airways
Sun, Aug 2 - Tue, Aug 18
ITA Airways Logo
3:00 pm - 2:40 pm
ORD
-
CTA
16h 40m
1 stop
ITA Airways Logo
9:30 pm - 1:10 pm
CTA
-
ORD
22h 40m
1 stop
$798ITA Airways
Sun, Aug 16 - Sun, Aug 23
Iberia Logo
4:55 pm - 7:05 pm
ORD
-
CTA
19h 10m
1 stop
Iberia Logo
12:00 pm - 2:25 pm
CTA
-
ORD
33h 25m
1 stop
$825Iberia
Sun, Oct 18 - Thu, Oct 22
TAP AIR PORTUGAL Logo
6:00 pm - 11:00 pm
ORD
-
SUF
22h 00m
2 stops
TAP AIR PORTUGAL Logo
6:15 am - 4:00 pm
SUF
-
ORD
40h 45m
2 stops
$985TAP AIR PORTUGAL
Sun, Oct 18 - Thu, Oct 22
TAP AIR PORTUGAL Logo
6:00 pm - 11:00 pm
ORD
-
SUF
22h 00m
2 stops
TAP AIR PORTUGAL Logo
6:15 am - 4:00 pm
SUF
-
ORD
40h 45m
2 stops
$986TAP AIR PORTUGAL
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 August.

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 March, when the average cost of round-trip tickets is $669 and $585 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$336
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 20% lower on average.
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.

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 1968 reviews
7.1Food
7.7Boarding
6.8Entertainment
7.4Comfort
8.3Crew
Airline reviews

3hr delay and then missed connecting flight with another 6hr wait at the airport before getting a continuation to my trip, worst trip ever in my 50+years of flight travel

4.0 OkayAnonymous, May 2026
TPA - ZRH
Read more SWISS reviews

3hr delay and then missed connecting flight with another 6hr wait at the airport before getting a continuation to my trip, worst trip ever in my 50+years of flight travel

Without a doubt, my “customer service” experience with SWISS was the worst of my life. Multiple disconnections in conversations, very cold and indifferent staff, failure to follow up with promised status updates — simply put, T. H. E. W. O. R. S. T. A full week later, and I am STILL waiting to hear from them. Never again for me with SWISS. Disgraceful.

The flight and all amenities were good to excellent. SWISS was awful to deal with. Every step of the way they nickel and dime you. Chose your seats? $14. Change your seats… No accounting for the prior payment. You get billed again. 17 pound restriction on overhead luggage, nonsense. It’s a weight in the plane whether it’s in the overhead or in check baggage. They just milk you for every cent they can and I resent it. The flight was excellent.

plenty of legspace, snacks, no pull face from flight attendants when asking for a wine. Also fast transfer ability at ZRH.

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.

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.

Entertainment system is okay, flight attendants were ok. Leg space very narrow, I couldn’t get what I wanted to eat, dinner nor breakfast.

Excellent experience with business class area. Staff was attentive and food was amazing. Only one bathroom for business class which was logistically difficult for the staff while preparing meals. Need to offer fluids with meals. I did not get enough water to drink. But overall I rate it 5 star.

On time, great food, good drink selection! Only down was alcohol-free lounge. Lufthansa had a much better offering!

Be honest of what you sell: This was sold as Business Class on all three legs, while the JetBlue plane didn't even have business class seats, and wanted $164 for extra legroom seats.

Seat assignments for family traveling with 2 children. Loud crowd during sleep time

Very good. I was happy that business seats were in a 1-2-1 configuration for the long haul flight. The shorter flight was a 2-2-2 configuration which I do not like as much, but it was a 3 hour flight that I slept through.

It was crowded… the bathrooms dirty and smelly. The seats have been made even smaller.

delayed to take off from detroit by 3 hours lost baggage in istanbul and now in venice without baggage

Seats were very tight with poor legroom - and I am average height. During the 12 hour flight, tiny paper cups of drinks we're only offered during the super and breakfast services, with the crew nowhere to be seen in between. One of the bathrooms was out of order, leading to long lines waiting to use the remaining two available to the economy class passengers.

short flight but we still got a very nice lunch and the crew did an excellent job in taking care of us

Never made it to Lufthansa because of Air Canadas negligence.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

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

ITA has these new Airbus A330 Neo that hates economy class passengers. The seats have absolutely no cushion to a point where it hits your spine constantly and reminds you to fork out for premium economy or don’t travel next time. The food was absolutely horrible, ETA mentioned 3 meals for 12 hour flight but it was mostly 1 meal and 2 light snacks. I am vegetarian, so my 2’d food was 1 slice of tomato, 1 cucumber on a dry cold bun. The other 2 meals were disgusting. My young one threw up the entire time. Flight attendants were the cherry on top - plain bad. They would skip servicing drinks to some passengers completely and if you call for an attendant, they will come and stop the button on top without even asking you what you need. I would avoid ITA by all means - there are plenty of options including SAS for same routes with better seats and humane treatment.

Nice flight. Uneventful, very good crew, comfortable seats. Pleasant experience.

Stews were nice. Plane was very old. Some of the mechanics for travelers outdated. Not enough bathrooms. Hideous food.

Our flight was changed to a day we could not travel so we cancelled it. Will never use kayak again

Comfortable flight Attendants are professional Had a luggage delay at one destination but was delivered the next day

ITA cancelled fligh rebooked with Lufthansa. Flight good, but 2hour connection in Frankfurt was HORRIBLE, took 1.9 hours to get through scanner, customs, another security, got to gate after running all the way, so caught it but stressful and terrible start to trip.

The boarding process was organized and efficient, and the crew was friendly and attentive throughout the flight. Food and drinks were typical economy class, but good. The aircraft was old, and the restroom was not very clean. However, we arrived on time, so overall the experience was good.

In Prem Econ, safe and timely flight, good amount of space, mostly comfortable seats. Little irritants: When lying down, seat kept shifting on me...as a short person w/light weight, my seat often reverted to semi-upright. Footrest was broken. TV screen didn't work, after I asked a few times a FA rebooted it to work again. And food was marginal. I don't expect much from airplane food...surprisingly, ITA didn't even meet expectations.

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

Information on your arrival and departure airports