$315 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 1/15. 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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Flight Deals

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

Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
6:30 pm - 11:25 pm
ORD
-
PMO
21h 55m2 stops
Multiple Airlines Logo
10:25 pm - 5:20 pm
PMO
-
ORD
25h 55m2 stops
$491Multiple Airlines
Sat, Apr 11 - Sat, Apr 18
Turkish Airlines Logo
11:25 am - 8:20 am
ORD
-
PMO
13h 55m1 stop
Turkish Airlines Logo
7:20 pm - 9:40 am
PMO
-
ORD
21h 20m1 stop
$518Turkish Airlines
Wed, Feb 11 - Tue, Feb 17
Turkish Airlines Logo
8:20 pm - 6:25 pm
ORD
-
CTA
15h 05m1 stop
Turkish Airlines Logo
7:25 pm - 10:05 am
CTA
-
ORD
21h 40m1 stop
$518Turkish Airlines
Wed, Feb 4 - Wed, Feb 11
Turkish Airlines Logo
8:20 pm - 8:30 am
ORD
-
PMO
29h 10m1 stop
Turkish Airlines Logo
6:45 pm - 10:05 am
PMO
-
ORD
22h 20m1 stop
$521Turkish Airlines
Tue, Feb 10 - Mon, Feb 16
SWISS Logo
6:50 pm - 8:40 pm
ORD
-
CTA
18h 50m1 stop
SWISS Logo
8:40 pm - 12:45 pm
CTA
-
ORD
23h 05m1 stop
$669SWISS
Tue, Feb 10 - Mon, Feb 16
SWISS Logo
5:50 pm - 8:40 pm
ORD
-
CTA
19h 50m2 stops
SWISS Logo
8:40 pm - 12:45 pm
CTA
-
ORD
23h 05m1 stop
$676SWISS
Sat, Jan 24 - Sat, Jan 31
KLM Logo
10:46 am - 1:40 pm
MDW
-
PMO
19h 54m2 stops
KLM Logo
6:10 am - 10:22 pm
PMO
-
MDW
23h 12m2 stops
$769KLM
Tue, Apr 7 - Wed, Apr 22
ITA Airways Logo
10:40 am - 6:30 pm
ORD
-
SUF
24h 50m2 stops
ITA Airways Logo
6:15 am - 1:10 pm
SUF
-
ORD
13h 55m1 stop
$829ITA Airways
Tue, Apr 7 - Wed, Apr 22
Lufthansa Logo
3:40 pm - 6:30 pm
ORD
-
SUF
19h 50m1 stop
Lufthansa Logo
6:15 am - 1:05 pm
SUF
-
ORD
13h 50m1 stop
$833Lufthansa
Fri, Jan 23 - Fri, Jan 30
KLM Logo
12:48 pm - 1:40 pm
MDW
-
PMO
17h 52m2 stops
KLM Logo
10:00 am - 10:22 pm
PMO
-
MDW
19h 22m2 stops
$1,297KLM
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 10 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$315
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago to Catania

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 4 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.
7.5
SWISSOverall score based on 1810 reviews
6.8Entertainment
7.1Food
8.3Crew
7.4Comfort
7.7Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Sep 2025
DEN - ZRH
Read more SWISS reviews

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

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

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.

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

nice and clean plane but the seats and the comfort was not what i expected. i expected more based on all the ads and reviews that i've read. I guess you get what you pay for in economy.

Overall it was good. Food was bad. I ordered gluten free vegetarian meal. But I got gluten free chicken for my long flight from Seattle to Istanbul. I don’t eat any kind of meat. Second meal I got eggplant with meat which I couldn’t eat. I don’t understand why we can’t get gluten free vegetarian meal for a 12 hour flight. I eat the bread and that was it.

Worse worse worse, i would not recommend this airline to anyone. Istanbul airport maybe State of the Art facility but staff is rude, only works if they get tips, and they push you to give tips even though my family had spent $50 in tips. Airline staff doesn't speak english so you really can't understand them. It was a nightmare travelling with Turkish. Never again.

As a big guy the seats are way too small for me. Would prefer more comfortable seats on these long haul flights.

My flight was canceled 1 minute before boarding. The customer service was owful, no one could tell us what was going happened. I spent 30hrs instead of 15 from Washington DC to Brussels. No apologie or help

Boeing 777 is a bad choice for a such a long flight.

The staff at IST airport could have been more helpful. Too much wasted time and the plane from IST to KHI was just horrible. The plane was not clean and smelled bad!

This is my 2nd time with the Turkish airline. Would definitely recommend. In stability we connected to Indiago would not recommend, very cramped seating. No inflight entertainment..service was inferior.

I wouldn't know what the flight was like. AI canceled my flight reservation!! There's no way to speak to an actual human to fix the issue! NEVER AGAIN! ALWAYS BOOK YOUR FLIGHT DIRECTLY WITH THE AIRLINE NEVER GO THROUGH KAYAK OR JUSTFLY.COM!!

Paying extra for premium seats was wasted. Turkish Airlines takes 2 seats for bassinet. The lady next to me had a baby with bassinet Bassinet was in front of my seat

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.

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 check in process is chaotic. It says partially checked-in. Never heard of such a thing. Then lost our reserved seats when we finally checked in at the airport. The seats don’t recline. Then we had to get mew boarding passes at the connection. Last, my companion lost her baggage and up to now there’s no update. We’re already half-way through our vacation and still no news what happened to the luggage.

Wonderful! Everyone very helpful and kind. Returning flight was cancelled but rebooking was easy.

Pretty normal flight was delayed due to traffic could have missed connecting flight to Venice but crew kept us well informed so we made it

Flight was on time and pretty standard. No Hiccups. I have no complaints, which is a lot to say about a 12 hour flight.

-The seats could be roomier -The entertainment in English could be more current! The moves were very old!!! -They served too many carbs! What happened to fruit and yogurt!!!!

We upgraded to premium economy and it made a difference in a 12 hr flight. I didn’t like that we had to deplane in the tarmac with our carryon luggage. Other than that, it was ok.

Everything was much better than I had expected, since I hadn’t heard of your airline before. I hope to take advantage of your excellent service again.

Staff were nice, we left on time and arrived early, food was good. Unfortunately, they lost one of our bags and have been unable to find it. So we are in Italy for a week for my husband‘s birthday and he does not have any of his clothing.

They gave us sandwiches as a meal twice. Snacks mid flight with cookies and a tuna panini. Then just the same tuna panini for dinner. That was it.

Top notch re cleanliness, comfort, operational. Attendants attentive, cheerful, courteous and professional. An unusually high-grade experience all around.

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.