$330 Find Cheap Flights from Chicago to Sicily - Compare and Save

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 9/13. 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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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

Mon, Sep 21 - Tue, Oct 20
Turkish Airlines Logo
8:10 pm - 6:40 pm
ORD
-
PMO
15h 30m
1 stop
Turkish Airlines Logo
7:40 pm - 9:40 am
PMO
-
ORD
21h 00m
1 stop
$692Turkish Airlines
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
8:10 pm - 11:50 pm
ORD
-
PMO
20h 40m
2 stops
Multiple Airlines Logo
6:15 am - 9:40 am
PMO
-
ORD
34h 25m
2 stops
$694Multiple Airlines
Mon, Sep 21 - Tue, Oct 20
Turkish Airlines Logo
8:10 pm - 6:40 pm
ORD
-
PMO
15h 30m
1 stop
Turkish Airlines Logo
7:40 pm - 9:40 am
PMO
-
ORD
21h 00m
1 stop
$696Turkish Airlines
Sun, Aug 16 - Thu, Aug 27
ITA Airways Logo
3:00 pm - 2:00 pm
ORD
-
PMO
16h 00m
1 stop
ITA Airways Logo
6:10 am - 1:10 pm
PMO
-
ORD
14h 00m
1 stop
$709ITA Airways
Mon, Sep 14 - Wed, Sep 23
Multiple Airlines Logo
11:25 am - 10:40 pm
ORD
-
PMO
28h 15m
2 stops
Multiple Airlines Logo
7:15 am - 9:40 am
PMO
-
ORD
33h 25m
2 stops
$735Multiple Airlines
Tue, Aug 18 - Thu, Aug 27
ITA Airways Logo
3:00 pm - 2:40 pm
ORD
-
CTA
16h 40m
1 stop
ITA Airways Logo
6:00 am - 1:10 pm
CTA
-
ORD
14h 10m
1 stop
$748ITA Airways
Mon, Aug 17 - Mon, Aug 31
SWISS Logo
2:20 pm - 2:05 pm
ORD
-
PMO
16h 45m
1 stop
SWISS Logo
9:45 am - 3:55 pm
PMO
-
ORD
13h 10m
1 stop
$809SWISS
Tue, Aug 25 - Mon, Aug 31
SWISS Logo
7:05 pm - 6:40 pm
ORD
-
PMO
16h 35m
1 stop
SWISS Logo
9:45 am - 3:55 pm
PMO
-
ORD
13h 10m
1 stop
$809SWISS
Sat, Aug 15 - Tue, Aug 25
Lufthansa Logo
7:45 pm - 7:15 am
ORD
-
PMO
28h 30m
1 stop
Lufthansa Logo
11:50 am - 11:40 pm
PMO
-
ORD
18h 50m
2 stops
$865Lufthansa
Sat, Aug 15 - Mon, Aug 24
Lufthansa Logo
9:40 pm - 5:30 pm
ORD
-
PMO
12h 50m
1 stop
Lufthansa Logo
6:10 pm - 12:55 pm
PMO
-
ORD
25h 45m
2 stops
$868Lufthansa
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.

How much is a round-trip flight from Chicago 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 to Sicily departing in November.

Flight prices are below average for this route right now.

Flights to Sicily from Chicago usually cost between $736 and $1,062 in November.
The lowest price found in the past 5 days was $698 on Turkish Airlines (Nov 19-Nov 24).

What is the cheapest month to fly from Chicago to Sicily?

To calculate monthly average prices, KAYAK takes all prices for each month 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 median of all values for each month.

The cheapest month for flights from Chicago to Sicily is January, when tickets cost $702 (return) on average. On the other hand, the most expensive months are May and June, when the average cost of round-trip tickets is $1,346 and $1,346 respectively.

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 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low season

November

Cheapest flight

$330
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago Midway Airport to Palermo

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.

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 2022 reviews
7.1Food
8.3Crew
7.7Boarding
7.4Comfort
6.8Entertainment
Airline reviews

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

2.0 MediocreAndrew, Dec 2025
ZRH - FCO
Read more SWISS reviews

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

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

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.

The seats had no space at all beyond the knees. The seat in-front literally reclined on your face, very uncomfortable plane. Was nothing like the normal SWISS experience. The food was okay but could be better.

They rebooked our flight and then canceled our trip halfway through the journey without any explanation. Needed to pay by ourselves for alternative flight options without any help from Swiss.

Easy boarding Seats were very uncomfortable no room arm rests didn't even go up all the way

Wonderful experience! The crew was outstanding and amazing from check in to gate to flight crew! Amazing. Thank you!

Carry on luggage size for economy passengers significantly smaller than other airlines, so nearly all ecomy passengers had their bags taken and checked.

Swiss ground crew was again at its prime and although I’m United 1K (Star Alliance Gold) they created problems with my hand luggage - while other passengers were boarding with more handbags and larger hand luggages, were critical on my 2 young kids attending the lounge with me and boarding the plane with me on the priority lane.

Missed connecting train since flight was late into Zurich and I had to stay at airport hotel because of it as well as I had to repurchase train ticket

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

My, Syed Zawar Hussein Shirazi frequently flyer membership number was not included on my boarding pass from O’Hare to Istanbul despite my reminder to the attendant at check in. Further she forgot to give me my boarding pass form Istanbul to Lahore and she needs to improve her customer service, please 🙏

Chicago to Istanbul was a much better experience than I expected since I’m more accustomed to Qatar Airways business class. The business lounge in the Istanbul airport was amazing - loved the lockers and phone charging stations, and the bathroom was a spa experience in itself. The onward leg from Istanbul to Karachi was utterly disappointing. Terrible plane, and I felt like I was in economy - the seats don’t come near to lying flat and the food was mediocre. What a sad downgrade - it isn’t as though the ticket on that leg was cheaper. So, on that front, there’s no contest with Qatar airways.

Second leg of Turkish Airline with Indigo is disaster for following reason. 1) You have to carry your cabin bags through ladder to boeing 777 because it was parked somewhere in parking lot and was not given a gate to board passengers and this seems to be people traveling to and fro from those flights and is not issue with flight itself. 2) I choose non vegetarian food on Turkish portal way ahead of checkin to entire trip, However the Indigo flight gave me random veg food saying they code veg food code from Turkish. 3) Indigo did not served any alcoholic beverages stating some weird reason which is non nonsensical. 4)Indigo have TV screens in front of you but it displays nothing except "Welcome Onboard" with annoying white black ground in dark flight. This is the most stupidest and annoying part because you are held hostage for 7 hours and only thing you could do is stare back at white screen which does not have entertainment package or even flight tracker. Such a shame.

During mid flight, try to get a flight attendant to help I couldn’t find one Otherwise, everything was perfect

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

7 stars hospitality and an excellent service by the Turkish Airline entire team. Somehow, our membership numbers for mileage points were not indicated on our boarding passes issued at O’Hare Airport by the Turkish Airlines check in desk. During transit in Istanbul, I brought to attention of customer service Turkish Airlines. Please have our mileage points posted to our membership account from O’Hare Chicago to Lahore for both my wife Kaukab Shirazi Thank you

Terrible boarding process, no proper line maintained even for business class, crews are not very attentive, business class food quality / variety / quantity have gone down, everything has become cheap.

Food quality and the overall service of the staff and significantly decreased. The flight was delayed at the Istanbul airport and the passengers were kept onboard for more than 3 hours. The staff didn’t kept the passengers informed and everyone was upset.

Turkish Airlines apparently no longer gives you 2 checked bags allowance on international flights, so that pleasure cost me $165 for my second suitcase at the airport. On top of that, they damaged that very suitcase, which happens to be a designer one and part of a set - ripped one of the four wheels right off.

It was okay. Mothers with rowdy children should be invited to sit in front of them.

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.

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

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.

Flew Premium Economy. The seats were comfortable and tilted back far enough to sleep. Food was okay and service friendly and efficient. We bought tickets through Kayak partner Underpricer and the price was good.

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.

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.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

It was fine. I wish there were more or better selections for entertainment.

The worst part about the trip was the seat. It looked old, with a sagging cushion and crumbs on it before I sat down. When I sat down I saw that the back of the seat was broken and it would only stay in one (reclined) position. I had purposefully paid extra ($65) for that seat because a) I can only sleep on translatlantic flights if I am next to the window and b) I wanted to be close to the front because I had a tight connecting flight in Rome. One flight attendant didn't care about the problem while another offered me a middle seat in the back of the plane. Of course he did not mention a refund for the fee I had paid for this seat. The food was mediocre, not even close to the good food in Alitalia, back in the day. The entertainment system did not work when I tried to "follow the flight". English of announcements was often impossible to understand (spoke poorly and too fast).

The boarding was delayed and they didn’t let us know why until after we sat on the plane (the plane was delayed getting in) but they had us waiting in line for over 1/2 hour for some reason which I didn’t understand.

Terrible service, uninterested employees, inefficient boarding process, and marginal set up on plane. Staff make the airline - good luck with this one.

Long delay, lack of space at the seats (not comfortable).

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.