$299 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 4/14. 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

Sun, Aug 16 - Thu, Aug 27
SWISS Logo
2:20 pm - 9:00 am
ORD
-
PMO
11h 40m
1 stop
SWISS Logo
9:45 am - 3:55 pm
PMO
-
ORD
13h 10m
1 stop
$487SWISS
Wed, Apr 15 - Wed, Apr 22
SWISS Logo
2:20 pm - 9:00 am
ORD
-
PMO
11h 40m
1 stop
SWISS Logo
2:55 pm - 12:35 pm
PMO
-
ORD
28h 40m
1 stop
$496SWISS
Sun, Aug 16 - Thu, Aug 27
SWISS Logo
7:05 pm - 9:00 am
ORD
-
PMO
30h 55m
1 stop
SWISS Logo
9:45 am - 12:35 pm
PMO
-
ORD
33h 50m
1 stop
$512SWISS
Sun, Aug 16 - Thu, Aug 27
Austrian Airlines Logo
4:20 pm - 8:50 am
ORD
-
PMO
33h 30m
1 stop
Austrian Airlines Logo
8:10 pm - 6:37 pm
PMO
-
ORD
29h 27m
2 stops
$527Austrian Airlines
Sun, Aug 16 - Thu, Aug 27
SWISS Logo
2:20 pm - 9:00 am
ORD
-
PMO
11h 40m
1 stop
SWISS Logo
9:45 am - 3:55 pm
PMO
-
ORD
13h 10m
1 stop
$532SWISS
Wed, Apr 15 - Wed, Apr 22
Lufthansa Logo
9:40 pm - 5:20 pm
ORD
-
PMO
12h 40m
1 stop
Lufthansa Logo
6:10 pm - 12:55 pm
PMO
-
ORD
25h 45m
2 stops
$533Lufthansa
Tue, Apr 14 - Thu, Apr 30
Turkish Airlines Logo
8:10 pm - 8:25 am
ORD
-
PMO
29h 15m
1 stop
Turkish Airlines Logo
9:25 am - 9:40 am
PMO
-
ORD
31h 15m
1 stop
$540Turkish Airlines
Wed, Apr 15 - Wed, Apr 22
Turkish Airlines Logo
8:10 pm - 6:25 pm
ORD
-
CTA
15h 15m
1 stop
Turkish Airlines Logo
9:25 am - 9:40 am
CTA
-
ORD
31h 15m
1 stop
$542Turkish Airlines
Thu, Aug 6 - Mon, Sep 7
ITA Airways Logo
8:40 am - 10:30 am
ORD
-
SUF
18h 50m
2 stops
ITA Airways Logo
6:15 am - 1:10 pm
SUF
-
ORD
13h 55m
1 stop
$899ITA Airways
Thu, Aug 6 - Mon, Sep 7
ITA Airways Logo
3:00 pm - 10:30 am
ORD
-
SUF
12h 30m
1 stop
ITA Airways Logo
7:15 pm - 1:10 pm
SUF
-
ORD
24h 55m
1 stop
$900ITA Airways
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 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 November, when tickets cost $535 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,335 and $1,243 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$299
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago O'Hare 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 1901 reviews
8.3Crew
7.4Comfort
7.7Boarding
7.1Food
6.8Entertainment
Airline reviews

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.

6.0 GoodSonja, Jan 2026
BOS - ZRH
Read more SWISS reviews

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.

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.

IAH to Istanbul was outstanding across the board. The flight from Istanbul to Male was good, not great.

the cabin was kept too hot. couldn't sleep as a result

It was an amazing experience. Flight crew's service, hospitality, and the food were phenomenal. I don't think I'd want to try any other airline company after this. I would definitely recommend to friends and family. Thank you Turkish Airlines !

Business Class pods are horrible. If you're petite, you might be able to sleep on the uncomfortable seat and bed. Crew and food are fantastic.

I have travelled many times on Turkish, but they always board at least 30-40 minutes past the stated time. If informed properly, passengers can choose to spend more time in the .lounge instead of standing around by the gate waiting to board. The new lounge at DFW was a big disappointment. The aircraft itself was a shock. In the past I have flown this sector with regular business class seating configuration of 1-2-1, The 2-3-2 seating is very disappointing after paying such high prices for tickets. The DFW to Istanbul segment was slightly better, but the Istanbul to Delhi segment was no better than premium economy. I will try to travel more on airlines which give business class passengers more value for their money.

Good overall. Seat spacing a bit tight between IST and ISB.

Excellent staff despite some trying passenger situations. Very impressed with their good attitudes and kindness.

Crew were unfriendly, touch screen for movies didn't work very well, seats were tight and uncomfortable

After arriving in Istanbul, the transit information on the electronic board showed a tight departure time, and the gate changed in the middle, making it difficult to make it on time.

Typically good service onboard but baggage delay in airport was significant

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

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.

The flight was canceled and we have not received the refund

They lost my checked in bag and have not helped me.

First, ITA lost my bag and the baggage team showed no regard in trying to find it. Second, I had paid for priority boarding as part of a first class ticket and instead they disregarded boarding groups and we all boarded at the same time. Third, wasn't allowed to select my seat in advance even with a first class ticket. When I was assigned bulkhead, I was told I would need to pay to change my seat. Overall, very disappointing experience.

The seats needs to be spruced up , for a long flight very uncomfortable , cushions are worn out but everything else is very good , crew is great.

I guess that was fine with ITA but the Rome airport is so difficult to navigate with so many checkpoints getting new tickets from what was originally given to me

My seat was broken and ducted taped and my monitor did not work the entire time over 8 hrs sitting. And I had no books or anything with me

my flight from Rome to Boston was on a very old plane. My video and audio did not work.

Good with timing of flights. The crew was exceptionally unfriendly. I heard more than one person say this. And even with the aisle, it seemed more uncomfortable than usual. The movie selection was old and poor, but the dinner was great - the lasagna and tiramisu.

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.

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.