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Find cheap flights from Chicago to Sicily from $306

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 8/22. 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
Thu 7/11
Thu 7/18

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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$559

Good to know

Low season

January

High season

September

Cheapest flight

$306
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 10% 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 to Sicily from Chicago 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 to Sicily with an airline and back to Chicago 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 to Sicily from Chicago 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 15% cheaper than an evening flight, on average*.
  • 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.
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 Chicago to Sicily

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.
7.8
Cathay PacificOverall score based on 1029 reviews
7.8Comfort
7.5Food
8.2Crew
8.0Boarding
8.0Entertainment
Airline reviews

Bad experience. Departure time delayed from 1610 to 1740. After the flight was pushed back, pilot said there was a technical issue on the aircraft and we couldn’t take off. Delayed another hour to solve it.

2.0 MediocreAnonymous, Jun 2024TPE - HKG
Read more about Cathay Pacific reviews

Bad experience. Departure time delayed from 1610 to 1740. After the flight was pushed back, pilot said there was a technical issue on the aircraft and we couldn’t take off. Delayed another hour to solve it.

Great, the flight attendants were very friendly and the food was also good.

The first economy rows have remote space in the seat which eats in the seating space. The seats are also smaller compared to other airlines.

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.

I cancelled the flights in good time but could only get a partial refund. I was not warned of this.

Not good. Flight was purchased for my father who needed medical assistance to board and transfer due to a heart condition. No one at Hong Kong from Cathay was there to assist and he barely made the connection. When I talked to him he could barely breath and was not sure he was going to make it. Really poor service even though the ticket stated he needed a wheelchair assistance.

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

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?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

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.

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Sicily

Recent round-trip flight deals

9/23Mon
1 stopScandinavian Airlines
30h 35mORD-PMO
10/16Wed
1 stopScandinavian Airlines
14h 45mPMO-ORD
$559
10/7Mon
1 stopScandinavian Airlines
30h 35mORD-PMO
10/16Wed
1 stopScandinavian Airlines
14h 45mPMO-ORD
$589
10/13Sun
1 stopTurkish Airlines
14h 45mORD-CTA
10/21Mon
1 stopTurkish Airlines
21h 25mCTA-ORD
$660
9/24Tue
1 stopTurkish Airlines
15h 00mORD-PMO
10/16Wed
1 stopTurkish Airlines
21h 10mPMO-ORD
$664
11/3Sun
1 stopLufthansa
18h 20mORD-CTA
11/17Sun
1 stopLufthansa
31h 50mCTA-ORD
$819
11/3Sun
1 stopLufthansa
18h 20mORD-CTA
11/10Sun
2 stopsLufthansa
26h 50mCTA-ORD
$857
8/4Sun
1 stopDelta
33h 25mORD-PMO
8/20Tue
2 stopsDelta
24h 44mPMO-ORD
$862
11/6Wed
2 stopsAir France
20h 35mORD-CTA
11/11Mon
2 stopsAir France
36h 40mCTA-ORD
$934
7/30Tue
2 stopsDelta
20h 01mORD-PMO
8/13Tue
2 stopsDelta
21h 19mPMO-ORD
$956
9/11Wed
2 stopsAir France
34h 15mORD-CTA
9/16Mon
2 stopsAir France
35h 49mCTA-ORD
$1,067

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Recent one-way flight deals

8/22Thu
3 stops
27h 10mORD-PMO
$306
9/14Sat
2 stops
32h 28mORD-PMO
$358
10/11Fri
2 stops
23h 48mORD-CTA
$410
7/1Mon
3 stops
37h 29mMDW-PMO
$414
10/11Fri
3 stops
25h 28mORD-CTA
$435
10/2Wed
1 stopITA Airways
13h 55mORD-PMO
$624
8/22Thu
1 stopITA Airways
13h 55mORD-PMO
$664
10/15Tue
1 stopTurkish Airlines
15h 00mORD-PMO
$707
6/27Thu
1 stopScandinavian Airlines
16h 00mORD-PMO
$821
6/27Thu
2 stopsDelta
17h 11mMDW-PMO
$3,270

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Last minute flights from Chicago to Sicily

Last minute flight, train and bus deals

6/16Sun
multi-stopITA Airways
18h 30mORD-PMO
6/23Sun
multi-stopITA Airways
25h 05mPMO-ORD
$1,156
6/16Sun
multi-stop
17h 15mORD-CTA
7/1Mon
multi-stop
15h 00mCTA-ORD
$1,252
6/15Sat
multi-stop
12h 10mORD-CTA
6/26Wed
multi-stop
21h 40mCTA-ORD
$1,265
6/15Sat
multi-stop
12h 10mORD-CTA
7/2Tue
multi-stop
21h 55mCTA-ORD
$1,269
6/15Sat
multi-stopBritish Airways
18h 45mORD-CTA
7/1Mon
multi-stopBritish Airways
32h 30mCTA-ORD
$1,274
6/15Sat
multi-stopBritish Airways
18h 45mORD-CTA
6/28Fri
multi-stopBritish Airways
30h 30mCTA-ORD
$1,324
6/16Sun
multi-stopIberia
23h 25mORD-CTA
6/27Thu
multi-stopIberia
25h 30mCTA-ORD
$1,405
6/16Sun
multi-stopLufthansa
29h 35mORD-PMO
6/23Sun
multi-stopLufthansa
25h 20mPMO-ORD
$1,499
6/15Sat
multi-stopKLM
15h 35mORD-CTA
6/26Wed
multi-stopKLM
25h 20mCTA-ORD
$1,716
6/15Sat
multi-stopKLM
15h 35mORD-CTA
7/2Tue
multi-stopKLM
24h 20mCTA-ORD
$1,774

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Flights to Sicily

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