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Find cheap flights from Chicago to Sicily from $437

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 6/27. 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
Sat 6/29
Sat 7/6

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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$776

Good to know

Low season

January

High season

September

Cheapest flight

$437
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 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 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 1% more expensive 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.
8.3
EVA AirOverall score based on 1500 reviews
8.6Crew
8.4Boarding
8.2Comfort
8.0Entertainment
7.9Food
Airline reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

8.0 ExcellentYue, May 2024IAH - TPE
Read more about EVA Air reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

The hygiene of the bathrooms were terrible. Urine smells leaked out into the cabin and the seats were really tight, even for a petite woman like myself. Flight attendants did not go through the cabin enough to offer refreshments.

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant, comfortable, and entertaining. All told, ZERO issues with it. And sadly, so far the flight was WAY more comfortable than the hellhole that is "Lambug Beach Resort" at Badian Beach!

It was a pleasant fly with Eva Air from NYC to Taipei. The crew were friendly and the food was exceeded my expectation.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Overall the flight was what might be expected for a long haul flight to Asia in economy class. The cabin crew was attentive and the food was good. Boarding was fairly fast and easy. The one thing I found frustrating was the EVA app. It is terrible. Trying to do anything on it was almost impossible.

EVA would not help with ticket issue since they were purchased through a travel agency. Even though it was EVA ticket stock. Travel agency Budget Air didn't reissue ticket after airline change which I didn’t learn until trying to checkin on Christmas Day and there was no contact number for the agency to help. I will never use Budget Air to purchase flight again and disappointed in EVA’s refusal to help. Thankfully just under 12 hrs before departure someone from the agency was available to reissue tickets. I was starting to think we would not be flying and the stress trying to resolve was completely unacceptable.

seamless check in/ friendly staff, food is good, always love flying Eva Air

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?

The flight experience was very good! Especially the United Club!

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.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Chicago to Sicily

Recent round-trip flight deals

10/13Sun
2 stopsTAP AIR PORTUGAL
22h 15mORD-CTA
10/21Mon
2 stopsTAP AIR PORTUGAL
55h 45mCTA-ORD
$636
11/3Sun
1 stopTurkish Airlines
13h 40mORD-CTA
11/12Tue
1 stopTurkish Airlines
30h 00mCTA-ORD
$660
10/3Thu
1 stopTurkish Airlines
14h 45mORD-CTA
10/10Thu
1 stopTurkish Airlines
29h 30mCTA-ORD
$690
11/2Sat
2 stopsAir Canada
35h 35mORD-CTA
11/11Mon
3 stopsAir Canada
37h 27mCTA-ORD
$795
11/2Sat
2 stopsLufthansa
38h 00mORD-CTA
11/11Mon
1 stopLufthansa
33h 00mCTA-ORD
$811
11/2Sat
2 stopsDelta
21h 35mMDW-CTA
11/12Tue
2 stopsDelta
22h 44mCTA-MDW
$1,044
7/15Mon
2 stopsAmerican Airlines
35h 55mORD-PMO
7/29Mon
1 stopAmerican Airlines
22h 00mPMO-ORD
$1,125
7/15Mon
2 stopsAmerican Airlines
35h 40mORD-PMO
7/29Mon
2 stopsAmerican Airlines
27h 33mPMO-ORD
$1,130
8/4Sun
1 stopDelta
33h 25mORD-PMO
8/15Thu
2 stopsDelta
21h 59mPMO-ORD
$1,150
10/3Thu
2 stopsLufthansa
18h 25mORD-CTA
10/10Thu
2 stopsLufthansa
25h 20mCTA-ORD
$1,325

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Recent one-way flight deals

6/27Thu
3 stops
57h 54mMDW-PMO
$437
6/27Thu
2 stops
20h 34mMDW-PMO
$479
6/28Fri
2 stops
55h 45mORD-PMO
$483
6/27Thu
3 stops
43h 38mORD-PMO
$507
6/28Fri
3 stops
44h 30mORD-PMO
$508
6/27Thu
2 stops
51h 58mORD-PMO
$527
8/22Thu
1 stopITA Airways
13h 55mORD-PMO
$666
6/28Fri
1 stopTurkish Airlines
15h 00mORD-PMO
$872
6/27Thu
1 stopSWISS
11h 35mORD-PMO
$932
6/28Fri
2 stopsDelta
18h 45mMDW-PMO
$3,270

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Last minute flights from Chicago to Sicily

Last minute flight, train and bus deals

5/31Fri
multi-stopSWISS
29h 55mORD-CTA
6/11Tue
multi-stopSWISS
33h 20mCTA-ORD
$1,129
5/31Fri
multi-stopLufthansa
13h 25mORD-CTA
6/11Tue
multi-stopLufthansa
33h 55mCTA-ORD
$1,183
5/31Fri
multi-stopLufthansa
19h 30mORD-CTA
6/11Tue
multi-stopLufthansa
33h 15mCTA-ORD
$1,186
5/31Fri
multi-stopLufthansa
28h 45mORD-CTA
6/11Tue
multi-stopLufthansa
33h 15mCTA-ORD
$1,316
5/31Fri
multi-stop
20h 25mORD-CTA
6/11Tue
multi-stop
30h 10mCTA-ORD
$1,491
5/31Fri
multi-stopDelta
15h 54mMDW-CTA
6/8Sat
multi-stopDelta
22h 48mCTA-MDW
$3,253

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