What airlines fly to Sicily?

ITA Airways, Turkish Airlines and SWISS are the top three most popular airlines that fly to Sicily from Chicago according to our data. ITA Airways is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Sicily. Keep in mind that there are 4 different airlines that fly to Sicily on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Sicily?

Aer Lingus, ITA Airways, and Turkish Airlines are the most popular carriers operating from Chicago to Sicily

When did momondo last update prices for flights from Chicago to Sicily?

Prices for flights from Chicago to Sicily were last updated today.

How many operators does momondo search for flights from Chicago to Sicily?

As of November 2025, there are 4 operators available to choose from for flights from Chicago to Sicily.

How old do you have to be to fly from Chicago to Sicily?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Sicily.

What documentation or ID do you need to fly to Sicily?

The required travel and health documents for your Sicily trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Sicily. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$331 Cheap Flights from Chicago to Sicily in 2025/26

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Find the cheapest flights from Chicago to Sicily

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:20 pm - 8:35 amORD-CTA

29h 15m1 stop

7:25 pm - 10:05 amCTA-ORD

21h 40m1 stop

$537Turkish Airlines

Find Deal

Mon, Jan 12 - Tue, Feb 10

12:50 pm - 6:25 pmORD-CTA

23h 35m1 stop

7:25 pm - 7:25 pmCTA-ORD

30h 00m1 stop

$563Turkish Airlines

Find Deal

Thu, Mar 19 - Thu, Mar 26

11:25 am - 8:20 amORD-PMO

13h 55m1 stop

7:20 pm - 6:15 pmPMO-ORD

29h 55m1 stop

$564Turkish Airlines

Find Deal

Wed, Apr 29 - Wed, May 20

7:15 am - 2:15 pmORD-PMO

24h 00m3 stops

10:05 am - 8:10 pmPMO-ORD

17h 05m2 stops

$570Multiple Airlines

Find Deal

Tue, Feb 10 - Tue, Feb 17

7:10 pm - 6:20 pmORD-PMO

16h 10m2 stops

12:25 pm - 3:25 pmPMO-ORD

34h 00m2 stops

$623Multiple Airlines

Find Deal

Wed, Jan 14 - Thu, Feb 26

8:25 pm - 2:40 pmORD-CTA

35h 15m2 stops

2:05 pm - 3:00 pmCTA-ORD

31h 55m2 stops

$624TAP AIR PORTUGAL

Find Deal

Sun, Jan 11 - Tue, Feb 10

4:45 pm - 11:00 pmORD-SUF

24h 15m1 stop

11:15 am - 2:10 pmSUF-ORD

32h 55m1 stop

$1,221Lufthansa

Find Deal

Mon, Mar 9 - Thu, Mar 12

4:45 pm - 6:30 pmORD-SUF

19h 45m1 stop

11:15 am - 4:20 pmSUF-ORD

35h 05m2 stops

$1,223Lufthansa

Find Deal

Mon, Mar 9 - Thu, Mar 12

1:14 pm - 10:25 amMDW-PMO

14h 11m2 stops

6:10 am - 5:26 pmPMO-MDW

18h 16m2 stops

$1,244KLM

Find Deal

Tue, Dec 16 - Tue, Dec 23

5:59 pm - 11:00 pmMDW-SUF

47h 01m2 stops

11:15 am - 9:46 pmSUF-MDW

40h 31m2 stops

$1,298KLM

Find Deal

Mon, Mar 9 - Thu, Mar 12

Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Jan 12

ORD8:20 pmChicago O'Hare Intl

29h 15m

1 stop

CTA8:35 amCatania Fontanarossa

Feb 10

CTA7:25 pmCatania Fontanarossa

21h 40m

1 stop

ORD10:05 amChicago O'Hare Intl

$537

Find similar

Turkish Airlines

Mar 19

ORD12:50 pmChicago O'Hare Intl

23h 35m

1 stop

CTA6:25 pmCatania Fontanarossa

Mar 26

CTA7:25 pmCatania Fontanarossa

30h 00m

1 stop

ORD7:25 pmChicago O'Hare Intl

$563

Find similar

Turkish Airlines

Apr 29

ORD11:25 amChicago O'Hare Intl

13h 55m

1 stop

PMO8:20 amPalermo Punta Raisi

May 20

PMO7:20 pmPalermo Punta Raisi

29h 55m

1 stop

ORD6:15 pmChicago O'Hare Intl

$564

Find similar

TAP AIR PORTUGAL flights from Chicago to Sicily

Our best TAP AIR PORTUGAL deals on Chicago to Sicily flight tickets

TAP AIR PORTUGAL

Jan 11

ORD8:25 pmChicago O'Hare Intl

35h 15m

2 stops

CTA2:40 pmCatania Fontanarossa

Feb 10

CTA2:05 pmCatania Fontanarossa

31h 55m

2 stops

ORD3:00 pmChicago O'Hare Intl

$624

Find similar

TAP AIR PORTUGAL

Jan 11

ORD8:25 pmChicago O'Hare Intl

35h 15m

2 stops

CTA2:40 pmCatania Fontanarossa

Feb 9

CTA3:25 pmCatania Fontanarossa

54h 35m

2 stops

ORD3:00 pmChicago O'Hare Intl

$661

Find similar

TAP AIR PORTUGAL

Jan 7

ORD7:10 pmChicago O'Hare Intl

35h 30m

2 stops

PMO1:40 pmPalermo Punta Raisi

Feb 26

PMO10:00 amPalermo Punta Raisi

36h 25m

2 stops

ORD3:25 pmChicago O'Hare Intl

$683

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 1/12

8:20 pm-8:35 am

1 stop29h 15m

Catania Fontanarossa

Tue 2/10

7:25 pm-10:05 am

1 stop21h 40m

$537

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Thu 3/19

12:50 pm-6:25 pm

1 stop23h 35m

Catania Fontanarossa

Thu 3/26

7:25 pm-7:25 pm

1 stop30h 00m

$563

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 4/29

11:25 am-8:20 am

1 stop13h 55m

Palermo Punta Raisi

Wed 5/20

7:20 pm-6:15 pm

1 stop29h 55m

$564

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 2/10

7:15 am-2:15 pm

3 stops24h 00m

Palermo Punta Raisi

Tue 2/17

10:05 am-8:10 pm

2 stops17h 05m

$570

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 1/14

7:10 pm-6:20 pm

2 stops16h 10m

Palermo Punta Raisi

Thu 2/26

12:25 pm-3:25 pm

2 stops34h 00m

$623

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 1/11

8:25 pm-2:40 pm

2 stops35h 15m

Catania Fontanarossa

Tue 2/10

2:05 pm-3:00 pm

2 stops31h 55m

$624

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Mon 3/9

4:45 pm-11:00 pm

1 stop24h 15m

Lamezia Terme Intl

Thu 3/12

11:15 am-2:10 pm

1 stop32h 55m

$1,221

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Mon 3/9

4:45 pm-6:30 pm

1 stop19h 45m

Lamezia Terme Intl

Thu 3/12

11:15 am-4:20 pm

2 stops35h 05m

$1,223

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Tue 12/16

1:14 pm-10:25 am

2 stops14h 11m

Palermo Punta Raisi

Tue 12/23

6:10 am-5:26 pm

2 stops18h 16m

$1,244

ChicagoLamezia Terme

MDW - SUF

MDWSUF

Chicago Midway

Mon 3/9

5:59 pm-11:00 pm

2 stops47h 01m

Lamezia Terme Intl

Thu 3/12

11:15 am-9:46 pm

2 stops40h 31m

$1,298

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Sicily

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Sicily?

In general, January is the cheapest month to fly from Chicago to Sicily. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $606. If you don’t want to visit Sicily in January, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $611.

What is the cheapest day to depart on your flight to Sicily?

Our data shows that Wednesday is the least expensive day to fly to Sicily. Tickets to fly out on this day can be as low as $781. Flights from Chicago to Sicily on a Thursday will generally be more expensive and average around $1,355. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Sicily?

Our data shows that the cheapest Chicago to Sicily flights are usually those with departure times in the morning. Our users have found flights to Sicily in the morning for as low as $839. Flights to Sicily are more costly in the afternoon, with an average ticket price of $1,091. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Chicago to Sicily flights?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Sicily flight.

Cheap Chicago to Sicily flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Sicily

Direct flights	None

There are no direct flights from Chicago to Sicily. There are no popular flight routes from Chicago to Sicily.

Search flight deals

When did momondo last update prices for flights from Chicago to Sicily?
Prices for flights from Chicago to Sicily were last updated today.
How many operators does momondo search for flights from Chicago to Sicily?
As of November 2025, there are 4 operators available to choose from for flights from Chicago to Sicily.
How old do you have to be to fly from Chicago to Sicily?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Sicily.
What documentation or ID do you need to fly to Sicily?
The required travel and health documents for your Sicily trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Sicily. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Sicily

Compare and see reviews for airlines that fly from Chicago to Sicily with momondo

Airline	Rating	Free Cancellation	Price
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 4,047 reviews	Search Turkish Airlines flights
Lufthansa	PriceFrom $776	Free Cancellation	Rating 6.8 7,576 reviews	Search Lufthansa flights
ITA Airways	PriceFrom $783	Free Cancellation	Rating 6.7 1,083 reviews	Search ITA Airways flights
SWISS	PriceFrom $801	Free Cancellation	Rating 7.5 1,788 reviews	Search SWISS flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sicily?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Sicily from Chicago.

Can I find flights from Chicago to Sicily with flexible booking policies on momondo?

Yes. All flights to Sicily from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Sicily?

Once all potential Chicago to Sicily flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Sicily right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Sicily now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Sicily and let you know when they change.