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 44% 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?

ITA Airways, Turkish Airlines, and TAP AIR PORTUGAL 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 October 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.

$272 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

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:20 pm - 6:25 pmORD-CTA

15h 05m1 stop

7:25 pm - 10:05 amCTA-ORD

21h 40m1 stop

$528Turkish Airlines

Find Deal

Mon, Oct 27 - Fri, Nov 7

7:05 am - 8:35 pmORD-CTA

30h 30m3 stops

9:40 pm - 1:10 pmCTA-ORD

22h 30m2 stops

$570Multiple Airlines

Find Deal

Sun, Nov 9 - Mon, Nov 17

1:12 pm - 9:30 amORD-CTA

14h 18m2 stops

6:00 am - 1:10 pmCTA-ORD

14h 10m1 stop

$652ITA Airways

Find Deal

Tue, Mar 24 - Sun, Mar 29

6:50 pm - 8:40 pmORD-CTA

18h 50m1 stop

8:50 am - 4:20 pmCTA-ORD

14h 30m1 stop

$698SWISS

Find Deal

Tue, Feb 10 - Fri, Feb 20

6:50 pm - 2:00 pmORD-SUF

12h 10m1 stop

7:05 pm - 4:20 pmSUF-ORD

28h 15m2 stops

$708SWISS

Find Deal

Thu, Nov 6 - Mon, Nov 17

11:05 am - 9:20 amORD-PMO

15h 15m2 stops

6:10 am - 6:10 pmPMO-ORD

19h 00m2 stops

$727ITA Airways

Find Deal

Mon, Oct 20 - Wed, Nov 5

4:20 pm - 2:00 pmORD-SUF

38h 40m2 stops

2:50 pm - 1:10 pmSUF-ORD

29h 20m2 stops

$733Lufthansa

Find Deal

Wed, Nov 5 - Fri, Nov 21

4:20 pm - 2:00 pmORD-SUF

14h 40m2 stops

2:50 pm - 1:10 pmSUF-ORD

29h 20m2 stops

$783Lufthansa

Find Deal

Thu, Nov 6 - Fri, Nov 21

6:23 pm - 6:55 amMDW-CTA

53h 32m2 stops

9:55 am - 8:40 amCTA-MDW

29h 45m2 stops

$1,463Delta

Find Deal

Fri, Oct 17 - Tue, Oct 21

6:00 am - 6:55 amMDW-CTA

17h 55m2 stops

9:55 am - 10:14 pmCTA-MDW

19h 19m2 stops

$1,763Delta

Find Deal

Sun, Oct 12 - Wed, Oct 15

Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Oct 27

ORD9:20 pmChicago O'Hare Intl

15h 05m

1 stop

CTA6:25 pmCatania Fontanarossa

Nov 7

CTA7:25 pmCatania Fontanarossa

21h 40m

1 stop

ORD10:05 amChicago O'Hare Intl

$528

Find similar

Turkish Airlines

Mar 18

ORD12:50 pmChicago O'Hare Intl

23h 35m

1 stop

CTA6:25 pmCatania Fontanarossa

Apr 6

CTA9:30 amCatania Fontanarossa

31h 10m

1 stop

ORD9:40 amChicago O'Hare Intl

$575

Find similar

Turkish Airlines

Mar 18

ORD9:20 pmChicago O'Hare Intl

15h 05m

1 stop

CTA6:25 pmCatania Fontanarossa

Apr 6

CTA9:30 amCatania Fontanarossa

31h 10m

1 stop

ORD9:40 amChicago O'Hare Intl

$584

Find similar

SWISS flights from Chicago to Sicily

Our best SWISS deals on Chicago to Sicily flight tickets

SWISS

Feb 10

ORD6:50 pmChicago O'Hare Intl

18h 50m

1 stop

CTA8:40 pmCatania Fontanarossa

Feb 20

CTA8:50 amCatania Fontanarossa

14h 30m

1 stop

ORD4:20 pmChicago O'Hare Intl

$698

Find similar

SWISS

Nov 6

ORD6:50 pmChicago O'Hare Intl

12h 10m

1 stop

SUF2:00 pmLamezia Terme Intl

Nov 17

SUF7:05 pmLamezia Terme Intl

28h 15m

2 stops

ORD4:20 pmChicago O'Hare Intl

$708

Find similar

SWISS

Feb 8

ORD6:50 pmChicago O'Hare Intl

18h 00m

2 stops

CTA7:50 pmCatania Fontanarossa

Feb 23

CTA8:40 pmCatania Fontanarossa

26h 40m

1 stop

ORD4:20 pmChicago O'Hare Intl

$709

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 10/27

9:20 pm-6:25 pm

1 stop15h 05m

Catania Fontanarossa

Fri 11/7

7:25 pm-10:05 am

1 stop21h 40m

$528

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 11/9

7:05 am-8:35 pm

3 stops30h 30m

Catania Fontanarossa

Mon 11/17

9:40 pm-1:10 pm

2 stops22h 30m

$570

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 3/24

1:12 pm-9:30 am

2 stops14h 18m

Catania Fontanarossa

Sun 3/29

6:00 am-1:10 pm

1 stop14h 10m

$652

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 2/10

6:50 pm-8:40 pm

1 stop18h 50m

Catania Fontanarossa

Fri 2/20

8:50 am-4:20 pm

1 stop14h 30m

$698

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Thu 11/6

6:50 pm-2:00 pm

1 stop12h 10m

Lamezia Terme Intl

Mon 11/17

7:05 pm-4:20 pm

2 stops28h 15m

$708

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 10/20

11:05 am-9:20 am

2 stops15h 15m

Palermo Punta Raisi

Wed 11/5

6:10 am-6:10 pm

2 stops19h 00m

$727

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 11/5

4:20 pm-2:00 pm

2 stops38h 40m

Lamezia Terme Intl

Fri 11/21

2:50 pm-1:10 pm

2 stops29h 20m

$733

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Thu 11/6

4:20 pm-2:00 pm

2 stops14h 40m

Lamezia Terme Intl

Fri 11/21

2:50 pm-1:10 pm

2 stops29h 20m

$783

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Fri 10/17

6:23 pm-6:55 am

2 stops53h 32m

Catania Fontanarossa

Tue 10/21

9:55 am-8:40 am

2 stops29h 45m

$1,463

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Sun 10/12

6:00 am-6:55 am

2 stops17h 55m

Catania Fontanarossa

Wed 10/15

9:55 am-10:14 pm

2 stops19h 19m

$1,763

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 $620.

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 38% 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 October 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 3,984 reviews	Search Turkish Airlines flights
Lufthansa	PriceFrom $754	Free Cancellation	Rating 6.8 7,443 reviews	Search Lufthansa flights
ITA Airways	PriceFrom $760	Free Cancellation	Rating 6.7 1,055 reviews	Search ITA Airways flights
SWISS	PriceFrom $801	Free Cancellation	Rating 7.5 1,754 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.