What airlines fly to Sicily?

Turkish Airlines, Lufthansa and SWISS are the top three most popular airlines that fly to Sicily from Chicago according to our data. Turkish Airlines is the first choice among our users, with 29% 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?

KLM, SWISS, and Delta 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 August 2026, 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.

$291 Cheap Flights from Chicago to Sicily in 2026

Discover deals from 900+ travel sites with momondo.

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.

8:15 pm - 6:10 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

14h 55m1 stop Istanbul

9:40 am - 10:00 amCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

31h 20m1 stop Istanbul

$690Turkish Airlines

Wed, Nov 25 - Wed, Dec 2

8:10 pm - 6:40 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

15h 30m1 stop Istanbul

7:40 pm - 9:40 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

21h 00m1 stop Istanbul

$696Turkish Airlines

Mon, Sep 21 - Tue, Oct 20

6:30 pm - 7:10 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

17h 40m2 stops Reykjavik Keflavik Intl Rome Fiumicino

6:30 am - 5:20 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

17h 50m2 stops Rome Fiumicino Reykjavik Keflavik Intl

$715Multiple Airlines

Thu, Nov 5 - Sat, Nov 14

2:20 pm - 2:05 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 45m1 stop Zurich

7:25 pm - 12:35 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

24h 10m1 stop Zurich

$748SWISS

Wed, Aug 19 - Wed, Aug 26

11:25 am - 7:10 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

24h 45m2 stops Istanbul Naples

11:40 am - 9:40 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

29h 00m2 stops Naples Istanbul

$758Multiple Airlines

Wed, Oct 14 - Fri, Oct 23

2:20 pm - 9:00 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

11h 40m1 stop Zurich

9:45 am - 3:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

13h 10m1 stop Zurich

$764SWISS

Wed, Aug 19 - Tue, Aug 25

3:00 pm - 6:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 20m1 stop Rome Fiumicino

7:05 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 05m1 stop Rome Fiumicino

$778ITA Airways

Wed, Aug 19 - Tue, Aug 25

3:00 pm - 6:35 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 35m2 stops Rome Fiumicino Milan Linate

3:20 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

28h 50m1 stop Rome Fiumicino

$795ITA Airways

Wed, Aug 19 - Wed, Aug 26

1:55 pm - 5:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 25m2 stops Charlotte Douglas Munich Franz Josef Strauss

6:10 pm - 12:35 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 25m1 stop Munich Franz Josef Strauss

$818Lufthansa

Wed, Aug 19 - Tue, Aug 25

9:50 pm - 5:45 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 55m1 stop Munich Franz Josef Strauss

12:15 pm - 6:25 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

13h 10m1 stop Munich Franz Josef Strauss

$876Lufthansa

Sat, Nov 14 - Sat, Nov 21

Cheap last minute flights

Enter your travel dates to find the best prices.

3:00 pm - 8:45 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

22h 45m1 stop Rome Fiumicino

4:30 pm - 1:10 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

27h 40m1 stop Rome Fiumicino

$744ITA Airways

Sun, Aug 9 - Mon, Aug 24

2:20 pm - 2:05 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 45m1 stop Zurich

7:25 pm - 12:35 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

24h 10m1 stop Zurich

$764SWISS

Wed, Aug 12 - Wed, Aug 19

3:00 pm - 2:00 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 00m1 stop Rome Fiumicino

7:05 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 05m1 stop Rome Fiumicino

$767ITA Airways

Sun, Aug 9 - Tue, Aug 25

3:00 pm - 2:40 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

16h 40m1 stop Rome Fiumicino

4:30 pm - 1:10 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

27h 40m1 stop Rome Fiumicino

$787ITA Airways

Sun, Aug 9 - Mon, Aug 24

2:20 pm - 9:00 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

11h 40m1 stop Zurich

2:55 pm - 3:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

32h 00m1 stop Zurich

$802SWISS

Wed, Aug 12 - Wed, Aug 19

2:20 pm - 9:00 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

11h 40m1 stop Zurich

2:55 pm - 12:35 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

28h 40m1 stop Zurich

$803SWISS

Wed, Aug 12 - Wed, Aug 19

3:00 pm - 3:45 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

17h 45m1 stop Rome Fiumicino

7:15 pm - 1:10 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

24h 55m1 stop Rome Fiumicino

$803ITA Airways

Sun, Aug 9 - Mon, Aug 24

11:05 am - 9:00 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

14h 55m2 stops Montreal Pierre Elliott Trudeau Intl Zurich

7:25 pm - 12:35 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

24h 10m1 stop Zurich

$809Multiple Airlines

Wed, Aug 12 - Wed, Aug 19

1:50 pm - 3:00 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

18h 10m2 stops Atlanta Hartsfield-Jackson Paris Charles de Gaulle

3:45 pm - 4:17 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 32m2 stops Paris Charles de Gaulle Detroit Metropolitan Wayne County

$834Delta

Wed, Aug 12 - Wed, Aug 19

11:22 am - 3:00 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 38m2 stops Detroit Metropolitan Wayne County Paris Charles de Gaulle

3:45 pm - 4:17 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 32m2 stops Paris Charles de Gaulle Detroit Metropolitan Wayne County

$834Delta

Wed, Aug 12 - Wed, Aug 19

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Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Nov 25

ORD8:15 pmChicago O'Hare Intl

14h 55m

1 stop

CTA6:10 pmCatania Fontanarossa

Dec 2

CTA9:40 amCatania Fontanarossa

31h 20m

1 stop

ORD10:00 amChicago O'Hare Intl

$690

Turkish Airlines

Sep 21

ORD8:10 pmChicago O'Hare Intl

15h 30m

1 stop

PMO6:40 pmPalermo Punta Raisi

Oct 20

PMO7:40 pmPalermo Punta Raisi

21h 00m

1 stop

ORD9:40 amChicago O'Hare Intl

$696

Turkish Airlines

Jan 13

ORD8:15 pmChicago O'Hare Intl

14h 55m

1 stop

CTA6:10 pmCatania Fontanarossa

Jan 26

CTA7:10 pmCatania Fontanarossa

30h 10m

1 stop

ORD6:20 pmChicago O'Hare Intl

$697

KLM flights from Chicago to Sicily

Our best KLM deals on Chicago to Sicily flight tickets

KLM

Oct 20

MDW1:27 pmChicago Midway

17h 13m

2 stops

PMO1:40 pmPalermo Punta Raisi

Oct 28

PMO10:05 amPalermo Punta Raisi

18h 28m

2 stops

MDW10:33 pmChicago Midway

$921

KLM

Sep 14

MDW1:19 pmChicago Midway

17h 21m

2 stops

PMO1:40 pmPalermo Punta Raisi

Sep 23

PMO9:50 amPalermo Punta Raisi

19h 54m

2 stops

MDW10:44 pmChicago Midway

$995

KLM

Sep 14

MDW1:19 pmChicago Midway

17h 21m

2 stops

PMO1:40 pmPalermo Punta Raisi

Sep 21

PMO6:10 amPalermo Punta Raisi

19h 23m

2 stops

MDW6:33 pmChicago Midway

$1,055

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCatania

ORD Chicago O'Hare Intl - CTA Catania Fontanarossa

ORDCTA

Chicago O'Hare Intl

Wed 11/25

8:15 pm-6:10 pm

1 stop14h 55m

Catania Fontanarossa

Wed 12/2

9:40 am-10:00 am

1 stop31h 20m

$690

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Mon 9/21

8:10 pm-6:40 pm

1 stop15h 30m

Palermo Punta Raisi

Tue 10/20

7:40 pm-9:40 am

1 stop21h 00m

$696

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Thu 11/5

6:30 pm-7:10 pm

2 stops17h 40m

Palermo Punta Raisi

Sat 11/14

6:30 am-5:20 pm

2 stops17h 50m

$715

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 8/19

2:20 pm-2:05 pm

1 stop16h 45m

Palermo Punta Raisi

Wed 8/26

7:25 pm-12:35 pm

1 stop24h 10m

$748

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 10/14

11:25 am-7:10 pm

2 stops24h 45m

Palermo Punta Raisi

Fri 10/23

11:40 am-9:40 am

2 stops29h 00m

$758

Quickest round-trip

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 8/19

2:20 pm-9:00 am

1 stop11h 40m

Palermo Punta Raisi

Tue 8/25

9:45 am-3:55 pm

1 stop13h 10m

$764

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 8/19

3:00 pm-6:20 pm

1 stop20h 20m

Palermo Punta Raisi

Tue 8/25

7:05 pm-1:10 pm

1 stop25h 05m

$778

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 8/19

3:00 pm-6:35 pm

2 stops20h 35m

Palermo Punta Raisi

Wed 8/26

3:20 pm-1:10 pm

1 stop28h 50m

$795

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 8/19

1:55 pm-5:20 pm

2 stops20h 25m

Palermo Punta Raisi

Tue 8/25

6:10 pm-12:35 pm

1 stop25h 25m

$818

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sat 11/14

9:50 pm-5:45 pm

1 stop12h 55m

Palermo Punta Raisi

Sat 11/21

12:15 pm-6:25 pm

1 stop13h 10m

$876

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 $702. If you don’t want to visit Sicily in January, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $769.

Can stopping save me money on Chicago to Sicily flights?

You could potentially save up to 18% 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

Fastest flight time	12h 00m
Direct flights	None

The fastest flight from Chicago to Sicily takes 12h 00m

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

Search flight deals

Frequently asked questions about flying 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 August 2026, 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 7.4 4,475 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $596	Free Cancellation	Rating 7.5 2,031 reviews	Search SWISS flights
ITA Airways	PriceFrom $695	Free Cancellation	Rating 6.7 1,308 reviews	Search ITA Airways flights
Lufthansa	PriceFrom $865	Free Cancellation	Rating 6.8 8,177 reviews	Search Lufthansa 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.