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

Turkish Airlines is the most popular carrier operating from Chicago to Sicily

What airlines fly to Sicily?

SWISS, Lufthansa and Turkish Airlines are the top three most popular airlines that fly to Sicily from Chicago according to our data. SWISS is the first choice among our users, with 28% 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.

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 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.

$387 Cheap Flights from Chicago to Sicily in 2026/27

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.

11:45 am - 6:10 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

23h 25m1 stop Istanbul

7:10 pm - 10:00 amCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

21h 50m1 stop Istanbul

$685Turkish Airlines

Thu, Jan 14 - Thu, Jan 21

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

14h 55m1 stop Istanbul

9:35 am - 6:20 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

15h 45m1 stop Istanbul

$685Turkish Airlines

Wed, Jan 13 - Wed, Jan 20

6:30 pm - 9:50 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 20m2 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

$699Multiple Airlines

Fri, Jan 15 - Sat, Feb 13

6:30 pm - 9:50 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 20m2 stops Reykjavik Keflavik Intl Rome Fiumicino

10:25 pm - 5:20 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 55m2 stops Rome Fiumicino Reykjavik Keflavik Intl

$729Multiple Airlines

Thu, Nov 26 - Tue, Dec 1

7:50 pm - 2:00 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 10m1 stop Zurich

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

13h 10m1 stop Zurich

$980SWISS

Mon, Mar 22 - Mon, Mar 29

7:05 pm - 2:05 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 00m1 stop Zurich

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

13h 10m1 stop Zurich

$1,034SWISS

Sun, Apr 4 - Fri, Apr 23

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

18h 00m2 stops Frankfurt am Main Munich Franz Josef Strauss

11:50 am - 7:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

15h 05m2 stops Munich Franz Josef Strauss Frankfurt am Main

$1,060Lufthansa

Sun, Mar 21 - Tue, Mar 30

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

18h 00m2 stops Frankfurt am Main Munich Franz Josef Strauss

11:50 am - 7:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

15h 05m2 stops Munich Franz Josef Strauss Frankfurt am Main

$1,076Lufthansa

Sun, Mar 21 - Tue, Mar 30

8:52 am - 9:20 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

17h 28m2 stops Washington, D.C. Dulles Intl Rome Fiumicino

6:10 am - 6:50 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

19h 40m2 stops Rome Fiumicino Washington, D.C. Dulles Intl

$1,633ITA Airways

Tue, Dec 1 - Tue, Mar 2

12:06 pm - 9:20 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

14h 14m2 stops New York John F Kennedy Intl Rome Fiumicino

6:10 am - 6:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

19h 45m2 stops Rome Fiumicino New York John F Kennedy Intl

$1,822ITA Airways

Sun, Jan 17 - Fri, Jan 22

Cheap last minute flights

Enter your travel dates to find the best prices.

1:55 pm - 7:10 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

22h 15m2 stops Montreal Pierre Elliott Trudeau Intl Rome Fiumicino

10:25 pm - 3:00 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

47h 35m2 stops Rome Fiumicino Montreal Pierre Elliott Trudeau Intl

$802Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

8:10 pm - 9:50 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

18h 40m2 stops Lisbon Humberto Delgado Rome Fiumicino

7:15 pm - 3:30 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

27h 15m2 stops Madrid Barajas Lisbon Humberto Delgado

$806Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

8:10 pm - 9:20 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

30h 10m2 stops Lisbon Humberto Delgado Rome Fiumicino

10:05 am - 3:30 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

36h 25m2 stops Rome Fiumicino Lisbon Humberto Delgado

$859Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

8:15 pm - 8:35 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

29h 20m1 stop Istanbul

9:35 am - 10:00 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 25m1 stop Istanbul

$862Turkish Airlines

Sat, Nov 14 - Fri, Nov 20

8:10 pm - 11:35 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

32h 25m3 stops Lisbon Humberto Delgado Paris Orly Milan Linate

8:10 pm - 3:30 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

26h 20m2 stops Paris Orly Lisbon Humberto Delgado

$884Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

3:55 pm - 7:25 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

20h 30m1 stop Dublin

5:55 am - 3:30 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

40h 35m2 stops Barcelona-El Prat Lisbon Humberto Delgado

$929Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

6:50 pm - 6:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 30m3 stops Zurich Nice Côte d'Azur Rome Fiumicino

7:15 pm - 3:30 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

27h 15m2 stops Madrid Barajas Lisbon Humberto Delgado

$952Multiple Airlines

Sun, Nov 15 - Sat, Nov 21

6:10 pm - 11:20 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

34h 10m1 stop Frankfurt am Main

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

34h 05m1 stop Rome Fiumicino

$1,905Lufthansa

Tue, Nov 10 - Tue, Nov 17

9:50 pm - 7:50 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

15h 00m2 stops Munich Franz Josef Strauss Rome Fiumicino

12:10 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

32h 00m1 stop Frankfurt am Main

$2,586Lufthansa

Sun, Nov 15 - Sat, Nov 21

4:20 pm - 11:20 amORD Chicago O'Hare Intl-CTA Catania Fontanarossa

12h 00m1 stop Frankfurt am Main

6:25 pm - 6:25 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

31h 00m1 stop Munich Franz Josef Strauss

$6,397Lufthansa

Sun, Nov 15 - Fri, Nov 20

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Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Jan 13

ORD8:15 pmChicago O'Hare Intl

14h 55m

1 stop

CTA6:10 pmCatania Fontanarossa

Jan 20

CTA9:35 amCatania Fontanarossa

15h 45m

1 stop

ORD6:20 pmChicago O'Hare Intl

$685

Turkish Airlines

Apr 21

ORD11:20 amChicago O'Hare Intl

24h 15m

1 stop

PMO6:35 pmPalermo Punta Raisi

Apr 28

PMO9:20 amPalermo Punta Raisi

15h 50m

1 stop

ORD6:10 pmChicago O'Hare Intl

$694

Turkish Airlines

Jan 13

ORD8:15 pmChicago O'Hare Intl

29h 20m

1 stop

PMO8:35 amPalermo Punta Raisi

Jan 27

PMO6:45 pmPalermo Punta Raisi

30h 35m

1 stop

ORD6:20 pmChicago O'Hare Intl

$696

British Airways flights from Chicago to Sicily

Our best British Airways deals on Chicago to Sicily flight tickets

British Airways

Apr 18

ORD5:00 pmChicago O'Hare Intl

18h 40m

1 stop

PMO6:40 pmPalermo Punta Raisi

Apr 28

PMO12:40 pmPalermo Punta Raisi

13h 19m

1 stop

ORD6:59 pmChicago O'Hare Intl

$801

British Airways

Apr 19

ORD7:25 pmChicago O'Hare Intl

16h 30m

1 stop

CTA6:55 pmCatania Fontanarossa

Apr 22

CTA12:05 pmCatania Fontanarossa

35h 20m

1 stop

ORD4:25 pmChicago O'Hare Intl

$814

British Airways

Feb 10

ORD12:06 pmChicago O'Hare Intl

16h 44m

2 stops

PMO11:50 amPalermo Punta Raisi

Feb 21

PMO1:05 pmPalermo Punta Raisi

13h 10m

1 stop

ORD7:15 pmChicago O'Hare Intl

$815

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

Thu 1/14

11:45 am-6:10 pm

1 stop23h 25m

Catania Fontanarossa

Thu 1/21

7:10 pm-10:00 am

1 stop21h 50m

$685

ChicagoCatania

ORD Chicago O'Hare Intl - CTA Catania Fontanarossa

ORDCTA

Chicago O'Hare Intl

Wed 1/13

8:15 pm-6:10 pm

1 stop14h 55m

Catania Fontanarossa

Wed 1/20

9:35 am-6:20 pm

1 stop15h 45m

$685

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Fri 1/15

6:30 pm-9:50 pm

2 stops20h 20m

Palermo Punta Raisi

Sat 2/13

6:30 am-5:20 pm

2 stops17h 50m

$699

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Thu 11/26

6:30 pm-9:50 pm

2 stops20h 20m

Palermo Punta Raisi

Tue 12/1

10:25 pm-5:20 pm

2 stops25h 55m

$729

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Mon 3/22

7:50 pm-2:00 pm

1 stop12h 10m

Palermo Punta Raisi

Mon 3/29

9:45 am-3:55 pm

1 stop13h 10m

$980

Quickest round-trip

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sun 4/4

7:05 pm-2:05 pm

1 stop12h 00m

Palermo Punta Raisi

Fri 4/23

9:45 am-3:55 pm

1 stop13h 10m

$1,034

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sun 3/21

5:20 pm-5:20 pm

2 stops18h 00m

Palermo Punta Raisi

Tue 3/30

11:50 am-7:55 pm

2 stops15h 05m

$1,060

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sun 3/21

5:20 pm-5:20 pm

2 stops18h 00m

Palermo Punta Raisi

Tue 3/30

11:50 am-7:55 pm

2 stops15h 05m

$1,076

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Tue 12/1

8:52 am-9:20 am

2 stops17h 28m

Palermo Punta Raisi

Tue 3/2

6:10 am-6:50 pm

2 stops19h 40m

$1,633

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sun 1/17

12:06 pm-9:20 am

2 stops14h 14m

Palermo Punta Raisi

Fri 1/22

6:10 am-6:55 pm

2 stops19h 45m

$1,822

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 $724. 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 $774.

Can stopping save me money on Chicago to Sicily flights?

You could potentially save up to 17% 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

Best Price Found	$387
Fastest flight time	13h 50m
Direct flights	None

The best one-way flight to Sicily from Chicago in the past 72 hours is $387. The best round-trip flight deal from Chicago to Sicily found on momondo in the last 72 hours is $685.

The fastest flight from Chicago to Sicily takes 13h 50m

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 November 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 $574	Free Cancellation	Rating 7.4 4,467 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $596	Free Cancellation	Rating 7.5 2,116 reviews	Search SWISS flights
ITA Airways	PriceFrom $645	Free Cancellation	Rating 6.8 1,413 reviews	Search ITA Airways flights
Lufthansa	PriceFrom $868	Free Cancellation	Rating 6.8 8,292 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.