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

SWISS, United Airlines, and Air Canada are the most popular carriers operating from Chicago to Sicily

What airlines fly to Sicily?

SWISS, Lufthansa and ITA Airways 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 27% 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 September 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.

$263 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.

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

$522Multiple Airlines

Sat, Nov 14 - Sun, Nov 22

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

$549Multiple Airlines

Fri, Dec 4 - Sat, Dec 12

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

$667Turkish Airlines

Mon, Oct 5 - Tue, Oct 20

11:25 am - 8:25 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

14h 00m1 stop Istanbul

6:45 pm - 11:00 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

22h 15m1 stop Istanbul

$675Turkish Airlines

Wed, Oct 21 - Wed, Oct 28

7:05 pm - 9:00 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

30h 55m1 stop Zurich

9:45 am - 4:15 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

13h 30m1 stop Zurich

$720SWISS

Wed, Oct 21 - Thu, Dec 3

2:40 pm - 2:05 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 25m1 stop Zurich

9:45 am - 4:15 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

13h 30m1 stop Zurich

$720SWISS

Tue, Oct 20 - Thu, Dec 3

9:40 pm - 5:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 40m1 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

$728Lufthansa

Wed, Oct 21 - Fri, Dec 4

9:40 pm - 5:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 40m1 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

$728Lufthansa

Tue, Oct 20 - Fri, Dec 4

3:00 pm - 11:30 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

13h 30m1 stop Rome Fiumicino

6:10 am - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

14h 00m1 stop Rome Fiumicino

$827ITA Airways

Fri, Oct 16 - Fri, Oct 23

3:00 pm - 11:30 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

13h 30m1 stop Rome Fiumicino

6:10 am - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

14h 00m1 stop Rome Fiumicino

$828ITA Airways

Fri, Oct 16 - Fri, Oct 23

Cheap last minute flights

Enter your travel dates to find the best prices.

3:00 pm - 10:30 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 30m1 stop Rome Fiumicino

6:20 am - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

13h 50m1 stop Rome Fiumicino

$934Multiple Airlines

Sun, Sep 27 - Sun, Oct 11

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

15h 30m1 stop Istanbul

9:25 am - 9:40 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 15m1 stop Istanbul

$945Turkish Airlines

Mon, Sep 28 - Fri, Oct 9

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

15h 30m1 stop Istanbul

9:25 am - 9:40 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 15m1 stop Istanbul

$956Turkish Airlines

Mon, Sep 28 - Thu, Oct 8

7:05 pm - 11:45 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

33h 40m1 stop London Heathrow

12:05 pm - 3:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

34h 50m1 stop London Heathrow

$1,009British Airways

Mon, Sep 28 - Thu, Oct 8

7:05 pm - 11:45 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

33h 40m1 stop London Heathrow

12:05 pm - 3:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

34h 50m1 stop London Heathrow

$1,010British Airways

Mon, Sep 28 - Thu, Oct 8

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

20h 20m1 stop Rome Fiumicino

6:10 am - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

14h 00m1 stop Rome Fiumicino

$1,081ITA Airways

Sun, Sep 27 - Sun, Oct 18

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

15h 30m1 stop Istanbul

9:25 am - 9:40 amPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

31h 15m1 stop Istanbul

$1,122Turkish Airlines

Fri, Sep 25 - Fri, Oct 9

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

20h 20m1 stop Rome Fiumicino

6:10 am - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

14h 00m1 stop Rome Fiumicino

$1,298ITA Airways

Sun, Sep 27 - Fri, Oct 2

10:30 pm - 10:20 amORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

28h 50m1 stop Frankfurt am Main

6:10 pm - 12:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 45m1 stop Frankfurt am Main

$6,142Lufthansa

Sun, Sep 27 - Sun, Oct 11

3:35 pm - 5:20 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

18h 45m1 stop Munich Franz Josef Strauss

5:45 pm - 7:55 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

33h 10m1 stop Frankfurt am Main

$6,513Lufthansa

Fri, Sep 25 - Fri, Oct 9

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Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Oct 5

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

$667

Turkish Airlines

Oct 21

ORD11:25 amChicago O'Hare Intl

14h 00m

1 stop

PMO8:25 amPalermo Punta Raisi

Oct 28

PMO6:45 pmPalermo Punta Raisi

22h 15m

1 stop

ORD11:00 amChicago O'Hare Intl

$675

Turkish Airlines

Feb 11

ORD8:15 pmChicago O'Hare Intl

14h 55m

1 stop

CTA6:10 pmCatania Fontanarossa

Feb 23

CTA7:10 pmCatania Fontanarossa

30h 10m

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

Sep 28

ORD7:05 pmChicago O'Hare Intl

33h 40m

1 stop

PMO11:45 amPalermo Punta Raisi

Oct 8

PMO12:05 pmPalermo Punta Raisi

34h 50m

1 stop

ORD3:55 pmChicago O'Hare Intl

$1,009

British Airways

Sep 28

ORD10:11 amChicago O'Hare Intl

18h 09m

2 stops

PMO11:20 amPalermo Punta Raisi

Oct 8

PMO12:05 pmPalermo Punta Raisi

34h 50m

1 stop

ORD3:55 pmChicago O'Hare Intl

$1,013

British Airways

Oct 5

ORD5:55 pmChicago O'Hare Intl

34h 50m

2 stops

PMO11:45 amPalermo Punta Raisi

Oct 20

PMO12:15 pmPalermo Punta Raisi

34h 56m

2 stops

ORD4:11 pmChicago O'Hare Intl

$1,016

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sat 11/14

6:30 pm-7:10 pm

2 stops17h 40m

Palermo Punta Raisi

Sun 11/22

6:30 am-5:20 pm

2 stops17h 50m

$522

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Fri 12/4

6:30 pm-9:50 pm

2 stops20h 20m

Palermo Punta Raisi

Sat 12/12

6:30 am-5:20 pm

2 stops17h 50m

$549

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Mon 10/5

8:10 pm-6:40 pm

1 stop15h 30m

Palermo Punta Raisi

Tue 10/20

7:40 pm-9:40 am

1 stop21h 00m

$667

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 10/21

11:25 am-8:25 am

1 stop14h 00m

Palermo Punta Raisi

Wed 10/28

6:45 pm-11:00 am

1 stop22h 15m

$675

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 10/21

7:05 pm-9:00 am

1 stop30h 55m

Palermo Punta Raisi

Thu 12/3

9:45 am-4:15 pm

1 stop13h 30m

$720

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Tue 10/20

2:40 pm-2:05 pm

1 stop16h 25m

Palermo Punta Raisi

Thu 12/3

9:45 am-4:15 pm

1 stop13h 30m

$720

Quickest round-trip

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 10/21

9:40 pm-5:20 pm

1 stop12h 40m

Palermo Punta Raisi

Fri 12/4

12:15 pm-6:25 pm

1 stop13h 10m

$728

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Tue 10/20

9:40 pm-5:20 pm

1 stop12h 40m

Palermo Punta Raisi

Fri 12/4

12:15 pm-6:25 pm

1 stop13h 10m

$728

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Fri 10/16

3:00 pm-11:30 am

1 stop13h 30m

Palermo Punta Raisi

Fri 10/23

6:10 am-1:10 pm

1 stop14h 00m

$827

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Fri 10/16

3:00 pm-11:30 am

1 stop13h 30m

Palermo Punta Raisi

Fri 10/23

6:10 am-1:10 pm

1 stop14h 00m

$828

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 $804.

Can stopping save me money on Chicago to Sicily flights?

You could potentially save up to 4% 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	$263
Fastest flight time	12h 00m
Direct flights	None

The best one-way flight to Sicily from Chicago in the past 72 hours is $263. The best round-trip flight deal from Chicago to Sicily found on momondo in the last 72 hours is $522.

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 September 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 $554	Free Cancellation	Rating 7.4 4,460 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $596	Free Cancellation	Rating 7.5 2,082 reviews	Search SWISS flights
ITA Airways	PriceFrom $645	Free Cancellation	Rating 6.8 1,365 reviews	Search ITA Airways flights
Lufthansa	PriceFrom $868	Free Cancellation	Rating 6.8 8,235 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.