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

SWISS, KLM, and Delta are the most popular carriers operating from Chicago to Sicily

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 31% 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 April 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.

$349 Cheap Flights from Chicago to Sicily in 2026

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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.

8:10 pm - 6:35 pm

ORD

PMO

15h 25m

1 stop

9:25 am - 9:40 am

PMO

ORD

31h 15m

1 stop

$572Turkish Airlines

Mon, Sep 28 - Thu, Oct 8

8:10 pm - 6:35 pm

ORD

PMO

15h 25m

1 stop

9:25 am - 9:40 am

PMO

ORD

31h 15m

1 stop

$574Turkish Airlines

Mon, Sep 28 - Thu, Oct 8

8:10 pm - 6:35 pm

ORD

PMO

15h 25m

1 stop

9:25 am - 9:40 am

PMO

ORD

31h 15m

1 stop

$583Turkish Airlines

Mon, Sep 28 - Fri, Oct 9

2:20 pm - 9:00 am

ORD

PMO

11h 40m

1 stop

9:45 am - 3:55 pm

PMO

ORD

13h 10m

1 stop

$624SWISS

Sun, Aug 16 - Thu, Aug 27

3:00 pm - 2:35 pm

ORD

SUF

16h 35m

1 stop

7:15 pm - 1:10 pm

SUF

ORD

24h 55m

1 stop

$959ITA Airways

Sat, Aug 15 - Mon, Sep 21

8:10 pm - 6:30 pm

ORD

SUF

39h 20m

2 stops

3:20 pm - 9:40 am

SUF

ORD

25h 20m

2 stops

$969Multiple Airlines

Sat, Aug 15 - Mon, Sep 21

3:00 pm - 11:35 pm

ORD

SUF

25h 35m

2 stops

11:15 am - 1:10 pm

SUF

ORD

32h 55m

1 stop

$985ITA Airways

Sat, Aug 15 - Mon, Sep 21

10:30 am - 6:55 pm

MDW

PMO

25h 25m

3 stops

6:30 am - 2:35 pm

PMO

MDW

39h 05m

3 stops

$986Multiple Airlines

Wed, May 27 - Wed, Jun 3

1:24 pm - 2:25 pm

MDW

PMO

18h 01m

2 stops

6:10 am - 6:33 pm

PMO

MDW

19h 23m

2 stops

$996KLM

Wed, May 6 - Wed, May 13

10:41 am - 10:30 am

MDW

PMO

16h 49m

2 stops

6:10 am - 6:36 pm

PMO

MDW

19h 26m

2 stops

$1,026KLM

Wed, Apr 22 - Sun, Apr 26

Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Sep 28

ORD8:10 pmChicago O'Hare Intl

15h 25m

1 stop

PMO6:35 pmPalermo Punta Raisi

Oct 8

PMO9:25 amPalermo Punta Raisi

31h 15m

1 stop

ORD9:40 amChicago O'Hare Intl

$572

Turkish Airlines

Sep 28

ORD8:10 pmChicago O'Hare Intl

15h 25m

1 stop

PMO6:35 pmPalermo Punta Raisi

Oct 8

PMO9:25 amPalermo Punta Raisi

31h 15m

1 stop

ORD9:40 amChicago O'Hare Intl

$574

Turkish Airlines

Sep 28

ORD8:10 pmChicago O'Hare Intl

15h 25m

1 stop

PMO6:35 pmPalermo Punta Raisi

Oct 9

PMO9:25 amPalermo Punta Raisi

31h 15m

1 stop

ORD9:40 amChicago O'Hare Intl

$583

Scandinavian Airlines flights from Chicago to Sicily

Our best Scandinavian Airlines deals on Chicago to Sicily flight tickets

Scandinavian Airlines

Aug 15

ORD7:15 pmChicago O'Hare Intl

15h 35m

1 stop

CTA5:50 pmCatania Fontanarossa

Aug 23

CTA6:40 pmCatania Fontanarossa

28h 30m

1 stop

ORD4:10 pmChicago O'Hare Intl

$765

Scandinavian Airlines

Aug 15

ORD6:00 amChicago O'Hare Intl

28h 50m

2 stops

CTA5:50 pmCatania Fontanarossa

Aug 23

CTA6:40 pmCatania Fontanarossa

28h 30m

1 stop

ORD4:10 pmChicago O'Hare Intl

$817

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/28

8:10 pm-6:35 pm

1 stop15h 25m

Palermo Punta Raisi

Thu 10/8

9:25 am-9:40 am

1 stop31h 15m

$572

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/28

8:10 pm-6:35 pm

1 stop15h 25m

Palermo Punta Raisi

Thu 10/8

9:25 am-9:40 am

1 stop31h 15m

$574

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/28

8:10 pm-6:35 pm

1 stop15h 25m

Palermo Punta Raisi

Fri 10/9

9:25 am-9:40 am

1 stop31h 15m

$583

Quickest round-trip

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 8/16

2:20 pm-9:00 am

1 stop11h 40m

Palermo Punta Raisi

Thu 8/27

9:45 am-3:55 pm

1 stop13h 10m

$624

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sat 8/15

3:00 pm-2:35 pm

1 stop16h 35m

Lamezia Terme Intl

Mon 9/21

7:15 pm-1:10 pm

1 stop24h 55m

$959

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sat 8/15

8:10 pm-6:30 pm

2 stops39h 20m

Lamezia Terme Intl

Mon 9/21

3:20 pm-9:40 am

2 stops25h 20m

$969

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sat 8/15

3:00 pm-11:35 pm

2 stops25h 35m

Lamezia Terme Intl

Mon 9/21

11:15 am-1:10 pm

1 stop32h 55m

$985

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 5/27

10:30 am-6:55 pm

3 stops25h 25m

Palermo Punta Raisi

Wed 6/3

6:30 am-2:35 pm

3 stops39h 05m

$986

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 5/6

1:24 pm-2:25 pm

2 stops18h 01m

Palermo Punta Raisi

Wed 5/13

6:10 am-6:33 pm

2 stops19h 23m

$996

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 4/22

10:41 am-10:30 am

2 stops16h 49m

Palermo Punta Raisi

Sun 4/26

6:10 am-6:36 pm

2 stops19h 26m

$1,026

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, February 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 $593. If you don’t want to visit Sicily in February, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $674.

Can stopping save me money on Chicago to Sicily flights?

You could potentially save up to 6% 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	11h 40m
Direct flights	None

The fastest flight from Chicago to Sicily takes 11h 40m

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 April 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 7.3 4,304 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $597	Free Cancellation	Rating 7.5 1,921 reviews	Search SWISS flights
ITA Airways	PriceFrom $704	Free Cancellation	Rating 6.7 1,184 reviews	Search ITA Airways flights
Lufthansa	PriceFrom $812	Free Cancellation	Rating 6.8 7,921 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.