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

ITA Airways is the most popular carrier 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 47% 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 July 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.

$247 Cheap Flights from Chicago to Sicily in 2025

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Find the cheapest flights from Chicago to Sicily

Round-trip

One-way

Last minute

Cheap round-trip flights

11:25 am - 8:20 amORD-PMO

13h 55m1 stop

7:15 pm - 9:40 amPMO-ORD

21h 25m1 stop

$491Turkish Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 24

11:25 am - 8:25 amORD-CTA

14h 00m1 stop

7:10 pm - 9:40 amCTA-ORD

21h 30m1 stop

$491Turkish Airlines

Find Deal

Tue, Oct 14 - Tue, Oct 21

7:50 pm - 1:55 pmORD-SUF

12h 05m1 stop

2:50 pm - 4:20 pmSUF-ORD

32h 30m1 stop

$647SWISS

Find Deal

Sun, Oct 26 - Mon, Nov 3

3:35 pm - 10:55 amORD-SUF

12h 20m1 stop

2:50 pm - 9:05 pmSUF-ORD

36h 15m2 stops

$703Lufthansa

Find Deal

Wed, Oct 22 - Fri, Oct 31

3:35 pm - 10:55 amORD-SUF

12h 20m1 stop

11:40 am - 6:15 pmSUF-ORD

13h 35m1 stop

$706Lufthansa

Find Deal

Wed, Oct 15 - Thu, Oct 23

3:00 pm - 6:30 pmORD-CTA

20h 30m1 stop

6:00 am - 1:10 pmCTA-ORD

14h 10m1 stop

$727ITA Airways

Find Deal

Mon, Aug 11 - Wed, Aug 27

7:50 pm - 2:00 pmORD-SUF

12h 10m1 stop

2:50 pm - 4:20 pmSUF-ORD

32h 30m1 stop

$729SWISS

Find Deal

Thu, Oct 30 - Fri, Nov 7

3:00 pm - 11:00 pmORD-SUF

25h 00m1 stop

6:15 am - 1:10 pmSUF-ORD

13h 55m1 stop

$751ITA Airways

Find Deal

Wed, Aug 27 - Wed, Sep 3

9:31 am - 3:00 pmMDW-PMO

22h 29m2 stops

3:45 pm - 5:37 pmPMO-MDW

32h 52m2 stops

$771Delta

Find Deal

Mon, Aug 11 - Mon, Aug 25

1:08 pm - 3:00 pmMDW-PMO

18h 52m2 stops

3:45 pm - 6:37 pmPMO-MDW

33h 52m2 stops

$831Delta

Find Deal

Mon, Aug 11 - Fri, Aug 29

Turkish Airlines flights from Chicago to Sicily

Our best Turkish Airlines deals on Chicago to Sicily flight tickets

Turkish Airlines

Oct 14

ORD11:25 amChicago O'Hare Intl

14h 00m

1 stop

CTA8:25 amCatania Fontanarossa

Oct 21

CTA7:10 pmCatania Fontanarossa

21h 30m

1 stop

ORD9:40 amChicago O'Hare Intl

$491

Find similar

Turkish Airlines

Oct 6

ORD11:45 pmChicago O'Hare Intl

25h 40m

1 stop

CTA8:25 amCatania Fontanarossa

Oct 15

CTA9:25 amCatania Fontanarossa

31h 15m

1 stop

ORD9:40 amChicago O'Hare Intl

$500

Find similar

Turkish Airlines

Sep 1

ORD11:45 pmChicago O'Hare Intl

35h 30m

1 stop

PMO6:15 pmPalermo Punta Raisi

Sep 11

PMO9:20 amPalermo Punta Raisi

31h 20m

1 stop

ORD9:40 amChicago O'Hare Intl

$501

Find similar

British Airways flights from Chicago to Sicily

Our best British Airways deals on Chicago to Sicily flight tickets

British Airways

Aug 12

ORD10:35 pmChicago O'Hare Intl

15h 25m

1 stop

CTA9:00 pmCatania Fontanarossa

Aug 25

CTA6:45 pmCatania Fontanarossa

24h 10m

1 stop

ORD11:55 amChicago O'Hare Intl

$621

Find similar

British Airways

Aug 12

ORD8:35 pmChicago O'Hare Intl

17h 25m

1 stop

CTA9:00 pmCatania Fontanarossa

Aug 25

CTA6:45 pmCatania Fontanarossa

28h 09m

2 stops

ORD3:54 pmChicago O'Hare Intl

$636

Find similar

British Airways

Oct 14

ORD4:52 pmChicago O'Hare Intl

21h 08m

2 stops

CTA9:00 pmCatania Fontanarossa

Oct 21

CTA7:55 pmCatania Fontanarossa

24h 55m

1 stop

ORD1:50 pmChicago O'Hare Intl

$644

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 9/10

11:25 am-8:20 am

1 stop13h 55m

Palermo Punta Raisi

Wed 9/24

7:15 pm-9:40 am

1 stop21h 25m

$491

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 10/14

11:25 am-8:25 am

1 stop14h 00m

Catania Fontanarossa

Tue 10/21

7:10 pm-9:40 am

1 stop21h 30m

$491

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sun 10/26

7:50 pm-1:55 pm

1 stop12h 05m

Lamezia Terme Intl

Mon 11/3

2:50 pm-4:20 pm

1 stop32h 30m

$647

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 10/22

3:35 pm-10:55 am

1 stop12h 20m

Lamezia Terme Intl

Fri 10/31

2:50 pm-9:05 pm

2 stops36h 15m

$703

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 10/15

3:35 pm-10:55 am

1 stop12h 20m

Lamezia Terme Intl

Thu 10/23

11:40 am-6:15 pm

1 stop13h 35m

$706

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 8/11

3:00 pm-6:30 pm

1 stop20h 30m

Catania Fontanarossa

Wed 8/27

6:00 am-1:10 pm

1 stop14h 10m

$727

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Thu 10/30

7:50 pm-2:00 pm

1 stop12h 10m

Lamezia Terme Intl

Fri 11/7

2:50 pm-4:20 pm

1 stop32h 30m

$729

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 8/27

3:00 pm-11:00 pm

1 stop25h 00m

Lamezia Terme Intl

Wed 9/3

6:15 am-1:10 pm

1 stop13h 55m

$751

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Mon 8/11

9:31 am-3:00 pm

2 stops22h 29m

Palermo Punta Raisi

Mon 8/25

3:45 pm-5:37 pm

2 stops32h 52m

$771

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Mon 8/11

1:08 pm-3:00 pm

2 stops18h 52m

Palermo Punta Raisi

Fri 8/29

3:45 pm-6:37 pm

2 stops33h 52m

$831

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.

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	$247
Fastest flight time	11h 50m
Direct flights	None
Airports in Sicily	3 airports

The best one-way flight to Sicily from Chicago in the past 72 hours is $247. The best round-trip flight deal from Chicago to Sicily found on momondo in the last 72 hours is $491.

The fastest flight from Chicago to Sicily takes 11h 50m

There are no direct flights from Chicago to Sicily. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - Palermo Punta Raisi Airport, Chicago O'Hare Intl Airport - Catania Fontanarossa Airport and Chicago O'Hare Intl Airport - Lamezia Terme Intl Airport.

There are 3 airports near Sicily: Catania Fontanarossa (CTA), Palermo Punta Raisi (PMO), Lamezia Terme Intl (SUF)

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 July 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 $556	Free Cancellation	Rating 7.3 3,933 reviews	Search Turkish Airlines flights
Lufthansa	PriceFrom $754	Free Cancellation	Rating 6.8 7,275 reviews	Search Lufthansa flights
ITA Airways	PriceFrom $766	Free Cancellation	Rating 6.7 1,011 reviews	Search ITA Airways flights
SWISS	PriceFrom $775	Free Cancellation	Rating 7.5 1,686 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.