What airlines fly to Sicily?

SWISS, Lufthansa and ITA Airways are the top three most popular airlines that fly to Sicily from Chicago O'Hare Intl Airport 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.

What is the cheapest airline that flies from Chicago O'Hare Intl to Sicily?

Lufthansa, SWISS, and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Sicily

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Sicily?

Prices for flights from Chicago O'Hare Intl Airport to Sicily are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Sicily?

The number of operators available for flights from Chicago O'Hare Intl Airport to Sicily is 4 as of September 2026.

How old do you have to be to fly from Chicago O'Hare Intl Airport to Sicily?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Sicily.

What documentation or ID do you need to fly to Sicily?

The travel and health documents required for your trip to Sicily can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sicily. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$339 Cheap Flights from Chicago O'Hare Intl Airport to Sicily in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to Sicily

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

$572Multiple Airlines

Wed, Dec 2 - Sun, Dec 13

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

$572Multiple Airlines

Wed, Dec 2 - Mon, Dec 14

12:45 pm - 6:10 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

23h 25m1 stop Istanbul

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

15h 45m1 stop Istanbul

$661Turkish Airlines

Thu, Oct 29 - Wed, Nov 18

8:10 pm - 6:25 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

15h 15m1 stop Istanbul

9:20 am - 9:40 amCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

31h 20m1 stop Istanbul

$665Turkish Airlines

Mon, Oct 5 - Wed, Oct 21

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

$822ITA Airways

Fri, Oct 16 - 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

$829SWISS

Fri, Oct 16 - Fri, Oct 23

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

12h 55m1 stop Munich Franz Josef Strauss

6:30 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 40m2 stops Munich Franz Josef Strauss Frankfurt am Main

$847Lufthansa

Sat, Feb 6 - Sun, Feb 21

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

12h 55m1 stop Munich Franz Josef Strauss

6:30 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

25h 40m2 stops Munich Franz Josef Strauss Frankfurt am Main

$847Lufthansa

Sat, Jan 16 - Sun, Jan 31

3:00 pm - 2:10 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

16h 10m1 stop Rome Fiumicino

1:45 pm - 1:10 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

30h 25m2 stops Milan Linate Rome Fiumicino

$854ITA Airways

Wed, Oct 7 - Thu, Oct 15

6:50 pm - 1:55 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

12h 05m1 stop Zurich

9:10 am - 4:15 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

14h 05m1 stop Zurich

$1,970SWISS

Sat, Dec 19 - Tue, Dec 29

Cheap last minute flights

Enter your travel dates to find the best prices.

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

24h 30m1 stop Rome Fiumicino

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

14h 00m1 stop Rome Fiumicino

$844ITA Airways

Sun, Sep 20 - Wed, Oct 14

3:00 pm - 7:45 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

21h 45m1 stop Rome Fiumicino

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

29h 00m1 stop Rome Fiumicino

$844ITA Airways

Sun, Sep 20 - Tue, Oct 13

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

15h 00m1 stop Rome Fiumicino

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

29h 00m1 stop Rome Fiumicino

$846ITA Airways

Sun, Sep 20 - Thu, Oct 15

6:00 pm - 10:30 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

21h 30m2 stops Lisbon Humberto Delgado Rome Fiumicino

3:10 pm - 12:40 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

28h 30m2 stops Rome Fiumicino Lisbon Humberto Delgado

$897TAP AIR PORTUGAL

Sun, Sep 20 - Wed, Oct 14

6:00 pm - 2:25 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

37h 25m2 stops Lisbon Humberto Delgado Rome Fiumicino

4:10 pm - 12:40 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

27h 30m2 stops Rome Fiumicino Lisbon Humberto Delgado

$897TAP AIR PORTUGAL

Sun, Sep 20 - Wed, Oct 14

6:00 pm - 10:30 pmORD Chicago O'Hare Intl-PMO Palermo Punta Raisi

21h 30m2 stops Lisbon Humberto Delgado Rome Fiumicino

4:10 pm - 4:00 pmPMO Palermo Punta Raisi-ORD Chicago O'Hare Intl

30h 50m2 stops Rome Fiumicino Lisbon Humberto Delgado

$918TAP AIR PORTUGAL

Sun, Sep 20 - Tue, Oct 13

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

$973Turkish Airlines

Mon, Sep 21 - Tue, Oct 20

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

$1,132Turkish Airlines

Mon, Sep 21 - Tue, Oct 20

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

$1,163Turkish Airlines

Mon, Sep 21 - Tue, Oct 20

6:00 pm - 5:45 pmORD Chicago O'Hare Intl-CTA Catania Fontanarossa

16h 45m2 stops Brussels Bruxelles-National Munich Franz Josef Strauss

4:30 pm - 6:15 pmCTA Catania Fontanarossa-ORD Chicago O'Hare Intl

32h 45m2 stops Rome Fiumicino Munich Franz Josef Strauss

$1,870Lufthansa

Fri, Sep 18 - Sun, Sep 20

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Turkish Airlines flights from Chicago O'Hare Intl Airport to Sicily

Our best Turkish Airlines deals on Chicago O'Hare Intl Airport to Sicily flight tickets

Turkish Airlines

Oct 29

ORD12:45 pmChicago O'Hare Intl

23h 25m

1 stop

CTA6:10 pmCatania Fontanarossa

Nov 18

CTA9:35 amCatania Fontanarossa

15h 45m

1 stop

ORD6:20 pmChicago O'Hare Intl

$661

Turkish Airlines

Oct 5

ORD8:10 pmChicago O'Hare Intl

15h 15m

1 stop

CTA6:25 pmCatania Fontanarossa

Oct 21

CTA9:20 amCatania Fontanarossa

31h 20m

1 stop

ORD9:40 amChicago O'Hare Intl

$665

Turkish Airlines

Oct 13

ORD8:10 pmChicago O'Hare Intl

15h 30m

1 stop

PMO6:40 pmPalermo Punta Raisi

Oct 28

PMO6:45 pmPalermo Punta Raisi

22h 15m

1 stop

ORD11:00 amChicago O'Hare Intl

$675

ITA Airways flights from Chicago O'Hare Intl Airport to Sicily

Our best ITA Airways deals on Chicago O'Hare Intl Airport to Sicily flight tickets

ITA Airways

Oct 16

ORD3:00 pmChicago O'Hare Intl

13h 30m

1 stop

PMO11:30 amPalermo Punta Raisi

Oct 23

PMO6:10 amPalermo Punta Raisi

14h 00m

1 stop

ORD1:10 pmChicago O'Hare Intl

$822

ITA Airways

Sep 20

ORD3:00 pmChicago O'Hare Intl

21h 45m

1 stop

PMO7:45 pmPalermo Punta Raisi

Oct 13

PMO3:10 pmPalermo Punta Raisi

29h 00m

1 stop

ORD1:10 pmChicago O'Hare Intl

$844

ITA Airways

Sep 20

ORD3:00 pmChicago O'Hare Intl

15h 00m

1 stop

PMO1:00 pmPalermo Punta Raisi

Oct 15

PMO3:10 pmPalermo Punta Raisi

29h 00m

1 stop

ORD1:10 pmChicago O'Hare Intl

$846

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Sicily that are best for you.

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

Wed 12/2

6:30 pm-9:50 pm

2 stops20h 20m

Palermo Punta Raisi

Sun 12/13

6:30 am-5:20 pm

2 stops17h 50m

$572

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 12/2

6:30 pm-9:50 pm

2 stops20h 20m

Palermo Punta Raisi

Mon 12/14

6:30 am-5:20 pm

2 stops17h 50m

$572

ChicagoCatania

ORD Chicago O'Hare Intl - CTA Catania Fontanarossa

ORDCTA

Chicago O'Hare Intl

Thu 10/29

12:45 pm-6:10 pm

1 stop23h 25m

Catania Fontanarossa

Wed 11/18

9:35 am-6:20 pm

1 stop15h 45m

$661

ChicagoCatania

ORD Chicago O'Hare Intl - CTA Catania Fontanarossa

ORDCTA

Chicago O'Hare Intl

Mon 10/5

8:10 pm-6:25 pm

1 stop15h 15m

Catania Fontanarossa

Wed 10/21

9:20 am-9:40 am

1 stop31h 20m

$665

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

$822

Quickest round-trip

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Fri 10/16

2:20 pm-9:00 am

1 stop11h 40m

Palermo Punta Raisi

Fri 10/23

9:45 am-3:55 pm

1 stop13h 10m

$829

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sat 2/6

9:50 pm-5:45 pm

1 stop12h 55m

Palermo Punta Raisi

Sun 2/21

6:30 pm-1:10 pm

2 stops25h 40m

$847

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sat 1/16

9:50 pm-5:45 pm

1 stop12h 55m

Palermo Punta Raisi

Sun 1/31

6:30 pm-1:10 pm

2 stops25h 40m

$847

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Wed 10/7

3:00 pm-2:10 pm

1 stop16h 10m

Palermo Punta Raisi

Thu 10/15

1:45 pm-1:10 pm

2 stops30h 25m

$854

ChicagoPalermo

ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi

ORDPMO

Chicago O'Hare Intl

Sat 12/19

6:50 pm-1:55 pm

1 stop12h 05m

Palermo Punta Raisi

Tue 12/29

9:10 am-4:15 pm

1 stop14h 05m

$1,970

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 O'Hare Intl Airport 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 O'Hare Intl Airport to Sicily. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $662. If you don’t want to visit Sicily in January, then you should wait until August to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $805.

Can stopping save me money on Chicago O'Hare Intl Airport to Sicily flights?

You could potentially save up to 11% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Sicily flight.

Cheap Chicago O'Hare Intl Airport to Sicily flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Sicily

Best Price Found	$339
Fastest flight time	12h 10m
Direct flights	None

The best one-way flight to Sicily from Chicago O'Hare Intl Airport in the past 72 hours is $339. The best round-trip flight deal from Chicago O'Hare Intl Airport to Sicily found on momondo in the last 72 hours is $572.

The fastest flight from Chicago O'Hare Intl Airport to Sicily takes 12h 10m

There are no direct flights from Chicago O'Hare Intl Airport to Sicily. There are no popular flight routes from Chicago O'Hare Intl Airport to Sicily.

Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Sicily

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Sicily?
Prices for flights from Chicago O'Hare Intl Airport to Sicily are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Sicily?
The number of operators available for flights from Chicago O'Hare Intl Airport to Sicily is 4 as of September 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Sicily?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Sicily.
What documentation or ID do you need to fly to Sicily?
The travel and health documents required for your trip to Sicily can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sicily. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago O'Hare Intl Airport to Sicily

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Sicily with momondo

Airline	Rating	Free Cancellation	Price
Turkish Airlines	PriceFrom $554	Free Cancellation	Rating 7.4 4,463 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $597	Free Cancellation	Rating 7.5 2,074 reviews	Search SWISS flights
ITA Airways	PriceFrom $645	Free Cancellation	Rating 6.7 1,355 reviews	Search ITA Airways flights
Lufthansa	PriceFrom $868	Free Cancellation	Rating 6.8 8,231 reviews	Search Lufthansa flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sicily?

It is quick and easy to find Chicago to Sicily flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Sicily that suits you.

Can I find flights from Chicago to Sicily with flexible booking policies on momondo?

Flights from Chicago to Sicily with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Sicily?

Once you have performed a search for Chicago to Sicily flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Sicily right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Sicily, momondo offers a useful price alert feature which will track prices for flights to Sicily from Chicago and alert you when they change.