HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sicily

$383+ Cheap flights from Chicago (CHI) to Sicily

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Sicily with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Sicily

Cheapest flights from Chicago to Sicily
Explore the most affordable flight options available from Chicago to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.

This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:10 pm
ORD
-
PMO
1 stop15h 25m
Turkish Airlines
Thu 10/89:25 am
PMO
-
ORD
1 stop31h 15m
Turkish Airlines
Deal found 5/11$726
This oojo deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:10 pm
ORD
-
PMO
1 stop15h 25m
Turkish Airlines
Wed 10/77:35 pm
PMO
-
ORD
1 stop21h 05m
Turkish Airlines
Deal found 5/7$732
This FlightHub deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:10 pm
ORD
-
PMO
1 stop29h 15m
Turkish Airlines
Tue 9/157:35 pm
PMO
-
ORD
1 stop21h 05m
Turkish Airlines
Deal found 5/7$744
This Cheapflightsfares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
-
PMO
1 stop11h 40m
SWISS
Thu 8/279:45 am
PMO
-
ORD
1 stop13h 10m
SWISS
Deal found 5/12$762
This FlightHub deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:10 pm
ORD
-
PMO
1 stop15h 25m
Turkish Airlines
Tue 9/87:35 pm
PMO
-
ORD
1 stop21h 05m
Turkish Airlines
Deal found 5/10$768
This Expedia deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:11 pm
ORD
-
CTA
2 stops22h 44m
Finnair
Tue 8/2510:30 am
CTA
-
ORD
1 stop14h 20m
Finnair
Deal found 5/11$772
This oojo deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:10 pm
ORD
-
PMO
1 stop15h 25m
Turkish Airlines
Wed 9/97:35 pm
PMO
-
ORD
1 stop21h 05m
Turkish Airlines
Deal found 5/8$773
This oojo deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:25 am
ORD
-
PMO
1 stop14h 00m
Turkish Airlines
Sun 9/279:25 am
PMO
-
ORD
1 stop31h 15m
Turkish Airlines
Deal found 5/9$780
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:10 pm
ORD
-
PMO
1 stop15h 25m
Turkish Airlines
Sun 9/279:25 am
PMO
-
ORD
1 stop31h 15m
Turkish Airlines
Deal found 5/11$782
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:15 pm
ORD
-
CTA
1 stop16h 50m
Multiple Airlines
Tue 8/2510:30 am
CTA
-
ORD
1 stop14h 20m
Multiple Airlines
Deal found 5/11$804
This FlightHub deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:25 am
ORD
-
CTA
1 stop24h 00m
Turkish Airlines
Mon 10/129:25 am
CTA
-
ORD
1 stop15h 50m
Turkish Airlines
Deal found 5/7$812
This FlightHub deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1511:50 am
ORD
-
CTA
1 stop13h 45m
Turkish Airlines
Tue 11/247:25 pm
CTA
-
ORD
1 stop30h 00m
Turkish Airlines
Deal found 5/6$814

Find flight deals from Chicago to Sicily

Keep the following information in mind while searching for Chicago to Sicily flight deals. Data was last updated May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$726
(FlightHub)

One-way from

$383
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$1,016
Provider with most accurate pricing for Chicago (CHI)-Catania Fontanarossa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Catania Fontanarossa flights.
Search Deals
From Chicago (CHI) to Sicily
Search Deals
One-way flight from Chicago (CHI) to Sicily
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($249 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sicily that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2026.
Use the filters below to find and compare flights from Chicago to Sicily that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 8/15

1:27 pm-12:15 pm

2 stops15h 48m

Palermo Punta Raisi

Mon 8/24

3:45 pm-4:15 pm

2 stops31h 30m

$886

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 8/4

2:12 pm-1:40 pm

2 stops16h 28m

Palermo Punta Raisi

Tue 8/18

6:10 am-8:22 pm

2 stops21h 12m

$922
Quickest round-trip

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 7/14

9:40 pm-5:45 pm

1 stop13h 05m

Catania Fontanarossa

Wed 7/22

10:40 am-8:16 pm

2 stops16h 36m

$973

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 7/14

6:00 am-7:55 am

1 stop18h 55m

Catania Fontanarossa

Wed 7/22

9:55 am-9:52 pm

1 stop18h 57m

$977

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 7/15

10:00 am-7:55 am

1 stop14h 55m

Catania Fontanarossa

Wed 7/22

9:55 am-9:52 pm

1 stop18h 57m

$977

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/28

1:15 pm-1:40 pm

2 stops17h 25m

Palermo Punta Raisi

Thu 10/8

10:15 am-8:24 pm

2 stops17h 09m

$991

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 7/5

6:05 am-3:00 pm

2 stops25h 55m

Palermo Punta Raisi

Fri 7/17

3:45 pm-9:52 pm

2 stops37h 07m

$993

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/28

1:30 pm-1:40 pm

2 stops17h 10m

Palermo Punta Raisi

Fri 10/9

10:05 am-10:04 pm

2 stops18h 59m

$996

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Tue 7/7

12:41 pm-3:00 pm

2 stops19h 19m

Palermo Punta Raisi

Tue 7/21

3:45 pm-6:25 pm

2 stops33h 40m

$1,000

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sun 7/5

1:26 pm-3:00 pm

2 stops18h 34m

Palermo Punta Raisi

Tue 7/21

3:45 pm-6:25 pm

2 stops33h 40m

$1,000

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Chicago to Sicily

Have a flexible travel schedule? Discover the best time to fly to Sicily from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sicily

How far ahead should I book a flight from Chicago to Sicily?

Booking 19 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Sicily. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Sicily?

Currently, August is the cheapest month in which you can book a flight from Chicago to Sicily (average of $56). Flying from Chicago to Sicily in December is currently the most expensive (average of $642). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Sicily?

Reviews of airlines servicing Sicily

Get insights into the airlines that provide service to Sicily. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sicily. Reviews last updated May 12, 2026.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS,Turkish Airlines, andLufthansa. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.6
Good
1,942 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.6

Boarding

7.7

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
SWISS
7.6
Good
1,942 reviews
SWISS
7.6
Good
1,942 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.6

Boarding

7.7

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
Turkish Airlines
7.4
Good
4,358 reviews
SWISS
7.6
Good
1,942 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.6

Boarding

7.7

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
Lufthansa
6.8
Okay
7,992 reviews
SWISS
7.6
Good
1,942 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.6

Boarding

7.7

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
ITA Airways
6.7
Okay
1,213 reviews
SWISS
7.6
Good
1,942 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.6

Boarding

7.7

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sicily. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Sicily?

    Departing from Chicago to Sicily will take you 15h 30m. Chicago and Sicily are separated by a distance of 5001 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Sicily one-way?

    The cheapest airline one-way is ITA Airways, with whom users have recently found tickets for as low as $286. However, be on the lookout for offers from Lufthansa and Turkish Airlines, as they are both options that can get you from Chicago to Sicily for a low price.

  • What are the most popular routes from Chicago to Sicily?

    The most popular flight routes from Chicago to Sicily are Chicago O'Hare Intl - Palermo Punta Raisi, Chicago O'Hare Intl - Catania Fontanarossa and Chicago Midway - Palermo Punta Raisi.

  • Can I find deals for flights from Chicago to Sicily that include hotel bookings?

    Yes. In addition to deals on Chicago to Sicily flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Sicily?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sicily.

  • Can I find deals for business class flights from Chicago to Sicily?

    Yes. Cheapflights offers flight deals from Chicago to Sicily by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Sicily?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Sicily (average of $56). Flying from Chicago to Sicily in December is currently the most expensive (average of $642). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Chicago to Sicily

Discover the top 4 airlines that operate flights from Chicago to Sicily. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$488Average$730FlexibilityNo cancel feeOn-time77%
SWISSCheapest$596Average$969FlexibilityNo cancel feeOn-time79%
ITA AirwaysCheapest$704Average$1,079FlexibilityNo cancel feeOn-time81%
LufthansaCheapest$812Average$1,327FlexibilityNo cancel feeOn-time76%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights