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Sicily

$314+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Chicago to Sicily

Keep the following information in mind while searching for Chicago to Sicily flight deals. Data was last updated November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$489
(FlightHub)

One-way from

$314
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$886
Provider with most accurate pricing for Chicago (CHI)-Catania Fontanarossa flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Catania Fontanarossa flights.
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From Chicago (CHI) to Sicily
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One-way flight from Chicago (CHI) to Sicily
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Highest demand for flights based on searches. 18% potential increase in price ($208 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 4, 2025.

This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:30 pmORD - PMO
2 stops18h 15mMultiple Airlines
Wed 12/106:00 amPMO - ORD
2 stops18h 20mMultiple Airlines
Deal found 11/3$508
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/911:50 amORD - CTA
1 stop13h 45mTurkish Airlines
Sat 11/229:35 amCTA - ORD
1 stop31h 30mTurkish Airlines
Deal found 11/2$531
This FlightHub deal was found by Cheapflights users on 11/2. 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 11/58:20 pmORD - PMO
1 stop29h 10mTurkish Airlines
Wed 11/126:45 pmPMO - ORD
1 stop30h 40mTurkish Airlines
Deal found 11/2$546
This oojo deal was found by Cheapflights users on 11/2. 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 11/511:50 amORD - PMO
2 stops18h 55mMultiple Airlines
Wed 11/126:45 pmPMO - ORD
1 stop30h 40mMultiple Airlines
Deal found 11/2$549
This FlightHub deal was found by Cheapflights users on 11/2. 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 12/211:50 amORD - PMO
1 stop22h 55mMultiple Airlines
Tue 12/93:15 pmPMO - ORD
2 stops25h 50mMultiple Airlines
Deal found 11/2$555
This FlightHub deal was found by Cheapflights users on 11/2. 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 11/1611:50 amORD - PMO
2 stops23h 35mMultiple Airlines
Wed 11/262:30 pmPMO - ORD
2 stops26h 35mMultiple Airlines
Deal found 11/2$571
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:05 amORD - PMO
2 stops23h 25mMultiple Airlines
Tue 12/236:05 amPMO - ORD
2 stops17h 15mMultiple Airlines
Deal found 11/3$602
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:00 amORD - PMO
3 stops22h 30mMultiple Airlines
Wed 12/108:05 pmPMO - ORD
2 stops24h 05mMultiple Airlines
Deal found 11/3$616
This FlightHub deal was found by Cheapflights users on 11/2. 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.
Thu 11/611:50 amORD - CTA
1 stop23h 35mTurkish Airlines
Sat 11/89:35 amCTA - ORD
1 stop55h 30mTurkish Airlines
Deal found 11/2$624
This oojo deal was found by Cheapflights users on 11/2. 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 11/268:20 pmORD - PMO
1 stop29h 10mTurkish Airlines
Wed 12/36:45 pmPMO - ORD
1 stop22h 20mTurkish Airlines
Deal found 11/2$642
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/173:55 pmORD - PMO
2 stops16h 40mMultiple Airlines
Thu 11/277:25 amPMO - ORD
2 stops19h 40mMultiple Airlines
Deal found 11/2$649
This KLM deal was found by Cheapflights users on 11/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:15 pmMDW - PMO
2 stops14h 10mKLM
Tue 12/96:10 amPMO - MDW
2 stops18h 50mKLM
Deal found 11/3$670

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 November 4, 2025.
Use the filters below to find and compare flights from Chicago to Sicily that are best for you.

Fly from

Chicago

Fly to

Sicily

Route

Depart

Return

Price

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Thu 3/26

9:20 pm-9:15 am

2 stops29h 55m

Palermo Punta Raisi

Sat 4/4

7:20 pm-9:40 am

1 stop21h 20m

$547

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Fri 3/13

9:20 pm-9:15 am

2 stops29h 55m

Palermo Punta Raisi

Mon 3/23

9:30 am-11:05 am

1 stop31h 35m

$547

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sat 1/10

11:50 am-6:25 pm

1 stop23h 35m

Catania Fontanarossa

Wed 1/21

9:35 am-10:05 am

1 stop31h 30m

$557

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 12/2

11:50 am-11:00 pm

2 stops28h 10m

Palermo Punta Raisi

Tue 12/9

3:15 pm-10:05 am

2 stops25h 50m

$571

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 12/3

11:50 am-11:00 pm

2 stops28h 10m

Palermo Punta Raisi

Wed 12/10

3:15 pm-10:05 am

2 stops25h 50m

$571

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 11/16

11:50 am-6:25 pm

2 stops23h 35m

Palermo Punta Raisi

Wed 11/26

2:30 pm-10:05 am

2 stops26h 35m

$571

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 4/28

7:00 am-6:00 pm

2 stops28h 00m

Palermo Punta Raisi

Sun 5/10

5:35 pm-4:10 pm

1 stop29h 35m

$609

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 4/27

11:25 am-6:20 pm

1 stop23h 55m

Palermo Punta Raisi

Sat 5/9

7:20 pm-9:40 am

1 stop21h 20m

$619

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Fri 2/27

8:15 pm-1:40 pm

2 stops34h 25m

Palermo Punta Raisi

Thu 3/12

2:25 pm-4:25 pm

2 stops32h 00m

$649

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Tue 11/18

1:15 pm-10:25 am

2 stops14h 10m

Palermo Punta Raisi

Tue 12/9

6:10 am-6:00 pm

2 stops18h 50m

$670

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 36 results
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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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Sicily (average of $346). Flying from Chicago to Sicily in June is currently the most expensive (average of $975). 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.

What is the cheapest time of day to fly from CHI to SI?

Find hourly flight availability from Chicago to Sicily. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

It’s typically best to fly out from Chicago to Sicily in the morning. Doing so could potentially save you 40% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago to Sicily?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sicily. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Sicily flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 4, 2025.
Read through reviews of airlines operating flights from Chicago to Sicily, such as Delta, SWISS, and Turkish Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
SWISS
7.5
Good
1,776 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Turkish Airlines
7.3
Good
4,039 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Lufthansa
6.8
Okay
7,545 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
ITA Airways
6.7
Okay
1,079 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 12h 10m. Chicago and Sicily are separated by a distance of 5097 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 - Catania Fontanarossa.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Sicily (average of $346). Flying from Chicago to Sicily in June is currently the most expensive (average of $975). 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

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Alternative routes for Chicago to Sicily

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Malpensa flights
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Linate flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Florence flights
Midway to Malpensa flights
O'Hare Intl to Bergamo flights
O'Hare Intl to Ciampino flights
O'Hare Intl to Naples flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Linate flights
O'Hare Intl to Bologna flights
Midway to Florence flights
O'Hare Intl to Palermo flights
Midway to Vicenza flights
Midway to Naples flights
St. Louis to Vicenza flights
O'Hare Intl to Treviso A. Canova flights
O'Hare Intl to Catania flights
St. Louis to Malpensa flights
St. Louis to Linate flights
O'Hare Intl to Verona flights
Peoria to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Pisa flights
Midway to Catania flights
St. Louis to Naples flights
O'Hare Intl to Bari flights
Moline to Leonardo da Vinci/Fiumicino flights
Midway to Bologna flights
O'Hare Intl to Turin flights
O'Hare Intl to Trieste flights
O'Hare Intl to Genoa flights
St. Louis to Catania flights
O'Hare Intl to Lamezia Terme flights
St. Louis to Bologna flights
Midway to Turin flights
Evansville to Leonardo da Vinci/Fiumicino flights
Midway to Palermo flights
St. Louis to Florence flights
Springfield to Leonardo da Vinci/Fiumicino flights
Moline to Vicenza flights
St. Louis to Verona flights
O'Hare Intl to Cagliari flights
O'Hare Intl to Brindisi flights
St. Louis to Turin flights
St. Louis to Ciampino flights

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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$488Average$790FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$776Average$1,225FlexibilityNo cancel feeOn-time76%
ITA AirwaysCheapest$783Average$1,098FlexibilityNo cancel feeOn-time81%
SWISSCheapest$801Average$1,313FlexibilityNo cancel feeOn-time79%

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