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Sicily

$285+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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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 December 18, 2025.

This Mytrip deal was found by Cheapflights users on 12/16. 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 12/316:30 pmORD - PMO
3 stops21h 00mMultiple Airlines
Tue 1/610:05 amPMO - ORD
2 stops35h 55mMultiple Airlines
Deal found 12/16$1,200
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:40 pmORD - CTA
1 stop32h 05mMultiple Airlines
Thu 1/811:15 pmCTA - ORD
2 stops46h 42mMultiple Airlines
Deal found 12/15$1,837
This FlightHub deal was found by Cheapflights users on 12/16. 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 12/2411:50 amORD - CTA
1 stop23h 35mTurkish Airlines
Sun 1/47:25 pmCTA - ORD
1 stop30h 00mTurkish Airlines
Deal found 12/16$1,866
This KAYAK deal was found by Cheapflights users on 12/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:50 pmORD - CTA
2 stops43h 50mSWISS
Thu 1/89:10 amCTA - ORD
2 stops38h 50mSWISS
Deal found 12/15$1,907
This FlightHub deal was found by Cheapflights users on 12/15. 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.
Fri 12/2611:50 amORD - PMO
2 stops19h 40mMultiple Airlines
Fri 1/29:30 amPMO - ORD
1 stop15h 55mMultiple Airlines
Deal found 12/15$2,058
This FlightHub deal was found by Cheapflights users on 12/15. 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 12/2211:50 amORD - CTA
1 stop37h 45mTurkish Airlines
Thu 1/87:25 pmCTA - ORD
1 stop30h 00mTurkish Airlines
Deal found 12/15$2,234
This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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.
Wed 12/249:05 pmORD - CTA
2 stops28h 00mSWISS
Sun 1/48:40 pmCTA - ORD
2 stops22h 30mSWISS
Deal found 12/16$2,376
This FlightHub deal was found by Cheapflights users on 12/17. 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.
Fri 12/264:20 pmORD - PMO
1 stop12h 05mMultiple Airlines
Sat 1/37:55 pmPMO - ORD
1 stop23h 50mMultiple Airlines
Deal found 12/17$2,628
This FlightHub deal was found by Cheapflights users on 12/15. 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 12/2211:50 amORD - PMO
2 stops19h 40mMultiple Airlines
Wed 1/76:45 pmPMO - ORD
1 stop30h 40mMultiple Airlines
Deal found 12/15$2,666
This KLM deal was found by Cheapflights users on 12/16. 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.
Wed 12/319:50 amMDW - PMO
2 stops17h 35mKLM
Tue 1/66:10 amPMO - MDW
2 stops18h 24mKLM
Deal found 12/16$3,237
This FlightHub deal was found by Cheapflights users on 12/16. 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 12/2911:50 amORD - CTA
1 stop23h 35mTurkish Airlines
Mon 1/59:35 amCTA - ORD
1 stop63h 50mTurkish Airlines
Deal found 12/16$3,934
This Air Canada deal was found by Cheapflights users on 12/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:05 amORD - CTA
2 stops24h 35mAir Canada
Sun 1/410:05 amCTA - ORD
3 stops28h 58mAir Canada
Deal found 12/16$4,569

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$542
(FlightHub)

One-way from

$285
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$1,057
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. 19% potential increase in price ($237 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 4/27

11:25 am-6:20 pm

1 stop23h 55m

Catania Fontanarossa

Wed 5/6

9:30 am-9:40 am

1 stop31h 10m

$570

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 2/17

6:30 pm-5:40 pm

2 stops16h 10m

Palermo Punta Raisi

Wed 3/4

7:10 am-5:20 pm

2 stops17h 10m

$607

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 4/27

7:50 pm-6:20 pm

1 stop15h 30m

Palermo Punta Raisi

Sat 5/9

7:20 pm-9:40 am

1 stop21h 20m

$614

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 3/25

9:20 pm-8:30 am

1 stop29h 10m

Palermo Punta Raisi

Sun 3/29

9:20 am-6:15 pm

1 stop15h 55m

$621

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Fri 1/16

11:50 am-8:35 am

1 stop13h 45m

Catania Fontanarossa

Wed 1/21

9:35 am-10:05 am

1 stop31h 30m

$623

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Fri 1/30

11:50 am-8:35 am

1 stop13h 45m

Catania Fontanarossa

Fri 2/6

7:25 pm-10:05 am

1 stop21h 40m

$623

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 3/24

12:50 pm-8:35 am

1 stop13h 45m

Catania Fontanarossa

Sun 3/29

7:20 pm-9:40 am

1 stop21h 20m

$627

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 2/1

11:50 am-8:35 am

1 stop13h 45m

Catania Fontanarossa

Sun 2/8

7:25 pm-10:05 am

1 stop21h 40m

$646

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 4/11

11:25 am-8:20 am

1 stop13h 55m

Palermo Punta Raisi

Sat 4/18

7:20 pm-9:40 am

1 stop21h 20m

$651

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 3/23

12:50 pm-3:55 pm

2 stops21h 05m

Catania Fontanarossa

Tue 3/31

6:10 am-9:40 am

2 stops34h 30m

$652

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 47 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 $1,055). 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 December 18, 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.

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 December 18, 2025.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS, Turkish Airlines, and Lufthansa. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.5
Good
1,817 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
6.0
Good

Madhukar,Nov 2024

ZRH - BOM

Indian Veg food selection and quality definitely needs a better chef.
SWISS
7.5
Good
1,817 reviews
SWISS
7.5
Good
1,817 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
6.0
Good

Madhukar,Nov 2024

ZRH - BOM

Indian Veg food selection and quality definitely needs a better chef.
Turkish Airlines
7.3
Good
4,103 reviews
SWISS
7.5
Good
1,817 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
6.0
Good

Madhukar,Nov 2024

ZRH - BOM

Indian Veg food selection and quality definitely needs a better chef.
Lufthansa
6.8
Okay
7,637 reviews
SWISS
7.5
Good
1,817 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
6.0
Good

Madhukar,Nov 2024

ZRH - BOM

Indian Veg food selection and quality definitely needs a better chef.
ITA Airways
6.7
Okay
1,108 reviews
SWISS
7.5
Good
1,817 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

Comfort

7.4

Reviews

1 / 20
6.0
Good

Madhukar,Nov 2024

ZRH - BOM

Indian Veg food selection and quality definitely needs a better chef.

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 20h 44m. Chicago and Sicily are separated by a distance of 5002 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 - 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 $1,055). 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.
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Evansville to Leonardo da Vinci/Fiumicino flights
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$488Average$762FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$764Average$1,106FlexibilityNo cancel feeOn-time81%
SWISSCheapest$774Average$1,301FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$776Average$1,218FlexibilityNo cancel feeOn-time76%

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