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Sicily

$279+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$701
(lol.travel)

One-way from

$279
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$1,321
From Chicago (CHI) to Sicily
Search Deals
One-way flight from Chicago (CHI) to Sicily
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This lol.travel deal was found by Cheapflights users on 6/15. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/103:00 pmORD - CTA
1 stop12h 55mITA Airways
Tue 8/267:15 pmCTA - ORD
1 stop24h 55mITA Airways
Deal found 6/15$701
This Mytrip deal was found by Cheapflights users on 6/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:00 pmORD - CTA
2 stops18h 30mMultiple Airlines
Tue 8/267:05 pmCTA - ORD
2 stops41h 55mMultiple Airlines
Deal found 6/15$730
This Iberia deal was found by Cheapflights users on 6/14. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:30 pmORD - CTA
1 stop19h 35mIberia
Tue 9/1612:00 pmCTA - ORD
1 stop33h 15mIberia
Deal found 6/14$767
This Gotogate deal was found by Cheapflights users on 6/14. 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.
Tue 7/294:00 pmORD - CTA
1 stop16h 25mLufthansa
Tue 8/56:00 amCTA - ORD
1 stop13h 30mLufthansa
Deal found 6/14$810
This FlightHub deal was found by Cheapflights users on 6/14. 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 8/183:00 pmORD - SUF
1 stop20h 30mITA Airways
Mon 9/16:15 amSUF - ORD
1 stop13h 55mITA Airways
Deal found 6/14$828
This Lufthansa deal was found by Cheapflights users on 6/14. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/183:35 pmORD - SUF
2 stops33h 45mLufthansa
Mon 9/18:40 amSUF - ORD
2 stops34h 50mLufthansa
Deal found 6/14$860
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/73:00 pmORD - PMO
1 stop11h 55mMultiple Airlines
Sat 7/1211:40 pmPMO - ORD
1 stop20h 30mMultiple Airlines
Deal found 6/15$893
This FlightHub deal was found by Cheapflights users on 6/15. 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 7/73:00 pmORD - PMO
1 stop17h 25mITA Airways
Tue 7/1512:15 pmPMO - ORD
1 stop31h 55mITA Airways
Deal found 6/15$904
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 9/2810:30 pmORD - PMO
2 stops29h 30mLufthansa
Sun 10/196:05 pmPMO - ORD
2 stops25h 50mLufthansa
Deal found 6/14$911
This FlightHub deal was found by Cheapflights users on 6/13. 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 9/47:50 pmORD - SUF
2 stops20h 10mMultiple Airlines
Mon 9/293:20 pmSUF - ORD
2 stops25h 20mMultiple Airlines
Deal found 6/13$913
This FlightHub deal was found by Cheapflights users on 6/15. 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.
Thu 10/26:00 pmORD - CTA
2 stops36h 25mTAP AIR PORTUGAL
Mon 10/134:30 pmCTA - ORD
2 stops54h 40mTAP AIR PORTUGAL
Deal found 6/15$924
This FlightHub deal was found by Cheapflights users on 6/13. 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 10/67:50 pmORD - CTA
1 stop15h 20mTurkish Airlines
Wed 10/159:25 amCTA - ORD
1 stop15h 30mTurkish Airlines
Deal found 6/13$930

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 June 16, 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

Sun 8/10

3:00 pm-10:55 am

1 stop12h 55m

Catania Fontanarossa

Tue 8/26

7:15 pm-1:10 pm

1 stop24h 55m

$701

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 8/10

6:00 pm-7:30 pm

2 stops18h 30m

Catania Fontanarossa

Tue 8/26

7:05 pm-6:00 am

2 stops41h 55m

$730

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 9/10

4:30 pm-7:05 pm

1 stop19h 35m

Catania Fontanarossa

Tue 9/16

12:00 pm-2:15 pm

1 stop33h 15m

$767

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 7/29

4:00 pm-3:25 pm

1 stop16h 25m

Catania Fontanarossa

Tue 8/5

6:00 am-12:30 pm

1 stop13h 30m

$810

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Mon 8/18

3:00 pm-6:30 pm

1 stop20h 30m

Lamezia Terme Intl

Mon 9/1

6:15 am-1:10 pm

1 stop13h 55m

$828

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Mon 8/18

3:35 pm-8:20 am

2 stops33h 45m

Lamezia Terme Intl

Mon 9/1

8:40 am-12:30 pm

2 stops34h 50m

$860

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 7/7

3:00 pm-9:55 am

1 stop11h 55m

Palermo Punta Raisi

Sat 7/12

11:40 pm-1:10 pm

1 stop20h 30m

$893

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 7/7

3:00 pm-3:25 pm

1 stop17h 25m

Palermo Punta Raisi

Tue 7/15

12:15 pm-1:10 pm

1 stop31h 55m

$904

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Thu 9/4

7:50 pm-11:00 pm

2 stops20h 10m

Lamezia Terme Intl

Mon 9/29

3:20 pm-9:40 am

2 stops25h 20m

$913

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 9/1

3:35 pm-11:00 am

1 stop12h 25m

Palermo Punta Raisi

Mon 9/15

11:25 am-7:55 pm

1 stop15h 30m

$921

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 55 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 $667). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,318). 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 June 16, 2025.

When flying from Chicago to Sicily, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Sicily by month

Plan your trip to Sicily by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Sicily ranges from 0.2 - 3.9 inches per month. October is typically the wettest month, when rainfall can reach 3.9 in. July is typically the driest time to visit Sicily when rainfall is around 0.2 in.

Temperature in Sicily by month

Plan your trip to Sicily by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Sicily, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 55.4 F).

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 June 16, 2025.
Peruse reviews from past customers who have flown with Emirates, Delta and KLM from Chicago to Sicily to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Emirates
8.1
Very good
3,266 reviews
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Delta
8.0
Very good
7,963 reviews
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
KLM
7.8
Good
1,361 reviews
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Austrian Airlines
7.6
Good
803 reviews
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.
Air France
7.5
Good
1,463 reviews
Emirates
8.1
Very good
3,266 reviews

Crew

8.3

Comfort

8.0

Entertainment

8.2

Boarding

8.1

Food

7.8

Overall

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

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.

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

    The cheapest airline one-way is Lufthansa, with whom users have recently found tickets for as low as $516. However, be on the lookout for offers from Iberia and ITA Airways, 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, January is the cheapest month in which you can book a flight from Chicago to Sicily (average of $667). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,318). 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

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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 Naples flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Florence flights
Midway to Malpensa flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Naples flights
Midway to Vicenza flights
St. Louis to Vicenza flights
O'Hare Intl to Bergamo flights
O'Hare Intl to Bari flights
O'Hare Intl to Palermo flights
Midway to Linate flights
O'Hare Intl to Ciampino flights
Midway to Florence flights
O'Hare Intl to Catania flights
St. Louis to Malpensa flights
O'Hare Intl to Bologna flights
St. Louis to Linate flights
O'Hare Intl to Pisa flights
Midway to Palermo flights
Midway to Bari flights
O'Hare Intl to Olbia flights
O'Hare Intl to Lamezia Terme flights
St. Louis to Florence flights
Midway to Catania flights
O'Hare Intl to Genoa flights
O'Hare Intl to Verona flights
O'Hare Intl to Trieste flights
O'Hare Intl to Treviso A. Canova flights
Midway to Bologna flights
St. Louis to Naples flights
O'Hare Intl to Turin flights
O'Hare Intl to Brindisi flights
O'Hare Intl to Cagliari flights
Midway to Turin flights
St. Louis to Catania flights
Midway to Genoa flights
Moline to Leonardo da Vinci/Fiumicino flights
Evansville to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Ancona flights
St. Louis to Bergamo flights
Peoria to Leonardo da Vinci/Fiumicino flights

Top 7 airlines flying from Chicago to Sicily

Discover the top 7 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$656FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$613Average$833FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$656Average$1,039FlexibilityNo cancel feeOn-time81%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$819Average$1,243FlexibilityNo cancel feeOn-time76%
SWISSCheapest$852Average$1,325FlexibilityNo cancel feeOn-time79%

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