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$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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$673
(FlightHub)

One-way from

$408
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$1,074
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. 17% potential increase in price ($198 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This FlightHub deal was found by Cheapflights users on 4/23. 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 10/611:25 amORD - CTA
1 stop23h 45mTurkish Airlines
Wed 10/159:25 amCTA - ORD
1 stop31h 15mTurkish Airlines
Deal found 4/23$673
This FlightHub deal was found by Cheapflights users on 4/23. 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 8/3111:25 amORD - PMO
1 stop13h 55mTurkish Airlines
Sun 9/147:15 pmPMO - ORD
1 stop33h 45mTurkish Airlines
Deal found 4/23$736
This FlightHub deal was found by Cheapflights users on 4/23. 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 11/28:25 pmORD - PMO
2 stops32h 15mMultiple Airlines
Thu 11/132:25 pmPMO - ORD
2 stops31h 50mMultiple Airlines
Deal found 4/23$738
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Sat 11/228:25 pmORD - CTA
2 stops34h 45mMultiple Airlines
Mon 12/18:40 pmCTA - ORD
1 stop26h 35mMultiple Airlines
Deal found 4/23$752
This British Airways deal was found by Cheapflights users on 4/23. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/55:00 pmORD - PMO
1 stop12h 30mBritish Airways
Thu 11/132:35 pmPMO - ORD
1 stop30h 20mBritish Airways
Deal found 4/23$762
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sat 9/206:15 pmORD - CTA
2 stops20h 35mTAP AIR PORTUGAL
Mon 9/294:30 pmCTA - ORD
2 stops54h 40mTAP AIR PORTUGAL
Deal found 4/22$789
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sat 9/206:15 pmORD - PMO
2 stops38h 10mTAP AIR PORTUGAL
Mon 9/293:10 pmPMO - ORD
2 stops56h 00mTAP AIR PORTUGAL
Deal found 4/22$796
This Justfly.com deal was found by Cheapflights users on 4/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1210:10 amORD - PMO
2 stops23h 55mScandinavian Airlines
Sat 9/205:55 pmPMO - ORD
1 stop29h 15mScandinavian Airlines
Deal found 4/23$810
This oojo deal was found by Cheapflights users on 4/23. 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 8/63:00 pmORD - CTA
1 stop23h 50mITA Airways
Sat 8/236:00 amCTA - ORD
1 stop14h 10mITA Airways
Deal found 4/23$826
This FlightHub deal was found by Cheapflights users on 4/23. 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 8/82:20 pmORD - PMO
1 stop16h 40mSWISS
Mon 8/183:00 pmPMO - ORD
1 stop28h 10mSWISS
Deal found 4/23$874
This Gurufare deal was found by Cheapflights users on 4/23. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/183:00 pmORD - PMO
1 stop22h 30mITA Airways
Sun 5/256:10 amPMO - ORD
1 stop14h 00mITA Airways
Deal found 4/23$885
This Lufthansa deal was found by Cheapflights users on 4/23. 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.
Wed 11/53:55 pmORD - PMO
1 stop18h 10mLufthansa
Fri 11/1411:40 amPMO - ORD
2 stops15h 25mLufthansa
Deal found 4/23$920

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 April 24, 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 10/6

11:25 am-6:10 pm

1 stop23h 45m

Catania Fontanarossa

Wed 10/15

9:25 am-9:40 am

1 stop31h 15m

$673

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 5/6

7:25 pm-9:55 pm

2 stops19h 30m

Catania Fontanarossa

Fri 5/9

10:50 pm-8:55 am

3 stops41h 05m

$778

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sat 9/20

6:15 pm-9:50 pm

2 stops20h 35m

Catania Fontanarossa

Mon 9/29

4:30 pm-4:10 pm

2 stops54h 40m

$789

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 8/6

3:00 pm-9:50 pm

1 stop23h 50m

Catania Fontanarossa

Sat 8/23

6:00 am-1:10 pm

1 stop14h 10m

$826

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 5/5

8:15 pm-11:25 pm

2 stops20h 10m

Palermo Punta Raisi

Sun 5/11

5:35 pm-6:25 pm

2 stops31h 50m

$826

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 5/18

3:00 pm-8:30 pm

1 stop22h 30m

Palermo Punta Raisi

Sun 5/25

6:10 am-1:10 pm

1 stop14h 00m

$885

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 7/21

6:10 pm-7:45 pm

2 stops18h 35m

Palermo Punta Raisi

Thu 7/31

2:25 pm-4:10 pm

2 stops32h 45m

$934

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 8/19

9:15 pm-11:15 am

1 stop31h 00m

Catania Fontanarossa

Tue 9/2

7:55 pm-6:15 pm

1 stop29h 20m

$969

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Tue 7/29

1:00 pm-3:00 pm

2 stops19h 00m

Palermo Punta Raisi

Tue 8/12

7:20 am-9:47 pm

2 stops21h 27m

$1,042

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 7/8

11:25 am-6:15 pm

1 stop23h 50m

Palermo Punta Raisi

Mon 7/21

9:20 am-10:00 pm

1 stop19h 40m

$1,048

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 44 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 $1,347). 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 April 24, 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 - 4.2 inches per month. October is typically the wettest month, when rainfall can reach 4.2 in. June 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, August 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 51.8 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 April 24, 2025.
Peruse reviews from past customers who have flown with Emirates, Delta and Austrian Airlines 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
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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
8.0
Very good
3,205 reviews
Emirates
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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
7,920 reviews
Emirates
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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
780 reviews
Emirates
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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.
SWISS
7.5
Good
1,582 reviews
Emirates
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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
7.4
Good
1,442 reviews
Emirates
8.0
Very good
3,205 reviews

Crew

8.3

Boarding

8.1

Entertainment

8.2

Overall

8.0

Comfort

8.0

Food

7.8

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 United Airlines, with whom users have recently found tickets for as low as $608. However, be on the lookout for offers from Scandinavian Airlines 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, 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 $1,347). 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
Midway to Leonardo da Vinci/Fiumicino flights
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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$656FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$613Average$837FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$670Average$1,006FlexibilityNo cancel feeOn-time81%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$819Average$1,296FlexibilityNo cancel feeOn-time76%
SWISSCheapest$852Average$1,375FlexibilityNo cancel feeOn-time79%

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