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$286+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$608
(Mytrip)

One-way from

$286
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$620
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 ($213 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 21, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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 4/67:15 pmORD - CTA
2 stops20h 40mMultiple Airlines
Sun 4/1312:45 pmCTA - ORD
2 stops34h 25mMultiple Airlines
Deal found 2/20$608
This oojo deal was found by Cheapflights users on 2/19. 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 9/811:45 pmORD - PMO
1 stop35h 35mTurkish Airlines
Thu 9/189:20 amPMO - ORD
1 stop31h 20mTurkish Airlines
Deal found 2/19$613
This oojo deal was found by Cheapflights users on 2/19. 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 10/67:50 pmORD - CTA
1 stop29h 35mTurkish Airlines
Wed 10/159:25 amCTA - ORD
1 stop31h 15mTurkish Airlines
Deal found 2/19$613
This Mytrip deal was found by Cheapflights users on 2/20. 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 4/67:15 pmORD - PMO
2 stops20h 45mMultiple Airlines
Sun 4/1311:30 amPMO - ORD
2 stops35h 40mMultiple Airlines
Deal found 2/20$632
This Mytrip deal was found by Cheapflights users on 2/20. 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 4/67:15 pmORD - SUF
2 stops20h 15mMultiple Airlines
Sun 4/1311:15 amSUF - ORD
3 stops35h 55mMultiple Airlines
Deal found 2/20$639
This FlightHub deal was found by Cheapflights users on 2/20. 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 3/239:25 pmORD - PMO
2 stops34h 35mTAP AIR PORTUGAL
Wed 4/23:10 pmPMO - ORD
2 stops56h 00mTAP AIR PORTUGAL
Deal found 2/20$716
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/308:35 pmORD - PMO
1 stop15h 05mAmerican Airlines
Tue 4/812:20 pmPMO - ORD
1 stop35h 40mAmerican Airlines
Deal found 2/20$736
This lol.travel deal was found by Cheapflights users on 2/20. 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.
Thu 3/278:05 pmORD - SUF
1 stop12h 05mSWISS
Mon 3/318:50 pmSUF - ORD
1 stop22h 20mSWISS
Deal found 2/20$753
This FlightHub deal was found by Cheapflights users on 2/19. 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 10/133:25 pmCTA - ORD
2 stops55h 45mTAP AIR PORTUGAL
Deal found 2/19$774
This Gotogate deal was found by Cheapflights users on 2/19. 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.
Wed 4/24:00 pmORD - CTA
2 stops18h 45mLufthansa
Wed 4/911:55 amCTA - ORD
2 stops15h 00mLufthansa
Deal found 2/19$817
This Expedia deal was found by Cheapflights users on 2/19. 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 4/811:36 amORD - PMO
2 stops17h 09mBritish Airways
Wed 4/3012:55 pmPMO - ORD
1 stop32h 50mBritish Airways
Deal found 2/19$828
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2510:35 amORD - PMO
2 stops21h 25mDelta
Wed 5/76:10 amPMO - ORD
2 stops24h 56mDelta
Deal found 2/20$837

Find flights from Chicago to Sicily within your budget

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 February 21, 2025.

Fly from

Chicago

Fly to

Sicily

Route

Depart

Return

Price

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 4/6

7:15 pm-10:55 pm

2 stops20h 40m

Catania Fontanarossa

Sun 4/13

12:45 pm-4:10 pm

2 stops34h 25m

$608

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Tue 3/4

11:55 am-8:35 am

1 stop13h 40m

Catania Fontanarossa

Fri 5/9

7:15 pm-9:40 am

1 stop21h 25m

$613

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 4/6

7:15 pm-11:00 pm

2 stops20h 45m

Palermo Punta Raisi

Sun 4/13

11:30 am-4:10 pm

2 stops35h 40m

$632

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sun 4/6

7:15 pm-10:30 pm

2 stops20h 15m

Lamezia Terme Intl

Sun 4/13

11:15 am-4:10 pm

3 stops35h 55m

$639

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 3/11

12:55 pm-5:45 pm

1 stop22h 50m

Palermo Punta Raisi

Wed 4/23

7:20 pm-9:40 am

1 stop21h 20m

$648

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 3/23

9:25 pm-2:00 pm

2 stops34h 35m

Palermo Punta Raisi

Wed 4/2

3:10 pm-4:10 pm

2 stops56h 00m

$716

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 3/30

8:35 pm-6:40 pm

1 stop15h 05m

Palermo Punta Raisi

Tue 4/8

12:20 pm-5:00 pm

1 stop35h 40m

$736

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Thu 3/27

8:05 pm-2:10 pm

1 stop12h 05m

Lamezia Terme Intl

Mon 3/31

8:50 pm-12:10 pm

1 stop22h 20m

$753

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sat 4/5

6:15 pm-1:25 pm

2 stops36h 10m

Catania Fontanarossa

Mon 4/21

4:30 pm-4:10 pm

2 stops54h 40m

$801

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 4/2

4:00 pm-5:45 pm

2 stops18h 45m

Catania Fontanarossa

Wed 4/9

11:55 am-7:55 pm

2 stops15h 00m

$817

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 40 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.

Travel insights for flights from Chicago to Sicily

Get recent, data-driven insights about flights from Chicago to Sicily including ideal travel times, pricing trends, and more.

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 $1,380). 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 February 21, 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 February 21, 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
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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
3,276 reviews
Emirates
8.1
Very good
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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
8,219 reviews
Emirates
8.1
Very good
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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
1,333 reviews
Emirates
8.1
Very good
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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
773 reviews
Emirates
8.1
Very good
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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
1,568 reviews
Emirates
8.1
Very good
3,276 reviews

Food

7.9

Boarding

8.1

Comfort

8.0

Overall

8.1

Crew

8.3

Entertainment

8.2

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 Delta, with whom users have recently found tickets for as low as $598. However, be on the lookout for offers from British Airways 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 $667). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,380). 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
O'Hare Intl to Malpensa flights
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Midway to Malpensa flights
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O'Hare Intl to Bergamo flights
Midway to Florence flights
Midway to Naples flights
O'Hare Intl to Ciampino flights
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O'Hare Intl to Bari flights
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Midway to Bologna flights
O'Hare Intl to Verona flights
Midway to Catania flights
Midway to Palermo flights
O'Hare Intl to Treviso A. Canova flights
O'Hare Intl to Trieste flights
Moline to Leonardo da Vinci/Fiumicino flights
St. Louis to Florence flights
Midway to Bari flights
O'Hare Intl to Genoa flights
O'Hare Intl to Cagliari flights
O'Hare Intl to Olbia flights
Midway to Genoa flights
O'Hare Intl to Brindisi flights
St. Louis to Catania flights
St. Louis to Naples flights
O'Hare Intl to Turin flights
O'Hare Intl to Lamezia Terme flights
Midway to Turin flights
O'Hare Intl to Ancona flights
St. Louis to Pisa flights
Moline to Vicenza 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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$661FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$636Average$797FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$657Average$1,002FlexibilityNo cancel feeOn-time81%
SWISSCheapest$807Average$1,312FlexibilityNo cancel feeOn-time79%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$825Average$1,337FlexibilityNo cancel feeOn-time76%
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