HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sicily

$247+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Sicily with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Sicily

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sicily (ITSI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$597
(FlightHub)

One-way from

$247
(Kiwi.com)
From Chicago (CHI) to Sicily
Search Deals
One-way flight from Chicago (CHI) to Sicily
Search Deals

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 December 22, 2024.

This Mytrip deal was found by Cheapflights users on 12/21. 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 12/302:05 pmORD - PMO
2 stops21h 35mMultiple Airlines
Thu 1/910:45 pmPMO - ORD
3 stops27h 52mMultiple Airlines
Deal found 12/21$935
This SWISS deal was found by Cheapflights users on 12/21. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:05 pmORD - PMO
1 stop12h 50mSWISS
Thu 1/92:45 pmPMO - ORD
1 stop32h 30mSWISS
Deal found 12/21$1,474
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/253:35 pmORD - SUF
3 stops23h 25mMultiple Airlines
Sun 1/511:15 amSUF - ORD
2 stops53h 55mMultiple Airlines
Deal found 12/21$1,961
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/232:55 pmORD - PMO
2 stops20h 25mDelta
Mon 12/306:10 amPMO - ORD
2 stops24h 43mDelta
Deal found 12/21$2,454
This SmartFares deal was found by Cheapflights users on 12/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:05 pmORD - SUF
1 stop16h 45mSWISS
Sun 1/59:55 amSUF - ORD
1 stop13h 20mSWISS
Deal found 12/21$3,108
This TAP AIR PORTUGAL deal was found by Cheapflights users on 12/22. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2312:47 pmORD - PMO
3 stops18h 43mTAP AIR PORTUGAL
Mon 12/306:10 amPMO - ORD
3 stops34h 16mTAP AIR PORTUGAL
Deal found 12/22$3,490
This SWISS deal was found by Cheapflights users on 12/21. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/217:05 pmORD - CTA
1 stop17h 45mSWISS
Sat 12/288:20 pmCTA - ORD
1 stop23h 35mSWISS
Deal found 12/21$3,663
This Iberia deal was found by Cheapflights users on 12/22. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/234:45 pmORD - PMO
2 stops19h 05mIberia
Mon 12/3010:20 amPMO - ORD
2 stops35h 10mIberia
Deal found 12/22$3,932
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/2310:08 amMDW - PMO
2 stops20h 52mDelta
Mon 12/306:10 amPMO - MDW
2 stops22h 56mDelta
Deal found 12/21$4,379

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 2/17

8:30 pm-6:25 pm

1 stop14h 55m

Catania Fontanarossa

Wed 2/26

9:35 am-10:10 am

1 stop31h 35m

$597

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 2/5

8:30 pm-8:35 am

1 stop29h 05m

Palermo Punta Raisi

Wed 2/12

6:45 pm-10:10 am

1 stop22h 25m

$601

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 1/25

6:30 pm-6:40 pm

2 stops17h 10m

Palermo Punta Raisi

Mon 2/10

7:00 am-5:20 pm

2 stops17h 20m

$611

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Mon 2/3

7:05 pm-8:15 pm

2 stops18h 10m

Catania Fontanarossa

Mon 2/10

11:05 am-1:25 pm

2 stops33h 20m

$616

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 2/5

11:55 am-10:35 pm

2 stops27h 40m

Lamezia Terme Intl

Wed 2/12

10:10 am-10:10 am

2 stops31h 00m

$631

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sun 2/9

8:25 pm-2:35 pm

2 stops35h 10m

Catania Fontanarossa

Wed 2/26

3:20 pm-3:30 pm

2 stops55h 10m

$691

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 2/26

10:05 am-9:30 am

2 stops16h 25m

Catania Fontanarossa

Thu 3/6

9:20 pm-9:24 pm

2 stops31h 04m

$747

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Sat 3/29

7:30 pm-5:30 pm

2 stops16h 00m

Catania Fontanarossa

Thu 4/10

7:00 am-6:20 pm

2 stops18h 20m

$784

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 3/29

7:30 pm-5:15 pm

2 stops15h 45m

Palermo Punta Raisi

Fri 4/11

12:15 pm-9:15 pm

2 stops16h 00m

$790

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Fri 4/4

6:00 pm-6:15 pm

2 stops41h 15m

Palermo Punta Raisi

Mon 4/21

12:15 pm-4:10 pm

2 stops58h 55m

$803

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 36 results
1
2
3
4

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 $1,403). 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 22, 2024.

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 December 22, 2024.
Peruse reviews from past customers who have flown with TAP AIR PORTUGAL, ITA Airways 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.
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,594 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,342 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

SWISS
7.6
Good
1,605 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France
7.4
Good
1,501 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Turkish Airlines
7.3
Good
3,900 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 ITA Airways, with whom users have recently found tickets for as low as $531. However, be on the lookout for offers from Delta and TAP AIR PORTUGAL, 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 - Catania Fontanarossa, Chicago O'Hare Intl - Palermo Punta Raisi 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 $1,403). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Top 8 airlines flying from Chicago to Sicily

Discover the top 8 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 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$82FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$662FlexibilityNo cancel feeOn-time69%
TAP AIR PORTUGALCheapest$603Average$980FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$660Average$1,023FlexibilityNo cancel feeOn-time81%
Turkish AirlinesCheapest$660Average$859FlexibilityNo cancel feeOn-time77%
SWISSCheapest$802Average$1,245FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$806Average$1,284FlexibilityNo cancel feeOn-time76%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.