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$375+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
abr. 8 — abr. 151
mar. 4/8
mar. 4/15
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 abril 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$765
(Mytrip)

One-way from

$682
(Flightnetwork)

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. 16% potential increase in price ($198 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 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 abril 3, 2025.

This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/2511:25 amORD - CTA
1 stop23h 50mTurkish Airlines
sáb. 10/49:25 amCTA - ORD
1 stop19h 35mTurkish Airlines
Deal found 4/1$642
This oojo deal was found by Cheapflights users on 4/2. 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.
dom. 9/2811:25 amORD - PMO
1 stop13h 55mTurkish Airlines
dom. 10/197:15 pmPMO - ORD
1 stop33h 45mTurkish Airlines
Deal found 4/2$682
This Trip.com deal was found by Cheapflights users on 4/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/97:15 pmORD - PMO
2 stops20h 15mMultiple Airlines
vie. 9/197:20 amPMO - ORD
2 stops39h 50mMultiple Airlines
Deal found 4/2$698
This Mytrip deal was found by Cheapflights users on 4/2. 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.
dom. 5/46:35 pmORD - CTA
2 stops19h 00mMultiple Airlines
dom. 5/1110:35 pmCTA - ORD
2 stops21h 45mMultiple Airlines
Deal found 4/2$771
This FlightHub deal was found by Cheapflights users on 4/2. 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.
jue. 10/26:00 pmORD - CTA
2 stops19h 05mTAP AIR PORTUGAL
lun. 10/134:30 pmCTA - ORD
2 stops54h 40mTAP AIR PORTUGAL
Deal found 4/2$799
This CrystalTravel deal was found by Cheapflights users on 4/2. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/206:35 pmORD - PMO
1 stop21h 50mSWISS
mar. 4/295:50 amPMO - ORD
1 stop17h 05mSWISS
Deal found 4/2$801
This Orbitz deal was found by Cheapflights users on 4/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:00 pmORD - PMO
2 stops56h 10mBritish Airways
jue. 11/272:35 pmPMO - ORD
1 stop30h 20mBritish Airways
Deal found 4/2$832
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
dom. 4/209:40 pmORD - PMO
1 stop12h 35mLufthansa
mar. 4/295:55 pmPMO - ORD
2 stops26h 00mLufthansa
Deal found 4/2$865
This Aeromexico deal was found by Cheapflights users on 4/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/2011:15 amORD - PMO
2 stops24h 05mAir France
mar. 4/2910:05 amPMO - ORD
2 stops44h 54mAir France
Deal found 4/2$875
This Aeromexico deal was found by Cheapflights users on 4/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/209:52 amMDW - PMO
2 stops21h 33mAir France
mar. 4/293:10 pmPMO - MDW
2 stops38h 12mAir France
Deal found 4/2$875
This Gurufare deal was found by Cheapflights users on 4/2. 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.
mar. 9/2311:00 amORD - CTA
2 stops16h 55mITA Airways
lun. 9/296:00 amCTA - ORD
1 stop14h 10mITA Airways
Deal found 4/2$898
This oojo deal was found by Cheapflights users on 4/2. 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.
dom. 9/143:00 pmORD - PMO
2 stops16h 40mITA Airways
dom. 9/286:10 amPMO - ORD
1 stop14h 00mITA Airways
Deal found 4/2$910

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 abril 3, 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

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

jue. 5/15

10:00 am-11:10 pm

3 stops30h 10m

Palermo Punta Raisi

jue. 5/22

6:05 pm-4:10 pm

2 stops29h 05m

$765

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

dom. 5/4

6:35 pm-8:35 pm

2 stops19h 00m

Catania Fontanarossa

dom. 5/11

10:35 pm-1:20 pm

2 stops21h 45m

$771

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

dom. 4/20

6:35 pm-11:25 pm

1 stop21h 50m

Palermo Punta Raisi

mar. 4/29

5:50 am-3:55 pm

1 stop17h 05m

$801

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

mar. 4/29

2:20 pm-2:35 pm

2 stops17h 15m

Lamezia Terme Intl

lun. 5/19

3:20 pm-12:30 pm

2 stops28h 10m

$808

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

dom. 4/13

11:25 am-8:20 am

1 stop13h 55m

Palermo Punta Raisi

mié. 5/7

7:15 pm-9:40 am

1 stop21h 25m

$843

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

dom. 4/20

9:40 pm-5:15 pm

1 stop12h 35m

Palermo Punta Raisi

mar. 4/29

5:55 pm-12:55 pm

2 stops26h 00m

$865

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

dom. 4/20

11:15 am-6:20 pm

2 stops24h 05m

Palermo Punta Raisi

mar. 4/29

10:05 am-11:59 pm

2 stops44h 54m

$875

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

dom. 4/20

9:52 am-2:25 pm

2 stops21h 33m

Palermo Punta Raisi

mar. 4/29

3:10 pm-10:22 pm

2 stops38h 12m

$875

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

vie. 5/9

3:00 pm-10:30 pm

1 stop24h 30m

Catania Fontanarossa

dom. 5/25

6:00 am-1:10 pm

1 stop14h 10m

$906

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

mar. 4/8

10:40 am-1:40 pm

2 stops20h 00m

Palermo Punta Raisi

lun. 5/5

8:30 pm-5:55 pm

2 stops28h 25m

$941

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 42 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 abril 3, 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 abril 3, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Air Transat 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
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,323 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Transat
7.8
Good
382 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Austrian Airlines
7.6
Good
771 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
SWISS
7.5
Good
1,574 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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 British Airways, with whom users have recently found tickets for as low as $682. However, be on the lookout for offers from ITA Airways and KLM, 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 $1,347). 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
O'Hare Intl to Malpensa flights
O'Hare Intl to Linate flights
O'Hare Intl to Florence flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Naples flights
Midway to Malpensa flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Linate flights
Midway to Vicenza flights
Midway to Naples flights
O'Hare Intl to Ciampino flights
O'Hare Intl to Palermo flights
Midway to Florence flights
O'Hare Intl to Bari flights
O'Hare Intl to Bergamo flights
O'Hare Intl to Catania flights
O'Hare Intl to Bologna flights
Midway to Catania flights
St. Louis to Malpensa flights
St. Louis to Florence flights
St. Louis to Naples flights
St. Louis to Vicenza flights
O'Hare Intl to Pisa flights
Midway to Bologna flights
O'Hare Intl to Verona flights
O'Hare Intl to Lamezia Terme flights
O'Hare Intl to Genoa flights
St. Louis to Linate flights
Midway to Palermo flights
O'Hare Intl to Trieste flights
Midway to Bari flights
Midway to Genoa flights
O'Hare Intl to Treviso A. Canova flights
O'Hare Intl to Olbia flights
O'Hare Intl to Turin flights
O'Hare Intl to Cagliari flights
O'Hare Intl to Brindisi flights
Midway to Turin flights
St. Louis to Catania flights
Evansville to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Ancona flights
St. Louis to Bologna flights
Moline to Leonardo da Vinci/Fiumicino flights
Midway to Pisa flights
Peoria to Leonardo da Vinci/Fiumicino flights
St. Louis to Turin 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 abril 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$661FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$613Average$836FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$661Average$1,011FlexibilityNo cancel feeOn-time81%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$825Average$1,328FlexibilityNo cancel feeOn-time76%
SWISSCheapest$943Average$1,356FlexibilityNo cancel feeOn-time79%

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