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$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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$491
(FlightHub)

One-way from

$247
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$736
From Chicago (CHI) to Sicily
Search Deals
One-way flight from Chicago (CHI) to Sicily
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Highest demand for flights based on searches. 14% potential increase in price ($158 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/29. 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.
mar. 10/1411:25 amORD - CTA
1 stop14h 00mTurkish Airlines
mar. 10/217:10 pmCTA - ORD
1 stop21h 30mTurkish Airlines
Deal found 7/29$491
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/85:55 pmORD - SUF
2 stops37h 00mAir Canada
lun. 11/177:05 pmSUF - ORD
3 stops30h 40mAir Canada
Deal found 7/31$552
This Trip.com deal was found by Cheapflights users on 7/30. 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.
lun. 8/256:10 pmORD - CTA
2 stops22h 00mMultiple Airlines
mar. 9/97:15 pmCTA - ORD
2 stops46h 40mMultiple Airlines
Deal found 7/30$572
This Ovago deal was found by Cheapflights users on 7/31. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/1210:35 pmORD - CTA
1 stop15h 25mBritish Airways
lun. 8/256:45 pmCTA - ORD
1 stop24h 10mBritish Airways
Deal found 7/31$621
This SWISS deal was found by Cheapflights users on 7/31. 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.
dom. 10/267:50 pmORD - SUF
1 stop12h 05mSWISS
lun. 11/32:50 pmSUF - ORD
1 stop32h 30mSWISS
Deal found 7/31$647
This Iberia deal was found by Cheapflights users on 7/29. 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.
mié. 8/134:30 pmORD - CTA
1 stop19h 35mIberia
jue. 8/289:25 pmCTA - ORD
1 stop23h 05mIberia
Deal found 7/29$695
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/31. 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.
dom. 10/269:25 pmORD - SUF
2 stops19h 35mTAP AIR PORTUGAL
mar. 11/411:15 amSUF - ORD
2 stops34h 45mTAP AIR PORTUGAL
Deal found 7/31$700
This Lufthansa deal was found by Cheapflights users on 7/31. 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.
mié. 10/223:35 pmORD - SUF
1 stop12h 20mLufthansa
vie. 10/312:50 pmSUF - ORD
2 stops36h 15mLufthansa
Deal found 7/31$703
This oojo deal was found by Cheapflights users on 7/31. 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.
lun. 8/183:00 pmORD - PMO
1 stop15h 50mITA Airways
dom. 8/244:35 pmPMO - ORD
1 stop27h 35mITA Airways
Deal found 7/31$711
This Turkish Airlines deal was found by Cheapflights users on 7/29. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/1511:25 amORD - PMO
1 stop23h 50mTurkish Airlines
lun. 9/19:20 amPMO - ORD
1 stop31h 20mTurkish Airlines
Deal found 7/29$712
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
dom. 8/173:00 pmORD - PMO
1 stop19h 35mMultiple Airlines
mié. 9/37:55 pmPMO - ORD
2 stops33h 48mMultiple Airlines
Deal found 7/29$717
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 8/135:10 pmORD - PMO
1 stop14h 50mDelta
lun. 8/253:45 pmPMO - ORD
2 stops36h 50mDelta
Deal found 7/31$721

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 julio 31, 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

mar. 10/14

11:25 am-8:25 am

1 stop14h 00m

Catania Fontanarossa

mar. 10/21

7:10 pm-9:40 am

1 stop21h 30m

$491

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

lun. 8/25

6:10 pm-11:10 pm

2 stops22h 00m

Catania Fontanarossa

mar. 9/9

7:15 pm-10:55 am

2 stops46h 40m

$572

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

mar. 10/14

4:52 pm-9:00 pm

2 stops21h 08m

Catania Fontanarossa

mar. 10/21

7:55 pm-1:50 pm

1 stop24h 55m

$644

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

dom. 10/26

7:50 pm-1:55 pm

1 stop12h 05m

Lamezia Terme Intl

lun. 11/3

2:50 pm-4:20 pm

1 stop32h 30m

$647

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

mié. 8/13

4:30 pm-7:05 pm

1 stop19h 35m

Catania Fontanarossa

jue. 8/28

9:25 pm-1:30 pm

1 stop23h 05m

$695

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

dom. 10/26

9:25 pm-11:00 pm

2 stops19h 35m

Lamezia Terme Intl

mar. 11/4

11:15 am-3:00 pm

2 stops34h 45m

$700

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

mié. 10/22

3:35 pm-10:55 am

1 stop12h 20m

Lamezia Terme Intl

vie. 10/31

2:50 pm-9:05 pm

2 stops36h 15m

$703

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

lun. 8/18

3:00 pm-1:50 pm

1 stop15h 50m

Palermo Punta Raisi

dom. 8/24

4:35 pm-1:10 pm

1 stop27h 35m

$711

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

vie. 8/15

11:25 am-6:15 pm

1 stop23h 50m

Palermo Punta Raisi

lun. 9/1

9:20 am-9:40 am

1 stop31h 20m

$712

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

dom. 8/17

3:00 pm-5:35 pm

1 stop19h 35m

Palermo Punta Raisi

mié. 9/3

7:55 pm-10:43 pm

2 stops33h 48m

$717

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 50 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 $1,317). 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 julio 31, 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.

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 julio 31, 2025.
Read through reviews of airlines operating flights from Chicago to Sicily, such as Delta, KLM, and Austrian Airlines. 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
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
823 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
SWISS
7.5
Good
1,686 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $286. However, be on the lookout for offers from TAP AIR PORTUGAL and Iberia, 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 $1,317). 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
O'Hare Intl to Malpensa flights
Midway to Leonardo da Vinci/Fiumicino flights
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Midway to Malpensa flights
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St. Louis to Vicenza flights
St. Louis to Leonardo da Vinci/Fiumicino flights
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Midway to Naples flights
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Midway to Vicenza flights
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St. Louis to Florence flights
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Midway to Bologna flights
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O'Hare Intl to Turin flights
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Peoria to Leonardo da Vinci/Fiumicino flights
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O'Hare Intl to Trieste flights
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Midway to Genoa flights
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Midway to Turin flights
Midway to Bari flights
Evansville to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Ancona flights
St. Louis to Cagliari flights
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Top 4 airlines flying from Chicago to Sicily

Discover the top 4 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$556Average$813FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$754Average$1,194FlexibilityNo cancel feeOn-time76%
ITA AirwaysCheapest$766Average$1,092FlexibilityNo cancel feeOn-time81%
SWISSCheapest$775Average$1,308FlexibilityNo cancel feeOn-time79%

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