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$350+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Find cheap flights from Chicago to Sicily with Cheapflights

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Cheap 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 March 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
-
PMO
1 stop11h 40m
Multiple Airlines
Thu 8/278:10 pm
PMO
-
ORD
1 stop24h 10m
Multiple Airlines
Deal found 3/20$478
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
-
PMO
1 stop11h 40m
SWISS
Thu 8/279:45 am
PMO
-
ORD
1 stop13h 10m
SWISS
Deal found 3/20$486
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:20 pm
ORD
-
PMO
1 stop11h 40m
SWISS
Thu 8/279:45 am
PMO
-
ORD
1 stop13h 10m
SWISS
Deal found 3/21$508
This FlightHub deal was found by Cheapflights users on 3/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:20 pm
ORD
-
PMO
1 stop33h 30m
Multiple Airlines
Tue 8/252:55 pm
PMO
-
ORD
1 stop28h 40m
Multiple Airlines
Deal found 3/21$513
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:20 pm
ORD
-
PMO
1 stop33h 30m
Austrian Airlines
Thu 8/278:10 pm
PMO
-
ORD
1 stop24h 10m
Austrian Airlines
Deal found 3/21$517
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:35 pm
ORD
-
PMO
1 stop18h 45m
Lufthansa
Mon 8/246:10 pm
PMO
-
ORD
1 stop31h 05m
Lufthansa
Deal found 3/21$526
This KAYAK deal was found by Cheapflights users on 3/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:20 pm
ORD
-
PMO
1 stop33h 30m
Austrian Airlines
Thu 8/278:10 pm
PMO
-
ORD
2 stops29h 27m
Austrian Airlines
Deal found 3/20$527
This FlightHub deal was found by Cheapflights users on 3/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:20 pm
ORD
-
PMO
1 stop33h 30m
Multiple Airlines
Mon 8/246:10 pm
PMO
-
ORD
1 stop31h 05m
Multiple Airlines
Deal found 3/21$528
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:40 pm
ORD
-
PMO
2 stops29h 40m
Lufthansa
Thu 8/2711:50 am
PMO
-
ORD
1 stop13h 25m
Lufthansa
Deal found 3/20$534
This SmartFares deal was found by Cheapflights users on 3/21. 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.
Mon 8/32:20 pm
ORD
-
PMO
1 stop11h 40m
Multiple Airlines
Mon 8/246:10 pm
PMO
-
ORD
1 stop31h 05m
Multiple Airlines
Deal found 3/21$535
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:05 pm
ORD
-
PMO
1 stop16h 45m
SWISS
Tue 8/252:55 pm
PMO
-
ORD
1 stop28h 40m
SWISS
Deal found 3/20$538
This FlightHub deal was found by Cheapflights users on 3/19. 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.
Tue 4/711:25 am
ORD
-
CTA
1 stop14h 00m
Turkish Airlines
Tue 4/147:25 pm
CTA
-
ORD
1 stop21h 15m
Turkish Airlines
Deal found 3/19$552

Find flight deals from Chicago to Sicily

Keep the following information in mind while searching for Chicago to Sicily flight deals. Data was last updated March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$478
(Kiwi.com)

One-way from

$350
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$776
Provider with most accurate pricing for Chicago (CHI)-Catania Fontanarossa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Catania Fontanarossa flights.
Search Deals
From Chicago (CHI) to Sicily
Search Deals
One-way flight from Chicago (CHI) to Sicily
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($262 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 23, 2026.
Use the filters below to find and compare flights from Chicago to Sicily that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 8/15

2:00 pm-12:05 pm

2 stops15h 05m

Palermo Punta Raisi

Tue 8/25

6:10 am-6:31 pm

2 stops19h 21m

$819

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 8/12

1:35 pm-3:00 pm

2 stops18h 25m

Palermo Punta Raisi

Wed 8/19

3:45 pm-5:41 pm

2 stops32h 56m

$828

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 4/11

6:05 pm-11:05 pm

2 stops22h 00m

Palermo Punta Raisi

Sat 4/18

3:10 pm-4:00 pm

2 stops31h 50m

$829

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Thu 8/13

5:10 pm-3:00 pm

1 stop14h 50m

Palermo Punta Raisi

Wed 8/19

3:45 pm-8:06 am

2 stops23h 21m

$867

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 8/15

5:59 pm-3:00 pm

2 stops14h 01m

Palermo Punta Raisi

Mon 8/24

10:05 am-9:46 pm

2 stops18h 41m

$869

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Tue 4/7

8:10 pm-11:00 pm

2 stops19h 50m

Lamezia Terme Intl

Wed 4/22

6:15 am-9:40 am

2 stops58h 25m

$874

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 8/12

1:30 pm-3:00 pm

2 stops18h 30m

Palermo Punta Raisi

Sat 8/22

4:00 pm-3:10 pm

1 stop30h 10m

$874

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sun 8/30

6:00 pm-11:00 pm

2 stops22h 00m

Lamezia Terme Intl

Tue 9/15

7:15 pm-4:50 pm

2 stops28h 35m

$890

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 8/10

10:35 am-3:00 pm

2 stops21h 25m

Palermo Punta Raisi

Sat 9/5

4:45 pm-10:00 am

2 stops24h 15m

$912

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 4/18

6:05 pm-11:05 pm

2 stops46h 00m

Palermo Punta Raisi

Wed 4/22

2:30 pm-4:00 pm

2 stops56h 30m

$926

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 59 resultsSorted by cheapest first
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6

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, November is the cheapest month in which you can book a flight from Chicago to Sicily (average of $414). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,015). 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.

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 March 23, 2026.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS,Turkish Airlines, andLufthansa. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.5
Good
1,902 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.5

Entertainment

6.8

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
SWISS
7.5
Good
1,902 reviews
SWISS
7.5
Good
1,902 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.5

Entertainment

6.8

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
Turkish Airlines
7.3
Good
4,273 reviews
SWISS
7.5
Good
1,902 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.5

Entertainment

6.8

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
Lufthansa
6.8
Okay
7,862 reviews
SWISS
7.5
Good
1,902 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.5

Entertainment

6.8

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
ITA Airways
6.7
Okay
1,172 reviews
SWISS
7.5
Good
1,902 reviews

Food

7.1

Comfort

7.4

Crew

8.3

Overall

7.5

Entertainment

6.8

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.

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.

  • How long is the flight from Chicago to Sicily?

    Departing from Chicago to Sicily will take you 15h 25m. Chicago and Sicily are separated by a distance of 5114 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Turkish Airlines and Lufthansa, 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, November is the cheapest month in which you can book a flight from Chicago to Sicily (average of $414). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,015). 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.

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$488Average$754FlexibilityNo cancel feeOn-time77%
SWISSCheapest$607Average$1,157FlexibilityNo cancel feeOn-time79%
ITA AirwaysCheapest$704Average$1,061FlexibilityNo cancel feeOn-time81%
LufthansaCheapest$778Average$1,304FlexibilityNo cancel feeOn-time76%

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