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$354+ Cheap flights from Sicily to Chicago (CHI)

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Sicily to Chicago

Keep the following information in mind while searching for Sicily to Chicago flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$616
(lol.travel)

One-way from

$354
(Kiwi.com)
Provider with most accurate pricing for Catania Fontanarossa-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Catania Fontanarossa-Chicago (CHI) flights.
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From Sicily to Chicago (CHI)
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One-way flight from Sicily to Chicago (CHI)
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Find flight deals from Sicily to Chicago

Cheapest flights from Sicily to Chicago
Explore the most affordable flight options available from Sicily to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2712:15 pmPMO - ORD
1 stop14h 50mLufthansa
Wed 12/33:20 pmORD - PMO
1 stop12h 45mLufthansa
Deal found 11/1$617
This Air Canada deal was found by Cheapflights users on 11/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:40 pmCTA - ORD
2 stops49h 30mAir Canada
Tue 12/29:10 pmORD - CTA
2 stops51h 55mAir Canada
Deal found 11/2$633
This SWISS deal was found by Cheapflights users on 11/2. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:40 pmCTA - ORD
1 stop23h 05mSWISS
Tue 12/25:50 pmORD - CTA
2 stops19h 50mSWISS
Deal found 11/2$639
This Air Canada deal was found by Cheapflights users on 11/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2712:15 pmPMO - ORD
2 stops38h 15mAir Canada
Wed 12/310:00 amORD - PMO
2 stops18h 05mAir Canada
Deal found 11/1$648
This Gotogate deal was found by Cheapflights users on 11/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2712:15 pmPMO - ORD
1 stop14h 50mMultiple Airlines
Wed 12/37:05 amORD - PMO
2 stops21h 00mMultiple Airlines
Deal found 11/1$664
This Expedia deal was found by Cheapflights users on 11/3. 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.
Thu 11/206:15 amSUF - ORD
2 stops18h 56mAir France
Mon 11/241:25 pmORD - SUF
2 stops22h 05mAir France
Deal found 11/3$703
This lol.travel deal was found by Cheapflights users on 11/2. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2412:15 pmCTA - ORD
1 stop31h 55mMultiple Airlines
Tue 12/26:50 pmORD - CTA
1 stop18h 50mMultiple Airlines
Deal found 11/2$737
This lol.travel deal was found by Cheapflights users on 11/3. 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.
Wed 11/196:15 amSUF - ORD
2 stops21h 08mITA Airways
Sun 11/239:20 amORD - SUF
2 stops18h 05mITA Airways
Deal found 11/3$770
This KLM deal was found by Cheapflights users on 11/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2010:10 amCTA - ORD
1 stop35h 10mKLM
Mon 11/2411:19 amORD - CTA
2 stops20h 21mKLM
Deal found 11/2$773
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Thu 11/206:15 amSUF - ORD
3 stops18h 40mMultiple Airlines
Mon 11/247:40 pmORD - SUF
3 stops20h 20mMultiple Airlines
Deal found 11/3$812
This Trip.com deal was found by Cheapflights users on 11/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:00 pmPMO - ORD
2 stops52h 20mMultiple Airlines
Mon 12/83:55 pmORD - PMO
2 stops18h 45mMultiple Airlines
Deal found 11/1$903
This Mytrip deal was found by Cheapflights users on 11/3. 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 11/197:15 pmSUF - ORD
3 stops29h 40mMultiple Airlines
Sun 11/233:50 pmORD - SUF
2 stops24h 50mMultiple Airlines
Deal found 11/3$913

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sicily to Chicago 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 November 3, 2025.
Use the filters below to find and compare flights from Sicily to Chicago that are best for you.

Fly from

Sicily

Fly to

Chicago

Route

Depart

Return

Price

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Fri 2/13

8:50 am-4:20 pm

1 stop14h 30m

Chicago O'Hare Intl

Sat 2/21

6:50 pm-7:50 pm

1 stop18h 00m

$618

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 3/5

2:45 pm-4:20 pm

1 stop32h 35m

Chicago O'Hare Intl

Mon 3/9

7:50 pm-2:30 pm

1 stop12h 40m

$625

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Mon 11/24

8:40 pm-3:10 pm

2 stops49h 30m

Chicago O'Hare Intl

Tue 12/2

9:10 pm-8:05 am

2 stops51h 55m

$633

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Mon 11/24

8:40 pm-12:45 pm

1 stop23h 05m

Chicago O'Hare Intl

Tue 12/2

5:50 pm-8:40 pm

2 stops19h 50m

$639

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 11/27

12:15 pm-7:30 pm

2 stops38h 15m

Chicago O'Hare Intl

Wed 12/3

10:00 am-11:05 am

2 stops18h 05m

$648

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 11/27

12:15 pm-8:05 pm

1 stop14h 50m

Chicago O'Hare Intl

Wed 12/3

7:05 am-11:05 am

2 stops21h 00m

$664

Lamezia TermeChicago

SUF - ORD

SUFORD

Lamezia Terme Intl

Thu 11/20

6:15 am-6:11 pm

2 stops18h 56m

Chicago O'Hare Intl

Mon 11/24

1:25 pm-6:30 pm

2 stops22h 05m

$703

Lamezia TermeChicago

SUF - ORD

SUFORD

Lamezia Terme Intl

Wed 11/19

6:15 am-8:23 pm

2 stops21h 08m

Chicago O'Hare Intl

Sun 11/23

9:20 am-10:25 am

2 stops18h 05m

$770

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Thu 11/20

10:10 am-2:20 pm

1 stop35h 10m

Chicago O'Hare Intl

Mon 11/24

11:19 am-2:40 pm

2 stops20h 21m

$773

Lamezia TermeChicago

SUF - ORD

SUFORD

Lamezia Terme Intl

Thu 2/5

11:15 am-3:20 pm

2 stops35h 05m

Chicago O'Hare Intl

Mon 2/9

9:50 pm-11:00 pm

2 stops42h 10m

$799

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 34 results
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Best time to book a flight from Sicily to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sicily 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 Sicily to Chicago

What is the cheapest time of day to fly from SI to CHI?

Find hourly flight availability from Sicily to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

When flying from Sicily to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 51% versus a flight in the afternoon.

Related info for your journey

Find useful and relevant information for your journey from Sicily to Chicago. 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 Sicily to Chicago?

    SWISS, Air Canada, and Air France can get you from Sicily to Chicago in just under 14h 30m. Your travel time can differ by up to 35h. The distance from Sicily to Chicago is about 5114 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Sicily to Chicago?

    Most travelers choose Palermo Punta Raisi - Chicago Midway, Palermo Punta Raisi - Chicago O'Hare Intl or Catania Fontanarossa - Chicago O'Hare Intl when deciding on the best route from Sicily to Chicago.

  • Can I find deals for flights from Sicily to Chicago that include hotel bookings?

    Yes. In addition to deals on Sicily to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sicily to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sicily to Chicago.

  • Can I find deals for business class flights from Sicily to Chicago?

    Yes. Cheapflights offers flight deals from Sicily to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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