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$368+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$664
(Air Canada)

One-way from

$368
(Kiwi.com)

Popular in

August

Cheapest in

March

Average price

$745
From Sicily to Chicago (CHI)
Search Deals
One-way flight from Sicily to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This Air Canada deal was found by Cheapflights users on 6/10. 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.
Sun 10/198:10 pmPMO - ORD
2 stops28h 23mMultiple Airlines
Sun 11/24:00 pmORD - PMO
2 stops19h 25mMultiple Airlines
Deal found 6/10$664
This Lufthansa deal was found by Cheapflights users on 6/10. 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.
Wed 10/16:35 pmCTA - ORD
2 stops25h 20mLufthansa
Thu 10/99:40 pmORD - CTA
1 stop18h 50mLufthansa
Deal found 6/10$671
This lol.travel deal was found by Cheapflights users on 6/10. 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.
Sun 7/271:15 pmPMO - ORD
1 stop29h 40mBritish Airways
Sun 8/39:15 pmORD - PMO
1 stop14h 25mBritish Airways
Deal found 6/10$685
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Wed 10/15:40 pmCTA - ORD
1 stop26h 40mMultiple Airlines
Thu 10/99:40 pmORD - CTA
1 stop18h 50mMultiple Airlines
Deal found 6/12$696
This Austrian Airlines deal was found by Cheapflights users on 6/10. 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/15:40 pmCTA - ORD
1 stop26h 40mAustrian Airlines
Thu 10/94:20 pmORD - CTA
1 stop17h 30mAustrian Airlines
Deal found 6/10$697
This British Airways deal was found by Cheapflights users on 6/10. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:45 pmCTA - ORD
2 stops28h 07mBritish Airways
Mon 7/284:36 pmORD - CTA
2 stops19h 19mBritish Airways
Deal found 6/10$737
This Lufthansa deal was found by Cheapflights users on 6/10. 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.
Thu 10/3012:05 pmPMO - ORD
1 stop15h 00mLufthansa
Sat 11/89:50 pmORD - PMO
1 stop12h 35mLufthansa
Deal found 6/10$739
This KLM deal was found by Cheapflights users on 6/10. 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.
Fri 7/258:35 amCTA - ORD
2 stops17h 52mKLM
Fri 8/14:20 pmORD - CTA
1 stop33h 55mKLM
Deal found 6/10$747
This SWISS deal was found by Cheapflights users on 6/11. 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.
Sun 10/195:50 amPMO - ORD
1 stop17h 05mSWISS
Sun 11/25:55 pmORD - PMO
2 stops17h 30mSWISS
Deal found 6/11$769
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/31:15 pmPMO - ORD
1 stop34h 45mAmerican Airlines
Sun 8/103:17 pmORD - PMO
2 stops20h 23mAmerican Airlines
Deal found 6/12$771
This lol.travel deal was found by Cheapflights users on 6/10. 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 7/236:15 amSUF - ORD
1 stop13h 55mITA Airways
Wed 7/303:00 pmORD - SUF
1 stop20h 30mITA Airways
Deal found 6/10$780
This Delta deal was found by Cheapflights users on 6/11. 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.
Sun 6/2910:00 amCTA - ORD
1 stop18h 41mDelta
Mon 7/75:00 pmORD - CTA
2 stops18h 40mDelta
Deal found 6/11$812

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 June 12, 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

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 10/19

8:10 pm-5:33 pm

2 stops28h 23m

Chicago O'Hare Intl

Sun 11/2

4:00 pm-6:25 pm

2 stops19h 25m

$664

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Wed 10/1

6:35 pm-12:55 pm

2 stops25h 20m

Chicago O'Hare Intl

Thu 10/9

9:40 pm-11:30 pm

1 stop18h 50m

$671

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 7/27

1:15 pm-11:55 am

1 stop29h 40m

Chicago O'Hare Intl

Sun 8/3

9:15 pm-6:40 pm

1 stop14h 25m

$685

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Wed 10/1

5:40 pm-1:20 pm

1 stop26h 40m

Chicago O'Hare Intl

Thu 10/9

9:40 pm-11:30 pm

1 stop18h 50m

$696

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Wed 10/1

5:40 pm-1:20 pm

1 stop26h 40m

Chicago O'Hare Intl

Thu 10/9

4:20 pm-4:50 pm

1 stop17h 30m

$697

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Mon 7/21

6:45 pm-3:52 pm

2 stops28h 07m

Chicago O'Hare Intl

Mon 7/28

4:36 pm-6:55 pm

2 stops19h 19m

$737

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 10/30

12:05 pm-9:05 pm

1 stop15h 00m

Chicago O'Hare Intl

Sat 11/8

9:50 pm-5:25 pm

1 stop12h 35m

$739

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

Fri 7/25

8:35 am-7:27 pm

2 stops17h 52m

Chicago O'Hare Intl

Fri 8/1

4:20 pm-9:15 am

1 stop33h 55m

$747

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 10/19

5:50 am-3:55 pm

1 stop17h 05m

Chicago O'Hare Intl

Sun 11/2

5:55 pm-6:25 pm

2 stops17h 30m

$769

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sun 8/3

1:15 pm-5:00 pm

1 stop34h 45m

Chicago O'Hare Intl

Sun 8/10

3:17 pm-6:40 pm

2 stops20h 23m

$771

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 44 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 June 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Sicily to Chicago as you normally would.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 12, 2025.
Get a feel of what it's like to fly with Delta, KLM and Austrian Airlines from Sicily to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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
1,358 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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
802 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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
1,463 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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
1,623 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

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 Sicily to Chicago. 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 Sicily to Chicago one-way?

    The cheapest airlines for a one-way flight from Sicily to Chicago are Turkish Airlines ($555), Aer Lingus ($570), and American Airlines ($722).

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

    Most travelers choose Palermo Punta Raisi - Chicago O'Hare Intl, Catania Fontanarossa - Chicago O'Hare Intl or Palermo Punta Raisi - Chicago Midway 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.

  • What is the cheapest month to book a flight from Sicily to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Sicily to Chicago (average of $245). Flying from Sicily to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Sicily?

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

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Alternative routes for Sicily to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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