HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$382+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Sicily to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Sicily to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Sicily (ITSI) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$560
(SWISS)

One-way from

$382
(Kiwi.com)
From Sicily to Chicago (CHI)
Search Deals
One-way flight from Sicily to Chicago (CHI)
Search Deals

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 enero 21, 2025.

This SWISS deal was found by Cheapflights users on 1/20. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/38:50 pmCTA - ORD
1 stop26h 25mSWISS
mar. 3/118:05 pmORD - CTA
1 stop30h 00mSWISS
Deal found 1/20$560
This Flighttix deal was found by Cheapflights users on 1/21. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/22:45 pmPMO - ORD
1 stop29h 10mSWISS
dom. 3/98:05 pmORD - PMO
1 stop14h 55mSWISS
Deal found 1/21$565
This Lufthansa deal was found by Cheapflights users on 1/20. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/169:30 amPMO - ORD
1 stop13h 45mMultiple Airlines
sáb. 2/229:25 pmORD - PMO
1 stop13h 00mMultiple Airlines
Deal found 1/20$570
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/56:20 amSUF - ORD
2 stops22h 04mDelta
dom. 2/94:25 pmORD - SUF
2 stops35h 05mDelta
Deal found 1/20$570
This Gotogate deal was found by Cheapflights users on 1/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/52:30 pmSUF - ORD
2 stops29h 55mMultiple Airlines
dom. 2/97:05 pmORD - SUF
1 stop11h 55mMultiple Airlines
Deal found 1/20$590
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/36:05 amCTA - ORD
2 stops24h 44mDelta
mar. 3/116:20 pmORD - CTA
2 stops14h 15mDelta
Deal found 1/20$597
This lol.travel deal was found by Cheapflights users on 1/20. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/19:35 pmCTA - ORD
1 stop23h 20mBritish Airways
jue. 10/95:00 pmORD - CTA
1 stop17h 50mBritish Airways
Deal found 1/20$599
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/166:10 amPMO - ORD
2 stops24h 38mDelta
dom. 2/234:25 pmORD - PMO
2 stops18h 55mDelta
Deal found 1/20$606
This Lufthansa deal was found by Cheapflights users on 1/21. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/16:00 amCTA - ORD
1 stop19h 15mLufthansa
jue. 10/99:40 pmORD - CTA
1 stop19h 15mLufthansa
Deal found 1/21$617
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/310:10 amCTA - ORD
3 stops35h 55mMultiple Airlines
mar. 3/116:20 pmORD - CTA
3 stops34h 40mMultiple Airlines
Deal found 1/20$649
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/137:00 amPMO - ORD
1 stop13h 10mITA Airways
mié. 9/103:00 pmORD - PMO
1 stop14h 40mITA Airways
Deal found 1/21$697
This lol.travel deal was found by Cheapflights users on 1/21. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/266:45 pmPMO - ORD
1 stop30h 50mTurkish Airlines
mar. 4/87:50 pmORD - PMO
1 stop29h 30mTurkish Airlines
Deal found 1/21$750

Find flights from Sicily to Chicago within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

lun. 3/3

8:50 pm-4:15 pm

1 stop26h 25m

Chicago O'Hare Intl

mar. 3/11

8:05 pm-8:05 am

1 stop30h 00m

$560

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

dom. 3/2

2:45 pm-12:55 pm

1 stop29h 10m

Chicago O'Hare Intl

dom. 3/9

8:05 pm-5:00 pm

1 stop14h 55m

$565

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

dom. 2/16

9:30 am-4:15 pm

1 stop13h 45m

Chicago O'Hare Intl

sáb. 2/22

9:25 pm-5:25 pm

1 stop13h 00m

$570

Lamezia TermeChicago

SUF - ORD

SUFORD

Lamezia Terme Intl

mié. 2/5

6:20 am-9:24 pm

2 stops22h 04m

Chicago O'Hare Intl

dom. 2/9

4:25 pm-10:30 am

2 stops35h 05m

$570

Lamezia TermeChicago

SUF - ORD

SUFORD

Lamezia Terme Intl

mié. 2/5

2:30 pm-1:25 pm

2 stops29h 55m

Chicago O'Hare Intl

dom. 2/9

7:05 pm-2:00 pm

1 stop11h 55m

$590

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

lun. 3/3

6:05 am-11:49 pm

2 stops24h 44m

Chicago O'Hare Intl

mar. 3/11

6:20 pm-2:35 pm

2 stops14h 15m

$597

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

dom. 2/16

6:10 am-11:48 pm

2 stops24h 38m

Chicago O'Hare Intl

dom. 2/23

4:25 pm-6:20 pm

2 stops18h 55m

$606

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

lun. 3/3

10:10 am-3:05 pm

3 stops35h 55m

Chicago O'Hare Intl

mar. 3/11

6:20 pm-11:00 am

3 stops34h 40m

$649

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

mié. 3/26

6:45 pm-7:35 pm

1 stop30h 50m

Chicago O'Hare Intl

mar. 4/8

7:50 pm-8:20 am

1 stop29h 30m

$750

CataniaChicago

CTA - ORD

CTAORD

Catania Fontanarossa

jue. 7/10

6:00 am-7:55 pm

2 stops20h 55m

Chicago O'Hare Intl

jue. 7/24

9:40 pm-11:55 pm

1 stop19h 15m

$818

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 25 results
1
2
3

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.

Travel insights for flights from Sicily to Chicago

Get recent, data-driven insights about flights from Sicily to Chicago including ideal travel times, pricing trends, and more.

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 enero 21, 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 enero 21, 2025.
Get a feel of what it's like to fly with SWISS, Delta and TAP AIR PORTUGAL 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
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

SWISS
7.5
Good
1,600 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Turkish Airlines
7.3
Good
3,931 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

TAP AIR PORTUGAL
7.2
Good
1,869 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Iberia
7.0
Good
2,646 reviews
Delta
8.0
Very good
8,521 reviews

Crew

8.6

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 ($495), SWISS ($578), and Lufthansa ($614).

  • 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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.

Alternative routes for Sicily to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to Midway flights
Linate to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Naples to O'Hare Intl flights
Bologna to O'Hare Intl flights
Vicenza to Midway flights
Vicenza to St. Louis flights
Malpensa to St. Louis flights
Florence to O'Hare Intl flights
Bari to O'Hare Intl flights
Ciampino to O'Hare Intl flights
Verona to O'Hare Intl flights
Turin to O'Hare Intl flights
Palermo to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to St. Louis flights
Genoa to O'Hare Intl flights
Catania to O'Hare Intl flights
Pisa to O'Hare Intl flights
Genoa to Midway flights
Florence to St. Louis flights
Malpensa to Moline flights
Ancona to O'Hare Intl flights

Top airline flying from Sicily to Chicago

Discover the top airline that operate flights from Sicily to Chicago. 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
ITA AirwaysCheapest$535Average$663FlexibilityNo cancel feeOn-time81%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.