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$343+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Chicago to Sicily

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sicily (ITSI). 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 November 21, 2024.

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 November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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.
Mon 12/94:00 pmORD - CTA
3 stops35h 25mMultiple Airlines
Mon 12/168:45 pmCTA - ORD
3 stops29h 47mMultiple Airlines
Deal found 11/20$766
This Flighttix deal was found by Cheapflights users on 11/19. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:43 pmMDW - PMO
2 stops16h 12mKLM
Tue 12/1710:05 amPMO - MDW
2 stops19h 01mKLM
Deal found 11/19$921
This Mytrip deal was found by Cheapflights users on 11/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/252:05 pmORD - PMO
2 stops20h 35mMultiple Airlines
Tue 12/177:05 pmPMO - ORD
3 stops33h 05mMultiple Airlines
Deal found 11/21$1,027
This oojo deal was found by Cheapflights users on 11/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/297:05 pmORD - PMO
1 stop11h 40mSWISS
Thu 1/92:45 pmPMO - ORD
1 stop32h 30mSWISS
Deal found 11/21$1,076
This oojo deal was found by Cheapflights users on 11/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/248:25 pmORD - SUF
2 stops43h 40mTAP AIR PORTUGAL
Tue 12/36:20 amSUF - ORD
2 stops40h 10mTAP AIR PORTUGAL
Deal found 11/20$1,079
This Delta deal was found by Cheapflights users on 11/20. 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.
Tue 12/310:41 amMDW - PMO
2 stops18h 14mDelta
Tue 12/176:10 amPMO - MDW
2 stops22h 56mDelta
Deal found 11/20$1,142
This SWISS deal was found by Cheapflights users on 11/20. 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.
Mon 12/99:10 pmORD - CTA
2 stops51h 55mSWISS
Mon 12/168:40 pmCTA - ORD
1 stop26h 35mSWISS
Deal found 11/20$1,250
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/157:05 pmORD - SUF
1 stop11h 55mMultiple Airlines
Thu 1/97:55 amSUF - ORD
2 stops38h 55mMultiple Airlines
Deal found 11/20$1,406
This KAYAK deal was found by Cheapflights users on 11/20. 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.
Fri 12/133:55 pmORD - PMO
1 stop18h 10mLufthansa
Fri 12/2011:40 amPMO - ORD
1 stop13h 45mLufthansa
Deal found 11/20$1,495
This oojo deal was found by Cheapflights users on 11/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1911:55 amORD - CTA
1 stop23h 30mTurkish Airlines
Thu 12/267:25 pmCTA - ORD
1 stop21h 45mTurkish Airlines
Deal found 11/19$1,598
This KAYAK deal was found by Cheapflights users on 11/20. 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.
Sat 12/1410:35 pmORD - SUF
2 stops32h 25mLufthansa
Mon 1/62:50 pmSUF - ORD
2 stops58h 35mLufthansa
Deal found 11/20$1,752
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/168:30 pmORD - SUF
2 stops19h 35mTurkish Airlines
Mon 1/611:15 amSUF - ORD
2 stops29h 55mTurkish Airlines
Deal found 11/20$2,038

Find flights from Chicago to Sicily within your budget

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 2,612,795 searches. Data last updated November 21, 2024.

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Depart

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Price

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Thu 2/20

11:55 am-6:25 pm

1 stop23h 30m

Catania Fontanarossa

Mon 3/3

9:25 am-6:35 pm

1 stop16h 10m

$552

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 2/12

7:15 pm-10:00 pm

2 stops19h 45m

Lamezia Terme Intl

Sat 2/22

7:20 am-3:30 pm

2 stops39h 10m

$553

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 2/5

8:30 pm-8:35 am

1 stop29h 05m

Palermo Punta Raisi

Wed 4/9

7:20 pm-9:50 am

1 stop21h 30m

$572

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Wed 2/12

7:15 pm-11:05 pm

2 stops20h 50m

Lamezia Terme Intl

Tue 3/11

11:15 am-4:30 pm

2 stops35h 15m

$632

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Wed 3/5

7:15 pm-2:00 pm

2 stops35h 45m

Palermo Punta Raisi

Mon 3/10

12:40 pm-4:30 pm

2 stops57h 50m

$642

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Wed 1/22

7:15 pm-6:30 pm

2 stops16h 15m

Catania Fontanarossa

Wed 1/29

3:20 pm-3:30 pm

2 stops55h 10m

$650

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Tue 1/28

2:00 pm-6:20 pm

2 stops21h 20m

Palermo Punta Raisi

Tue 2/11

3:15 pm-9:28 pm

2 stops37h 13m

$678

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Fri 1/17

8:20 pm-6:20 pm

2 stops15h 00m

Palermo Punta Raisi

Wed 1/22

3:15 pm-3:30 pm

2 stops55h 15m

$697

ChicagoLamezia Terme

ORD - SUF

ORDSUF

Chicago O'Hare Intl

Sun 2/9

11:05 am-10:30 am

2 stops40h 25m

Lamezia Terme Intl

Tue 3/11

6:20 am-9:15 pm

2 stops20h 55m

$720

ChicagoCatania

ORD - CTA

ORDCTA

Chicago O'Hare Intl

Fri 1/10

8:20 pm-2:35 pm

2 stops35h 15m

Catania Fontanarossa

Fri 1/17

3:20 pm-3:30 pm

2 stops55h 10m

$742

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 34 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.

Travel insights for flights from Chicago to Sicily

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

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 $685). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,365). 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 November 21, 2024.

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.

Rainfall in Sicily by month

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

In terms of precipitation, rainfall in Sicily ranges from 0.2 - 4.2 inches per month. October is typically the wettest month, when rainfall can reach 4.2 in. June is typically the driest time to visit Sicily when rainfall is around 0.2 in.

Temperature in Sicily by month

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

If weather is an important factor for your trip to Sicily, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 November 21, 2024.
Peruse reviews from past customers who have flown with TAP AIR PORTUGAL, KLM and Lufthansa from Chicago to Sicily to help guide your decision. 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
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,755 reviews
Delta
8.0
Very good
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,349 reviews
Delta
8.0
Very good
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

SWISS
7.6
Good
1,636 reviews
Delta
8.0
Very good
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France
7.4
Good
1,525 reviews
Delta
8.0
Very good
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Turkish Airlines
7.4
Good
3,920 reviews
Delta
8.0
Very good
8,755 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 Delta, with whom users have recently found tickets for as low as $448. However, be on the lookout for offers from Turkish Airlines and SWISS, 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 $685). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,365). 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
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Malpensa flights
O'Hare Intl to Linate flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Florence flights
Midway to Malpensa flights
Midway to Vicenza flights
St. Louis to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Naples flights
Midway to Florence flights
O'Hare Intl to Bergamo flights
Midway to Linate flights
O'Hare Intl to Palermo flights
O'Hare Intl to Bari flights
Midway to Naples flights
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O'Hare Intl to Verona flights
St. Louis to Malpensa flights
St. Louis to Vicenza flights
Midway to Bologna flights
O'Hare Intl to Pisa flights
St. Louis to Linate flights
O'Hare Intl to Ciampino flights
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O'Hare Intl to Genoa flights
Moline to Leonardo da Vinci/Fiumicino flights
Midway to Palermo flights
O'Hare Intl to Turin flights
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O'Hare Intl to Treviso A. Canova flights
O'Hare Intl to Brindisi flights
Midway to Genoa flights
St. Louis to Turin flights
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Midway to Bari flights
O'Hare Intl to Lamezia Terme flights
Midway to Turin flights
Evansville to Leonardo da Vinci/Fiumicino flights
Peoria to Leonardo da Vinci/Fiumicino flights
St. Louis to Naples flights
O'Hare Intl to Trieste flights
St. Louis to Verona flights
O'Hare Intl to Ancona flights
Springfield to Leonardo da Vinci/Fiumicino flights

Top 8 airlines flying from Chicago to Sicily

Discover the top 8 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$82FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$662FlexibilityNo cancel feeOn-time69%
TAP AIR PORTUGALCheapest$603Average$980FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$662Average$1,014FlexibilityNo cancel feeOn-time81%
Turkish AirlinesCheapest$680Average$861FlexibilityNo cancel feeOn-time77%
SWISSCheapest$792Average$1,270FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$806Average$1,283FlexibilityNo cancel feeOn-time76%
DeltaCheapest$813Average$943FlexibilityNo cancel feeOn-timeN/A
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