$400+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Jun 11 — Jun 181
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Sicily to ChicagoExplore 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 May 12, 2026.
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 May 12, 2026.
This British Airways deal was found by Cheapflights users on 5/11. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:40 pm
PMO
- ORD
1 stop34h 15m
British Airways
Sun 10/45:15 pm
ORD
- PMO
2 stops35h 05m
British Airways
Deal found 5/11![British Airways logo]()
$639
This Air Canada deal was found by Cheapflights users on 5/7. 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.
Wed 6/1710:40 am
CTA
- ORD
1 stop30h 36m
Air Canada
Thu 9/311:05 am
ORD
- CTA
1 stop15h 00m
Air Canada
Deal found 5/7![Air Canada logo]()
$675
This Air Canada deal was found by Cheapflights users on 5/7. 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 6/189:00 am
CTA
- ORD
2 stops37h 50m
Air Canada
Thu 9/311:05 am
ORD
- CTA
1 stop15h 00m
Air Canada
Deal found 5/7![Air Canada logo]()
$677
This Air Canada deal was found by Cheapflights users on 5/10. 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.
Wed 6/1710:40 am
CTA
- ORD
1 stop16h 25m
Air Canada
Tue 9/18:45 am
ORD
- CTA
1 stop17h 20m
Air Canada
Deal found 5/10![Air Canada logo]()
$678
This ITA Airways deal was found by Cheapflights users on 5/10. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Tue 9/293:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Deal found 5/10![ITA Airways logo]()
$678
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:05 pm
PMO
- ORD
1 stop25h 05m
ITA Airways
Sun 9/273:00 pm
ORD
- PMO
1 stop13h 30m
ITA Airways
Deal found 5/10![ITA Airways logo]()
$684
This KLM deal was found by Cheapflights users on 5/9. 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 5/219:55 am
CTA
- ORD
1 stop18h 41m
Multiple Airlines
Sat 5/306:31 pm
ORD
- CTA
1 stop30h 24m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$701
This Expedia deal was found by Cheapflights users on 5/8. 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 5/2110:40 am
CTA
- ORD
2 stops20h 19m
KLM
Thu 5/288:20 pm
ORD
- CTA
1 stop14h 10m
KLM
Deal found 5/8![KLM logo]()
$707
This ITA Airways deal was found by Cheapflights users on 5/10. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Sun 9/273:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Deal found 5/10![ITA Airways logo]()
$707
This lol.travel deal was found by Cheapflights users on 5/8. 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.
Thu 6/186:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Sat 6/273:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Deal found 5/8![ITA Airways logo]()
$709
This KLM deal was found by Cheapflights users on 5/10. 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.
Thu 5/219:55 am
CTA
- ORD
1 stop34h 21m
Multiple Airlines
Thu 5/285:10 pm
ORD
- CTA
1 stop17h 20m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$710
This Air France deal was found by Cheapflights users on 5/10. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:05 am
PMO
- ORD
2 stops18h 42m
Multiple Airlines
Sun 9/274:20 pm
ORD
- PMO
1 stop33h 05m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$714
Best flights from Sicily to ChicagoDiscover carefully curated flight deals from Sicily to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
Discover carefully curated flight deals from Sicily to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
This British Airways deal was found by Cheapflights users on 5/8. 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.
Wed 9/3012:40 pm
PMO
- ORD
1 stop34h 15m
British Airways
Sun 10/45:15 pm
ORD
- PMO
2 stops35h 05m
British Airways
Deal found 5/8![British Airways logo]()
$639
This Air Canada deal was found by Cheapflights users on 5/10. 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.
Wed 6/1710:40 am
CTA
- ORD
2 stops33h 30m
Air Canada
Tue 9/18:45 am
ORD
- CTA
1 stop17h 20m
Air Canada
Deal found 5/10![Air Canada logo]()
$678
This ITA Airways deal was found by Cheapflights users on 5/10. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Sun 9/273:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Deal found 5/10![ITA Airways logo]()
$707
This KLM deal was found by Cheapflights users on 5/10. 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.
Tue 6/99:10 am
PMO
- ORD
2 stops18h 21m
KLM
Mon 6/155:57 pm
ORD
- PMO
2 stops17h 23m
KLM
Deal found 5/10![KLM logo]()
$720
This KLM deal was found by Cheapflights users on 5/12. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:00 am
CTA
- ORD
2 stops17h 26m
Multiple Airlines
Sat 6/206:00 pm
ORD
- CTA
1 stop30h 55m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$727
This Turkish Airlines deal was found by Cheapflights users on 5/11. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:25 pm
CTA
- ORD
1 stop21h 15m
Turkish Airlines
Mon 9/288:10 pm
ORD
- CTA
1 stop15h 15m
Turkish Airlines
Deal found 5/11![Turkish Airlines logo]()
$767
This United Airlines deal was found by Cheapflights users on 5/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:15 am
SUF
- ORD
2 stops20h 57m
United Airlines
Mon 10/264:40 pm
ORD
- SUF
1 stop11h 50m
United Airlines
Deal found 5/10![United Airlines logo]()
$856
This KLM deal was found by Cheapflights users on 5/8. 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 6/119:55 am
CTA
- ORD
1 stop18h 53m
KLM
Sat 6/202:35 pm
ORD
- CTA
2 stops15h 50m
KLM
Deal found 5/8![KLM logo]()
$734
This KLM deal was found by Cheapflights users on 5/12. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:10 am
PMO
- MDW
2 stops19h 23m
KLM
Mon 6/151:26 pm
MDW
- PMO
2 stops17h 14m
KLM
Deal found 5/12![KLM logo]()
$816
This lol.travel deal was found by Cheapflights users on 5/12. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:15 pm
SUF
- ORD
1 stop24h 55m
ITA Airways
Tue 6/163:00 pm
ORD
- SUF
1 stop25h 00m
ITA Airways
Deal found 5/12![ITA Airways logo]()
$911
This Mytrip deal was found by Cheapflights users on 5/9. 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.
Tue 6/237:15 pm
SUF
- ORD
3 stops26h 15m
Multiple Airlines
Tue 6/305:10 pm
ORD
- SUF
2 stops23h 25m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$1,010
This ITA Airways deal was found by Cheapflights users on 5/9. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Fri 5/2910:25 am
ORD
- SUF
2 stops17h 05m
ITA Airways
Deal found 5/9![ITA Airways logo]()
$973
This KLM deal was found by Cheapflights users on 5/10. 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.
Tue 6/96:10 am
PMO
- MDW
2 stops19h 21m
KLM
Mon 6/1512:50 pm
MDW
- PMO
2 stops17h 50m
KLM
Deal found 5/10![KLM logo]()
$902
This Mytrip deal was found by Cheapflights users on 5/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:15 am
SUF
- ORD
2 stops22h 10m
Multiple Airlines
Sat 5/307:25 pm
ORD
- SUF
2 stops16h 05m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,016
This Gotogate deal was found by Cheapflights users on 5/7. 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.
Sun 6/2111:35 am
SUF
- ORD
2 stops56h 35m
ITA Airways
Sun 6/283:00 pm
ORD
- SUF
1 stop12h 30m
ITA Airways
Deal found 5/7![ITA Airways logo]()
$1,015
This Trip.com deal was found by Cheapflights users on 5/8. 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.
Thu 6/189:10 am
PMO
- MDW
2 stops20h 07m
Multiple Airlines
Sat 6/271:49 pm
MDW
- PMO
2 stops19h 01m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,059
This KLM deal was found by Cheapflights users on 5/9. 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.
Tue 6/239:10 am
PMO
- MDW
2 stops20h 07m
KLM
Tue 6/301:26 pm
MDW
- PMO
2 stops17h 14m
KLM
Deal found 5/9![KLM logo]()
$1,028
This Mytrip deal was found by Cheapflights users on 5/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:05 am
PMO
- MDW
3 stops34h 30m
Multiple Airlines
Mon 6/153:20 pm
MDW
- PMO
3 stops24h 35m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,140
Last-minute flights from Sicily to ChicagoDiscover last-minute flight deals from Sicily to Chicago. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Sicily to Chicago. Data last updated May 12, 2026 and is based on user searches.
This ITA Airways deal was found by Cheapflights users on 5/7. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Wed 7/223:00 pm
ORD
- CTA
1 stop15h 25m
ITA Airways
Deal found 5/7![ITA Airways logo]()
$729
This Expedia deal was found by Cheapflights users on 5/9. 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.
Mon 5/183:10 pm
PMO
- ORD
2 stops33h 39m
Air France
Tue 5/265:41 pm
ORD
- PMO
2 stops17h 39m
Air France
Deal found 5/9![Air France logo]()
$730
This KLM deal was found by Cheapflights users on 5/9. 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 5/219:55 am
CTA
- ORD
1 stop18h 41m
Multiple Airlines
Sat 5/306:31 pm
ORD
- CTA
1 stop30h 24m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$701
This Expedia deal was found by Cheapflights users on 5/8. 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 5/2110:40 am
CTA
- ORD
2 stops20h 19m
KLM
Thu 5/288:20 pm
ORD
- CTA
1 stop14h 10m
KLM
Deal found 5/8![KLM logo]()
$707
This KLM deal was found by Cheapflights users on 5/10. 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.
Thu 5/219:55 am
CTA
- ORD
1 stop34h 21m
Multiple Airlines
Thu 5/285:10 pm
ORD
- CTA
1 stop17h 20m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$710
This KLM deal was found by Cheapflights users on 5/10. 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.
Thu 5/216:10 am
PMO
- ORD
2 stops18h 44m
Multiple Airlines
Sat 5/305:41 pm
ORD
- PMO
2 stops15h 09m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$718
This KLM deal was found by Cheapflights users on 5/10. 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.
Tue 6/99:10 am
PMO
- ORD
2 stops18h 21m
KLM
Mon 6/155:57 pm
ORD
- PMO
2 stops17h 23m
KLM
Deal found 5/10![KLM logo]()
$720
This KLM deal was found by Cheapflights users on 5/12. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:55 am
CTA
- ORD
1 stop18h 53m
Multiple Airlines
Sat 6/206:00 pm
ORD
- CTA
1 stop30h 55m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$718
This Air Canada deal was found by Cheapflights users on 5/7. 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.
Wed 6/1710:40 am
CTA
- ORD
1 stop30h 36m
Air Canada
Thu 9/311:05 am
ORD
- CTA
1 stop15h 00m
Air Canada
Deal found 5/7![Air Canada logo]()
$675
This Air Canada deal was found by Cheapflights users on 5/10. 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.
Wed 6/1710:40 am
CTA
- ORD
1 stop16h 25m
Air Canada
Tue 9/18:45 am
ORD
- CTA
1 stop17h 20m
Air Canada
Deal found 5/10![Air Canada logo]()
$678
This Air Canada deal was found by Cheapflights users on 5/7. 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 6/189:00 am
CTA
- ORD
2 stops37h 50m
Air Canada
Tue 9/18:45 am
ORD
- CTA
1 stop17h 20m
Air Canada
Deal found 5/7![Air Canada logo]()
$677
This lol.travel deal was found by Cheapflights users on 5/8. 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.
Thu 6/186:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Sat 6/273:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Deal found 5/8![ITA Airways logo]()
$709
One-way flights from Sicily to ChicagoSearch for one-way flight options from Sicily to Chicago. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
Search for one-way flight options from Sicily to Chicago. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:15 am
CTA
- ORD
3 stops42h 35m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 10/46:15 am
CTA
- ORD
3 stops42h 35m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Tue 10/139:35 am
CTA
- ORD
3 stops39h 15m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:15 am
CTA
- ORD
3 stops22h 10m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Sat 9/265:50 am
CTA
- ORD
3 stops43h 00m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$442
This Mytrip deal was found by Cheapflights users on 5/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:40 pm
PMO
- ORD
3 stops27h 45m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Tue 8/258:15 am
PMO
- ORD
3 stops40h 35m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:55 am
CTA
- ORD
3 stops42h 55m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Mon 9/289:45 am
CTA
- ORD
2 stops40h 30m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Tue 6/2310:25 pm
PMO
- ORD
3 stops44h 25m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:20 am
SUF
- ORD
3 stops36h 30m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Tue 6/236:40 pm
PMO
- MDW
3 stops50h 55m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$500
Find flight deals from Sicily to Chicago
Keep the following information in mind while searching for Sicily to Chicago flight deals. Data was last updated May 12, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $639 (British Airways) |
One-way from | $400 (Kiwi.com) |
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 May 12, 2026.
Use the filters below to find and compare flights from Sicily to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Wed 9/30
12:40 pm-3:55 pm
1 stop34h 15m
Chicago O'Hare Intl
Sun 10/4
5:15 pm-11:20 am
2 stops35h 05m
$639
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Wed 6/17
10:40 am-1:10 pm
2 stops33h 30m
Chicago O'Hare Intl
Tue 9/1
8:45 am-9:05 am
1 stop17h 20m
$678
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Tue 9/1
8:30 pm-1:10 pm
1 stop23h 40m
Chicago O'Hare Intl
Sun 9/27
3:00 pm-1:40 pm
1 stop15h 40m
$707
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Tue 6/9
9:10 am-8:31 pm
2 stops18h 21m
Chicago O'Hare Intl
Mon 6/15
5:57 pm-6:20 pm
2 stops17h 23m
$720
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 6/11
6:00 am-4:26 pm
2 stops17h 26m
Chicago O'Hare Intl
Sat 6/20
6:00 pm-7:55 am
1 stop30h 55m
$727
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 6/11
9:55 am-9:48 pm
1 stop18h 53m
Chicago O'Hare Intl
Sat 6/20
2:35 pm-1:25 pm
2 stops15h 50m
$734
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 9/24
7:25 pm-9:40 am
1 stop21h 15m
Chicago O'Hare Intl
Mon 9/28
8:10 pm-6:25 pm
1 stop15h 15m
$767
PalermoChicago
PMO - MDW
PMOMDW
Palermo Punta Raisi
Mon 6/1
6:10 am-6:33 pm
2 stops19h 23m
Chicago Midway
Mon 6/15
1:26 pm-1:40 pm
2 stops17h 14m
$816
Lamezia TermeChicago
SUF - ORD
SUFORD
Lamezia Terme Intl
Thu 10/22
6:15 am-8:12 pm
2 stops20h 57m
Chicago O'Hare Intl
Mon 10/26
4:40 pm-10:30 am
1 stop11h 50m
$856
PalermoChicago
PMO - MDW
PMOMDW
Palermo Punta Raisi
Tue 6/9
6:10 am-6:31 pm
2 stops19h 21m
Chicago Midway
Mon 6/15
12:50 pm-1:40 pm
2 stops17h 50m
$902
Showing 1-10 of 37 resultsSorted by cheapest first
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.
CTA-ORD
PMO-ORD
SUF-ORD
PMO-MDW
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
ITSI-CHI
CTA-ORD
PMO-ORD
SUF-ORD
PMO-MDW
No data available for this route at this time. Please check back soon.
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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