$356+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Mar 4 — Mar 111
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 February 2, 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 February 2, 2026.
This SWISS deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:45 pm
PMO
- ORD
1 stop32h 35m
SWISS
Mon 3/26:50 pm
ORD
- PMO
1 stop12h 40m
SWISS
Deal found 2/2![SWISS logo]()
$624
This SWISS deal was found by Cheapflights users on 2/1. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:40 pm
CTA
- ORD
1 stop26h 40m
SWISS
Tue 3/34:10 pm
ORD
- CTA
1 stop21h 30m
SWISS
Deal found 2/1![SWISS logo]()
$625
This Booking.com deal was found by Cheapflights users on 2/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:15 pm
CTA
- ORD
1 stop14h 50m
Multiple Airlines
Tue 3/35:50 pm
ORD
- CTA
2 stops19h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$637
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:15 pm
PMO
- ORD
1 stop14h 50m
Multiple Airlines
Mon 3/23:45 pm
ORD
- PMO
2 stops15h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$637
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Thu 10/297:50 pm
ORD
- PMO
1 stop31h 05m
SWISS
Deal found 2/1![SWISS logo]()
$665
This KLM deal was found by Cheapflights users on 2/2. 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.
Mon 4/2010:35 pm
CTA
- ORD
1 stop22h 40m
KLM
Wed 4/2911:08 am
ORD
- CTA
1 stop13h 47m
KLM
Deal found 2/2![KLM logo]()
$714
This KLM deal was found by Cheapflights users on 2/2. 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.
Mon 4/209:55 am
CTA
- ORD
2 stops17h 45m
Multiple Airlines
Wed 4/2911:08 am
ORD
- CTA
1 stop13h 47m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$734
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:10 pm
CTA
- ORD
2 stops34h 41m
ITA Airways
Wed 3/2511:05 am
ORD
- CTA
2 stops20h 20m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$736
This ITA Airways deal was found by Cheapflights users on 2/1. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:10 am
PMO
- ORD
1 stop14h 00m
Multiple Airlines
Thu 10/291:12 pm
ORD
- PMO
2 stops14h 08m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$745
This ITA Airways deal was found by Cheapflights users on 2/1. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:15 pm
SUF
- ORD
1 stop24h 55m
ITA Airways
Mon 9/2110:40 am
ORD
- SUF
2 stops16h 50m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$750
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:10 am
PMO
- ORD
2 stops18h 25m
ITA Airways
Wed 3/2511:05 am
ORD
- PMO
2 stops18h 35m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$771
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Wed 3/186:00 am
PMO
- ORD
3 stops24h 22m
Multiple Airlines
Wed 3/256:01 pm
ORD
- PMO
2 stops18h 19m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$773
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 February 2, 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 February 2, 2026.
This SWISS deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:45 pm
PMO
- ORD
1 stop32h 35m
SWISS
Mon 3/26:50 pm
ORD
- PMO
1 stop12h 40m
SWISS
Deal found 2/2![SWISS logo]()
$624
This Booking.com deal was found by Cheapflights users on 2/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:15 pm
CTA
- ORD
1 stop14h 50m
Multiple Airlines
Tue 3/35:50 pm
ORD
- CTA
2 stops19h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$637
This KLM deal was found by Cheapflights users on 2/2. 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.
Mon 4/2010:35 pm
CTA
- ORD
1 stop22h 40m
KLM
Wed 4/2911:08 am
ORD
- CTA
1 stop13h 47m
KLM
Deal found 2/2![KLM logo]()
$714
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:10 pm
CTA
- ORD
2 stops34h 41m
ITA Airways
Wed 3/2511:05 am
ORD
- CTA
2 stops20h 20m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$736
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:25 pm
PMO
- MDW
2 stops41h 06m
Air France
Mon 3/210:49 am
MDW
- PMO
2 stops29h 11m
Air France
Deal found 2/2![Air France logo]()
$783
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:15 am
SUF
- ORD
1 stop13h 50m
United Airlines
Sat 5/29:20 pm
ORD
- SUF
2 stops30h 10m
United Airlines
Deal found 2/1![United Airlines logo]()
$814
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:45 pm
PMO
- ORD
1 stop30h 40m
Turkish Airlines
Wed 3/259:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Deal found 2/1![Turkish Airlines logo]()
$849
This Air Canada deal was found by Cheapflights users on 1/31. 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 3/59:10 am
CTA
- ORD
2 stops17h 35m
Air Canada
Mon 3/91:12 pm
ORD
- CTA
2 stops18h 13m
Air Canada
Deal found 1/31![Air Canada logo]()
$864
This SWISS deal was found by Cheapflights users on 2/1. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:40 pm
CTA
- ORD
1 stop26h 40m
SWISS
Tue 3/34:10 pm
ORD
- CTA
1 stop21h 30m
SWISS
Deal found 2/1![SWISS logo]()
$625
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:15 pm
PMO
- ORD
1 stop14h 50m
Multiple Airlines
Mon 3/23:45 pm
ORD
- PMO
2 stops15h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$637
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:10 am
PMO
- ORD
2 stops18h 25m
ITA Airways
Wed 3/2511:05 am
ORD
- PMO
2 stops18h 35m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$771
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:25 pm
PMO
- MDW
2 stops41h 06m
KLM
Mon 3/210:49 am
MDW
- PMO
2 stops29h 11m
KLM
Deal found 2/2![KLM logo]()
$783
This KLM deal was found by Cheapflights users on 2/2. 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.
Mon 4/209:55 am
CTA
- ORD
2 stops17h 45m
Multiple Airlines
Wed 4/2911:08 am
ORD
- CTA
1 stop13h 47m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$734
This Turkish Airlines deal was found by Cheapflights users on 2/1. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:25 pm
CTA
- ORD
1 stop30h 00m
Turkish Airlines
Mon 3/912:50 pm
ORD
- CTA
1 stop23h 35m
Turkish Airlines
Deal found 2/1![Turkish Airlines logo]()
$862
This Air Canada deal was found by Cheapflights users on 1/31. 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 2/238:40 pm
CTA
- ORD
2 stops29h 00m
Air Canada
Tue 3/33:55 pm
ORD
- CTA
2 stops14h 30m
Air Canada
Deal found 1/31![Air Canada logo]()
$868
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:05 am
CTA
- ORD
2 stops20h 51m
KLM
Tue 3/32:12 pm
ORD
- CTA
2 stops17h 48m
KLM
Deal found 2/2![KLM logo]()
$799
This Trip.com deal was found by Cheapflights users on 2/1. 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.
Wed 3/1812:25 pm
CTA
- ORD
1 stop14h 40m
Multiple Airlines
Wed 3/257:50 pm
ORD
- CTA
1 stop30h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$800
This Air Canada deal was found by Cheapflights users on 1/30. 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 3/512:15 pm
PMO
- ORD
2 stops38h 30m
Air Canada
Mon 3/97:10 am
ORD
- PMO
2 stops24h 30m
Air Canada
Deal found 1/30![Air Canada logo]()
$957
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Wed 3/186:00 am
PMO
- ORD
3 stops24h 22m
Multiple Airlines
Wed 3/255:05 am
ORD
- PMO
3 stops31h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$840
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Tue 2/178:05 pm
SUF
- ORD
3 stops35h 35m
Multiple Airlines
Sat 2/213:35 pm
ORD
- SUF
2 stops43h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$990
This Turkish Airlines deal was found by Cheapflights users on 1/31. 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.
Mon 2/1611:15 am
SUF
- ORD
2 stops38h 10m
Turkish Airlines
Fri 2/208:20 pm
ORD
- SUF
2 stops39h 10m
Turkish Airlines
Deal found 1/31![Turkish Airlines logo]()
$1,538
This Gotogate deal was found by Cheapflights users on 1/31. 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.
Mon 2/1611:15 am
SUF
- ORD
2 stops62h 10m
Multiple Airlines
Fri 2/208:15 pm
ORD
- SUF
2 stops15h 15m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$1,154
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:10 am
PMO
- MDW
2 stops22h 21m
Multiple Airlines
Wed 3/2512:47 pm
MDW
- PMO
2 stops16h 53m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,792
Last-minute flights from Sicily to ChicagoDiscover last-minute flight deals from Sicily to Chicago. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Sicily to Chicago. Data last updated February 2, 2026 and is based on user searches.
This SWISS deal was found by Cheapflights users on 2/1. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:40 pm
CTA
- ORD
1 stop26h 40m
SWISS
Tue 3/34:10 pm
ORD
- CTA
1 stop21h 30m
SWISS
Deal found 2/1![SWISS logo]()
$625
This Booking.com deal was found by Cheapflights users on 2/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:15 pm
CTA
- ORD
1 stop14h 50m
Multiple Airlines
Tue 3/35:50 pm
ORD
- CTA
2 stops19h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$637
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:05 am
CTA
- ORD
2 stops20h 51m
KLM
Tue 3/32:12 pm
ORD
- CTA
2 stops17h 48m
KLM
Deal found 2/2![KLM logo]()
$799
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:15 pm
CTA
- ORD
2 stops31h 30m
Lufthansa
Tue 3/34:05 pm
ORD
- CTA
1 stop12h 30m
Lufthansa
Deal found 2/2![Lufthansa logo]()
$840
This SWISS deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:45 pm
PMO
- ORD
1 stop32h 35m
SWISS
Mon 3/26:50 pm
ORD
- PMO
1 stop12h 40m
SWISS
Deal found 2/2![SWISS logo]()
$624
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:15 pm
PMO
- ORD
1 stop14h 50m
Multiple Airlines
Mon 3/23:45 pm
ORD
- PMO
2 stops15h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$637
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:25 pm
PMO
- MDW
2 stops41h 06m
KLM
Mon 3/210:49 am
MDW
- PMO
2 stops29h 11m
KLM
Deal found 2/2![KLM logo]()
$783
This Trip.com deal was found by Cheapflights users on 1/31. 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 2/263:15 pm
PMO
- MDW
2 stops55h 06m
Air France
Mon 3/210:49 am
MDW
- PMO
2 stops24h 36m
Air France
Deal found 1/31![Air France logo]()
$790
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:10 pm
CTA
- ORD
2 stops34h 41m
ITA Airways
Wed 3/2511:05 am
ORD
- CTA
2 stops20h 20m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$736
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:10 am
PMO
- ORD
2 stops18h 25m
ITA Airways
Wed 3/2511:05 am
ORD
- PMO
2 stops18h 35m
ITA Airways
Deal found 2/1![ITA Airways logo]()
$771
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Wed 3/186:00 am
PMO
- ORD
3 stops24h 22m
Multiple Airlines
Wed 3/256:01 pm
ORD
- PMO
2 stops18h 19m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$773
This Trip.com deal was found by Cheapflights users on 2/1. 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.
Wed 3/1812:25 pm
CTA
- ORD
1 stop14h 40m
Multiple Airlines
Wed 3/257:50 pm
ORD
- CTA
1 stop30h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$800
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 February 2, 2026.
Search for one-way flight options from Sicily to Chicago. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1710:05 pm
CTA
- ORD
3 stops45h 55m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$356
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Wed 3/187:30 am
CTA
- ORD
3 stops46h 52m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/164:00 pm
PMO
- ORD
2 stops37h 43m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:20 am
CTA
- ORD
3 stops42h 30m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:10 pm
CTA
- ORD
3 stops46h 05m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:15 pm
PMO
- MDW
3 stops44h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:00 am
PMO
- ORD
3 stops37h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:35 pm
CTA
- ORD
1 stop27h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$478
This British Airways deal was found by Cheapflights users on 2/2. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:25 pm
CTA
- ORD
2 stops26h 39m
British Airways
Deal found 2/2![British Airways logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:15 pm
PMO
- ORD
2 stops35h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$488
This Iberia deal was found by Cheapflights users on 2/2. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:10 pm
CTA
- ORD
1 stop21h 10m
Iberia
Deal found 2/2![Iberia logo]()
$489
This Mytrip deal was found by Cheapflights users on 1/31. 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 5/287:05 pm
PMO
- ORD
3 stops27h 55m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$499
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 February 2, 2026.
Round-trip from | $624 (SWISS) |
|---|---|
One-way from | $356 (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 February 2, 2026.
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
Thu 2/26
2:45 pm-4:20 pm
1 stop32h 35m
Chicago O'Hare Intl
Mon 3/2
6:50 pm-2:30 pm
1 stop12h 40m
$624
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Mon 2/23
8:40 pm-4:20 pm
1 stop26h 40m
Chicago O'Hare Intl
Tue 3/3
4:10 pm-8:40 pm
1 stop21h 30m
$625
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Mon 2/23
12:15 pm-8:05 pm
1 stop14h 50m
Chicago O'Hare Intl
Tue 3/3
5:50 pm-8:40 pm
2 stops19h 50m
$637
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Thu 2/26
12:15 pm-8:05 pm
1 stop14h 50m
Chicago O'Hare Intl
Mon 3/2
3:45 pm-2:30 pm
2 stops15h 45m
$637
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Mon 4/20
10:35 pm-2:15 pm
1 stop22h 40m
Chicago O'Hare Intl
Wed 4/29
11:08 am-7:55 am
1 stop13h 47m
$714
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Mon 4/20
9:55 am-8:40 pm
2 stops17h 45m
Chicago O'Hare Intl
Wed 4/29
11:08 am-7:55 am
1 stop13h 47m
$734
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Wed 3/18
2:10 pm-6:51 pm
2 stops34h 41m
Chicago O'Hare Intl
Wed 3/25
11:05 am-1:25 pm
2 stops20h 20m
$736
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Wed 3/18
6:10 am-6:35 pm
2 stops18h 25m
Chicago O'Hare Intl
Wed 3/25
11:05 am-11:40 am
2 stops18h 35m
$771
PalermoChicago
PMO - MDW
PMOMDW
Palermo Punta Raisi
Thu 2/26
12:25 pm-10:31 pm
2 stops41h 06m
Chicago Midway
Mon 3/2
10:49 am-11:00 pm
2 stops29h 11m
$783
PalermoChicago
PMO - MDW
PMOMDW
Palermo Punta Raisi
Thu 2/26
12:25 pm-10:31 pm
2 stops41h 06m
Chicago Midway
Mon 3/2
10:49 am-11:00 pm
2 stops29h 11m
$783
Showing 1-10 of 44 results
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.
PMO-ORD
CTA-ORD
PMO-MDW
SUF-ORD
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
PMO-ORD
CTA-ORD
PMO-MDW
SUF-ORD
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor