$381+ Cheap flights from Sicily to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Jul 31 — Aug 71
Round-trip
1 adult, Economy
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Find cheap flights from Sicily to Chicago with Cheapflights
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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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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 July 1, 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 July 1, 2026.
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Fri 9/183:20 pm
SUF
- ORD
1 stop28h 50m
ITA Airways
Wed 9/303:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$586
This lol.travel deal was found by Cheapflights users on 7/1. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Tue 9/13:00 pm
ORD
- PMO
1 stop24h 30m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$616
This lol.travel deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Tue 9/13:00 pm
ORD
- CTA
1 stop22h 45m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$619
This British Airways deal was found by Cheapflights users on 6/27. 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 8/226:55 pm
PMO
- ORD
2 stops29h 03m
British Airways
Sat 8/298:58 pm
ORD
- PMO
2 stops38h 42m
British Airways
Deal found 6/27![British Airways logo]()
$621
This ITA Airways deal was found by Cheapflights users on 6/30. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Sun 10/113:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$634
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Sat 8/227:05 pm
PMO
- ORD
1 stop25h 05m
ITA Airways
Sat 8/293:00 pm
ORD
- PMO
1 stop21h 45m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$643
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Sat 8/227:15 pm
CTA
- ORD
1 stop24h 55m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$644
This oojo deal was found by Cheapflights users on 6/26. 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.
Mon 8/313:10 pm
PMO
- ORD
1 stop29h 00m
ITA Airways
Thu 9/173:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Deal found 6/26![ITA Airways logo]()
$647
This British Airways deal was found by Cheapflights users on 6/27. 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.
Sun 8/239:50 pm
CTA
- ORD
1 stop27h 25m
British Airways
Tue 9/19:56 am
ORD
- CTA
2 stops28h 09m
British Airways
Deal found 6/27![British Airways logo]()
$654
This lol.travel deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:20 pm
SUF
- ORD
1 stop28h 50m
ITA Airways
Sun 7/193:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$672
This lol.travel deal was found by Cheapflights users on 6/29. 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 7/166:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Mon 7/203:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$673
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Fri 8/217:15 pm
CTA
- ORD
1 stop24h 55m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$696
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 July 1, 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 July 1, 2026.
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Fri 9/183:20 pm
SUF
- ORD
1 stop28h 50m
ITA Airways
Wed 9/303:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$586
This British Airways deal was found by Cheapflights users on 6/28. 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.
Sun 8/239:50 pm
CTA
- ORD
1 stop27h 25m
British Airways
Tue 9/19:56 am
ORD
- CTA
2 stops28h 09m
British Airways
Deal found 6/28![British Airways logo]()
$654
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:55 am
CTA
- ORD
1 stop18h 57m
Delta
Wed 8/121:59 pm
ORD
- CTA
2 stops21h 41m
Delta
Deal found 6/30![Delta logo]()
$758
This KLM deal was found by Cheapflights users on 6/26. 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 8/109:50 am
PMO
- ORD
2 stops19h 54m
Multiple Airlines
Mon 8/175:10 pm
ORD
- PMO
1 stop14h 50m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$777
This KLM deal was found by Cheapflights users on 6/29. 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.
Sun 8/236:10 am
PMO
- ORD
2 stops17h 07m
KLM
Tue 9/14:20 pm
ORD
- PMO
1 stop34h 05m
KLM
Deal found 6/29![KLM logo]()
$844
This Icelandair deal was found by Cheapflights users on 6/26. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:20 am
SUF
- ORD
2 stops18h 00m
Icelandair
Thu 1/146:30 pm
ORD
- SUF
2 stops17h 00m
Icelandair
Deal found 6/26![Icelandair logo]()
$848
This Turkish Airlines deal was found by Cheapflights users on 6/26. 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.
Wed 10/219:25 am
CTA
- ORD
1 stop31h 15m
Turkish Airlines
Sun 10/2512:45 pm
ORD
- CTA
1 stop13h 55m
Turkish Airlines
Deal found 6/26![Turkish Airlines logo]()
$849
This lol.travel deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Tue 9/13:00 pm
ORD
- CTA
1 stop22h 45m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$619
This ITA Airways deal was found by Cheapflights users on 6/30. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Sun 10/113:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$634
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/173:25 pm
CTA
- ORD
2 stops32h 55m
Multiple Airlines
Fri 1/156:30 pm
ORD
- CTA
2 stops21h 50m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$779
This oojo deal was found by Cheapflights users on 6/27. 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.
Mon 8/313:10 pm
PMO
- ORD
1 stop29h 00m
ITA Airways
Thu 9/173:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$648
This British Airways deal was found by Cheapflights users on 6/27. 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 8/229:25 pm
CTA
- ORD
2 stops26h 33m
British Airways
Sat 8/297:05 pm
ORD
- CTA
1 stop18h 50m
British Airways
Deal found 6/27![British Airways logo]()
$802
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:50 pm
CTA
- ORD
1 stop32h 40m
Delta
Tue 9/19:30 am
ORD
- CTA
1 stop15h 25m
Delta
Deal found 6/28![Delta logo]()
$850
This KLM deal was found by Cheapflights users on 6/27. 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 11/510:10 am
CTA
- ORD
2 stops17h 20m
Multiple Airlines
Sun 11/153:35 pm
ORD
- CTA
2 stops16h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$793
This Turkish Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 7/179:25 am
PMO
- ORD
1 stop31h 15m
Turkish Airlines
Tue 7/2111:25 am
ORD
- PMO
1 stop24h 10m
Turkish Airlines
Deal found 7/1![Turkish Airlines logo]()
$873
This Icelandair deal was found by Cheapflights users on 6/26. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:20 am
SUF
- ORD
2 stops18h 00m
Icelandair
Sat 1/96:30 pm
ORD
- SUF
2 stops17h 00m
Icelandair
Deal found 6/26![Icelandair logo]()
$896
This KLM deal was found by Cheapflights users on 6/26. 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 8/139:50 am
PMO
- ORD
2 stops19h 02m
KLM
Thu 9/104:20 pm
ORD
- PMO
2 stops15h 15m
KLM
Deal found 6/26![KLM logo]()
$919
This Delta deal was found by Cheapflights users on 6/27. 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 8/113:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Tue 8/1810:54 am
MDW
- PMO
2 stops21h 01m
Delta
Deal found 6/27![Delta logo]()
$878
This KLM deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:15 am
CTA
- ORD
2 stops20h 35m
Multiple Airlines
Mon 11/163:35 pm
ORD
- CTA
2 stops16h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$804
This Gotogate deal was found by Cheapflights users on 6/26. 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.
Thu 8/206:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/26![ITA Airways logo]()
$731
This Icelandair deal was found by Cheapflights users on 6/26. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/136:20 am
SUF
- ORD
2 stops18h 00m
Icelandair
Sat 1/96:30 pm
ORD
- SUF
2 stops17h 00m
Icelandair
Deal found 6/26![Icelandair logo]()
$896
This British Airways deal was found by Cheapflights users on 6/29. 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.
Sun 8/2312:05 pm
PMO
- ORD
1 stop34h 50m
British Airways
Tue 9/110:30 pm
ORD
- PMO
1 stop29h 40m
British Airways
Deal found 6/29![British Airways logo]()
$931
This Icelandair deal was found by Cheapflights users on 6/29. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:20 am
SUF
- ORD
2 stops18h 00m
Icelandair
Fri 1/86:30 pm
ORD
- SUF
2 stops17h 00m
Icelandair
Deal found 6/29![Icelandair logo]()
$897
This Air Canada deal was found by Cheapflights users on 6/27. 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 8/319:45 am
PMO
- ORD
2 stops17h 20m
Multiple Airlines
Thu 9/1711:05 am
ORD
- PMO
2 stops14h 55m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$836
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:00 pm
PMO
- MDW
2 stops33h 33m
Delta
Sat 8/299:24 am
MDW
- PMO
2 stops22h 31m
Delta
Deal found 6/30![Delta logo]()
$953
This ITA Airways deal was found by Cheapflights users on 7/1. 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.
Sun 8/236:10 am
PMO
- ORD
1 stop14h 00m
Multiple Airlines
Tue 9/110:50 am
ORD
- PMO
2 stops15h 30m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$858
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Sat 7/117:20 am
PMO
- MDW
2 stops21h 55m
Multiple Airlines
Wed 7/151:18 pm
MDW
- PMO
2 stops18h 42m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$977
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/233:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Tue 9/17:25 pm
MDW
- PMO
2 stops31h 00m
Delta
Deal found 6/28![Delta logo]()
$1,237
This KLM deal was found by Cheapflights users on 6/29. 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 9/106:10 am
PMO
- MDW
2 stops17h 47m
Multiple Airlines
Fri 9/115:45 pm
MDW
- PMO
2 stops15h 05m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$1,868
This Delta deal was found by Cheapflights users on 6/27. 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.
Wed 8/53:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Wed 8/269:59 am
MDW
- PMO
2 stops22h 01m
Delta
Deal found 6/27![Delta logo]()
$5,302
Last-minute flights from Sicily to ChicagoDiscover last-minute flight deals from Sicily to Chicago. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from Sicily to Chicago. Data last updated July 1, 2026 and is based on user searches.
This ITA Airways deal was found by Cheapflights users on 6/29. 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 7/68:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Thu 7/303:00 pm
ORD
- PMO
1 stop12h 50m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$772
This KLM deal was found by Cheapflights users on 6/29. 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 7/74:20 pm
CTA
- ORD
1 stop29h 10m
KLM
Fri 7/174:20 pm
ORD
- CTA
1 stop12h 40m
KLM
Deal found 6/29![KLM logo]()
$764
This lol.travel deal was found by Cheapflights users on 7/1. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:05 pm
PMO
- ORD
1 stop25h 05m
ITA Airways
Thu 7/163:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$823
This lol.travel deal was found by Cheapflights users on 7/1. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Wed 7/153:00 pm
ORD
- PMO
1 stop21h 45m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$849
This lol.travel deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:20 pm
SUF
- ORD
1 stop28h 50m
ITA Airways
Sun 7/193:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$672
This lol.travel deal was found by Cheapflights users on 6/29. 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 7/166:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Mon 7/203:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$673
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:55 am
CTA
- ORD
1 stop18h 57m
Delta
Wed 8/125:10 pm
ORD
- CTA
1 stop18h 30m
Delta
Deal found 6/30![Delta logo]()
$758
This Gotogate deal was found by Cheapflights users on 6/26. 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.
Thu 8/206:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/26![ITA Airways logo]()
$731
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Fri 8/217:15 pm
CTA
- ORD
1 stop24h 55m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$696
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Sat 8/227:15 pm
CTA
- ORD
1 stop24h 55m
ITA Airways
Sat 8/293:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$644
This lol.travel deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Tue 9/13:00 pm
ORD
- CTA
1 stop22h 45m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$619
This British Airways deal was found by Cheapflights users on 6/27. 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.
Sun 8/239:50 pm
CTA
- ORD
1 stop27h 25m
British Airways
Tue 9/19:56 am
ORD
- CTA
2 stops28h 09m
British Airways
Deal found 6/27![British Airways logo]()
$654
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 July 1, 2026.
Search for one-way flight options from Sicily to Chicago. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 9/92:05 pm
PMO
- ORD
3 stops34h 45m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$381
This Priceline deal was found by Cheapflights users on 6/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:50 pm
PMO
- ORD
1 stop26h 10m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:50 pm
CTA
- ORD
3 stops45h 35m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 9/911:15 pm
PMO
- MDW
3 stops53h 43m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 10/198:00 am
CTA
- ORD
3 stops40h 50m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 8/238:45 pm
PMO
- MDW
3 stops44h 00m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 8/299:05 pm
PMO
- ORD
3 stops48h 20m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$462
This Mytrip deal was found by Cheapflights users on 6/26. 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.
Sat 8/296:55 pm
PMO
- ORD
1 stop28h 00m
British Airways
Deal found 6/26![British Airways logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 8/239:05 am
PMO
- ORD
3 stops43h 20m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$517
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:15 am
PMO
- ORD
3 stops37h 25m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$518
This KAYAK deal was found by Cheapflights users on 6/26. 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.
Wed 9/912:40 pm
PMO
- ORD
1 stop30h 50m
British Airways
Deal found 6/26![British Airways logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 8/48:20 am
CTA
- ORD
3 stops44h 05m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$583
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 July 1, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $586 (lol.travel) |
One-way from | $381 (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 July 1, 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
Lamezia TermeChicago
SUF - ORD
SUFORD
Lamezia Terme Intl
Fri 9/18
3:20 pm-1:10 pm
1 stop28h 50m
Chicago O'Hare Intl
Wed 9/30
3:00 pm-6:30 pm
1 stop20h 30m
$586
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Sun 8/23
6:00 am-1:10 pm
1 stop14h 10m
Chicago O'Hare Intl
Tue 9/1
3:00 pm-8:45 pm
1 stop22h 45m
$619
Lamezia TermeChicago
SUF - ORD
SUFORD
Lamezia Terme Intl
Wed 10/7
6:15 am-1:10 pm
1 stop13h 55m
Chicago O'Hare Intl
Sun 10/11
3:00 pm-6:30 pm
1 stop20h 30m
$634
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Mon 8/31
3:10 pm-1:10 pm
1 stop29h 00m
Chicago O'Hare Intl
Thu 9/17
3:00 pm-1:40 pm
1 stop15h 40m
$648
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Sun 8/23
9:50 pm-6:15 pm
1 stop27h 25m
Chicago O'Hare Intl
Tue 9/1
9:56 am-9:05 pm
2 stops28h 09m
$654
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 8/20
6:00 am-1:10 pm
1 stop14h 10m
Chicago O'Hare Intl
Sat 8/29
3:00 pm-2:40 pm
1 stop16h 40m
$731
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Tue 8/4
9:55 am-9:52 pm
1 stop18h 57m
Chicago O'Hare Intl
Wed 8/12
1:59 pm-6:40 pm
2 stops21h 41m
$758
PalermoChicago
PMO - ORD
PMOORD
Palermo Punta Raisi
Mon 8/10
9:50 am-10:44 pm
2 stops19h 54m
Chicago O'Hare Intl
Mon 8/17
5:10 pm-3:00 pm
1 stop14h 50m
$777
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 12/17
3:25 pm-5:20 pm
2 stops32h 55m
Chicago O'Hare Intl
Fri 1/15
6:30 pm-11:20 pm
2 stops21h 50m
$779
CataniaChicago
CTA - ORD
CTAORD
Catania Fontanarossa
Thu 11/5
10:10 am-8:30 pm
2 stops17h 20m
Chicago O'Hare Intl
Sun 11/15
3:35 pm-2:40 pm
2 stops16h 05m
$793
Showing 1-10 of 48 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.
SUF-ORD
PMO-ORD
CTA-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
SUF-ORD
PMO-ORD
CTA-ORD
PMO-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
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Traveling to a place near Chicago?
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Hammond
Lansing
Merrillville
Valparaiso
Porter
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