$387+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — CHI
Sep 20 — Sep 271
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 August 21, 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 August 21, 2026.
This lol.travel deal was found by Cheapflights users on 8/17. 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.
Tue 9/16:10 am -
1 stop14h 00m
Tue 9/153:00 pm -
1 stop20h 20m
Deal found 8/17![ITA Airways logo]()
$627
This lol.travel deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 am -
1 stop14h 00m
Wed 10/73:00 pm -
1 stop25h 05m
Deal found 8/19![ITA Airways logo]()
$641
This lol.travel deal was found by Cheapflights users on 8/17. 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 9/57:05 pm -
1 stop25h 05m
Sat 9/123:00 pm -
1 stop23h 05m
Deal found 8/17![ITA Airways logo]()
$653
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/1911:05 pm -
1 stop22h 10m
Sun 9/274:15 pm -
1 stop22h 05m
Deal found 8/17![KLM logo]()
$660
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/56:35 am -
2 stops21h 50m
Sat 9/127:25 pm -
2 stops21h 10m
Deal found 8/17![Multiple Airlines logo]()
$665
This British Airways deal was found by Cheapflights users on 8/17. 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 10/106:55 pm -
1 stop28h 00m
Mon 10/1910:05 am -
2 stops18h 15m
Deal found 8/17![British Airways logo]()
$666
This oojo deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:20 pm -
1 stop31h 50m
Thu 9/103:00 pm -
1 stop15h 25m
Deal found 8/19![ITA Airways logo]()
$670
This KLM deal was found by Cheapflights users on 8/17. 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.
Sat 9/56:10 am -
2 stops17h 49m
Sat 9/125:37 pm -
2 stops15h 13m
Deal found 8/17![Multiple Airlines logo]()
$670
This British Airways deal was found by Cheapflights users on 8/17. 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.
Thu 9/1012:05 pm -
2 stops35h 41m
Mon 9/1410:11 am -
2 stops18h 09m
Deal found 8/17![British Airways logo]()
$672
This Delta deal was found by Cheapflights users on 8/18. 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 9/54:45 pm -
1 stop29h 25m
Sat 9/1211:30 am -
2 stops21h 20m
Deal found 8/18![Delta logo]()
$673
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/1911:05 pm -
1 stop22h 10m
Sat 9/264:15 pm -
1 stop16h 55m
Deal found 8/17![KLM logo]()
$674
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:45 pm -
1 stop29h 25m
Sat 9/2611:17 am -
2 stops21h 33m
Deal found 8/20![Delta logo]()
$675
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 August 21, 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 August 21, 2026.
This lol.travel deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:55 pm -
1 stop23h 15m
Sat 9/123:00 pm -
1 stop24h 30m
Deal found 8/20![ITA Airways logo]()
$660
This British Airways deal was found by Cheapflights users on 8/16. 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 10/106:55 pm -
1 stop28h 00m
Mon 10/1910:05 am -
2 stops18h 15m
Deal found 8/16![British Airways logo]()
$666
This KLM deal was found by Cheapflights users on 8/17. 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.
Sat 9/56:10 am -
2 stops17h 07m
Sat 9/125:10 pm -
1 stop15h 40m
Deal found 8/17![Multiple Airlines logo]()
$670
This Expedia deal was found by Cheapflights users on 8/15. 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.
Sat 9/1911:05 pm -
1 stop22h 10m
Sat 9/2610:25 am -
1 stop14h 30m
Deal found 8/15![KLM logo]()
$672
This Delta deal was found by Cheapflights users on 8/18. 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 9/54:45 pm -
2 stops31h 14m
Sat 9/125:37 pm -
2 stops15h 13m
Deal found 8/18![Delta logo]()
$678
This Expedia deal was found by Cheapflights users on 8/15. 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.
Sat 9/196:35 pm -
2 stops25h 40m
Sat 9/264:05 pm -
1 stop16h 25m
Deal found 8/15![Lufthansa logo]()
$879
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/198:55 am -
1 stop34h 40m
Sat 9/266:05 pm -
2 stops18h 45m
Deal found 8/17![SWISS logo]()
$881
This Expedia deal was found by Cheapflights users on 8/15. 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.
Sat 9/193:25 pm -
2 stops30h 45m
Sat 9/265:10 pm -
2 stops17h 45m
Deal found 8/15![Air France logo]()
$881
This Turkish Airlines deal was found by Cheapflights users on 8/16. 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 10/216:15 am -
2 stops43h 00m
Sun 10/259:15 pm -
2 stops19h 45m
Deal found 8/16![Turkish Airlines logo]()
$1,133
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 10/216:15 am -
1 stop13h 55m
Sun 10/254:40 pm -
1 stop11h 50m
Deal found 8/18![United Airlines logo]()
$1,254
This KLM deal was found by Cheapflights users on 8/17. 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.
Sat 9/56:10 am -
2 stops17h 49m
Sat 9/125:37 pm -
2 stops15h 13m
Deal found 8/17![Multiple Airlines logo]()
$670
This British Airways deal was found by Cheapflights users on 8/18. 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.
Fri 10/27:50 pm -
2 stops27h 56m
Fri 10/94:26 pm -
2 stops18h 29m
Deal found 8/18![British Airways logo]()
$672
This ITA Airways deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:30 pm -
1 stop23h 40m
Sun 10/183:00 pm -
1 stop16h 10m
Deal found 8/20![ITA Airways logo]()
$721
This British Airways deal was found by Cheapflights users on 8/17. 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.
Thu 9/1012:05 pm -
2 stops35h 41m
Mon 9/1410:11 am -
2 stops18h 09m
Deal found 8/17![British Airways logo]()
$672
This KLM deal was found by Cheapflights users on 8/18. 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 11/210:55 am -
2 stops19h 57m
Sun 11/86:10 am -
1 stop19h 45m
Deal found 8/18![KLM logo]()
$748
This KLM deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
2 stops21h 30m
Wed 11/41:55 pm -
2 stops17h 45m
Deal found 8/20![Multiple Airlines logo]()
$705
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:05 pm -
1 stop25h 05m
Thu 9/173:00 pm -
1 stop13h 20m
Deal found 8/20![ITA Airways logo]()
$740
This oojo deal was found by Cheapflights users on 8/16. 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.
Sat 9/199:30 pm -
1 stop22h 40m
Sat 9/263:00 pm -
1 stop15h 25m
Deal found 8/16![ITA Airways logo]()
$745
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:00 pm -
1 stop33h 10m
Sun 9/2710:25 am -
1 stop14h 30m
Deal found 8/19![Delta logo]()
$916
This KLM deal was found by Cheapflights users on 8/18. 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 11/210:55 am -
2 stops19h 57m
Sun 11/81:55 pm -
2 stops17h 45m
Deal found 8/18![Multiple Airlines logo]()
$769
This British Airways deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:55 am -
1 stop35h 00m
Sat 9/1210:11 am -
2 stops18h 04m
Deal found 8/19![British Airways logo]()
$800
This Gotogate deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:15 pm -
1 stop24h 55m
Tue 9/83:00 pm -
2 stops15h 20m
Deal found 8/19![ITA Airways logo]()
$754
This lol.travel deal was found by Cheapflights users on 8/18. 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 9/311:40 am -
1 stop13h 35m
Mon 9/74:20 pm -
1 stop34h 00m
Deal found 8/18![Multiple Airlines logo]()
$797
This KLM deal was found by Cheapflights users on 8/17. 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 9/19:55 am -
2 stops19h 41m
Tue 9/151:19 pm -
2 stops18h 06m
Deal found 8/17![KLM logo]()
$1,118
This ITA Airways deal was found by Cheapflights users on 8/16. 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 9/246:00 am -
1 stop14h 10m
Mon 9/288:50 am -
2 stops17h 40m
Deal found 8/16![ITA Airways logo]()
$919
This KLM deal was found by Cheapflights users on 8/16. 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.
Sat 10/106:10 am -
2 stops18h 50m
Mon 10/191:27 pm -
2 stops17h 43m
Deal found 8/16![KLM logo]()
$1,125
This Air France Smart Connect deal was found by Cheapflights users on 8/16. 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 Smart Connect is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:00 pm -
1 stop26h 10m
Sat 9/265:10 pm -
1 stop33h 45m
Deal found 8/16![Multiple Airlines logo]()
$953
This KLM deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 am -
2 stops19h 23m
Wed 10/710:59 am -
2 stops17h 31m
Deal found 8/19![KLM logo]()
$1,224
This ITA Airways deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:15 am -
2 stops19h 45m
Tue 9/83:00 pm -
1 stop12h 30m
Deal found 8/19![Multiple Airlines logo]()
$1,123
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:45 pm -
2 stops30h 30m
Sat 9/261:19 pm -
2 stops19h 31m
Deal found 8/20![Delta logo]()
$1,734
Last-minute flights from Sicily to ChicagoDiscover last-minute flight deals from Sicily to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Sicily to Chicago. Data last updated August 21, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 8/17. 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.
Tue 9/16:10 am -
1 stop14h 00m
Tue 9/153:00 pm -
1 stop20h 20m
Deal found 8/17![ITA Airways logo]()
$627
This oojo deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:20 pm -
1 stop31h 50m
Thu 9/103:00 pm -
1 stop15h 25m
Deal found 8/19![ITA Airways logo]()
$670
This lol.travel deal was found by Cheapflights users on 8/17. 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 9/57:05 pm -
1 stop25h 05m
Sat 9/123:00 pm -
1 stop23h 05m
Deal found 8/17![ITA Airways logo]()
$653
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/56:35 am -
2 stops21h 50m
Sat 9/127:25 pm -
2 stops21h 10m
Deal found 8/17![Multiple Airlines logo]()
$665
This KLM deal was found by Cheapflights users on 8/17. 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.
Sat 9/56:10 am -
2 stops17h 49m
Sat 9/125:37 pm -
2 stops15h 13m
Deal found 8/17![Multiple Airlines logo]()
$670
This Delta deal was found by Cheapflights users on 8/18. 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 9/54:45 pm -
1 stop29h 25m
Sat 9/1211:30 am -
2 stops21h 20m
Deal found 8/18![Delta logo]()
$673
This Delta deal was found by Cheapflights users on 8/18. 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 9/54:45 pm -
2 stops31h 14m
Sat 9/125:37 pm -
2 stops15h 13m
Deal found 8/18![Delta logo]()
$678
This British Airways deal was found by Cheapflights users on 8/16. 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.
Thu 9/1012:05 pm -
2 stops35h 41m
Mon 9/148:38 pm -
2 stops32h 07m
Deal found 8/16![British Airways logo]()
$672
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/1911:05 pm -
1 stop22h 10m
Sun 9/274:15 pm -
1 stop22h 05m
Deal found 8/17![KLM logo]()
$660
This Expedia deal was found by Cheapflights users on 8/17. 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.
Sat 9/1911:05 pm -
1 stop22h 10m
Sat 9/264:15 pm -
1 stop16h 55m
Deal found 8/17![KLM logo]()
$674
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:45 pm -
1 stop29h 25m
Sat 9/2611:17 am -
2 stops21h 33m
Deal found 8/20![Delta logo]()
$675
This lol.travel deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 am -
1 stop14h 00m
Wed 10/73:00 pm -
1 stop25h 05m
Deal found 8/19![ITA Airways logo]()
$641
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 August 21, 2026.
Search for one-way flight options from Sicily to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/2412:35 am -
3 stops49h 15m
Deal found 8/17![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/2710:40 pm -
3 stops49h 40m
Deal found 8/16![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:10 pm -
3 stops35h 40m
Deal found 8/20![Multiple Airlines logo]()
$404
This Expedia deal was found by Cheapflights users on 8/16. 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.
Tue 10/276:40 pm -
2 stops31h 05m
Deal found 8/16![Iberia logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 11/18:15 pm -
2 stops25h 55m
Deal found 8/16![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:05 pm -
3 stops32h 15m
Deal found 8/19![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:25 pm -
3 stops48h 05m
Deal found 8/19![Multiple Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/1510:25 pm -
3 stops45h 15m
Deal found 8/16![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/66:05 am -
3 stops42h 45m
Deal found 8/16![Multiple Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:55 am -
1 stop16h 48m
Deal found 8/19![Delta logo]()
$518
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:50 pm -
1 stop26h 10m
Deal found 8/20![American Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:35 pm -
2 stops31h 24m
Deal found 8/20![Multiple Airlines logo]()
$532
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 August 21, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $627 (lol.travel) |
One-way from | $387 (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 7,457,451 searches. Data last updated August 21, 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 Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Sat 9/5
8:55 pm-1:10 pm
1 stop23h 15m
Chicago O'Hare Intl
Sat 9/12
3:00 pm-10:30 pm
1 stop24h 30m
$660
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Sat 10/10
6:55 pm-3:55 pm
1 stop28h 00m
Chicago O'Hare Intl
Mon 10/19
10:05 am-11:20 am
2 stops18h 15m
$666
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Sat 9/5
6:10 am-4:17 pm
2 stops17h 07m
Chicago O'Hare Intl
Sat 9/12
5:10 pm-3:50 pm
1 stop15h 40m
$670
PalermoChicago
PMO Palermo Punta Raisi - MDW Chicago Midway
PMOMDW
Palermo Punta Raisi
Sat 9/5
6:10 am-4:59 pm
2 stops17h 49m
Chicago Midway
Sat 9/12
5:37 pm-3:50 pm
2 stops15h 13m
$670
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Sat 9/19
11:05 pm-2:15 pm
1 stop22h 10m
Chicago O'Hare Intl
Sat 9/26
10:25 am-7:55 am
1 stop14h 30m
$672
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Fri 10/2
7:50 pm-4:46 pm
2 stops27h 56m
Chicago O'Hare Intl
Fri 10/9
4:26 pm-5:55 pm
2 stops18h 29m
$672
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Thu 9/10
12:05 pm-4:46 pm
2 stops35h 41m
Chicago O'Hare Intl
Mon 9/14
10:11 am-11:20 am
2 stops18h 09m
$672
PalermoChicago
PMO Palermo Punta Raisi - MDW Chicago Midway
PMOMDW
Palermo Punta Raisi
Sat 9/5
4:45 pm-4:59 pm
2 stops31h 14m
Chicago Midway
Sat 9/12
5:37 pm-3:50 pm
2 stops15h 13m
$678
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Thu 10/8
6:00 am-8:30 pm
2 stops21h 30m
Chicago O'Hare Intl
Wed 11/4
1:55 pm-2:40 pm
2 stops17h 45m
$705
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Thu 10/15
8:30 pm-1:10 pm
1 stop23h 40m
Chicago O'Hare Intl
Sun 10/18
3:00 pm-2:10 pm
1 stop16h 10m
$721
Showing 1-10 of 45 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.
PMO-ORD
CTA-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
PMO-ORD
CTA-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
Valparaiso
Hammond
Saint Joseph
Porter
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