$324+ Cheap flights from Chicago (CHI) to Sicily
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Sep 21 — Sep 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Sicily 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 Chicago to Sicily
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Cheapest flights from Chicago to SicilyExplore the most affordable flight options available from Chicago to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
Explore the most affordable flight options available from Chicago to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:50 pm -
1 stop18h 50m
Tue 11/1010:25 pm -
2 stops27h 00m
Deal found 8/21![Multiple Airlines logo]()
$612
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:35 pm -
1 stop12h 25m
Sun 10/187:45 pm -
2 stops25h 15m
Deal found 8/21![Multiple Airlines logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:20 pm -
1 stop12h 00m
Tue 11/1010:25 pm -
2 stops27h 00m
Deal found 8/21![Multiple Airlines logo]()
$625
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:55 pm -
1 stop12h 40m
Sun 10/252:25 pm -
2 stops30h 45m
Deal found 8/21![Multiple Airlines logo]()
$627
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:40 pm -
1 stop20h 05m
Mon 11/26:00 am -
2 stops39h 00m
Deal found 8/21![Multiple Airlines logo]()
$632
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:50 pm -
1 stop18h 05m
Fri 11/610:25 pm -
2 stops22h 35m
Deal found 8/21![Multiple Airlines logo]()
$633
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:40 pm -
1 stop20h 05m
Tue 11/1710:25 pm -
2 stops27h 00m
Deal found 8/21![Multiple Airlines logo]()
$638
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:50 pm -
1 stop18h 05m
Wed 11/49:25 pm -
2 stops23h 35m
Deal found 8/21![Multiple Airlines logo]()
$644
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:55 pm -
1 stop12h 40m
Mon 10/266:40 am -
2 stops18h 45m
Deal found 8/21![Multiple Airlines logo]()
$646
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:55 pm -
1 stop20h 55m
Sun 10/259:40 pm -
2 stops23h 30m
Deal found 8/21![Multiple Airlines logo]()
$651
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:20 pm -
1 stop12h 00m
Wed 11/49:25 pm -
2 stops23h 35m
Deal found 8/21![Multiple Airlines logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:35 pm -
1 stop12h 25m
Mon 10/1210:25 pm -
2 stops46h 35m
Deal found 8/21![Multiple Airlines logo]()
$660
Best flights from Chicago to SicilyDiscover carefully curated flight deals from Chicago to Sicily that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
Discover carefully curated flight deals from Chicago to Sicily that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
This Turkish Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:10 pm -
1 stop15h 15m
Tue 10/207:25 pm -
1 stop21h 15m
Deal found 8/21![Turkish Airlines logo]()
$699
This TAP AIR PORTUGAL deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:10 pm -
2 stops19h 50m
Thu 11/196:20 am -
2 stops40h 10m
Deal found 8/21![TAP AIR PORTUGAL logo]()
$881
This Air France 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/710:35 am -
2 stops17h 55m
Wed 1/2010:05 am -
2 stops19h 05m
Deal found 8/17![Multiple Airlines logo]()
$886
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.
Sun 9/203:00 pm -
1 stop13h 20m
Thu 10/158:30 pm -
1 stop23h 40m
Deal found 8/19![ITA Airways logo]()
$888
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
2 stops19h 55m
Tue 11/2410:55 am -
2 stops28h 55m
Deal found 8/21![Delta logo]()
$1,036
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 10/51:19 pm -
2 stops17h 06m
Tue 10/206:00 am -
2 stops19h 00m
Deal found 8/18![KLM logo]()
$1,044
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/95:50 pm -
2 stops34h 40m
Tue 1/196:10 am -
2 stops38h 03m
Deal found 8/17![United Airlines logo]()
$1,053
This Lufthansa deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:30 pm -
1 stop29h 10m
Mon 10/128:40 am -
2 stops16h 35m
Deal found 8/21![Lufthansa logo]()
$1,229
This Turkish Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:25 am -
1 stop14h 00m
Thu 10/159:25 am -
1 stop31h 15m
Deal found 8/21![Turkish Airlines logo]()
$768
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:10 pm -
1 stop15h 15m
Sun 10/185:40 pm -
1 stop23h 00m
Deal found 8/20![Turkish Airlines logo]()
$769
This Turkish Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:25 am -
1 stop14h 00m
Fri 10/169:25 am -
1 stop31h 15m
Deal found 8/21![Turkish Airlines logo]()
$793
This TAP AIR PORTUGAL 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 pm -
2 stops38h 10m
Tue 10/134:10 pm -
2 stops30h 50m
Deal found 8/20![TAP AIR PORTUGAL logo]()
$964
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:00 pm -
1 stop12h 55m
Sat 10/179:30 pm -
1 stop22h 40m
Deal found 8/17![ITA Airways logo]()
$973
This Trip.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:45 pm -
2 stops24h 50m
Mon 10/126:35 am -
2 stops19h 40m
Deal found 8/21![Multiple Airlines logo]()
$1,021
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 10/23:00 pm -
1 stop16h 10m
Fri 10/96:10 am -
1 stop14h 00m
Deal found 8/19![ITA Airways logo]()
$974
This KLM deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/131:27 pm -
2 stops17h 43m
Tue 10/206:10 am -
2 stops18h 50m
Deal found 8/22![KLM logo]()
$1,076
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:10 pm -
1 stop29h 10m
Tue 10/67:25 pm -
1 stop21h 15m
Deal found 8/18![Turkish Airlines logo]()
$850
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:05 am -
2 stops27h 20m
Wed 1/67:55 am -
2 stops16h 25m
Deal found 8/20![Multiple Airlines logo]()
$1,043
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:00 pm -
1 stop16h 00m
Wed 10/76:10 am -
1 stop14h 00m
Deal found 8/18![ITA Airways logo]()
$974
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.
Thu 10/17:01 pm -
2 stops37h 49m
Sat 10/316:40 pm -
2 stops34h 53m
Deal found 8/18![Delta logo]()
$1,280
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:00 pm -
1 stop12h 55m
Mon 9/149:30 pm -
1 stop22h 40m
Deal found 8/18![ITA Airways logo]()
$976
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.
Fri 9/187:01 pm -
2 stops14h 09m
Fri 9/256:00 am -
2 stops19h 33m
Deal found 8/19![KLM logo]()
$1,182
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:10 pm -
1 stop15h 15m
Fri 10/307:10 pm -
1 stop21h 50m
Deal found 8/19![Turkish Airlines logo]()
$890
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:40 pm -
1 stop11h 50m
Thu 11/196:20 am -
1 stop13h 50m
Deal found 8/20![United Airlines logo]()
$1,418
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:10 pm -
1 stop29h 10m
Tue 10/67:25 pm -
1 stop21h 15m
Deal found 8/18![Turkish Airlines logo]()
$890
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.
Thu 9/103:00 pm -
1 stop15h 40m
Mon 9/288:30 pm -
1 stop23h 40m
Deal found 8/19![ITA Airways logo]()
$1,017
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.
Tue 12/153:40 pm -
1 stop24h 20m
Tue 1/57:15 pm -
2 stops27h 05m
Deal found 8/17![Multiple Airlines logo]()
$1,239
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:25 am -
1 stop14h 00m
Fri 10/309:35 am -
1 stop31h 25m
Deal found 8/17![Turkish Airlines logo]()
$913
This KLM deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:19 pm -
2 stops17h 06m
Mon 10/1210:05 am -
2 stops19h 28m
Deal found 8/21![KLM logo]()
$1,342
This Air France 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:35 am -
2 stops16h 20m
Tue 10/610:15 am -
2 stops19h 18m
Deal found 8/18![Multiple Airlines logo]()
$1,333
Last-minute flights from Chicago to SicilyDiscover last-minute flight deals from Chicago to Sicily. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sicily. Data last updated August 22, 2026 and is based on user searches.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm -
1 stop23h 45m
Sat 8/292:10 pm -
1 stop30h 00m
Deal found 8/18![ITA Airways logo]()
$868
This oojo deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/233:00 pm -
1 stop20h 20m
Sun 8/306:10 am -
1 stop14h 00m
Deal found 8/22![ITA Airways logo]()
$827
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:00 pm -
1 stop13h 20m
Tue 9/156:00 am -
2 stops20h 15m
Deal found 8/21![Multiple Airlines logo]()
$782
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:40 pm -
1 stop16h 25m
Mon 8/319:45 am -
1 stop13h 10m
Deal found 8/18![SWISS logo]()
$793
This oojo deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:00 pm -
1 stop16h 35m
Thu 9/106:10 am -
1 stop14h 00m
Deal found 8/21![ITA Airways logo]()
$812
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:00 pm -
1 stop13h 20m
Tue 9/156:00 am -
2 stops20h 15m
Deal found 8/21![Multiple Airlines logo]()
$797
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:00 pm -
1 stop13h 20m
Wed 9/93:30 pm -
1 stop28h 40m
Deal found 8/18![ITA Airways logo]()
$805
This Turkish Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/218:10 pm -
1 stop15h 30m
Tue 10/207:40 pm -
1 stop21h 00m
Deal found 8/22![Turkish Airlines logo]()
$722
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:35 pm -
1 stop12h 25m
Sat 10/310:30 pm -
2 stops46h 30m
Deal found 8/21![Multiple Airlines logo]()
$824
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:35 pm -
1 stop12h 25m
Sun 10/46:15 am -
2 stops38h 45m
Deal found 8/21![Multiple Airlines logo]()
$837
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:35 pm -
1 stop12h 25m
Mon 10/58:00 am -
2 stops18h 15m
Deal found 8/21![Multiple Airlines logo]()
$872
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:10 pm -
1 stop29h 10m
Tue 10/67:25 pm -
1 stop21h 15m
Deal found 8/18![Turkish Airlines logo]()
$850
One-way flights from Chicago to SicilySearch for one-way flight options from Chicago to Sicily. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
Search for one-way flight options from Chicago to Sicily. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:25 pm -
3 stops31h 45m
Deal found 8/21![Multiple Airlines logo]()
$324
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.
Sun 10/1810:25 pm -
3 stops39h 45m
Deal found 8/20![Multiple Airlines logo]()
$325
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:30 pm -
3 stops22h 25m
Deal found 8/18![Multiple Airlines logo]()
$340
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:30 pm -
3 stops17h 35m
Deal found 8/18![Multiple Airlines logo]()
$343
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:30 pm -
3 stops20h 45m
Deal found 8/18![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:46 pm -
3 stops42h 29m
Deal found 8/22![Multiple Airlines logo]()
$356
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.
Mon 11/96:30 pm -
3 stops31h 20m
Deal found 8/17![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:50 pm -
2 stops45h 25m
Deal found 8/22![Multiple Airlines logo]()
$359
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.
Wed 10/217:25 pm -
3 stops31h 15m
Deal found 8/19![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:25 pm -
3 stops29h 50m
Deal found 8/21![Multiple Airlines logo]()
$361
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:30 pm -
2 stops20h 20m
Deal found 8/18![Multiple Airlines logo]()
$362
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.
Mon 11/306:30 pm -
2 stops17h 00m
Deal found 8/19![Multiple Airlines logo]()
$364
Find flight deals from Chicago to Sicily
Keep the following information in mind while searching for Chicago to Sicily flight deals. Data was last updated August 22, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $612 (Kiwi.com) |
One-way from | $324 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $850 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Sicily that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 22, 2026.
Use the filters below to find and compare flights from Chicago to Sicily that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Mon 10/5
8:10 pm-6:25 pm
1 stop15h 15m
Catania Fontanarossa
Tue 10/20
7:25 pm-9:40 am
1 stop21h 15m
$699
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Wed 10/7
11:25 am-8:25 am
1 stop14h 00m
Palermo Punta Raisi
Thu 10/15
9:25 am-9:40 am
1 stop31h 15m
$768
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Wed 10/14
8:10 pm-6:25 pm
1 stop15h 15m
Catania Fontanarossa
Sun 10/18
5:40 pm-9:40 am
1 stop23h 00m
$769
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Wed 10/7
11:25 am-8:25 am
1 stop14h 00m
Palermo Punta Raisi
Fri 10/16
9:25 am-9:40 am
1 stop31h 15m
$793
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Mon 9/28
8:10 pm-8:20 am
1 stop29h 10m
Catania Fontanarossa
Tue 10/6
7:25 pm-9:40 am
1 stop21h 15m
$850
ChicagoLamezia Terme
ORD Chicago O'Hare Intl - SUF Lamezia Terme Intl
ORDSUF
Chicago O'Hare Intl
Sun 11/15
8:10 pm-11:00 pm
2 stops19h 50m
Lamezia Terme Intl
Thu 11/19
6:20 am-3:30 pm
2 stops40h 10m
$881
ChicagoPalermo
MDW Chicago Midway - PMO Palermo Punta Raisi
MDWPMO
Chicago Midway
Thu 1/7
10:35 am-11:30 am
2 stops17h 55m
Palermo Punta Raisi
Wed 1/20
10:05 am-10:10 pm
2 stops19h 05m
$886
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Sun 9/20
3:00 pm-11:20 am
1 stop13h 20m
Palermo Punta Raisi
Thu 10/15
8:30 pm-1:10 pm
1 stop23h 40m
$888
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Wed 10/21
8:10 pm-6:25 pm
1 stop15h 15m
Catania Fontanarossa
Fri 10/30
7:10 pm-11:00 am
1 stop21h 50m
$890
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Sat 9/26
8:10 pm-8:20 am
1 stop29h 10m
Catania Fontanarossa
Tue 10/6
7:25 pm-9:40 am
1 stop21h 15m
$890
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Sicily
Have a flexible travel schedule? Discover the best time to fly to Sicily from Chicago with our price prediction graph.
ORD-SUF
ORD-CTA
ORD-PMO
MDW-PMO
MDW-CTA
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 Chicago to Sicily
CHI-ITSI
ORD-SUF
ORD-CTA
ORD-PMO
MDW-PMO
What is the cheapest month to book a flight from Chicago to Sicily?
Currently, January is the cheapest month in which you can book a flight from Chicago to Sicily (average of $702). Flying from Chicago to Sicily in May is currently the most expensive (average of $1,385). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to Sicily?
Airfare is below average for this route at the moment.
Chicago to Sicily flights typically cost between $834 and $1,149 in November.The cheapest round-trip price found within the last 5 days was $612 on Multiple Airlines (Nov 3-Nov 10).
How far ahead should I book a flight from Chicago to Sicily?
Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Sicily. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Sicily
Get insights into the airlines that provide service to Sicily. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sicily. Reviews last updated August 22, 2026.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS,Turkish Airlines, andLufthansa. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Related info for your journey
Find useful and relevant information for your journey from Chicago to Sicily. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Sicily
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Complete your trip
Complete your trip to Sicily by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Sicily by cabin class
Find flights from Chicago to Sicily, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Sicily flights
Browse other Chicago and Sicily flight options. Last updated on August 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Sicily
Discover the top 4 airlines that operate flights from Chicago to Sicily. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$554 | Average$710 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$596 | Average$1,010 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$705 | Average$1,080 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$868 | Average$1,334 | FlexibilityNo cancel fee | On-time76% |