$311+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Aug 2 — Aug 91
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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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 July 3, 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 July 3, 2026.
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.
Sat 9/57:15 pm
ORD
- PMO
1 stop14h 30m
Scandinavian Airlines
Wed 9/236:50 pm
PMO
- ORD
1 stop28h 20m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$672
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
ORD
- PMO
1 stop14h 30m
Scandinavian Airlines
Fri 9/256:50 pm
PMO
- ORD
1 stop28h 20m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$701
This Gotogate deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/93:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Mon 8/248:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$703
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/93:00 pm
ORD
- CTA
1 stop12h 50m
ITA Airways
Mon 8/242:10 pm
CTA
- ORD
1 stop30h 00m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$703
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:00 pm
ORD
- PMO
1 stop18h 40m
Multiple Airlines
Wed 8/269:45 pm
PMO
- ORD
1 stop22h 25m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$705
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:25 pm
ORD
- PMO
2 stops20h 20m
Multiple Airlines
Wed 9/99:45 pm
PMO
- ORD
2 stops29h 03m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$706
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:05 am
ORD
- PMO
2 stops28h 10m
Multiple Airlines
Tue 8/1810:40 pm
PMO
- ORD
2 stops23h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$707
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Thu 8/276:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$711
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Wed 8/193:10 pm
PMO
- ORD
1 stop29h 00m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$713
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Mon 8/248:00 am
CTA
- ORD
1 stop36h 10m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$735
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Tue 8/256:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$738
This Bravofly 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:00 pm
ORD
- CTA
1 stop24h 30m
ITA Airways
Thu 8/206:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$753
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 July 3, 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 July 3, 2026.
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.
Thu 8/133:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Thu 8/206:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$764
This Turkish Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 9/238:10 pm
ORD
- PMO
1 stop29h 15m
Turkish Airlines
Wed 10/77:35 pm
PMO
- ORD
1 stop21h 05m
Turkish Airlines
Deal found 7/3![Turkish Airlines logo]()
$798
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 8/411:22 am
ORD
- PMO
2 stops20h 38m
Delta
Tue 8/183:45 pm
PMO
- ORD
2 stops31h 32m
Delta
Deal found 6/30![Delta logo]()
$833
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:28 pm
MDW
- PMO
2 stops17h 12m
KLM
Tue 11/2410:05 am
PMO
- MDW
2 stops19h 05m
KLM
Deal found 7/1![KLM logo]()
$835
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/174:20 pm
ORD
- SUF
1 stop34h 00m
Multiple Airlines
Mon 8/248:40 am
SUF
- ORD
1 stop34h 55m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$843
This SWISS deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:20 pm
ORD
- PMO
1 stop11h 40m
SWISS
Mon 8/242:55 pm
PMO
- ORD
1 stop28h 40m
SWISS
Deal found 7/3![SWISS logo]()
$855
This TAP AIR PORTUGAL 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 pm
ORD
- PMO
2 stops22h 05m
TAP AIR PORTUGAL
Tue 10/204:10 pm
PMO
- ORD
2 stops30h 50m
TAP AIR PORTUGAL
Deal found 6/29![TAP AIR PORTUGAL logo]()
$932
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:45 pm
ORD
- CTA
2 stops29h 40m
Finnair
Wed 9/96:55 pm
CTA
- ORD
2 stops30h 20m
Finnair
Deal found 6/30![Finnair logo]()
$979
This ITA Airways deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- PMO
1 stop16h 15m
ITA Airways
Sun 8/236:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$770
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Tue 10/207:35 pm
PMO
- ORD
1 stop29h 40m
Turkish Airlines
Deal found 6/30![Turkish Airlines logo]()
$798
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.
Mon 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Tue 8/183:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$834
This ITA Airways deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- SUF
1 stop16h 35m
ITA Airways
Sun 8/236:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$793
This TAP AIR PORTUGAL 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:10 pm
ORD
- CTA
2 stops35h 30m
TAP AIR PORTUGAL
Thu 12/103:25 pm
CTA
- ORD
2 stops31h 05m
TAP AIR PORTUGAL
Deal found 6/29![TAP AIR PORTUGAL logo]()
$948
This Turkish Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:10 pm
ORD
- PMO
1 stop29h 15m
Turkish Airlines
Fri 11/279:35 am
PMO
- ORD
1 stop15h 45m
Turkish Airlines
Deal found 7/2![Turkish Airlines logo]()
$868
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.
Sat 8/153:00 pm
ORD
- SUF
1 stop12h 30m
ITA Airways
Sat 8/226:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$798
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/151:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Mon 8/243:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 7/3![Delta logo]()
$883
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 8/201:25 pm
MDW
- SUF
2 stops18h 10m
KLM
Tue 8/256:35 am
SUF
- MDW
2 stops23h 01m
KLM
Deal found 6/29![KLM logo]()
$974
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:25 pm
ORD
- SUF
2 stops20h 35m
Multiple Airlines
Sat 8/227:15 pm
SUF
- ORD
3 stops33h 10m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$1,009
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:24 am
MDW
- PMO
2 stops22h 36m
Delta
Thu 8/203:45 pm
PMO
- MDW
2 stops33h 48m
Delta
Deal found 6/29![Delta logo]()
$883
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 9/134:20 pm
ORD
- CTA
1 stop22h 00m
KLM
Mon 10/510:05 pm
CTA
- ORD
1 stop23h 10m
KLM
Deal found 6/29![KLM logo]()
$975
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.
Sat 8/153:00 pm
ORD
- PMO
1 stop13h 20m
ITA Airways
Sat 8/226:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$807
This Turkish Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 11/238:15 pm
ORD
- CTA
1 stop29h 25m
Turkish Airlines
Mon 12/79:40 am
CTA
- ORD
1 stop31h 20m
Turkish Airlines
Deal found 7/3![Turkish Airlines logo]()
$890
This Expedia deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:30 pm
ORD
- SUF
2 stops26h 10m
Multiple Airlines
Sun 8/2311:40 am
SUF
- ORD
2 stops17h 25m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$1,053
This Turkish Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Sat 10/37:35 pm
PMO
- ORD
1 stop21h 05m
Turkish Airlines
Deal found 7/2![Turkish Airlines logo]()
$898
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 9/23:00 pm
ORD
- CTA
1 stop12h 55m
ITA Airways
Tue 9/156:00 am
CTA
- ORD
1 stop14h 10m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$845
This KLM deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:28 pm
MDW
- PMO
2 stops17h 12m
KLM
Sat 10/316:10 am
PMO
- MDW
2 stops17h 55m
KLM
Deal found 7/2![KLM logo]()
$1,040
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 am
MDW
- CTA
2 stops18h 50m
Delta
Wed 9/309:55 am
CTA
- MDW
2 stops19h 50m
Delta
Deal found 6/29![Delta logo]()
$1,024
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
ORD
- SUF
2 stops17h 30m
ITA Airways
Tue 8/256:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$866
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.
Fri 8/1412:46 pm
MDW
- CTA
2 stops16h 14m
KLM
Fri 8/218:40 am
CTA
- MDW
2 stops20h 56m
KLM
Deal found 6/30![KLM logo]()
$1,100
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.
Mon 8/318:10 pm
ORD
- CTA
1 stop29h 15m
Turkish Airlines
Tue 9/227:25 pm
CTA
- ORD
1 stop21h 15m
Turkish Airlines
Deal found 7/1![Turkish Airlines logo]()
$1,015
Last-minute flights from Chicago to SicilyDiscover last-minute flight deals from Chicago to Sicily. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sicily. Data last updated July 3, 2026 and is based on user searches.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:00 pm
ORD
- PMO
1 stop24h 40m
ITA Airways
Tue 8/184:40 pm
PMO
- ORD
1 stop27h 30m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$714
This Gotogate deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/93:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Mon 8/248:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$703
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/93:00 pm
ORD
- CTA
1 stop12h 50m
ITA Airways
Mon 8/242:10 pm
CTA
- ORD
1 stop30h 00m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$703
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:05 am
ORD
- PMO
2 stops28h 10m
Multiple Airlines
Tue 8/1810:40 pm
PMO
- ORD
2 stops23h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$707
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Wed 8/193:10 pm
PMO
- ORD
1 stop29h 00m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$713
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Thu 8/276:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$711
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- CTA
1 stop16h 40m
ITA Airways
Mon 8/248:00 am
CTA
- ORD
1 stop36h 10m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$735
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:00 pm
ORD
- PMO
1 stop18h 40m
Multiple Airlines
Wed 8/269:45 pm
PMO
- ORD
1 stop22h 25m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$705
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:25 pm
ORD
- PMO
2 stops20h 20m
Multiple Airlines
Wed 9/99:45 pm
PMO
- ORD
2 stops29h 03m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$706
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:25 pm
ORD
- PMO
2 stops18h 25m
Multiple Airlines
Tue 9/87:35 pm
PMO
- ORD
2 stops29h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$716
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:00 pm
ORD
- PMO
1 stop21h 45m
ITA Airways
Wed 8/266:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$717
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
ORD
- SUF
1 stop20h 30m
ITA Airways
Tue 8/256:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$738
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 July 3, 2026.
Search for one-way flight options from Chicago to Sicily. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Trip.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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.
Fri 7/317:25 pm
ORD
- PMO
2 stops19h 25m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$311
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.
Tue 8/117:25 pm
ORD
- PMO
2 stops16h 05m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$312
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 8/310:25 pm
ORD
- PMO
2 stops43h 35m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$317
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 8/107:25 pm
ORD
- PMO
2 stops30h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$318
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 8/57:25 pm
ORD
- PMO
2 stops22h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$319
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 8/127:25 pm
ORD
- PMO
2 stops17h 20m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$323
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.
Sun 8/27:25 pm
ORD
- PMO
2 stops20h 15m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$326
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.
Sat 8/17:25 pm
ORD
- PMO
2 stops32h 05m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$327
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:25 pm
ORD
- CTA
3 stops33h 55m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:25 pm
ORD
- CTA
3 stops40h 25m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$350
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 pm
ORD
- CTA
1 stop17h 25m
SWISS
Deal found 6/30![SWISS logo]()
$383
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 9/14:20 pm
ORD
- CTA
1 stop34h 30m
KLM
Deal found 6/29![KLM logo]()
$390
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 July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $672 (Kiwi.com) |
One-way from | $311 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $1,178 |
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 2,558,603 searches. Data last updated July 3, 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
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Thu 8/13
3:00 pm-1:40 pm
1 stop15h 40m
Palermo Punta Raisi
Thu 8/20
6:10 am-1:10 pm
1 stop14h 00m
$764
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Sun 8/16
3:00 pm-2:15 pm
1 stop16h 15m
Palermo Punta Raisi
Sun 8/23
6:10 am-1:10 pm
1 stop14h 00m
$770
ChicagoLamezia Terme
ORD - SUF
ORDSUF
Chicago O'Hare Intl
Sun 8/16
3:00 pm-2:35 pm
1 stop16h 35m
Lamezia Terme Intl
Sun 8/23
6:15 am-1:10 pm
1 stop13h 55m
$793
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 9/23
8:10 pm-8:25 am
1 stop29h 15m
Palermo Punta Raisi
Wed 10/7
7:35 pm-9:40 am
1 stop21h 05m
$798
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Mon 9/21
8:10 pm-6:35 pm
1 stop15h 25m
Palermo Punta Raisi
Tue 10/20
7:35 pm-6:15 pm
1 stop29h 40m
$798
Quickest round-trip
ChicagoLamezia Terme
ORD - SUF
ORDSUF
Chicago O'Hare Intl
Sat 8/15
3:00 pm-10:30 am
1 stop12h 30m
Lamezia Terme Intl
Sat 8/22
6:15 am-1:10 pm
1 stop13h 55m
$798
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Sat 8/15
3:00 pm-11:20 am
1 stop13h 20m
Palermo Punta Raisi
Sat 8/22
6:10 am-1:10 pm
1 stop14h 00m
$807
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Tue 8/4
11:22 am-3:00 pm
2 stops20h 38m
Palermo Punta Raisi
Tue 8/18
3:45 pm-4:17 pm
2 stops31h 32m
$833
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Mon 8/10
1:25 pm-3:00 pm
2 stops18h 35m
Palermo Punta Raisi
Tue 8/18
3:45 pm-4:15 pm
2 stops31h 30m
$834
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Tue 10/20
1:28 pm-1:40 pm
2 stops17h 12m
Palermo Punta Raisi
Tue 11/24
10:05 am-10:10 pm
2 stops19h 05m
$835
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-CTA
ORD-PMO
ORD-SUF
MDW-CTA
MDW-PMO
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-CTA
ORD-PMO
ORD-SUF
MDW-CTA
What is the cheapest month to book a flight from Chicago to Sicily?
Currently, August is the cheapest month in which you can book a flight from Chicago to Sicily (average of $56). Flying from Chicago to Sicily in December is currently the most expensive (average of $642). 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?
How far ahead should I book a flight from Chicago to Sicily?
Booking 55 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 July 3, 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.
Comfort
7.4
Food
7.1
Overall
7.5
Boarding
7.7
Crew
8.3
Entertainment
6.8
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Food
7.1
Overall
7.5
Boarding
7.7
Crew
8.3
Entertainment
6.8
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Food
7.1
Overall
7.5
Boarding
7.7
Crew
8.3
Entertainment
6.8
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Food
7.1
Overall
7.5
Boarding
7.7
Crew
8.3
Entertainment
6.8
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Food
7.1
Overall
7.5
Boarding
7.7
Crew
8.3
Entertainment
6.8
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
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
See prices for flight routes from nearby airports that may be better suited for you.
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 July 3, 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 2,558,603 searches. Data last updated July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$710 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$596 | Average$932 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$683 | Average$1,080 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$778 | Average$1,332 | FlexibilityNo cancel fee | On-time76% |