$303+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Mar 2 — Mar 91
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 January 31, 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 January 31, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:05 pm
ORD
- PMO
1 stop12h 00m
SWISS
Thu 8/279:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Deal found 1/30![SWISS logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:20 pm
ORD
- PMO
1 stop11h 40m
SWISS
Thu 8/279:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Deal found 1/28![SWISS logo]()
$491
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:50 pm
ORD
- PMO
1 stop16h 35m
SWISS
Mon 3/27:15 pm
PMO
- ORD
1 stop28h 05m
SWISS
Deal found 1/30![SWISS logo]()
$496
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:50 pm
ORD
- PMO
1 stop16h 35m
SWISS
Tue 3/33:20 pm
PMO
- ORD
1 stop32h 00m
SWISS
Deal found 1/30![SWISS logo]()
$508
This KAYAK deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:20 pm
ORD
- PMO
1 stop11h 40m
SWISS
Mon 8/249:45 am
PMO
- ORD
1 stop33h 50m
SWISS
Deal found 1/28![SWISS logo]()
$509
This Justfly.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Sat 5/97:35 pm
PMO
- ORD
1 stop29h 40m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$521
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
- PMO
1 stop11h 40m
SWISS
Tue 8/259:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Deal found 1/30![SWISS logo]()
$524
This Justfly.com deal was found by Cheapflights users on 1/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:10 pm
ORD
- CTA
1 stop15h 15m
Turkish Airlines
Sun 5/37:25 pm
CTA
- ORD
1 stop21h 15m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$524
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:00 am
ORD
- PMO
2 stops18h 05m
Multiple Airlines
Mon 3/27:15 pm
PMO
- ORD
1 stop28h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:20 pm
ORD
- PMO
1 stop11h 40m
SWISS
Wed 8/269:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Deal found 1/28![SWISS logo]()
$530
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/48:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Wed 2/116:45 pm
PMO
- ORD
1 stop22h 20m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$532
This FlightHub deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Wed 3/186:45 pm
PMO
- ORD
1 stop22h 20m
Turkish Airlines
Deal found 1/31![Turkish Airlines logo]()
$533
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 January 31, 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 January 31, 2026.
This Justfly.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/311:25 am
ORD
- CTA
1 stop14h 00m
Turkish Airlines
Fri 5/87:25 pm
CTA
- ORD
1 stop21h 15m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$524
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:00 am
ORD
- PMO
2 stops18h 05m
Multiple Airlines
Mon 3/27:15 pm
PMO
- ORD
1 stop28h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$525
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:50 am
ORD
- CTA
2 stops20h 05m
ITA Airways
Sun 3/293:25 pm
CTA
- ORD
2 stops36h 10m
ITA Airways
Deal found 1/30![ITA Airways logo]()
$677
This KLM deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:45 pm
MDW
- PMO
2 stops18h 45m
KLM
Mon 3/26:10 am
PMO
- MDW
2 stops23h 21m
KLM
Deal found 1/30![KLM logo]()
$738
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:25 pm
ORD
- SUF
2 stops16h 05m
Icelandair
Tue 6/1611:15 am
SUF
- ORD
2 stops17h 10m
Icelandair
Deal found 1/30![Icelandair logo]()
$924
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/210:30 pm
ORD
- SUF
2 stops29h 20m
Lufthansa
Sat 4/1811:40 am
SUF
- ORD
1 stop13h 35m
Lufthansa
Deal found 1/30![Lufthansa logo]()
$931
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:40 pm
ORD
- SUF
1 stop11h 50m
United Airlines
Wed 4/226:15 am
SUF
- ORD
1 stop13h 50m
United Airlines
Deal found 1/28![United Airlines logo]()
$998
This Justfly.com deal was found by Cheapflights users on 1/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:25 am
ORD
- CTA
1 stop14h 00m
Turkish Airlines
Sun 5/37:25 pm
CTA
- ORD
1 stop29h 50m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$533
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:10 pm
ORD
- PMO
2 stops19h 20m
Multiple Airlines
Sat 5/97:35 pm
PMO
- ORD
1 stop29h 40m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$558
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Sat 5/97:35 pm
PMO
- ORD
1 stop21h 05m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$534
This Turkish Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:50 am
ORD
- PMO
2 stops19h 40m
Multiple Airlines
Fri 2/209:30 am
PMO
- ORD
1 stop31h 35m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$579
This oojo deal was found by Cheapflights users on 1/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Wed 3/186:45 pm
PMO
- ORD
1 stop30h 40m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
MDW
- CTA
2 stops18h 55m
Delta
Sun 5/39:55 am
CTA
- MDW
2 stops19h 33m
Delta
Deal found 1/30![Delta logo]()
$1,364
This FlightHub deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:50 am
ORD
- PMO
2 stops19h 40m
Multiple Airlines
Tue 3/33:15 pm
PMO
- ORD
2 stops25h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$596
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:25 am
ORD
- PMO
1 stop24h 10m
Turkish Airlines
Fri 5/159:25 am
PMO
- ORD
1 stop31h 15m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$569
This Ovago deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:00 pm
MDW
- PMO
2 stops17h 40m
Air Europa
Tue 7/284:10 pm
PMO
- MDW
2 stops31h 17m
Air Europa
Deal found 1/30![Air Europa logo]()
$1,539
This FlightHub deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:25 am
ORD
- PMO
2 stops23h 55m
Multiple Airlines
Wed 5/64:10 pm
PMO
- ORD
2 stops24h 30m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$596
This oojo deal was found by Cheapflights users on 1/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:20 am
ORD
- CTA
2 stops19h 35m
ITA Airways
Mon 4/69:30 pm
CTA
- ORD
2 stops27h 53m
ITA Airways
Deal found 1/29![ITA Airways logo]()
$827
This Turkish Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Sun 3/86:45 pm
PMO
- ORD
1 stop30h 40m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$582
This KLM deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:47 pm
MDW
- PMO
2 stops16h 53m
KLM
Wed 3/186:10 am
PMO
- MDW
2 stops22h 21m
KLM
Deal found 1/28![KLM logo]()
$875
This Turkish Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:20 pm
ORD
- CTA
1 stop15h 05m
Turkish Airlines
Sun 3/87:25 pm
CTA
- ORD
1 stop30h 00m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$583
This oojo deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:25 pm
ORD
- SUF
2 stops16h 05m
Multiple Airlines
Wed 4/2211:15 am
SUF
- ORD
2 stops38h 00m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$679
This oojo deal was found by Cheapflights users on 1/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:45 am
ORD
- SUF
2 stops18h 45m
ITA Airways
Sat 5/96:15 am
SUF
- ORD
1 stop13h 55m
ITA Airways
Deal found 1/29![ITA Airways logo]()
$983
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:50 pm
ORD
- CTA
2 stops20h 50m
Multiple Airlines
Fri 3/66:05 am
CTA
- ORD
2 stops19h 20m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$681
This oojo deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:25 am
ORD
- CTA
1 stop14h 00m
Turkish Airlines
Sat 5/99:25 am
CTA
- ORD
1 stop31h 15m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$738
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/211:25 am
ORD
- SUF
2 stops24h 05m
Multiple Airlines
Sat 4/187:15 pm
SUF
- ORD
2 stops30h 00m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$767
This KLM deal was found by Cheapflights users on 1/29. 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 5/1910:35 am
MDW
- PMO
2 stops17h 55m
KLM
Wed 5/276:10 am
PMO
- MDW
2 stops19h 21m
KLM
Deal found 1/29![KLM logo]()
$1,307
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:50 pm
ORD
- CTA
1 stop13h 45m
Turkish Airlines
Sun 3/297:25 pm
CTA
- ORD
1 stop21h 15m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$758
This Mytrip deal was found by Cheapflights users on 1/29. 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.
Sun 3/159:20 pm
ORD
- CTA
3 stops31h 35m
Multiple Airlines
Sun 3/228:35 am
CTA
- ORD
2 stops32h 30m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$774
This FlightHub deal was found by Cheapflights users on 1/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/218:40 pm
ORD
- CTA
3 stops41h 10m
Multiple Airlines
Sun 3/299:50 am
CTA
- ORD
1 stop34h 30m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$779
Last-minute flights from Chicago to SicilyDiscover last-minute flight deals from Chicago to Sicily. Data last updated January 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sicily. Data last updated January 31, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/111:50 am
ORD
- CTA
1 stop13h 45m
Turkish Airlines
Sat 2/149:35 am
CTA
- ORD
1 stop15h 50m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$554
This FlightHub deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:50 am
ORD
- CTA
1 stop23h 35m
Turkish Airlines
Sat 2/79:35 am
CTA
- ORD
1 stop31h 30m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$535
This Ovago deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:50 am
ORD
- CTA
1 stop23h 35m
Turkish Airlines
Sun 2/87:25 pm
CTA
- ORD
1 stop21h 40m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$558
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/48:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Wed 2/116:45 pm
PMO
- ORD
1 stop22h 20m
Turkish Airlines
Deal found 1/28![Turkish Airlines logo]()
$532
This oojo deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/411:50 am
ORD
- PMO
2 stops23h 35m
Multiple Airlines
Wed 2/116:45 pm
PMO
- ORD
1 stop22h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$558
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:50 am
ORD
- PMO
1 stop22h 55m
Turkish Airlines
Fri 2/209:30 am
PMO
- ORD
1 stop31h 35m
Turkish Airlines
Deal found 1/30![Turkish Airlines logo]()
$534
This Turkish Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:50 am
ORD
- PMO
2 stops19h 40m
Multiple Airlines
Fri 2/209:30 am
PMO
- ORD
1 stop31h 35m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$579
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:50 pm
ORD
- PMO
1 stop16h 35m
SWISS
Mon 3/27:15 pm
PMO
- ORD
1 stop28h 05m
SWISS
Deal found 1/30![SWISS logo]()
$496
This oojo deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:50 pm
ORD
- PMO
1 stop16h 35m
SWISS
Tue 3/33:20 pm
PMO
- ORD
1 stop32h 00m
SWISS
Deal found 1/30![SWISS logo]()
$508
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:00 am
ORD
- PMO
2 stops18h 05m
Multiple Airlines
Mon 3/27:15 pm
PMO
- ORD
1 stop28h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$525
This Cheapflightsfares deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:05 pm
ORD
- PMO
1 stop12h 20m
Lufthansa
Fri 3/612:10 pm
PMO
- ORD
1 stop13h 15m
Lufthansa
Deal found 1/28![Lufthansa logo]()
$559
This KAYAK deal was found by Cheapflights users on 1/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:20 pm
ORD
- PMO
1 stop14h 25m
Multiple Airlines
Sat 3/73:15 pm
PMO
- ORD
2 stops25h 50m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$566
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 January 31, 2026.
Search for one-way flight options from Chicago to Sicily. Find affordable one-way fares based on user searches. Data last updated January 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:30 pm
ORD
- CTA
2 stops31h 20m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Thu 3/1212:05 pm
ORD
- SUF
3 stops52h 05m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/158:25 pm
ORD
- PMO
2 stops29h 35m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Thu 3/127:30 am
MDW
- SUF
3 stops53h 30m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:15 am
MDW
- PMO
3 stops32h 20m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/153:45 pm
ORD
- PMO
3 stops25h 25m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/153:45 pm
ORD
- CTA
2 stops15h 45m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$449
This oojo deal was found by Cheapflights users on 1/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:20 am
ORD
- PMO
2 stops20h 20m
ITA Airways
Deal found 1/29![ITA Airways logo]()
$462
This Justfly.com deal was found by Cheapflights users on 1/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$468
This Justfly.com deal was found by Cheapflights users on 1/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:20 pm
ORD
- PMO
1 stop29h 10m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:50 pm
ORD
- PMO
1 stop16h 35m
SWISS
Deal found 1/30![SWISS logo]()
$495
This Justfly.com deal was found by Cheapflights users on 1/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:25 am
ORD
- CTA
1 stop14h 00m
Turkish Airlines
Deal found 1/29![Turkish Airlines logo]()
$496
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 January 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $496 (Kiwi.com) |
One-way from | $303 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $716 |
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 January 31, 2026.
Use the filters below to find and compare flights from Chicago to Sicily that are best for you.
Fly from
Chicago
Fly to
Sicily
Route
Depart
Return
Price
ChicagoCatania
ORD - CTA
ORDCTA
Chicago O'Hare Intl
Fri 4/3
11:25 am-8:25 am
1 stop14h 00m
Catania Fontanarossa
Fri 5/8
7:25 pm-9:40 am
1 stop21h 15m
$524
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 2/25
10:00 am-11:05 am
2 stops18h 05m
Palermo Punta Raisi
Mon 3/2
7:15 pm-4:20 pm
1 stop28h 05m
$525
ChicagoCatania
ORD - CTA
ORDCTA
Chicago O'Hare Intl
Fri 4/24
11:25 am-8:25 am
1 stop14h 00m
Catania Fontanarossa
Sun 5/3
7:25 pm-6:15 pm
1 stop29h 50m
$533
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Mon 4/27
8:10 pm-6:35 pm
1 stop15h 25m
Palermo Punta Raisi
Sat 5/9
7:35 pm-9:40 am
1 stop21h 05m
$534
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 3/11
9:20 pm-8:30 am
1 stop29h 10m
Palermo Punta Raisi
Wed 3/18
6:45 pm-7:25 pm
1 stop30h 40m
$534
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Mon 4/27
8:10 pm-10:30 pm
2 stops19h 20m
Palermo Punta Raisi
Sat 5/9
7:35 pm-6:15 pm
1 stop29h 40m
$558
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Mon 5/4
11:25 am-6:35 pm
1 stop24h 10m
Palermo Punta Raisi
Fri 5/15
9:25 am-9:40 am
1 stop31h 15m
$569
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Sat 2/14
11:50 am-2:30 pm
2 stops19h 40m
Palermo Punta Raisi
Fri 2/20
9:30 am-10:05 am
1 stop31h 35m
$579
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 3/4
8:20 pm-8:30 am
1 stop29h 10m
Palermo Punta Raisi
Sun 3/8
6:45 pm-7:25 pm
1 stop30h 40m
$582
ChicagoCatania
ORD - CTA
ORDCTA
Chicago O'Hare Intl
Wed 3/4
8:20 pm-6:25 pm
1 stop15h 05m
Catania Fontanarossa
Sun 3/8
7:25 pm-7:25 pm
1 stop30h 00m
$583
Showing 1-10 of 49 results
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
MDW-PMO
ORD-SUF
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-CTA
ORD-PMO
MDW-PMO
ORD-SUF
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 $332). Flying from Chicago to Sicily in June is currently the most expensive (average of $1,049). 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?
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 January 31, 2026.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS, Turkish Airlines, and Lufthansa. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Crew
8.3
Overall
7.6
Comfort
7.4
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodMadhukar,Nov 2024
ZRH - BOM
Entertainment
6.8
Crew
8.3
Overall
7.6
Comfort
7.4
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodMadhukar,Nov 2024
ZRH - BOM
Entertainment
6.8
Crew
8.3
Overall
7.6
Comfort
7.4
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodMadhukar,Nov 2024
ZRH - BOM
Entertainment
6.8
Crew
8.3
Overall
7.6
Comfort
7.4
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodMadhukar,Nov 2024
ZRH - BOM
Entertainment
6.8
Crew
8.3
Overall
7.6
Comfort
7.4
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodMadhukar,Nov 2024
ZRH - BOM
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Sicily
See prices for flight routes from nearby airports that may be better suited for you.
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 January 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$755 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$658 | Average$1,273 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$753 | Average$1,093 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$776 | Average$1,220 | FlexibilityNo cancel fee | On-time76% |