$322+ Cheap flights from Chicago (CHI) to Sicily
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CTA
Nov 8 — Nov 151
Round-trip
1 adult, Economy
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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 October 9, 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 October 9, 2026.
This Gotogate deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 10/198:10 pm -
1 stop29h 10m
Tue 11/37:10 pm -
1 stop22h 50m
Deal found 10/5![Turkish Airlines logo]()
$680
This Turkish Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/289:15 pm -
1 stop29h 20m
Fri 12/119:35 am -
1 stop31h 25m
Deal found 10/6![Turkish Airlines logo]()
$696
This FlightHub deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/249:15 pm -
1 stop14h 30m
Wed 10/286:45 pm -
1 stop22h 15m
Deal found 10/5![Turkish Airlines logo]()
$708
This oojo deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/249:15 pm -
1 stop29h 20m
Wed 10/289:35 am -
1 stop31h 25m
Deal found 10/5![Turkish Airlines logo]()
$737
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 11/95:55 am -
2 stops23h 25m
Tue 11/242:20 pm -
1 stop14h 58m
Deal found 10/5![United Airlines logo]()
$744
This Turkish Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/289:15 pm -
1 stop29h 20m
Sun 11/16:45 pm -
1 stop23h 15m
Deal found 10/8![Turkish Airlines logo]()
$756
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/107:45 pm -
2 stops33h 35m
Tue 11/242:20 pm -
1 stop14h 58m
Deal found 10/8![United Airlines logo]()
$758
This Booking.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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.
Fri 11/136:30 pm -
2 stops18h 25m
Tue 11/2411:50 am -
2 stops34h 40m
Deal found 10/6![Multiple Airlines logo]()
$784
This Turkish Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 11/148:15 pm -
1 stop14h 30m
Wed 11/186:45 pm -
1 stop30h 35m
Deal found 10/6![Turkish Airlines logo]()
$786
This Booking.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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.
Thu 11/126:30 pm -
2 stops19h 50m
Tue 11/2411:50 am -
2 stops34h 40m
Deal found 10/6![Multiple Airlines logo]()
$790
This United deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:39 am -
1 stop19h 41m
Thu 12/109:45 am -
1 stop13h 30m
Deal found 10/6![Multiple Airlines logo]()
$797
This Gotogate deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/288:45 am -
2 stops20h 35m
Fri 12/1112:15 pm -
1 stop13h 10m
Deal found 10/4![Multiple Airlines logo]()
$798
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 October 9, 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 October 9, 2026.
This Turkish Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/289:15 pm -
1 stop29h 20m
Fri 12/119:35 am -
1 stop31h 25m
Deal found 10/4![Turkish Airlines logo]()
$696
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 11/95:29 pm -
1 stop11h 51m
Tue 11/242:20 pm -
1 stop14h 58m
Deal found 10/5![United Airlines logo]()
$744
This Gotogate deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/288:45 am -
2 stops20h 35m
Fri 12/1112:15 pm -
1 stop13h 10m
Deal found 10/4![Multiple Airlines logo]()
$798
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/1210:30 am -
1 stop15h 40m
Sun 12/2011:10 am -
1 stop17h 29m
Deal found 10/8![Delta logo]()
$1,106
This KLM deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop20h 10m
Sat 12/1910:55 am -
1 stop17h 44m
Deal found 10/8![KLM logo]()
$1,106
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/107:45 pm -
2 stops33h 35m
Tue 11/242:20 pm -
2 stops26h 25m
Deal found 10/8![United Airlines logo]()
$758
This Booking.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Thu 3/1812:45 pm -
1 stop23h 25m
Sat 3/279:35 am -
1 stop30h 00m
Deal found 10/4![Turkish Airlines logo]()
$759
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:30 pm -
1 stop11h 50m
Thu 12/102:20 pm -
1 stop15h 07m
Deal found 10/4![United Airlines logo]()
$804
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 3/189:15 pm -
1 stop14h 55m
Sat 3/278:25 pm -
2 stops31h 00m
Deal found 10/4![Multiple Airlines logo]()
$983
This Turkish Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/168:15 pm -
1 stop14h 55m
Thu 11/197:10 pm -
1 stop21h 50m
Deal found 10/8![Turkish Airlines logo]()
$1,030
This Iberia deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/123:42 pm -
2 stops22h 28m
Sun 12/209:55 pm -
2 stops24h 00m
Deal found 10/8![Multiple Airlines logo]()
$1,041
Last-minute flights from Chicago to SicilyDiscover last-minute flight deals from Chicago to Sicily. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sicily. Data last updated October 9, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 10/198:10 pm -
1 stop29h 10m
Tue 11/37:10 pm -
1 stop22h 50m
Deal found 10/5![Turkish Airlines logo]()
$680
This FlightHub deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/249:15 pm -
1 stop14h 30m
Wed 10/286:45 pm -
1 stop22h 15m
Deal found 10/5![Turkish Airlines logo]()
$708
This oojo deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/249:15 pm -
1 stop29h 20m
Wed 10/289:35 am -
1 stop31h 25m
Deal found 10/5![Turkish Airlines logo]()
$737
This Turkish Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/289:15 pm -
1 stop29h 20m
Fri 12/119:35 am -
1 stop31h 25m
Deal found 10/6![Turkish Airlines logo]()
$696
This Turkish Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/289:15 pm -
1 stop29h 20m
Sun 11/16:45 pm -
1 stop23h 15m
Deal found 10/8![Turkish Airlines logo]()
$756
This United deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:39 am -
1 stop19h 41m
Thu 12/109:45 am -
1 stop13h 30m
Deal found 10/6![Multiple Airlines logo]()
$797
This Gotogate deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/288:45 am -
2 stops20h 35m
Fri 12/1112:15 pm -
1 stop13h 10m
Deal found 10/4![Multiple Airlines logo]()
$798
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 11/95:55 am -
2 stops23h 25m
Tue 11/242:20 pm -
1 stop14h 58m
Deal found 10/5![United Airlines logo]()
$744
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/107:45 pm -
2 stops33h 35m
Tue 11/242:20 pm -
1 stop14h 58m
Deal found 10/8![United Airlines logo]()
$758
This Booking.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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.
Thu 11/126:30 pm -
2 stops19h 50m
Tue 11/2411:50 am -
2 stops34h 40m
Deal found 10/6![Multiple Airlines logo]()
$790
This Booking.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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.
Fri 11/136:30 pm -
2 stops18h 25m
Tue 11/2411:50 am -
2 stops34h 40m
Deal found 10/6![Multiple Airlines logo]()
$784
This Turkish Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 11/148:15 pm -
1 stop14h 30m
Wed 11/186:45 pm -
1 stop30h 35m
Deal found 10/6![Turkish Airlines logo]()
$786
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 October 9, 2026.
Search for one-way flight options from Chicago to Sicily. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/208:30 am -
3 stops41h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/208:30 am -
3 stops39h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/148:30 am -
3 stops43h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/76:30 pm -
3 stops17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/96:30 pm -
3 stops20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/76:30 pm -
3 stops19h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/106:30 pm -
3 stops20h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/106:30 pm -
3 stops20h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 2/286:30 pm -
3 stops20h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 1/96:30 pm -
3 stops19h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$368
This Trip.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Wed 11/256:30 pm -
2 stops18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$373
This Trip.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 11/136:30 pm -
2 stops21h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$376
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 October 9, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $680 (Gotogate) |
One-way from | $322 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $1,182 |
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 October 9, 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
Tue 4/6
9:40 pm-9:10 am
2 stops28h 30m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$399
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Wed 3/17
10:05 am-10:50 am
3 stops18h 45m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$423
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Tue 10/20
8:10 pm-9:05 am
2 stops29h 55m
Palermo Punta Raisi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$436
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Thu 3/18
10:05 am-12:20 am
2 stops32h 15m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$437
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Sun 10/18
10:25 pm-10:45 am
3 stops29h 20m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$441
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Tue 1/5
9:50 pm-11:50 am
1 stop31h 00m
Palermo Punta Raisi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$472
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Mon 10/19
9:40 pm-11:55 pm
3 stops19h 15m
Palermo Punta Raisi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$494
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Wed 10/14
4:55 pm-12:05 am
1 stop24h 10m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$511
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Fri 10/16
6:00 pm-1:00 am
3 stops24h 00m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$516
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Thu 3/18
8:45 pm-12:00 pm
2 stops57h 15m
Palermo Punta Raisi
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$518
Showing 1-10 of 30 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
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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
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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 far ahead should I book a flight from Chicago to Sicily?
Booking 60 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 October 9, 2026.
Read through reviews of airlines operating flights from Chicago to Sicily, such as SWISS,Turkish Airlines, andITA Airways. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.2
Food
7.1
Overall
7.5
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Oct 2026
BOS - ZRH
Crew
8.2
Food
7.1
Overall
7.5
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Oct 2026
BOS - ZRH
Crew
8.2
Food
7.1
Overall
7.5
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Oct 2026
BOS - ZRH
Crew
8.2
Food
7.1
Overall
7.5
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Oct 2026
BOS - ZRH
Crew
8.2
Food
7.1
Overall
7.5
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Oct 2026
BOS - 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
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 October 9, 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 October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$554 | Average$714 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$596 | Average$1,011 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$736 | Average$1,046 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$868 | Average$1,359 | FlexibilityNo cancel fee | On-time76% |