$376+ Cheap flights from Italy to Chicago (CHI)
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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Oct 27 — Nov 31
Round-trip
1 adult, Economy
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Find cheap flights from Italy to Chicago with Cheapflights
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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 Italy to ChicagoExplore the most affordable flight options available from Italy to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 27, 2026.
Explore the most affordable flight options available from Italy to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 27, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop13h 55m
Wed 10/143:00 pm -
2 stops14h 30m
Deal found 9/22![United Airlines logo]()
$534
This Gotogate deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/43:55 pm -
1 stop12h 30m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/26![Icelandair logo]()
$552
This lol.travel deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:30 pm -
1 stop28h 40m
Wed 10/143:00 pm -
1 stop16h 45m
Deal found 9/27![ITA Airways logo]()
$559
This Gotogate deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/83:30 pm -
1 stop28h 40m
Wed 10/143:00 pm -
1 stop12h 20m
Deal found 9/27![ITA Airways logo]()
$578
This lol.travel deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Thu 10/85:25 pm -
Nonstop9h 35m
Deal found 9/24![Finnair logo]()
$582
This lol.travel deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:15 pm -
1 stop28h 55m
Fri 10/233:00 pm -
1 stop16h 30m
Deal found 9/25![ITA Airways logo]()
$582
This lol.travel deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Sun 10/115:25 pm -
Nonstop9h 35m
Deal found 9/24![Finnair logo]()
$583
This lol.travel deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Wed 10/75:25 pm -
Nonstop9h 35m
Deal found 9/23![Finnair logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:55 pm -
1 stop33h 20m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/24![Icelandair logo]()
$593
This lol.travel deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Thu 10/85:25 pm -
Nonstop9h 35m
Deal found 9/25![Iberia logo]()
$596
This Justfly.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1411:40 am -
1 stop14h 35m
Wed 10/213:45 pm -
1 stop11h 55m
Deal found 9/23![Aer Lingus logo]()
$601
This Gotogate deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Tue 10/133:55 pm -
1 stop33h 20m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/25![Icelandair logo]()
$610
Best flights from Italy to ChicagoDiscover carefully curated flight deals from Italy to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
Discover carefully curated flight deals from Italy to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
This British Airways deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:00 pm -
Nonstop10h 50m
Sun 10/187:05 pm -
1 stop19h 55m
Deal found 9/25![British Airways logo]()
$627
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:00 pm -
Nonstop10h 50m
Sun 10/185:25 pm -
Nonstop9h 35m
Deal found 9/24![American Airlines logo]()
$633
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Wed 10/146:05 am -
2 stops22h 38m
Wed 10/2110:30 am -
1 stop14h 40m
Deal found 9/23![Delta logo]()
$664
This Iberia deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Thu 11/1212:25 pm -
2 stops27h 34m
Tue 11/172:38 pm -
2 stops21h 42m
Deal found 9/24![Multiple Airlines logo]()
$670
This Scandinavian Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Fri 12/251:00 pm -
2 stops34h 45m
Tue 1/57:10 pm -
2 stops34h 00m
Deal found 9/24![Scandinavian Airlines logo]()
$672
This Expedia deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Mon 10/1210:05 pm -
1 stop23h 10m
Sun 10/181:55 pm -
2 stops16h 50m
Deal found 9/23![KLM logo]()
$673
This Turkish Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Sun 11/222:50 pm -
1 stop26h 10m
Sun 11/298:15 pm -
1 stop15h 10m
Deal found 9/24![Turkish Airlines logo]()
$684
This ITA Airways deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:40 pm -
1 stop24h 30m
Sun 10/183:00 pm -
2 stops19h 35m
Deal found 9/24![ITA Airways logo]()
$687
This SWISS deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/169:30 am -
1 stop13h 25m
Sun 10/257:50 pm -
1 stop12h 25m
Deal found 9/26![SWISS logo]()
$690
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop13h 55m
Fri 10/166:55 am -
2 stops19h 45m
Deal found 9/27![United Airlines logo]()
$691
This Lufthansa deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:30 pm -
1 stop13h 35m
Thu 11/263:40 pm -
Nonstop9h 05m
Deal found 9/24![Lufthansa logo]()
$697
This Flysmarter deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:10 am -
3 stops18h 38m
Sat 1/301:58 pm -
2 stops22h 57m
Deal found 9/26![Air Canada logo]()
$704
This Austrian Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:55 am -
1 stop35h 25m
Wed 10/285:20 pm -
1 stop14h 55m
Deal found 9/27![Austrian Airlines logo]()
$708
This British Airways deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:00 pm -
Nonstop10h 50m
Wed 10/213:37 pm -
1 stop14h 23m
Deal found 9/26![British Airways logo]()
$634
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:35 am -
2 stops16h 55m
Mon 10/125:29 pm -
2 stops13h 56m
Deal found 9/23![Delta logo]()
$668
This Scandinavian Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Wed 10/148:00 pm -
1 stop27h 10m
Fri 1/87:10 pm -
2 stops16h 50m
Deal found 9/23![Scandinavian Airlines logo]()
$677
This British Airways deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:50 am -
1 stop15h 20m
Wed 12/26:49 pm -
2 stops16h 06m
Deal found 9/26![Multiple Airlines logo]()
$684
This KLM deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/158:55 pm -
1 stop24h 30m
Sun 1/243:00 pm -
2 stops16h 30m
Deal found 9/24![KLM logo]()
$687
This Turkish Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Tue 11/247:25 pm -
1 stop29h 55m
Wed 12/28:15 pm -
1 stop30h 40m
Deal found 9/23![Turkish Airlines logo]()
$687
This SWISS deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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.
Thu 11/269:10 am -
1 stop14h 05m
Thu 1/284:10 pm -
1 stop12h 50m
Deal found 9/26![SWISS logo]()
$690
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/287:00 am -
1 stop13h 10m
Mon 12/286:10 pm -
2 stops17h 25m
Deal found 9/25![United Airlines logo]()
$697
This Lufthansa deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/169:55 am -
1 stop17h 10m
Tue 1/129:50 pm -
1 stop31h 00m
Deal found 9/24![Lufthansa logo]()
$710
This British Airways deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:50 pm -
2 stops32h 26m
Tue 11/246:30 pm -
1 stop34h 20m
Deal found 9/27![British Airways logo]()
$646
This Austrian Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:00 am -
1 stop13h 20m
Thu 10/154:20 pm -
1 stop19h 50m
Deal found 9/25![Austrian Airlines logo]()
$723
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 2/186:10 am -
2 stops19h 00m
Mon 3/225:45 pm -
2 stops15h 15m
Deal found 9/25![Delta logo]()
$687
This SWISS deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Mon 10/128:40 pm -
1 stop26h 15m
Sun 10/182:20 pm -
1 stop22h 35m
Deal found 9/23![SWISS logo]()
$694
This British Airways deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:20 am -
1 stop15h 45m
Thu 11/191:14 pm -
1 stop11h 51m
Deal found 9/24![Multiple Airlines logo]()
$699
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/2310:45 am -
1 stop16h 20m
Mon 1/44:10 pm -
1 stop14h 50m
Deal found 9/25![United Airlines logo]()
$701
This KLM deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 1/176:30 am -
2 stops19h 39m
Sun 1/243:00 pm -
2 stops16h 30m
Deal found 9/24![KLM logo]()
$703
This Scandinavian Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Tue 10/2712:55 pm -
2 stops34h 50m
Tue 11/37:10 pm -
2 stops33h 55m
Deal found 9/27![Scandinavian Airlines logo]()
$709
Last-minute flights from Italy to ChicagoDiscover last-minute flight deals from Italy to Chicago. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from Italy to Chicago. Data last updated September 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:55 pm -
1 stop33h 20m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/24![Icelandair logo]()
$593
This lol.travel deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Thu 10/85:25 pm -
Nonstop9h 35m
Deal found 9/24![Finnair logo]()
$582
This lol.travel deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Sun 10/115:25 pm -
Nonstop9h 35m
Deal found 9/24![Finnair logo]()
$583
This lol.travel deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Wed 10/75:25 pm -
Nonstop9h 35m
Deal found 9/23![Finnair logo]()
$585
This lol.travel deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
Nonstop10h 55m
Thu 10/85:25 pm -
Nonstop9h 35m
Deal found 9/25![Iberia logo]()
$596
This Gotogate deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/43:55 pm -
1 stop12h 30m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/26![Icelandair logo]()
$552
This lol.travel deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:30 pm -
1 stop28h 40m
Wed 10/143:00 pm -
1 stop16h 45m
Deal found 9/27![ITA Airways logo]()
$559
This Gotogate deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/83:30 pm -
1 stop28h 40m
Wed 10/143:00 pm -
1 stop12h 20m
Deal found 9/27![ITA Airways logo]()
$578
This lol.travel deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:15 pm -
1 stop28h 55m
Fri 10/233:00 pm -
1 stop16h 30m
Deal found 9/25![ITA Airways logo]()
$582
This Gotogate deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Tue 10/133:55 pm -
1 stop33h 20m
Sat 10/177:25 pm -
1 stop12h 20m
Deal found 9/25![Icelandair logo]()
$610
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop13h 55m
Wed 10/143:00 pm -
2 stops14h 30m
Deal found 9/22![United Airlines logo]()
$534
This Justfly.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1411:40 am -
1 stop14h 35m
Wed 10/213:45 pm -
1 stop11h 55m
Deal found 9/23![Aer Lingus logo]()
$601
One-way flights from Italy to ChicagoSearch for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
Search for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/249:15 pm -
2 stops27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/236:15 pm -
2 stops30h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 2/86:35 pm -
2 stops29h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 1/178:50 am -
2 stops37h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 1/1610:30 pm -
2 stops25h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/201:10 pm -
3 stops35h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 1/113:05 pm -
2 stops30h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/241:45 pm -
3 stops34h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/244:20 pm -
2 stops30h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 1/912:20 pm -
3 stops36h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:30 pm -
2 stops55h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/236:10 pm -
3 stops54h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$403
Find flight deals from Italy to Chicago
Keep the following information in mind while searching for Italy to Chicago flight deals. Data was last updated September 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $534 (United Airlines) |
One-way from | $376 (Kiwi.com) |
Popular in | July |
Cheapest in | April |
Average price | $682 |
Good round-trip deal | $725 or less |
Good one-way deal | $727 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Italy to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 27, 2026.
Use the filters below to find and compare flights from Italy to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Sun 1/17
8:50 am-2:55 pm
2 stops37h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$387
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Sat 1/16
10:30 pm-5:20 pm
2 stops25h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$388
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Mon 1/11
3:05 pm-2:55 pm
2 stops30h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$391
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Tue 11/24
4:20 pm-3:30 pm
2 stops30h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$395
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Wed 2/3
8:00 pm-2:55 pm
3 stops25h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$405
CataniaChicago
CTA Catania Fontanarossa - ORD Chicago O'Hare Intl
CTAORD
Catania Fontanarossa
Tue 2/9
4:30 pm-2:55 pm
2 stops29h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$412
VeniceChicago
VCE Venice Marco Polo - ORD Chicago O'Hare Intl
VCEORD
Venice Marco Polo
Mon 11/2
8:20 pm-3:30 pm
2 stops50h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$412
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Sun 11/22
12:15 pm-6:45 pm
1 stop13h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$452
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Thu 11/5
8:35 pm-2:45 pm
1 stop25h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$453
VeniceChicago
VCE Venice Marco Polo - ORD Chicago O'Hare Intl
VCEORD
Venice Marco Polo
Fri 10/16
8:30 pm-9:15 pm
1 stop31h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$474
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Italy to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Italy with our price prediction graph.
NAP-ORD
VCE-ORD
FLR-ORD
BLQ-ORD
CTA-ORD
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 Italy to Chicago
IT0-CHI
NAP-ORD
VCE-ORD
FLR-ORD
BLQ-ORD
What is the cheapest month to book a flight from Italy to Chicago?
Currently, November is the cheapest month in which you can book a flight from Italy to Chicago (average of $720). Flying from Italy to Chicago in July is currently the most expensive (average of $923). 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.
What is the cheapest time of day to fly from IT to CHI?
Find hourly flight availability from Italy to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 27, 2026.
When flying from Italy to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Italy to Chicago
Explore weekly flight availability from Italy to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 27, 2026.
The most flights from IT0 to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How often are flights from Italy to Chicago delayed?
About 16% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 190 minutes.
What is the most punctual flight time for Italy to Chicago flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Italy to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
How far ahead should I book a flight from Italy to Chicago?
The price you pay for your flight from Italy to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 27, 2026.
Read reviews from past customers who have flown Turkish Airlines,United Airlines, andITA Airways from Italy to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
7.3
Crew
7.8
Boarding
7.3
Food
7.5
Overall
7.4
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Entertainment
7.5
Comfort
7.3
Crew
7.8
Boarding
7.3
Food
7.5
Overall
7.4
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Entertainment
7.5
Comfort
7.3
Crew
7.8
Boarding
7.3
Food
7.5
Overall
7.4
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Entertainment
7.5
Comfort
7.3
Crew
7.8
Boarding
7.3
Food
7.5
Overall
7.4
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Entertainment
7.5
Comfort
7.3
Crew
7.8
Boarding
7.3
Food
7.5
Overall
7.4
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Related info for your journey
Find useful and relevant information for your journey from Italy to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
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Alternative routes for Italy to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 27, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Italy to Chicago by cabin class
Find flights from Italy to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Italy and Chicago flights
Browse other Italy and Chicago flight options. Last updated on September 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Italy to Chicago flights
Consider these flights traveling from Italy to Chicago.
Top 4 airlines flying from Italy to Chicago
Discover the top 4 airlines that operate flights from Italy to Chicago. 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 September 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$609 | Average$647 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$667 | Average$893 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$690 | Average$1,003 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$753 | Average$833 | FlexibilityNo cancel fee | On-time81% |