$362+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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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 November 10, 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 November 10, 2026.
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Thu 12/2410:30 pm -
2 stops25h 50m
Thu 12/316:30 pm -
2 stops19h 35m
Deal found 11/9![Multiple Airlines logo]()
$541
This oojo deal was found by Cheapflights users on 11/5. 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.
Thu 12/108:05 pm -
1 stop27h 40m
Sun 1/317:10 pm -
1 stop17h 05m
Deal found 11/5![Scandinavian Airlines logo]()
$606
This oojo deal was found by Cheapflights users on 11/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:20 am -
1 stop12h 25m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/6![Scandinavian Airlines logo]()
$611
This Booking.com deal was found by Cheapflights users on 11/6. 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.
Wed 11/1811:15 am -
1 stop14h 05m
Fri 11/273:55 pm -
1 stop11h 40m
Deal found 11/6![Aer Lingus logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:25 am -
1 stop36h 55m
Sat 12/56:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$620
This Icelandair deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:25 am -
1 stop12h 55m
Fri 11/276:30 pm -
1 stop12h 30m
Deal found 11/7![Icelandair logo]()
$623
This Icelandair deal was found by Cheapflights users on 11/6. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:25 am -
1 stop12h 55m
Sat 12/56:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$626
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 12/128:05 pm -
1 stop27h 40m
Sat 3/137:10 pm -
1 stop30h 40m
Deal found 11/5![Scandinavian Airlines logo]()
$627
This oojo deal was found by Cheapflights users on 11/5. 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 11/218:05 pm -
1 stop27h 40m
Wed 11/257:10 pm -
1 stop17h 05m
Deal found 11/5![Scandinavian Airlines logo]()
$629
This Super.com deal was found by Cheapflights users on 11/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1611:25 am -
1 stop12h 55m
Thu 1/76:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$631
This Gotogate deal was found by Cheapflights users on 11/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:20 am -
1 stop12h 25m
Sat 11/287:10 pm -
1 stop30h 40m
Deal found 11/8![Scandinavian Airlines logo]()
$634
This lol.travel deal was found by Cheapflights users on 11/5. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:10 pm -
1 stop28h 20m
Wed 11/257:00 pm -
1 stop34h 30m
Deal found 11/5![TAP AIR PORTUGAL logo]()
$638
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 November 10, 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 November 10, 2026.
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Thu 12/2410:30 pm -
2 stops25h 50m
Thu 12/316:30 pm -
2 stops19h 35m
Deal found 11/9![Multiple Airlines logo]()
$541
This British Airways deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 5/57:50 pm -
2 stops27h 10m
Sun 5/95:34 pm -
2 stops19h 26m
Deal found 11/7![British Airways logo]()
$579
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/168:05 pm -
2 stops32h 47m
Mon 1/187:10 pm -
1 stop17h 05m
Deal found 11/5![Scandinavian Airlines logo]()
$637
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/411:25 am -
1 stop12h 55m
Wed 12/96:30 pm -
1 stop12h 30m
Deal found 11/10![Icelandair logo]()
$662
This Iberia deal was found by Cheapflights users on 11/5. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:00 am -
1 stop15h 55m
Fri 2/125:40 pm -
1 stop21h 50m
Deal found 11/5![Iberia logo]()
$663
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Fri 2/127:05 am -
1 stop15h 15m
Fri 2/193:40 pm -
Nonstop9h 05m
Deal found 11/9![United Airlines logo]()
$667
This Gotogate deal was found by Cheapflights users on 11/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/32:50 pm -
1 stop34h 30m
Sat 2/1311:45 am -
1 stop23h 40m
Deal found 11/8![Turkish Airlines logo]()
$673
This Air Serbia deal was found by Cheapflights users on 11/6. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:30 pm -
1 stop27h 20m
Sat 1/27:30 pm -
1 stop30h 30m
Deal found 11/6![Air Serbia logo]()
$676
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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.
Fri 12/41:10 pm -
2 stops16h 22m
Wed 12/96:40 pm -
1 stop13h 15m
Deal found 11/10![American Airlines logo]()
$687
This TAP AIR PORTUGAL deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2112:20 pm -
1 stop34h 10m
Fri 11/278:10 pm -
1 stop32h 25m
Deal found 11/9![TAP AIR PORTUGAL logo]()
$737
This Delta deal was found by Cheapflights users on 11/8. 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.
Fri 12/46:10 am -
2 stops17h 07m
Wed 12/92:41 pm -
2 stops13h 49m
Deal found 11/8![Delta logo]()
$756
This Expedia deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:10 am -
2 stops17h 07m
Tue 12/152:41 pm -
2 stops16h 44m
Deal found 11/10![Air France logo]()
$778
This Air Canada deal was found by Cheapflights users on 11/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/119:10 am -
2 stops16h 30m
Mon 2/157:05 am -
2 stops24h 35m
Deal found 11/5![Air Canada logo]()
$847
This Expedia deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:45 pm -
2 stops32h 04m
Sun 11/294:25 pm -
1 stop19h 25m
Deal found 11/7![KLM logo]()
$919
This British Airways deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop15h 55m
Thu 12/102:44 pm -
2 stops17h 51m
Deal found 11/7![Multiple Airlines logo]()
$648
This British Airways deal was found by Cheapflights users on 11/8. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:05 pm -
2 stops34h 54m
Tue 12/156:40 pm -
1 stop34h 10m
Deal found 11/8![British Airways logo]()
$658
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/147:05 am -
1 stop13h 05m
Sun 2/218:40 am -
2 stops16h 15m
Deal found 11/9![United Airlines logo]()
$668
This Turkish Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/7![Turkish Airlines logo]()
$687
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/248:05 pm -
1 stop27h 40m
Sun 2/287:10 pm -
1 stop17h 15m
Deal found 11/5![Scandinavian Airlines logo]()
$697
This Iberia deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/36:00 am -
2 stops23h 30m
Mon 12/75:40 pm -
1 stop13h 40m
Deal found 11/9![Iberia logo]()
$706
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop15h 55m
Mon 12/75:40 pm -
1 stop13h 40m
Deal found 11/9![Multiple Airlines logo]()
$658
This British Airways deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/1012:40 pm -
2 stops25h 46m
Tue 12/156:40 pm -
1 stop34h 10m
Deal found 11/9![British Airways logo]()
$658
This Air Serbia deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:50 pm -
1 stop27h 00m
Wed 1/611:55 pm -
1 stop25h 00m
Deal found 11/7![Air Serbia logo]()
$726
This United Airlines deal was found by Cheapflights users on 11/6. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/187:05 am -
1 stop15h 15m
Mon 3/224:40 pm -
Nonstop9h 05m
Deal found 11/6![United Airlines logo]()
$673
This American Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/1012:40 pm -
1 stop13h 45m
Tue 12/158:48 pm -
2 stops32h 02m
Deal found 11/9![American Airlines logo]()
$752
This Turkish Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/2410:55 am -
1 stop30h 05m
Wed 12/211:45 am -
1 stop15h 10m
Deal found 11/7![Turkish Airlines logo]()
$687
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:10 am -
2 stops20h 35m
Thu 12/178:04 am -
1 stop17h 11m
Deal found 11/9![Delta logo]()
$759
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/17:55 pm -
1 stop27h 15m
Mon 4/56:00 am -
2 stops22h 30m
Deal found 11/5![Scandinavian Airlines logo]()
$698
This British Airways deal was found by Cheapflights users on 11/8. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1410:00 am -
Nonstop10h 30m
Thu 5/277:25 pm -
1 stop21h 20m
Deal found 11/8![British Airways logo]()
$667
This United Airlines deal was found by Cheapflights users on 11/8. 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 4/136:45 am -
1 stop13h 10m
Mon 5/314:00 pm -
1 stop12h 55m
Deal found 11/8![United Airlines logo]()
$681
Last-minute flights from Italy to ChicagoDiscover last-minute flight deals from Italy to Chicago. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Italy to Chicago. Data last updated November 10, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 11/6. 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.
Wed 11/1811:15 am -
1 stop14h 05m
Fri 11/273:55 pm -
1 stop11h 40m
Deal found 11/6![Aer Lingus logo]()
$618
This lol.travel deal was found by Cheapflights users on 11/5. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:10 pm -
1 stop28h 20m
Wed 11/257:00 pm -
1 stop34h 30m
Deal found 11/5![TAP AIR PORTUGAL logo]()
$638
This Icelandair deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:25 am -
1 stop12h 55m
Fri 11/276:30 pm -
1 stop12h 30m
Deal found 11/7![Icelandair logo]()
$623
This oojo deal was found by Cheapflights users on 11/5. 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 11/218:05 pm -
1 stop27h 40m
Wed 11/257:10 pm -
1 stop17h 05m
Deal found 11/5![Scandinavian Airlines logo]()
$629
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:25 am -
1 stop36h 55m
Sat 12/56:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$620
This Icelandair deal was found by Cheapflights users on 11/6. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:25 am -
1 stop12h 55m
Sat 12/56:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$626
This Gotogate deal was found by Cheapflights users on 11/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:20 am -
1 stop12h 25m
Sat 11/287:10 pm -
1 stop30h 40m
Deal found 11/8![Scandinavian Airlines logo]()
$634
This oojo deal was found by Cheapflights users on 11/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:20 am -
1 stop12h 25m
Sun 1/317:10 pm -
2 stops16h 30m
Deal found 11/6![Scandinavian Airlines logo]()
$611
This oojo deal was found by Cheapflights users on 11/5. 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.
Thu 12/108:05 pm -
1 stop27h 40m
Sun 1/317:10 pm -
1 stop17h 05m
Deal found 11/5![Scandinavian Airlines logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 12/128:05 pm -
1 stop27h 40m
Sat 3/137:10 pm -
1 stop30h 40m
Deal found 11/5![Scandinavian Airlines logo]()
$627
This Super.com deal was found by Cheapflights users on 11/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1611:25 am -
1 stop12h 55m
Thu 1/76:30 pm -
1 stop12h 30m
Deal found 11/6![Icelandair logo]()
$631
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Thu 12/2410:30 pm -
2 stops25h 50m
Thu 12/316:30 pm -
2 stops19h 35m
Deal found 11/9![Multiple Airlines logo]()
$541
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 November 10, 2026.
Search for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:05 am -
2 stops37h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 1/98:05 pm -
2 stops28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/99:20 am -
2 stops39h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$368
This Justfly.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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.
Sat 4/34:20 pm -
1 stop32h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Icelandair logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/119:50 pm -
2 stops26h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$372
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/319:20 am -
2 stops15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/309:20 am -
2 stops39h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/2210:35 pm -
3 stops49h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 1/179:40 pm -
3 stops50h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 2/256:10 am -
2 stops20h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/278:05 pm -
2 stops28h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 3/46:10 am -
2 stops19h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$385
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $541 (Mytrip) |
One-way from | $362 (Kiwi.com) |
Popular in | July |
Cheapest in | November |
Average price | $648 |
Good round-trip deal | $845 or less |
Good one-way deal | $611 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 November 10, 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
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Thu 1/21
11:05 am-5:20 pm
2 stops37h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$362
MilanChicago
MXP Milan Malpensa - ORD Chicago O'Hare Intl
MXPORD
Milan Malpensa
Sat 3/27
8:05 pm-6:15 pm
2 stops28h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$384
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Sat 4/17
11:55 am-6:59 pm
1 stop14h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$407
VeniceChicago
VCE Venice Marco Polo - ORD Chicago O'Hare Intl
VCEORD
Venice Marco Polo
Fri 12/11
9:20 pm-3:30 pm
2 stops49h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$407
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Wed 5/5
6:45 am-9:00 pm
2 stops21h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$410
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Wed 5/5
7:40 am-1:50 pm
1 stop13h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$410
BolognaChicago
BLQ Bologna Guglielmo Marconi - ORD Chicago O'Hare Intl
BLQORD
Bologna Guglielmo Marconi
Fri 1/15
5:05 pm-7:15 pm
2 stops33h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$411
BolognaChicago
BLQ Bologna Guglielmo Marconi - ORD Chicago O'Hare Intl
BLQORD
Bologna Guglielmo Marconi
Thu 1/14
3:50 pm-3:30 pm
2 stops30h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$413
PalermoChicago
PMO Palermo Punta Raisi - ORD Chicago O'Hare Intl
PMOORD
Palermo Punta Raisi
Sun 4/4
12:05 pm-1:50 pm
1 stop32h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$419
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Tue 4/13
10:00 am-1:30 pm
Nonstop10h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$420
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.
PMO-ORD
MXP-ORD
FCO-ORD
NAP-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
PMO-ORD
MXP-ORD
FCO-ORD
NAP-ORD
What is the cheapest month to book a flight from Italy to Chicago?
Currently, May is the cheapest month in which you can book a flight from Italy to Chicago (average of $743). Flying from Italy to Chicago in July is currently the most expensive (average of $932). 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 November 10, 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.
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 71 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 November 10, 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.
Overall
7.4
Food
7.5
Comfort
7.3
Boarding
7.3
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
Overall
7.4
Food
7.5
Comfort
7.3
Boarding
7.3
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
Overall
7.4
Food
7.5
Comfort
7.3
Boarding
7.3
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
Overall
7.4
Food
7.5
Comfort
7.3
Boarding
7.3
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
Overall
7.4
Food
7.5
Comfort
7.3
Boarding
7.3
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Italy to Chicago
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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 November 10, 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 November 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$620 | Average$647 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$667 | Average$853 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$690 | Average$1,003 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$753 | Average$833 | FlexibilityNo cancel fee | On-time81% |