$345+ Cheap flights from Italy to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Sep 8 — Sep 151
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 August 9, 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 August 9, 2026.
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:55 pm -
1 stop12h 30m
Fri 10/1610:25 pm -
1 stop33h 20m
Deal found 8/7![Icelandair logo]()
$525
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Fri 9/43:55 pm -
1 stop12h 30m
Mon 9/147:25 pm -
1 stop12h 20m
Deal found 8/9![Icelandair logo]()
$539
This Gotogate deal was found by Cheapflights users on 8/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:55 pm -
1 stop12h 30m
Sun 9/1310:25 pm -
1 stop33h 20m
Deal found 8/6![Icelandair logo]()
$541
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:55 pm -
1 stop33h 20m
Mon 9/287:25 pm -
1 stop12h 20m
Deal found 8/5![Icelandair logo]()
$543
This lol.travel deal was found by Cheapflights users on 8/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 pm -
1 stop27h 45m
Wed 10/216:00 pm -
1 stop34h 40m
Deal found 8/8![TAP AIR PORTUGAL logo]()
$572
This lol.travel deal was found by Cheapflights users on 8/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop13h 55m
Tue 9/223:00 pm -
1 stop16h 30m
Deal found 8/4![ITA Airways logo]()
$581
This lol.travel deal was found by Cheapflights users on 8/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:35 am -
1 stop13h 35m
Sun 9/203:00 pm -
1 stop12h 35m
Deal found 8/7![ITA Airways logo]()
$594
This lol.travel deal was found by Cheapflights users on 8/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:40 pm -
1 stop24h 30m
Thu 9/173:00 pm -
1 stop16h 20m
Deal found 8/6![ITA Airways logo]()
$595
This Gotogate deal was found by Cheapflights users on 8/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:55 pm -
1 stop33h 20m
Sun 9/1310:25 pm -
1 stop33h 20m
Deal found 8/6![Icelandair logo]()
$595
This ITA Airways deal was found by Cheapflights users on 8/4. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:10 pm -
1 stop25h 00m
Thu 9/243:00 pm -
1 stop24h 55m
Deal found 8/4![ITA Airways logo]()
$604
This lol.travel deal was found by Cheapflights users on 8/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:35 am -
1 stop14h 15m
Mon 9/75:30 pm -
Nonstop9h 30m
Deal found 8/4![Finnair logo]()
$615
This flugladen.de deal was found by Cheapflights users on 8/9. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:20 am -
1 stop32h 50m
Wed 9/303:00 pm -
1 stop12h 35m
Deal found 8/9![ITA Airways logo]()
$617
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 August 9, 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 August 9, 2026.
This ITA Airways deal was found by Cheapflights users on 8/4. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:40 pm -
1 stop24h 30m
Sun 9/63:00 pm -
1 stop16h 20m
Deal found 8/4![ITA Airways logo]()
$628
This Icelandair deal was found by Cheapflights users on 8/5. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:55 pm -
1 stop33h 20m
Sun 9/1310:25 pm -
1 stop33h 20m
Deal found 8/5![Icelandair logo]()
$649
This American Airlines deal was found by Cheapflights users on 8/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:00 pm -
Nonstop10h 45m
Thu 9/1710:25 pm -
1 stop13h 45m
Deal found 8/6![American Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:05 am -
1 stop16h 05m
Tue 9/2910:25 am -
2 stops18h 05m
Deal found 8/6![Delta logo]()
$675
This Scandinavian Airlines deal was found by Cheapflights users on 8/4. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:20 am -
1 stop13h 50m
Sat 10/247:15 pm -
1 stop18h 00m
Deal found 8/4![Scandinavian Airlines logo]()
$682
This British Airways deal was found by Cheapflights users on 8/4. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:40 am -
2 stops18h 40m
Tue 10/209:15 pm -
1 stop17h 45m
Deal found 8/4![British Airways logo]()
$685
This KLM deal was found by Cheapflights users on 8/7. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:00 am -
1 stop14h 00m
Fri 11/611:39 am -
1 stop13h 36m
Deal found 8/7![KLM logo]()
$697
This Condor deal was found by Cheapflights users on 8/4. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:10 am -
2 stops18h 16m
Tue 9/811:01 am -
2 stops15h 49m
Deal found 8/4![Multiple Airlines logo]()
$720
This Turkish Airlines deal was found by Cheapflights users on 8/4. 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.
Mon 9/142:00 pm -
1 stop26h 40m
Fri 9/258:10 pm -
1 stop29h 10m
Deal found 8/4![Turkish Airlines logo]()
$759
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 10/309:15 am -
1 stop13h 05m
Thu 11/59:35 pm -
Nonstop8h 40m
Deal found 8/4![United Airlines logo]()
$825
This ITA Airways deal was found by Cheapflights users on 8/7. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:10 pm -
1 stop25h 00m
Tue 9/13:00 pm -
1 stop24h 55m
Deal found 8/7![ITA Airways logo]()
$650
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:05 am -
1 stop16h 05m
Sat 9/266:00 pm -
2 stops17h 15m
Deal found 8/7![Delta logo]()
$676
This Icelandair deal was found by Cheapflights users on 8/6. 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 9/213:45 pm -
1 stop33h 30m
Wed 9/3010:25 pm -
1 stop33h 10m
Deal found 8/6![Icelandair logo]()
$703
This ITA Airways deal was found by Cheapflights users on 8/7. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:40 pm -
1 stop24h 30m
Tue 9/83:00 pm -
1 stop24h 45m
Deal found 8/7![ITA Airways logo]()
$664
This Scandinavian Airlines deal was found by Cheapflights users on 8/8. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:00 am -
1 stop12h 10m
Mon 9/147:15 pm -
1 stop31h 55m
Deal found 8/8![Scandinavian Airlines logo]()
$733
This Mytrip deal was found by Cheapflights users on 8/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
2 stops22h 25m
Tue 9/87:25 pm -
2 stops18h 45m
Deal found 8/6![Multiple Airlines logo]()
$739
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am -
2 stops18h 55m
Tue 10/2012:45 pm -
2 stops15h 45m
Deal found 8/6![Delta logo]()
$679
This KLM deal was found by Cheapflights users on 8/8. 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.
Thu 9/36:35 am -
2 stops16h 42m
Mon 9/74:50 pm -
1 stop15h 30m
Deal found 8/8![KLM logo]()
$766
This Scandinavian Airlines deal was found by Cheapflights users on 8/6. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:00 pm -
1 stop27h 10m
Sun 10/117:15 pm -
2 stops17h 35m
Deal found 8/6![Scandinavian Airlines logo]()
$735
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am -
2 stops18h 56m
Mon 9/71:19 pm -
2 stops18h 56m
Deal found 8/7![Delta logo]()
$681
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Wed 11/2511:20 am -
1 stop15h 45m
Sun 11/299:35 pm -
Nonstop8h 40m
Deal found 8/8![United Airlines logo]()
$828
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:45 am -
1 stop16h 30m
Sun 9/139:00 pm -
2 stops17h 00m
Deal found 8/7![Multiple Airlines logo]()
$773
This Icelandair deal was found by Cheapflights users on 8/6. 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.
Sun 9/204:20 pm -
1 stop12h 05m
Fri 9/2510:25 pm -
1 stop33h 45m
Deal found 8/6![Icelandair logo]()
$800
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:05 am -
2 stops19h 28m
Sat 9/269:59 am -
2 stops18h 31m
Deal found 8/7![Delta logo]()
$681
This United Airlines deal was found by Cheapflights users on 8/6. 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.
Sun 9/66:30 am -
1 stop15h 25m
Sun 9/139:00 am -
2 stops17h 05m
Deal found 8/6![United Airlines logo]()
$829
This ITA Airways deal was found by Cheapflights users on 8/4. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:20 am -
Nonstop10h 50m
Sat 9/53:00 pm -
Nonstop9h 25m
Deal found 8/4![ITA Airways logo]()
$755
This Scandinavian Airlines deal was found by Cheapflights users on 8/8. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:05 pm -
1 stop27h 40m
Sun 11/297:15 pm -
1 stop32h 15m
Deal found 8/8![Scandinavian Airlines logo]()
$771
This KLM deal was found by Cheapflights users on 8/7. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am -
2 stops17h 12m
Mon 9/75:10 pm -
1 stop18h 05m
Deal found 8/7![Multiple Airlines logo]()
$796
This Delta deal was found by Cheapflights users on 8/8. 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.
Wed 9/26:30 am -
1 stop15h 00m
Tue 9/85:10 pm -
2 stops16h 25m
Deal found 8/8![Delta logo]()
$682
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Sat 1/307:00 am -
1 stop13h 10m
Wed 2/106:50 pm -
1 stop12h 10m
Deal found 8/8![United Airlines logo]()
$829
Last-minute flights from Italy to ChicagoDiscover last-minute flight deals from Italy to Chicago. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Italy to Chicago. Data last updated August 9, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 8/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:55 pm -
1 stop12h 30m
Sun 9/1310:25 pm -
1 stop33h 20m
Deal found 8/6![Icelandair logo]()
$541
This lol.travel deal was found by Cheapflights users on 8/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:40 pm -
1 stop24h 30m
Thu 9/173:00 pm -
1 stop16h 20m
Deal found 8/6![ITA Airways logo]()
$595
This lol.travel deal was found by Cheapflights users on 8/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:35 am -
1 stop14h 15m
Mon 9/75:30 pm -
Nonstop9h 30m
Deal found 8/4![Finnair logo]()
$615
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Fri 9/43:55 pm -
1 stop12h 30m
Mon 9/147:25 pm -
1 stop12h 20m
Deal found 8/9![Icelandair logo]()
$539
This Gotogate deal was found by Cheapflights users on 8/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:55 pm -
1 stop33h 20m
Sun 9/1310:25 pm -
1 stop33h 20m
Deal found 8/6![Icelandair logo]()
$595
This lol.travel deal was found by Cheapflights users on 8/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:35 am -
1 stop13h 35m
Sun 9/203:00 pm -
1 stop12h 35m
Deal found 8/7![ITA Airways logo]()
$594
This ITA Airways deal was found by Cheapflights users on 8/4. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:10 pm -
1 stop25h 00m
Thu 9/243:00 pm -
1 stop24h 55m
Deal found 8/4![ITA Airways logo]()
$604
This lol.travel deal was found by Cheapflights users on 8/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop13h 55m
Tue 9/223:00 pm -
1 stop16h 30m
Deal found 8/4![ITA Airways logo]()
$581
This lol.travel deal was found by Cheapflights users on 8/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:35 am -
1 stop14h 15m
Sun 9/275:35 pm -
Nonstop9h 25m
Deal found 8/4![Finnair logo]()
$617
This Gotogate deal was found by Cheapflights users on 8/5. 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.
Thu 9/176:35 am -
1 stop13h 35m
Sat 9/263:00 pm -
1 stop16h 20m
Deal found 8/5![ITA Airways logo]()
$618
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:55 pm -
1 stop33h 20m
Mon 9/287:25 pm -
1 stop12h 20m
Deal found 8/5![Icelandair logo]()
$543
This oojo deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:20 am -
1 stop32h 50m
Tue 9/293:00 pm -
1 stop12h 35m
Deal found 8/3![ITA Airways logo]()
$619
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 August 9, 2026.
Search for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/256:10 am -
2 stops42h 40m
Deal found 8/5![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Tue 10/136:00 am -
3 stops42h 50m
Deal found 8/6![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/259:20 am -
3 stops39h 30m
Deal found 8/5![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Sat 10/106:50 pm -
3 stops30h 00m
Deal found 8/6![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sun 10/116:30 am -
3 stops42h 20m
Deal found 8/7![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 10/105:55 am -
3 stops42h 55m
Deal found 8/7![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
Fri 10/1611:00 pm -
3 stops49h 50m
Deal found 8/4![Multiple Airlines logo]()
$366
This Mytrip deal was found by Cheapflights users on 8/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:55 pm -
2 stops25h 20m
Deal found 8/4![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Sun 10/1810:15 pm -
3 stops50h 35m
Deal found 8/8![Multiple Airlines logo]()
$369
This Kissandfly.com deal was found by Cheapflights users on 8/4. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:15 pm -
1 stop22h 45m
Deal found 8/4![Aer Lingus logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/49:55 pm -
3 stops50h 55m
Deal found 8/5![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 10/173:20 pm -
3 stops57h 30m
Deal found 8/4![Multiple Airlines logo]()
$372
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 August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $525 (Mytrip) |
One-way from | $345 (Kiwi.com) |
Popular in | July |
Cheapest in | September |
Average price | $848 |
Good round-trip deal | $599 or less |
Good one-way deal | $600 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 2,558,603 searches. Data last updated August 9, 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
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Wed 9/2
7:40 pm-1:10 pm
1 stop24h 30m
Chicago O'Hare Intl
Sun 9/6
3:00 pm-2:20 pm
1 stop16h 20m
$628
VeniceChicago
VCE Venice Marco Polo - ORD Chicago O'Hare Intl
VCEORD
Venice Marco Polo
Sun 9/6
3:55 pm-6:15 pm
1 stop33h 20m
Chicago O'Hare Intl
Sun 9/13
10:25 pm-2:45 pm
1 stop33h 20m
$649
VeniceChicago
VCE Venice Marco Polo - ORD Chicago O'Hare Intl
VCEORD
Venice Marco Polo
Tue 8/25
7:10 pm-1:10 pm
1 stop25h 00m
Chicago O'Hare Intl
Tue 9/1
3:00 pm-10:55 pm
1 stop24h 55m
$650
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Fri 9/4
7:40 pm-1:10 pm
1 stop24h 30m
Chicago O'Hare Intl
Tue 9/8
3:00 pm-10:45 pm
1 stop24h 45m
$664
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Tue 9/1
3:00 pm-6:45 pm
Nonstop10h 45m
Chicago O'Hare Intl
Thu 9/17
10:25 pm-7:10 pm
1 stop13h 45m
$665
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Wed 9/23
6:05 am-3:10 pm
1 stop16h 05m
Chicago O'Hare Intl
Tue 9/29
10:25 am-11:30 am
2 stops18h 05m
$675
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Thu 9/17
6:05 am-3:10 pm
1 stop16h 05m
Chicago O'Hare Intl
Sat 9/26
6:00 pm-6:15 pm
2 stops17h 15m
$676
NaplesChicago
NAP Naples - MDW Chicago Midway
NAPMDW
Naples
Tue 10/6
6:05 am-6:00 pm
2 stops18h 55m
Chicago Midway
Tue 10/20
12:45 pm-11:30 am
2 stops15h 45m
$679
NaplesChicago
NAP Naples - MDW Chicago Midway
NAPMDW
Naples
Thu 9/3
6:05 am-6:01 pm
2 stops18h 56m
Chicago Midway
Mon 9/7
1:19 pm-3:15 pm
2 stops18h 56m
$681
NaplesChicago
NAP Naples - MDW Chicago Midway
NAPMDW
Naples
Thu 9/17
6:05 am-6:33 pm
2 stops19h 28m
Chicago Midway
Sat 9/26
9:59 am-11:30 am
2 stops18h 31m
$681
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.
VCE-ORD
NAP-ORD
MXP-ORD
FCO-MDW
FCO-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
VCE-ORD
NAP-ORD
MXP-ORD
FCO-MDW
What is the cheapest month to book a flight from Italy to Chicago?
Currently, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $683). Flying from Italy to Chicago in July is currently the most expensive (average of $912). 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 August 9, 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 August 9, 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 22% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 193 minutes.
What is the most punctual flight time for Italy to Chicago flights?
Historically, flights departing at night 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 Monday 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, Ethiopian Air have had the lowest number of delays on this route, with just 18% 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 65 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 August 9, 2026.
Read reviews from past customers who have flown Turkish Airlines,United Airlines, andLufthansa 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.
Boarding
7.3
Crew
7.8
Overall
7.4
Entertainment
7.5
Food
7.5
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Crew
7.8
Overall
7.4
Entertainment
7.5
Food
7.5
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Crew
7.8
Overall
7.4
Entertainment
7.5
Food
7.5
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Crew
7.8
Overall
7.4
Entertainment
7.5
Food
7.5
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Crew
7.8
Overall
7.4
Entertainment
7.5
Food
7.5
Comfort
7.3
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
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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 August 9, 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
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Italy and Chicago flights
Browse other Italy and Chicago flight options. Last updated on August 9, 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 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$571 | Average$1,103 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$585 | Average$894 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$609 | Average$689 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$699 | Average$833 | FlexibilityNo cancel fee | On-time81% |