$279+ Cheap flights from Chicago (CHI) to Italy
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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Italy with Cheapflights
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Cheapest flights from Chicago to ItalyExplore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
This lol.travel deal was found by Cheapflights users on 8/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 pm -
1 stop34h 40m
Thu 10/17:15 pm -
1 stop27h 45m
Deal found 8/10![TAP AIR PORTUGAL logo]()
$610
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 pm -
1 stop17h 20m
Thu 10/157:15 pm -
1 stop27h 45m
Deal found 8/5![TAP AIR PORTUGAL logo]()
$623
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 pm -
1 stop12h 20m
Fri 9/43:55 pm -
1 stop12h 30m
Deal found 8/9![Icelandair logo]()
$636
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.
Wed 12/26:30 pm -
1 stop16h 15m
Sat 12/127:30 am -
1 stop16h 50m
Deal found 8/6![Multiple Airlines logo]()
$638
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm -
1 stop24h 40m
Wed 8/263:05 pm -
1 stop29h 05m
Deal found 8/6![ITA Airways logo]()
$638
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 pm -
1 stop12h 20m
Tue 9/13:55 pm -
1 stop12h 30m
Deal found 8/6![Icelandair logo]()
$639
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:05 pm -
1 stop17h 15m
Wed 10/2112:30 pm -
1 stop31h 10m
Deal found 8/9![TAP AIR PORTUGAL logo]()
$640
This Air Serbia deal was found by Cheapflights users on 8/10. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:30 pm -
1 stop32h 05m
Fri 12/188:30 pm -
1 stop27h 20m
Deal found 8/10![Air Serbia logo]()
$641
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sun 12/136:30 pm -
1 stop14h 10m
Thu 12/178:00 am -
1 stop16h 20m
Deal found 8/10![Multiple Airlines logo]()
$643
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.
Sun 11/16:30 pm -
1 stop14h 10m
Mon 11/96:10 am -
1 stop18h 10m
Deal found 8/9![Multiple Airlines logo]()
$648
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.
Sun 8/93:00 pm -
1 stop24h 40m
Tue 8/257:35 pm -
1 stop24h 35m
Deal found 8/7![ITA Airways logo]()
$648
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.
Wed 10/710:25 pm -
2 stops15h 15m
Wed 10/1411:55 pm -
2 stops25h 20m
Deal found 8/7![Multiple Airlines logo]()
$649
Best flights from Chicago to ItalyDiscover carefully curated flight deals from Chicago to Italy that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from Chicago to Italy that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:10 pm -
1 stop15h 30m
Tue 10/207:40 pm -
1 stop21h 00m
Deal found 8/5![Turkish Airlines logo]()
$697
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:40 pm -
Nonstop9h 05m
Wed 2/249:45 am -
Nonstop10h 25m
Deal found 8/9![United Airlines logo]()
$713
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/134:26 pm -
2 stops17h 04m
Tue 12/226:00 am -
2 stops20h 51m
Deal found 8/8![Multiple Airlines logo]()
$740
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.
Sun 11/810:59 am -
1 stop17h 21m
Sun 11/1510:00 am -
1 stop15h 04m
Deal found 8/6![Delta logo]()
$778
This TAP AIR PORTUGAL 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 pm -
1 stop23h 15m
Thu 10/85:55 am -
1 stop13h 45m
Deal found 8/8![TAP AIR PORTUGAL logo]()
$793
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 10/217:15 pm -
1 stop16h 55m
Sun 10/2511:20 am -
1 stop12h 25m
Deal found 8/8![Scandinavian Airlines logo]()
$797
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/201:05 pm -
2 stops13h 55m
Wed 1/276:30 am -
2 stops16h 55m
Deal found 8/6![KLM logo]()
$808
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.
Thu 8/203:00 pm -
1 stop16h 25m
Mon 9/77:05 pm -
1 stop25h 05m
Deal found 8/7![ITA Airways logo]()
$934
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:30 pm -
Nonstop9h 30m
Thu 9/103:00 pm -
Nonstop10h 55m
Deal found 8/6![Finnair logo]()
$1,008
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:50 pm -
1 stop13h 10m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 8/8![British Airways logo]()
$1,155
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:10 pm -
1 stop20h 25m
Wed 10/2110:50 am -
1 stop29h 50m
Deal found 8/8![Turkish Airlines logo]()
$700
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 11/83:40 pm -
Nonstop9h 05m
Sun 11/157:05 am -
1 stop15h 15m
Deal found 8/6![United Airlines logo]()
$761
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:25 am -
1 stop29h 10m
Thu 10/158:05 pm -
1 stop20h 35m
Deal found 8/7![Turkish Airlines logo]()
$710
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 12/11:22 pm -
2 stops15h 23m
Tue 12/81:05 pm -
1 stop16h 51m
Deal found 8/6![Delta logo]()
$796
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:10 pm -
1 stop11h 35m
Sat 12/512:25 pm -
2 stops25h 50m
Deal found 8/8![Multiple Airlines logo]()
$806
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:25 am -
2 stops19h 40m
Thu 9/179:40 am -
1 stop13h 30m
Deal found 8/9![Scandinavian Airlines logo]()
$827
This KLM deal was found by Cheapflights users on 8/10. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/171:22 pm -
2 stops13h 38m
Tue 12/16:30 am -
2 stops16h 44m
Deal found 8/10![KLM logo]()
$828
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/113:40 pm -
Nonstop9h 05m
Thu 12/177:05 am -
1 stop13h 05m
Deal found 8/5![United Airlines logo]()
$761
This Turkish Airlines deal was found by Cheapflights users on 8/10. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:25 am -
1 stop14h 00m
Fri 10/169:25 am -
1 stop31h 15m
Deal found 8/10![Turkish Airlines logo]()
$722
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.
Mon 10/261:27 pm -
2 stops15h 28m
Wed 11/412:00 pm -
2 stops17h 33m
Deal found 8/7![Delta logo]()
$816
This TAP AIR PORTUGAL 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 pm -
1 stop23h 40m
Sat 9/265:55 pm -
1 stop29h 05m
Deal found 8/6![TAP AIR PORTUGAL logo]()
$909
This Scandinavian Airlines deal was found by Cheapflights users on 8/10. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:25 am -
2 stops20h 40m
Tue 10/207:45 pm -
1 stop27h 25m
Deal found 8/10![Scandinavian Airlines logo]()
$849
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.
Thu 8/203:00 pm -
1 stop25h 05m
Tue 9/86:10 am -
1 stop14h 00m
Deal found 8/7![ITA Airways logo]()
$934
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:40 pm -
1 stop12h 00m
Wed 8/263:20 pm -
Nonstop9h 50m
Deal found 8/9![United Airlines logo]()
$784
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/251:20 pm -
2 stops15h 10m
Sat 5/1512:20 pm -
2 stops17h 27m
Deal found 8/6![Multiple Airlines logo]()
$870
This Turkish Airlines 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:45 pm -
1 stop14h 15m
Mon 11/96:55 pm -
1 stop30h 25m
Deal found 8/5![Turkish Airlines logo]()
$739
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.
Sun 10/44:15 pm -
1 stop12h 45m
Sat 10/176:40 am -
1 stop14h 35m
Deal found 8/7![KLM logo]()
$903
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:30 am -
1 stop20h 25m
Wed 9/211:05 am -
1 stop16h 50m
Deal found 8/5![Delta logo]()
$854
This ITA Airways 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:00 pm -
1 stop11h 40m
Sat 10/35:00 pm -
1 stop27h 10m
Deal found 8/9![ITA Airways logo]()
$950
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:35 pm -
Nonstop8h 40m
Sat 12/59:45 am -
1 stop13h 52m
Deal found 8/7![United Airlines logo]()
$787
Last-minute flights from Chicago to ItalyDiscover last-minute flight deals from Chicago to Italy. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Italy. Data last updated August 10, 2026 and is based on user searches.
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.
Sun 8/93:00 pm -
1 stop24h 40m
Tue 8/257:35 pm -
1 stop24h 35m
Deal found 8/7![ITA Airways logo]()
$648
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm -
1 stop24h 40m
Wed 8/263:05 pm -
1 stop29h 05m
Deal found 8/6![ITA Airways logo]()
$638
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.
Sun 8/163:00 pm -
1 stop20h 10m
Tue 9/17:00 am -
1 stop13h 10m
Deal found 8/6![ITA Airways logo]()
$671
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 pm -
1 stop12h 20m
Fri 9/43:55 pm -
1 stop12h 30m
Deal found 8/9![Icelandair logo]()
$636
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:25 pm -
1 stop12h 20m
Tue 9/13:55 pm -
1 stop12h 30m
Deal found 8/6![Icelandair logo]()
$639
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.
Sat 9/197:25 pm -
1 stop12h 20m
Sun 10/43:55 pm -
1 stop33h 20m
Deal found 8/5![Icelandair logo]()
$665
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.
Sun 9/208:10 pm -
1 stop14h 35m
Wed 9/307:45 pm -
1 stop20h 55m
Deal found 8/6![Turkish Airlines logo]()
$670
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.
Mon 9/217:25 pm -
1 stop12h 20m
Sun 10/43:55 pm -
1 stop33h 20m
Deal found 8/6![Icelandair logo]()
$667
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:10 pm -
1 stop20h 40m
Wed 9/307:45 pm -
1 stop20h 55m
Deal found 8/9![Turkish Airlines logo]()
$673
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:10 pm -
1 stop16h 40m
Wed 9/308:50 pm -
1 stop19h 50m
Deal found 8/9![Turkish Airlines logo]()
$673
This lol.travel deal was found by Cheapflights users on 8/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 pm -
1 stop34h 40m
Thu 10/17:15 pm -
1 stop27h 45m
Deal found 8/10![TAP AIR PORTUGAL logo]()
$610
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:25 pm -
1 stop12h 45m
Tue 10/64:20 pm -
1 stop32h 55m
Deal found 8/8![Icelandair logo]()
$672
One-way flights from Chicago to ItalySearch for one-way flight options from Chicago to Italy. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from Chicago to Italy. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:30 pm -
1 stop12h 30m
Deal found 8/7![Icelandair logo]()
$279
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:30 pm -
1 stop12h 30m
Deal found 8/7![Icelandair logo]()
$281
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:25 pm -
1 stop12h 00m
Deal found 8/5![Icelandair logo]()
$284
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:25 pm -
1 stop33h 10m
Deal found 8/7![Icelandair logo]()
$285
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:50 pm -
2 stops39h 40m
Deal found 8/9![Multiple Airlines logo]()
$286
This FlightHub deal was found by Cheapflights users on 8/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:25 pm -
1 stop12h 20m
Deal found 8/10![Icelandair logo]()
$286
This BusinessClass 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:45 pm -
2 stops55h 50m
Deal found 8/8![British Airways logo]()
$291
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 pm -
1 stop12h 30m
Deal found 8/6![Icelandair logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sat 8/227:25 pm -
1 stop12h 20m
Deal found 8/10![Icelandair logo]()
$296
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:25 pm -
2 stops16h 45m
Deal found 8/9![Multiple Airlines logo]()
$300
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 10/187:25 pm -
3 stops19h 00m
Deal found 8/5![Multiple Airlines logo]()
$301
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 10/1810:25 pm -
2 stops17h 00m
Deal found 8/5![Multiple Airlines logo]()
$301
Find flight deals from Chicago to Italy
Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated August 10, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $623 (oojo) |
One-way from | $279 (oojo) |
Popular in | June |
Cheapest in | January |
Average price | $759 |
Good round-trip deal | $785 or less |
Good one-way deal | $422 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Italy 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 10, 2026.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Mon 9/21
8:10 pm-6:40 pm
1 stop15h 30m
Palermo Punta Raisi
Tue 10/20
7:40 pm-9:40 am
1 stop21h 00m
$697
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Wed 10/7
8:10 pm-11:35 pm
1 stop20h 25m
Rome Fiumicino
Wed 10/21
10:50 am-9:40 am
1 stop29h 50m
$700
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Wed 10/7
11:25 am-11:35 pm
1 stop29h 10m
Rome Fiumicino
Thu 10/15
8:05 pm-9:40 am
1 stop20h 35m
$710
Quickest round-trip
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Wed 12/2
3:40 pm-7:45 am
Nonstop9h 05m
Rome Fiumicino
Wed 2/24
9:45 am-1:10 pm
Nonstop10h 25m
$713
ChicagoPalermo
ORD Chicago O'Hare Intl - PMO Palermo Punta Raisi
ORDPMO
Chicago O'Hare Intl
Wed 10/7
11:25 am-8:25 am
1 stop14h 00m
Palermo Punta Raisi
Fri 10/16
9:25 am-9:40 am
1 stop31h 15m
$722
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Thu 11/5
12:45 pm-10:00 am
1 stop14h 15m
Milan Malpensa
Mon 11/9
6:55 pm-6:20 pm
1 stop30h 25m
$739
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Sun 12/13
4:26 pm-4:30 pm
2 stops17h 04m
Naples
Tue 12/22
6:00 am-7:51 pm
2 stops20h 51m
$740
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Sun 11/8
3:40 pm-7:45 am
Nonstop9h 05m
Rome Fiumicino
Sun 11/15
7:05 am-3:20 pm
1 stop15h 15m
$761
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Fri 12/11
3:40 pm-7:45 am
Nonstop9h 05m
Rome Fiumicino
Thu 12/17
7:05 am-1:10 pm
1 stop13h 05m
$761
ChicagoRome
MDW Chicago Midway - FCO Rome Fiumicino
MDWFCO
Chicago Midway
Sun 11/8
10:59 am-11:20 am
1 stop17h 21m
Rome Fiumicino
Sun 11/15
10:00 am-6:04 pm
1 stop15h 04m
$778
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Italy
Have a flexible travel schedule? Discover the best time to fly to Italy from Chicago with our price prediction graph.
ORD-NAP
ORD-VCE
ORD-MXP
ORD-FCO
ORD-FLR
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Italy
CHI-IT0
ORD-NAP
ORD-VCE
ORD-MXP
ORD-FCO
What is the cheapest month to book a flight from Chicago to Italy?
Currently, February is the cheapest month in which you can book a flight from Chicago to Italy (average of $601). Flying from Chicago to Italy in June is currently the most expensive (average of $1,056). 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 CHI to IT?
Find hourly flight availability from Chicago to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 10, 2026.
When flying from Chicago to Italy, 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 Chicago to Italy
Explore weekly flight availability from Chicago to Italy. 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 10, 2026.
The most flights from CHI to IT0 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 Chicago to Italy delayed?
About 31% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 161 minutes.
What is the most punctual flight time for Chicago to Italy 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?
Saturday 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 Chicago to Italy flights?
Over the last year, ITA Airways have had the lowest number of delays on this route, with just 27% of flights being delayed.
How far ahead should I book a flight from Chicago to Italy?
The best time to book flights from Chicago to Italy is 6 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Italy
Get insights into the airlines that provide service to Italy. 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 Italy. Reviews last updated August 10, 2026.
Peruse reviews from past customers who have flown with Turkish Airlines,Scandinavian Airlines, andUnited Airlines from Chicago to Italy to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Overall
7.4
Comfort
7.3
Food
7.5
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Related info for your journey
Find useful and relevant information for your journey from Chicago to Italy. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Italy
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Italy by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Italy by cabin class
Find flights from Chicago to Italy, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Italy flights
Browse other Chicago and Italy flight options. Last updated on August 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Italy flights
Consider these flights traveling from Chicago to Italy.
Fly to Italy regions
Consider these flights traveling to Italy regions.
Top 10 airlines flying from Chicago to Italy
Discover the top 10 airlines that operate flights from Chicago to Italy. 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$337 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$369 | Average$681 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$384 | Average$914 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$395 | Average$699 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$420 | Average$666 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$455 | Average$861 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$493 | Average$1,125 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$496 | Average$1,034 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$502 | Average$900 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$504 | Average$1,043 | FlexibilityNo cancel fee | On-time77% |