$287+ Cheap flights from Chicago (CHI) to Italy
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VCE
Dec 12 — Dec 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Italy with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Italy
Cheapest
Best
Last-minute
One-way
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 November 12, 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 November 12, 2026.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Sat 12/1211:25 am -
1 stop12h 55m
Deal found 11/9![Icelandair logo]()
$564
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:30 pm -
1 stop12h 30m
Wed 12/1611:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$568
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:30 pm -
1 stop12h 30m
Wed 12/911:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$569
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Mon 12/711:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$570
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:30 pm -
1 stop12h 30m
Thu 1/2811:25 am -
1 stop12h 55m
Deal found 11/9![Icelandair logo]()
$574
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:30 pm -
1 stop12h 30m
Fri 12/1811:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$582
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.
Wed 12/26:30 pm -
1 stop12h 30m
Wed 12/911:25 am -
1 stop36h 55m
Deal found 11/10![Icelandair logo]()
$583
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Fri 12/1111:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$586
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.
Thu 12/106:30 pm -
1 stop12h 30m
Thu 2/2511:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$601
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:45 am -
2 stops15h 55m
Tue 12/155:50 pm -
1 stop26h 55m
Deal found 11/10![Multiple Airlines logo]()
$640
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:15 pm -
1 stop15h 20m
Tue 12/157:35 pm -
1 stop21h 25m
Deal found 11/9![Turkish Airlines logo]()
$648
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2911:45 am -
1 stop19h 05m
Tue 12/157:50 pm -
1 stop21h 10m
Deal found 11/9![Turkish Airlines logo]()
$667
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 November 12, 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 November 12, 2026.
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.
Fri 12/48:10 pm -
1 stop20h 55m
Tue 12/154:40 pm -
1 stop29h 50m
Deal found 11/9![TAP AIR PORTUGAL logo]()
$646
This British Airways deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 2/1011:45 am -
2 stops16h 50m
Wed 2/248:50 am -
1 stop16h 55m
Deal found 11/12![Multiple Airlines logo]()
$674
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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.
Tue 2/166:50 pm -
1 stop12h 25m
Tue 3/1610:45 am -
1 stop12h 30m
Deal found 11/11![SWISS logo]()
$687
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/68:05 pm -
1 stop30h 20m
Tue 4/137:20 pm -
1 stop29h 50m
Deal found 11/9![Turkish Airlines logo]()
$696
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.
Wed 2/179:10 am -
1 stop15h 45m
Tue 3/309:45 am -
Nonstop10h 20m
Deal found 11/8![United Airlines logo]()
$709
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/227:25 pm -
1 stop12h 30m
Tue 3/309:20 am -
1 stop11h 40m
Deal found 11/7![Delta logo]()
$737
This Booking.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 11/288:05 pm -
1 stop16h 50m
Thu 12/311:15 am -
1 stop14h 05m
Deal found 11/12![Aer Lingus logo]()
$750
This Air Canada 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/712:50 pm -
2 stops13h 45m
Thu 3/1110:15 am -
2 stops29h 53m
Deal found 11/7![Air Canada logo]()
$767
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/610:30 am -
2 stops25h 50m
Tue 4/138:05 pm -
1 stop27h 25m
Deal found 11/9![Scandinavian Airlines logo]()
$773
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:25 pm -
1 stop14h 25m
Tue 2/166:30 am -
2 stops19h 17m
Deal found 11/7![KLM logo]()
$815
This Expedia deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/124:55 pm -
2 stops21h 05m
Mon 4/199:45 pm -
2 stops23h 05m
Deal found 11/11![Iberia logo]()
$930
This KAYAK deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/611:45 am -
2 stops17h 15m
Sun 2/211:05 pm -
1 stop31h 40m
Deal found 11/12![British Airways logo]()
$985
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/129:50 pm -
1 stop15h 25m
Mon 6/1410:20 am -
2 stops33h 15m
Deal found 11/7![Lufthansa logo]()
$1,049
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:15 pm -
1 stop30h 40m
Wed 12/910:55 am -
1 stop38h 25m
Deal found 11/8![Turkish Airlines logo]()
$696
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/236:50 pm -
1 stop12h 25m
Fri 3/56:35 am -
2 stops15h 17m
Deal found 11/9![Multiple Airlines logo]()
$719
This United Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 11/293:40 pm -
Nonstop9h 05m
Tue 1/127:05 am -
1 stop15h 15m
Deal found 11/12![United Airlines logo]()
$720
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.
Sun 11/152:44 pm -
2 stops17h 16m
Tue 11/246:30 am -
2 stops19h 35m
Deal found 11/9![Delta logo]()
$743
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/511:20 am -
1 stop24h 05m
Thu 4/153:25 pm -
1 stop25h 10m
Deal found 11/9![Turkish Airlines logo]()
$700
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:40 pm -
Nonstop9h 05m
Mon 12/78:15 pm -
1 stop27h 00m
Deal found 11/10![Multiple Airlines logo]()
$719
This Scandinavian Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/247:10 pm -
1 stop30h 40m
Wed 1/138:05 pm -
1 stop27h 40m
Deal found 11/11![Scandinavian Airlines logo]()
$796
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.
Mon 12/77:00 am -
1 stop17h 55m
Sun 12/137:05 am -
2 stops15h 33m
Deal found 11/9![United Airlines logo]()
$732
This Turkish 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/138:05 pm -
1 stop16h 40m
Tue 5/49:00 am -
1 stop31h 35m
Deal found 11/10![Turkish Airlines logo]()
$700
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/216:35 pm -
1 stop17h 10m
Sun 5/23:55 pm -
1 stop31h 35m
Deal found 11/9![Scandinavian Airlines logo]()
$797
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.
Wed 12/303:56 pm -
2 stops14h 59m
Wed 1/136:30 am -
1 stop14h 55m
Deal found 11/8![Delta logo]()
$802
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.
Wed 2/174:29 pm -
1 stop12h 36m
Tue 2/239:45 am -
Nonstop10h 25m
Deal found 11/8![United Airlines logo]()
$733
This British Airways deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 1/2711:45 am -
2 stops16h 50m
Tue 2/28:30 pm -
1 stop25h 25m
Deal found 11/11![Multiple Airlines logo]()
$788
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/126:50 pm -
1 stop16h 20m
Mon 6/147:45 pm -
1 stop23h 50m
Deal found 11/7![SWISS logo]()
$964
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.
Tue 2/166:25 pm -
1 stop12h 30m
Thu 2/256:30 am -
1 stop14h 55m
Deal found 11/9![Delta logo]()
$802
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.
Sat 2/68:15 pm -
1 stop15h 20m
Wed 2/107:35 pm -
1 stop21h 25m
Deal found 11/7![Turkish Airlines logo]()
$732
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/127:10 pm -
2 stops16h 50m
Fri 3/1911:20 am -
1 stop12h 25m
Deal found 11/7![Scandinavian Airlines logo]()
$806
Last-minute flights from Chicago to ItalyDiscover last-minute flight deals from Chicago to Italy. Data last updated November 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Italy. Data last updated November 12, 2026 and is based on user searches.
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2911:45 am -
1 stop19h 05m
Tue 12/157:50 pm -
1 stop21h 10m
Deal found 11/9![Turkish Airlines logo]()
$667
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:15 pm -
1 stop15h 20m
Tue 12/157:35 pm -
1 stop21h 25m
Deal found 11/9![Turkish Airlines logo]()
$648
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Sat 12/1211:25 am -
1 stop12h 55m
Deal found 11/9![Icelandair logo]()
$564
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Mon 12/711:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$570
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.
Wed 12/26:30 pm -
1 stop12h 30m
Wed 12/911:25 am -
1 stop36h 55m
Deal found 11/10![Icelandair logo]()
$583
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:30 pm -
1 stop12h 30m
Fri 12/1111:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$586
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:30 pm -
1 stop12h 30m
Wed 12/911:25 am -
1 stop12h 55m
Deal found 11/8![Icelandair logo]()
$569
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:45 am -
2 stops15h 55m
Tue 12/155:50 pm -
1 stop26h 55m
Deal found 11/10![Multiple Airlines logo]()
$640
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:30 pm -
1 stop12h 30m
Fri 12/1811:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$582
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:30 pm -
1 stop12h 30m
Wed 12/1611:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$568
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.
Thu 12/106:30 pm -
1 stop12h 30m
Thu 2/2511:25 am -
1 stop12h 55m
Deal found 11/7![Icelandair logo]()
$601
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:30 pm -
1 stop12h 30m
Thu 1/2811:25 am -
1 stop12h 55m
Deal found 11/9![Icelandair logo]()
$574
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 November 12, 2026.
Search for one-way flight options from Chicago to Italy. Find affordable one-way fares based on user searches. Data last updated November 12, 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.
Wed 12/26:30 pm -
1 stop12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Icelandair logo]()
$287
This Gurufare 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/98:45 pm -
2 stops31h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![British Airways logo]()
$288
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:00 pm -
1 stop21h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![TAP AIR PORTUGAL logo]()
$290
This Booking.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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.
Sun 11/158:10 pm -
1 stop32h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![TAP AIR PORTUGAL logo]()
$290
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/126:30 pm -
1 stop12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Icelandair logo]()
$291
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:00 pm -
1 stop22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![TAP AIR PORTUGAL logo]()
$295
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.
Sun 1/106:30 pm -
2 stops14h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$296
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/137:00 pm -
1 stop33h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![TAP AIR PORTUGAL logo]()
$297
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:10 pm -
1 stop21h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![TAP AIR PORTUGAL logo]()
$302
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/37:00 pm -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![TAP AIR PORTUGAL logo]()
$304
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 2/76:30 pm -
3 stops19h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$308
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/16:30 pm -
2 stops21h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$309
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 November 12, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $564 (oojo) |
One-way from | $287 (Mytrip) |
Popular in | June |
Cheapest in | January |
Average price | $718 |
Good round-trip deal | $769 or less |
Good one-way deal | $518 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 7,457,451 searches. Data last updated November 12, 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
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Sat 3/20
3:45 pm-7:55 am
1 stop34h 10m
Rome Fiumicino
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$333
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 2/23
6:30 pm-4:40 pm
3 stops39h 10m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$336
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Tue 2/9
5:10 pm-4:55 pm
1 stop16h 45m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 3/16
10:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$346
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 3/16
1:35 pm-9:35 am
2 stops14h 00m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$351
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Sun 1/17
8:10 pm-5:00 pm
1 stop13h 50m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$363
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Sat 4/3
5:45 pm-7:05 pm
1 stop18h 20m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$366
ChicagoBari
ORD Chicago O'Hare Intl - BRI Bari Palese
ORDBRI
Chicago O'Hare Intl
Wed 4/21
10:25 pm-7:10 am
3 stops25h 45m
Bari Palese
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$367
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Mon 1/18
5:40 pm-10:45 pm
1 stop22h 05m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$379
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Wed 12/2
6:30 pm-1:45 pm
3 stops36h 15m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$381
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-FCO
ORD-NAP
ORD-VCE
ORD-LIN
ORD-BLQ
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-FCO
ORD-NAP
ORD-VCE
ORD-LIN
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 $654). Flying from Chicago to Italy in June is currently the most expensive (average of $1,085). 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 November 12, 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.
How often are flights from Chicago to Italy delayed?
About 30% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 160 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?
Friday tends to have the lowest number of delays on this route, whereas Wednesday 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 29% 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 18 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 November 12, 2026.
Peruse reviews from past customers who have flown with Scandinavian Airlines,Turkish 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
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
Boarding
7.7
Food
6.8
Entertainment
6.8
Crew
8.1
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
BOS - CPH
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Top regions
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 November 12, 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 7,457,451 searches. Data last updated November 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$612 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$362 | Average$710 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$420 | Average$706 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$433 | Average$715 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$455 | Average$912 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$504 | Average$1,046 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$514 | Average$992 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$522 | Average$1,192 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$549 | Average$1,099 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$554 | Average$935 | FlexibilityNo cancel fee | On-timeN/A |