$242+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Oct 23 — Oct 301
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 September 23, 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 September 23, 2026.
This Gotogate deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/27:15 pm -
1 stop17h 10m
Thu 11/198:05 pm -
1 stop27h 40m
Deal found 9/18![Scandinavian Airlines logo]()
$470
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/27:15 pm -
1 stop17h 10m
Wed 11/188:05 pm -
1 stop27h 40m
Deal found 9/20![Scandinavian Airlines logo]()
$471
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/137:15 pm -
1 stop32h 15m
Thu 11/2611:20 am -
1 stop12h 25m
Deal found 9/18![Scandinavian Airlines logo]()
$471
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 11/77:15 pm -
1 stop32h 15m
Fri 11/2011:20 am -
1 stop12h 25m
Deal found 9/20![Scandinavian Airlines logo]()
$480
This oojo deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:25 pm -
1 stop12h 20m
Tue 10/133:55 pm -
1 stop33h 20m
Deal found 9/20![Icelandair logo]()
$503
This FlightHub deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/1110:25 pm -
1 stop33h 20m
Fri 10/163:55 pm -
1 stop12h 30m
Deal found 9/19![Icelandair logo]()
$514
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 11/146:30 pm -
2 stops17h 40m
Sun 11/226:30 am -
2 stops17h 50m
Deal found 9/20![Multiple Airlines logo]()
$522
This British Airways deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/811:45 am -
2 stops16h 05m
Tue 11/2412:20 pm -
2 stops27h 19m
Deal found 9/22![Multiple Airlines logo]()
$542
This Mytrip deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/46:30 pm -
2 stops20h 20m
Sat 12/126:30 am -
2 stops17h 50m
Deal found 9/19![Multiple Airlines logo]()
$549
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 11/156:50 pm -
1 stop16h 40m
Tue 11/249:35 am -
1 stop13h 40m
Deal found 9/19![SWISS logo]()
$555
This deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/95:10 pm -
1 stop11h 30m
Fri 12/186:55 am -
1 stop13h 50m
Deal found 9/20![British Airways logo]()
$560
This deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Tue 12/89:50 pm -
1 stop12h 05m
Thu 12/1712:40 pm -
1 stop13h 05m
Deal found 9/20![British Airways logo]()
$561
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 September 23, 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 September 23, 2026.
This British Airways deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 2/211:45 am -
2 stops15h 55m
Tue 2/911:30 am -
2 stops19h 00m
Deal found 9/19![Multiple Airlines logo]()
$543
This British Airways deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/139:50 pm -
1 stop16h 30m
Mon 12/212:15 pm -
1 stop30h 30m
Deal found 9/21![British Airways logo]()
$578
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:45 pm -
1 stop34h 10m
Tue 12/19:45 am -
Nonstop10h 25m
Deal found 9/19![United Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/111:35 pm -
2 stops18h 25m
Wed 2/176:30 am -
1 stop14h 55m
Deal found 9/20![Delta logo]()
$666
This Turkish Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:10 pm -
1 stop29h 15m
Wed 10/286:45 pm -
1 stop22h 15m
Deal found 9/22![Turkish Airlines logo]()
$696
This Scandinavian Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/67:15 pm -
2 stops34h 40m
Wed 11/188:05 pm -
2 stops33h 31m
Deal found 9/19![Scandinavian Airlines logo]()
$705
This Finnair deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Mon 10/55:35 pm -
Nonstop9h 25m
Wed 10/213:00 pm -
Nonstop10h 50m
Deal found 9/19![Finnair logo]()
$737
This Air Serbia deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1711:20 pm -
1 stop26h 05m
Sat 10/249:25 am -
1 stop18h 50m
Deal found 9/21![Air Serbia logo]()
$744
This SWISS deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/207:50 pm -
1 stop16h 10m
Sun 3/287:45 pm -
1 stop27h 10m
Deal found 9/18![SWISS logo]()
$752
This FlightHub deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 1/88:10 pm -
2 stops35h 20m
Fri 1/153:15 pm -
2 stops55h 15m
Deal found 9/18![TAP AIR PORTUGAL logo]()
$855
This KLM deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:10 am -
1 stop18h 45m
Tue 10/2710:20 am -
2 stops17h 23m
Deal found 9/22![KLM logo]()
$985
This Icelandair deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:30 pm -
2 stops16h 50m
Fri 11/206:10 am -
2 stops18h 10m
Deal found 9/22![Icelandair logo]()
$1,110
This British Airways deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/75:10 pm -
1 stop13h 45m
Mon 12/146:00 pm -
1 stop31h 45m
Deal found 9/21![British Airways logo]()
$578
This British Airways deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/911:45 am -
2 stops16h 50m
Wed 3/38:50 am -
2 stops17h 39m
Deal found 9/21![Multiple Airlines logo]()
$579
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:00 pm -
1 stop12h 55m
Sat 10/179:30 pm -
1 stop22h 40m
Deal found 9/22![ITA Airways logo]()
$1,207
This British Airways deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/711:45 am -
2 stops17h 00m
Fri 1/1512:45 pm -
2 stops26h 54m
Deal found 9/19![Multiple Airlines logo]()
$601
This British Airways deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/145:10 pm -
1 stop20h 20m
Mon 12/216:00 pm -
1 stop26h 45m
Deal found 9/19![British Airways logo]()
$631
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:52 pm -
2 stops30h 48m
Tue 10/206:00 am -
2 stops23h 28m
Deal found 9/18![United Airlines logo]()
$697
This Turkish Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/49:15 pm -
1 stop28h 15m
Wed 11/118:15 pm -
1 stop20h 45m
Deal found 9/20![Turkish Airlines logo]()
$700
This Scandinavian Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/27:25 am -
2 stops29h 00m
Thu 11/198:05 pm -
1 stop27h 40m
Deal found 9/18![Scandinavian Airlines logo]()
$721
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/45:10 pm -
1 stop17h 50m
Wed 10/145:55 am -
2 stops18h 03m
Deal found 9/19![Delta logo]()
$721
This British Airways deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 -
2 stops17h 39m
Deal found 9/23![Multiple Airlines logo]()
$615
This Turkish Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/118:15 pm -
1 stop29h 15m
Fri 11/209:30 am -
1 stop31h 30m
Deal found 9/20![Turkish Airlines logo]()
$700
This British Airways deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 3/186:10 pm -
1 stop21h 25m
Mon 3/299:15 pm -
1 stop23h 35m
Deal found 9/21![British Airways logo]()
$637
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/244:40 pm -
Nonstop9h 05m
Wed 11/49:45 am -
Nonstop10h 25m
Deal found 9/19![United Airlines logo]()
$711
This Scandinavian Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/27:25 am -
2 stops29h 00m
Wed 11/188:05 pm -
1 stop27h 40m
Deal found 9/18![Scandinavian Airlines logo]()
$721
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:24 am -
2 stops17h 31m
Sun 11/16:05 am -
2 stops21h 25m
Deal found 9/23![Delta logo]()
$746
This British Airways deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 3/176:10 pm -
1 stop11h 30m
Sat 3/2710:45 am -
1 stop15h 00m
Deal found 9/18![British Airways logo]()
$638
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/227:05 pm -
1 stop12h 05m
Thu 11/56:30 am -
2 stops17h 14m
Deal found 9/21![United Airlines logo]()
$711
This Finnair deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:45 pm -
Nonstop9h 25m
Thu 10/2210:00 am -
Nonstop10h 40m
Deal found 9/22![Finnair logo]()
$893
Last-minute flights from Chicago to ItalyDiscover last-minute flight deals from Chicago to Italy. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Italy. Data last updated September 23, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:25 pm -
1 stop12h 20m
Tue 10/133:55 pm -
1 stop33h 20m
Deal found 9/20![Icelandair logo]()
$503
This FlightHub deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/1110:25 pm -
1 stop33h 20m
Fri 10/163:55 pm -
1 stop12h 30m
Deal found 9/19![Icelandair logo]()
$514
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/148:45 am -
2 stops30h 00m
Mon 10/1911:15 pm -
2 stops23h 40m
Deal found 9/20![Multiple Airlines logo]()
$624
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Wed 10/149:15 pm -
1 stop18h 00m
Mon 10/199:15 pm -
1 stop23h 35m
Deal found 9/20![British Airways logo]()
$626
This British Airways deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/199:15 pm -
1 stop15h 45m
Thu 11/57:00 am -
1 stop13h 45m
Deal found 9/20![British Airways logo]()
$578
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/195:29 pm -
2 stops17h 31m
Thu 11/52:15 pm -
1 stop26h 12m
Deal found 9/20![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:50 pm -
1 stop14h 30m
Thu 11/56:05 am -
2 stops22h 38m
Deal found 9/20![Delta logo]()
$602
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:35 pm -
1 stop12h 20m
Wed 11/116:20 am -
1 stop15h 45m
Deal found 9/22![American Airlines logo]()
$568
This British Airways deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:10 pm -
1 stop20h 20m
Wed 11/116:20 am -
2 stops17h 35m
Deal found 9/22![Multiple Airlines logo]()
$583
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 pm -
2 stops15h 30m
Wed 11/116:45 am -
2 stops16h 59m
Deal found 9/22![Air Canada logo]()
$613
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:30 pm -
1 stop12h 30m
Wed 11/1111:25 am -
1 stop12h 55m
Deal found 9/22![Icelandair logo]()
$626
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:27 am -
1 stop20h 48m
Fri 11/1312:30 pm -
1 stop14h 09m
Deal found 9/22![Delta logo]()
$627
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 September 23, 2026.
Search for one-way flight options from Chicago to Italy. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This British Airways deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1111:45 am -
2 stops16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$242
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm -
2 stops21h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$246
This British Airways deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/109:44 am -
2 stops18h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 stops31h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1110:25 pm -
3 stops35h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$261
This British Airways deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 3/21:18 pm -
2 stops14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1110:25 pm -
3 stops37h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1110:25 pm -
3 stops37h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/410:25 pm -
3 stops35h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/410:25 pm -
2 stops39h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/410:25 pm -
3 stops39h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:25 pm -
3 stops43h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$274
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 September 23, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $470 (Gotogate) |
One-way from | $242 (British Airways) |
Popular in | June |
Cheapest in | January |
Average price | $937 |
Good round-trip deal | $867 or less |
Good one-way deal | $532 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 September 23, 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
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Sun 10/4
10:25 pm-6:40 pm
3 stops37h 15m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$271
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Tue 10/20
7:25 pm-7:40 am
3 stops29h 15m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$310
ChicagoCatania
ORD Chicago O'Hare Intl - CTA Catania Fontanarossa
ORDCTA
Chicago O'Hare Intl
Mon 1/11
6:30 pm-9:55 pm
2 stops20h 25m
Catania Fontanarossa
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$317
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Tue 9/29
7:25 pm-4:10 pm
2 stops13h 45m
Milan Linate
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$320
ChicagoBari
ORD Chicago O'Hare Intl - BRI Bari Palese
ORDBRI
Chicago O'Hare Intl
Thu 1/28
6:30 pm-11:25 am
2 stops33h 55m
Bari Palese
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$322
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Sun 1/17
5:10 pm-2:30 pm
1 stop14h 20m
Rome Fiumicino
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$324
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Sun 3/21
7:50 pm-2:15 pm
1 stop12h 25m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$331
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Mon 3/22
6:10 pm-8:30 pm
1 stop20h 20m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$331
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Mon 3/22
7:50 pm-9:10 am
1 stop31h 20m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$333
ChicagoVenice
ORD Chicago O'Hare Intl - VCE Venice Marco Polo
ORDVCE
Chicago O'Hare Intl
Mon 10/5
7:25 pm-2:45 pm
1 stop12h 20m
Venice Marco Polo
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$334
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-VCE
ORD-FCO
ORD-PMO
ORD-MXP
ORD-NAP
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-VCE
ORD-FCO
ORD-PMO
ORD-MXP
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 $621). Flying from Chicago to Italy in June is currently the most expensive (average of $1,072). 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 September 23, 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 September 23, 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 157 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 September 23, 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.
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
7.3
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Comfort
7.3
Food
7.5
Crew
7.8
Overall
7.4
Entertainment
7.5
Boarding
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 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 September 23, 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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$338 | Average$581 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$362 | Average$701 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$396 | Average$707 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$420 | Average$697 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$455 | Average$854 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$504 | Average$1,049 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$507 | Average$962 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$514 | Average$990 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$522 | Average$1,148 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$549 | Average$1,104 | FlexibilityNo cancel fee | On-time69% |