$340+ Cheap flights from Italy to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Jul 24 — Jul 311
Round-trip
1 adult, Economy
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Cheapest flights from Italy to ChicagoExplore the most affordable flight options available from Italy to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
Explore the most affordable flight options available from Italy to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
This Mytrip deal was found by Cheapflights users on 6/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Mon 8/317:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/22![Icelandair logo]()
$519
This Mytrip deal was found by Cheapflights users on 6/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/304:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Sat 9/197:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/22![Icelandair logo]()
$520
This oojo deal was found by Cheapflights users on 6/20. 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.
Tue 8/254:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Sun 8/3010:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$521
This Justfly.com deal was found by Cheapflights users on 6/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Thu 9/247:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$531
This Justfly.com deal was found by Cheapflights users on 6/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Wed 9/2310:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$532
This Icelandair deal was found by Cheapflights users on 6/21. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/44:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Thu 10/157:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/21![Icelandair logo]()
$539
This Icelandair deal was found by Cheapflights users on 6/21. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/44:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Wed 10/1410:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/21![Icelandair logo]()
$540
This Icelandair deal was found by Cheapflights users on 6/21. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:10 pm
VCE
- ORD
1 stop33h 05m
Icelandair
Fri 10/1610:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/21![Icelandair logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Sat 9/267:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$551
This Icelandair deal was found by Cheapflights users on 6/20. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Mon 9/217:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$552
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Sun 9/2710:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$553
This Icelandair deal was found by Cheapflights users on 6/20. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:10 pm
VCE
- ORD
1 stop33h 05m
Icelandair
Thu 9/247:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$554
Best flights from Italy to ChicagoDiscover carefully curated flight deals from Italy to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
Discover carefully curated flight deals from Italy to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
This Icelandair deal was found by Cheapflights users on 6/20. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Wed 9/2310:25 pm
ORD
- VCE
1 stop33h 35m
Icelandair
Deal found 6/20![Icelandair logo]()
$554
This ITA Airways deal was found by Cheapflights users on 6/23. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:15 am
VCE
- ORD
1 stop13h 55m
ITA Airways
Sun 9/63:00 pm
ORD
- VCE
1 stop24h 50m
ITA Airways
Deal found 6/23![ITA Airways logo]()
$586
This KLM deal was found by Cheapflights users on 6/19. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:00 am
FCO
- MDW
1 stop15h 37m
Multiple Airlines
Tue 3/161:00 pm
MDW
- FCO
1 stop14h 35m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$657
This British Airways deal was found by Cheapflights users on 6/22. 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 11/810:20 am
MXP
- ORD
1 stop14h 18m
British Airways
Wed 11/1811:48 am
ORD
- MXP
2 stops15h 52m
British Airways
Deal found 6/22![British Airways logo]()
$690
This Delta deal was found by Cheapflights users on 6/22. 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 8/216:00 am
VCE
- MDW
2 stops19h 33m
Delta
Mon 8/315:45 pm
MDW
- VCE
2 stops15h 25m
Delta
Deal found 6/22![Delta logo]()
$702
This Scandinavian Airlines deal was found by Cheapflights users on 6/22. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:55 pm
LIN
- ORD
2 stops34h 50m
Scandinavian Airlines
Thu 12/37:15 pm
ORD
- LIN
2 stops33h 50m
Scandinavian Airlines
Deal found 6/22![Scandinavian Airlines logo]()
$719
This KLM deal was found by Cheapflights users on 6/22. 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.
Thu 10/2910:00 am
FCO
- MDW
1 stop14h 37m
KLM
Sun 11/151:05 pm
MDW
- FCO
1 stop12h 10m
KLM
Deal found 6/22![KLM logo]()
$745
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Wed 11/49:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Sun 11/83:40 pm
ORD
- FCO
Nonstop9h 05m
United Airlines
Deal found 6/19![United Airlines logo]()
$819
This Austrian Airlines deal was found by Cheapflights users on 6/20. 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
LIN
- ORD
2 stops16h 59m
Austrian Airlines
Thu 9/2412:55 pm
ORD
- LIN
2 stops23h 15m
Austrian Airlines
Deal found 6/20![Austrian Airlines logo]()
$831
This KLM deal was found by Cheapflights users on 6/23. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:40 am
LIN
- ORD
1 stop14h 35m
Multiple Airlines
Wed 9/165:10 pm
ORD
- LIN
1 stop11h 10m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$691
This British Airways deal was found by Cheapflights users on 6/20. 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.
Tue 9/158:45 am
VCE
- ORD
1 stop14h 10m
British Airways
Tue 9/226:30 pm
ORD
- VCE
2 stops16h 10m
British Airways
Deal found 6/20![British Airways logo]()
$700
This Delta deal was found by Cheapflights users on 6/23. 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.
Thu 10/81:20 pm
VCE
- ORD
1 stop15h 13m
Delta
Mon 10/125:45 pm
ORD
- VCE
2 stops15h 25m
Delta
Deal found 6/23![Delta logo]()
$702
This Scandinavian Airlines deal was found by Cheapflights users on 6/22. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:10 am
FCO
- ORD
2 stops38h 35m
Scandinavian Airlines
Sat 11/147:15 pm
ORD
- FCO
1 stop16h 30m
Scandinavian Airlines
Deal found 6/22![Scandinavian Airlines logo]()
$733
This ITA Airways deal was found by Cheapflights users on 6/22. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Sat 7/253:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Deal found 6/22![ITA Airways logo]()
$736
This Delta deal was found by Cheapflights users on 6/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
VCE
- ORD
1 stop15h 15m
Delta
Sat 9/196:00 pm
ORD
- VCE
2 stops17h 00m
Delta
Deal found 6/21![Delta logo]()
$703
This KLM deal was found by Cheapflights users on 6/21. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:00 am
FCO
- MDW
1 stop16h 33m
KLM
Thu 8/2010:54 am
MDW
- FCO
1 stop13h 41m
KLM
Deal found 6/21![KLM logo]()
$796
This British Airways deal was found by Cheapflights users on 6/23. 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.
Sun 8/161:45 pm
MXP
- ORD
1 stop33h 10m
British Airways
Sun 8/308:45 pm
ORD
- MXP
1 stop19h 50m
British Airways
Deal found 6/23![British Airways logo]()
$746
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Fri 9/189:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Fri 10/23:35 pm
ORD
- FCO
1 stop11h 25m
United Airlines
Deal found 6/19![United Airlines logo]()
$824
This Finnair deal was found by Cheapflights users on 6/22. 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 7/810:00 am
FCO
- ORD
Nonstop10h 40m
Multiple Airlines
Sun 7/1210:30 pm
ORD
- FCO
1 stop12h 45m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$759
This Scandinavian Airlines deal was found by Cheapflights users on 6/23. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:00 am
VCE
- ORD
1 stop12h 10m
Scandinavian Airlines
Sun 9/610:30 am
ORD
- VCE
2 stops16h 40m
Scandinavian Airlines
Deal found 6/23![Scandinavian Airlines logo]()
$769
This Delta deal was found by Cheapflights users on 6/22. 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.
Sun 8/3011:45 am
VCE
- ORD
2 stops15h 45m
Delta
Sat 9/196:00 pm
ORD
- VCE
2 stops17h 00m
Delta
Deal found 6/22![Delta logo]()
$708
This ITA Airways deal was found by Cheapflights users on 6/19. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Sun 8/23:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 6/19![ITA Airways logo]()
$798
This British Airways deal was found by Cheapflights users on 6/20. 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.
Thu 8/139:05 am
VCE
- ORD
1 stop13h 50m
British Airways
Fri 8/289:15 pm
ORD
- VCE
1 stop18h 00m
British Airways
Deal found 6/20![British Airways logo]()
$748
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:15 pm
BGY
- ORD
3 stops26h 55m
Multiple Airlines
Sun 8/307:15 pm
ORD
- BGY
2 stops16h 15m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$778
This Delta deal was found by Cheapflights users on 6/20. 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.
Sat 10/311:05 pm
MXP
- MDW
1 stop15h 05m
Delta
Sun 11/86:30 pm
MDW
- MXP
2 stops15h 55m
Delta
Deal found 6/20![Delta logo]()
$708
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/243:20 pm
MXP
- ORD
Nonstop9h 50m
United Airlines
Mon 8/319:40 pm
ORD
- MXP
Nonstop8h 40m
United Airlines
Deal found 6/22![United Airlines logo]()
$858
This British Airways deal was found by Cheapflights users on 6/20. 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.
Thu 7/161:30 pm
FCO
- ORD
1 stop15h 30m
British Airways
Thu 7/305:30 pm
ORD
- FCO
2 stops17h 25m
British Airways
Deal found 6/20![British Airways logo]()
$754
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 11/256:05 am
VCE
- MDW
2 stops19h 32m
Delta
Fri 12/41:05 pm
MDW
- VCE
2 stops15h 05m
Delta
Deal found 6/24![Delta logo]()
$710
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:20 pm
MXP
- ORD
3 stops29h 50m
Multiple Airlines
Sun 8/307:15 pm
ORD
- MXP
3 stops20h 55m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$823
This British Airways deal was found by Cheapflights users on 6/22. 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.
Fri 7/311:10 pm
FCO
- ORD
1 stop18h 40m
British Airways
Sun 8/167:05 pm
ORD
- FCO
1 stop15h 00m
British Airways
Deal found 6/22![British Airways logo]()
$761
Last-minute flights from Italy to ChicagoDiscover last-minute flight deals from Italy to Chicago. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Italy to Chicago. Data last updated June 24, 2026 and is based on user searches.
This Flighttix deal was found by Cheapflights users on 6/19. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:15 pm
FCO
- ORD
1 stop16h 15m
British Airways
Thu 7/911:40 am
ORD
- FCO
1 stop12h 25m
British Airways
Deal found 6/19![British Airways logo]()
$660
This British Airways deal was found by Cheapflights users on 6/20. 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.
Sat 6/2710:00 am
FCO
- ORD
Nonstop10h 30m
British Airways
Fri 7/1010:30 pm
ORD
- FCO
1 stop16h 55m
British Airways
Deal found 6/20![British Airways logo]()
$661
This British Airways deal was found by Cheapflights users on 6/18. 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.
Sat 6/2710:00 am
FCO
- ORD
Nonstop10h 30m
British Airways
Sat 7/117:05 pm
ORD
- FCO
1 stop20h 55m
British Airways
Deal found 6/18![British Airways logo]()
$662
This Rumbo deal was found by Cheapflights users on 6/20. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:00 am
FCO
- ORD
Nonstop10h 30m
Multiple Airlines
Fri 7/104:55 pm
ORD
- FCO
1 stop12h 40m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$666
This Rumbo deal was found by Cheapflights users on 6/21. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2810:00 am
FCO
- ORD
Nonstop10h 30m
Multiple Airlines
Sat 7/1110:30 pm
ORD
- FCO
1 stop13h 35m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$659
This Flighttix deal was found by Cheapflights users on 6/21. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:10 pm
FCO
- ORD
1 stop16h 25m
British Airways
Sat 7/115:07 am
ORD
- FCO
1 stop22h 13m
British Airways
Deal found 6/21![British Airways logo]()
$665
This lol.travel deal was found by Cheapflights users on 6/23. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:00 am
FCO
- ORD
Nonstop10h 40m
Finnair
Tue 7/145:00 pm
ORD
- FCO
Nonstop9h 10m
Finnair
Deal found 6/23![Finnair logo]()
$663
This deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:15 am
VCE
- ORD
1 stop13h 55m
ITA Airways
Sat 8/13:00 pm
ORD
- VCE
1 stop16h 30m
ITA Airways
Deal found 6/21![ITA Airways logo]()
$644
This deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Sat 8/13:00 pm
ORD
- LIN
1 stop11h 40m
ITA Airways
Deal found 6/21![ITA Airways logo]()
$655
This deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Sun 8/23:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 6/21![ITA Airways logo]()
$657
This deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:15 am
VCE
- ORD
1 stop13h 55m
ITA Airways
Sun 8/23:00 pm
ORD
- VCE
1 stop12h 30m
ITA Airways
Deal found 6/21![ITA Airways logo]()
$645
This deal was found by Cheapflights users on 6/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Sat 8/13:00 pm
ORD
- LIN
1 stop11h 40m
ITA Airways
Deal found 6/21![ITA Airways logo]()
$656
One-way flights from Italy to ChicagoSearch for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
Search for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:20 pm
MXP
- MDW
2 stops41h 20m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 pm
BGY
- ORD
3 stops29h 50m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:45 pm
BGY
- ORD
3 stops50h 05m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
Thu 10/226:45 am
BGY
- ORD
3 stops42h 05m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Sat 10/310:55 am
BGY
- ORD
3 stops37h 55m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$366
This Mytrip deal was found by Cheapflights users on 6/19. 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.
Thu 8/2711:20 pm
MXP
- ORD
2 stops27h 32m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$368
This Mytrip deal was found by Cheapflights users on 6/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/74:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Deal found 6/22![Icelandair logo]()
$370
This Mytrip deal was found by Cheapflights users on 6/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:10 pm
VCE
- ORD
1 stop12h 15m
Icelandair
Deal found 6/23![Icelandair logo]()
$371
This oojo deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/234:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Deal found 6/24![Icelandair logo]()
$372
This oojo deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 6/24![Icelandair logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
Wed 10/218:35 pm
BGY
- ORD
2 stops28h 15m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$373
This oojo deal was found by Cheapflights users on 6/23. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 6/23![Icelandair logo]()
$374
Find flight deals from Italy to Chicago
Keep the following information in mind while searching for Italy to Chicago flight deals. Data was last updated June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $519 (Mytrip) |
One-way from | $340 (Kiwi.com) |
Popular in | August |
Cheapest in | September |
Average price | $814 |
Good round-trip deal | $658 or less |
Good one-way deal | $623 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Italy to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 24, 2026.
Use the filters below to find and compare flights from Italy to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Sun 9/20
4:10 pm-9:25 pm
1 stop12h 15m
Chicago O'Hare Intl
Wed 9/23
10:25 pm-3:00 pm
1 stop33h 35m
$554
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Wed 9/2
6:15 am-1:10 pm
1 stop13h 55m
Chicago O'Hare Intl
Sun 9/6
3:00 pm-10:50 pm
1 stop24h 50m
$586
RomeChicago
FCO - MDW
FCOMDW
Rome Fiumicino
Wed 12/16
10:00 am-6:37 pm
1 stop15h 37m
Chicago Midway
Tue 3/16
1:00 pm-9:35 am
1 stop14h 35m
$657
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
Sun 11/8
10:20 am-5:38 pm
1 stop14h 18m
Chicago O'Hare Intl
Wed 11/18
11:48 am-10:40 am
2 stops15h 52m
$690
MilanChicago
LIN - ORD
LINORD
Milan Linate
Fri 9/4
6:40 am-2:15 pm
1 stop14h 35m
Chicago O'Hare Intl
Wed 9/16
5:10 pm-11:20 am
1 stop11h 10m
$691
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Tue 9/15
8:45 am-3:55 pm
1 stop14h 10m
Chicago O'Hare Intl
Tue 9/22
6:30 pm-5:40 pm
2 stops16h 10m
$700
VeniceChicago
VCE - MDW
VCEMDW
Venice Marco Polo
Fri 8/21
6:00 am-6:33 pm
2 stops19h 33m
Chicago Midway
Mon 8/31
5:45 pm-4:10 pm
2 stops15h 25m
$702
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Thu 10/8
1:20 pm-9:33 pm
1 stop15h 13m
Chicago O'Hare Intl
Mon 10/12
5:45 pm-4:10 pm
2 stops15h 25m
$702
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Sat 8/29
6:00 am-2:15 pm
1 stop15h 15m
Chicago O'Hare Intl
Sat 9/19
6:00 pm-6:00 pm
2 stops17h 00m
$703
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Sun 8/30
11:45 am-8:30 pm
2 stops15h 45m
Chicago O'Hare Intl
Sat 9/19
6:00 pm-6:00 pm
2 stops17h 00m
$708
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Italy to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Italy with our price prediction graph.
VCE-ORD
FCO-MDW
MXP-ORD
VCE-MDW
LIN-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Italy to Chicago
IT0-CHI
VCE-ORD
FCO-MDW
MXP-ORD
VCE-MDW
What is the cheapest month to book a flight from Italy to Chicago?
Currently, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $356). Flying from Italy to Chicago in August is currently the most expensive (average of $1,605). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from IT to CHI?
Find hourly flight availability from Italy to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 24, 2026.
When flying from Italy to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Italy to Chicago
Explore weekly flight availability from Italy to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 24, 2026.
The most flights from IT0 to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How often are flights from Italy to Chicago delayed?
About 21% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 191 minutes.
What is the most punctual flight time for Italy to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Italy to Chicago flights?
Over the last year, Ethiopian Air have had the lowest number of delays on this route, with just 15% of flights being delayed.
How far ahead should I book a flight from Italy to Chicago?
The price you pay for your flight from Italy to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 24, 2026.
Read reviews from past customers who have flown Turkish Airlines,United Airlines, andLufthansa from Italy to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.8
Boarding
7.3
Comfort
7.3
Overall
7.4
Entertainment
7.5
Food
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Crew
7.8
Boarding
7.3
Comfort
7.3
Overall
7.4
Entertainment
7.5
Food
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Crew
7.8
Boarding
7.3
Comfort
7.3
Overall
7.4
Entertainment
7.5
Food
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Crew
7.8
Boarding
7.3
Comfort
7.3
Overall
7.4
Entertainment
7.5
Food
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Crew
7.8
Boarding
7.3
Comfort
7.3
Overall
7.4
Entertainment
7.5
Food
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Related info for your journey
Find useful and relevant information for your journey from Italy to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Italy to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 24, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Italy to Chicago by cabin class
Find flights from Italy to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Italy and Chicago flights
Browse other Italy and Chicago flight options. Last updated on June 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Italy to Chicago flights
Consider these flights traveling from Italy to Chicago.
Top 4 airlines flying from Italy to Chicago
Discover the top 4 airlines that operate flights from Italy to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$571 | Average$1,103 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$585 | Average$811 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$609 | Average$658 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$699 | Average$885 | FlexibilityNo cancel fee | On-time81% |