$368+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Jun 7 — Jun 141
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 May 8, 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 May 8, 2026.
This Mytrip deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:10 pm
VCE
- ORD
1 stop33h 05m
Icelandair
Sat 6/207:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 5/3![Icelandair logo]()
$530
This Mytrip deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Mon 6/157:25 pm
ORD
- MXP
1 stop19h 30m
Icelandair
Deal found 5/5![Icelandair logo]()
$533
This Mytrip deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Mon 6/1510:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/6![Icelandair logo]()
$535
This Mytrip deal was found by Cheapflights users on 5/7. 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.
Sat 9/54:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Sat 9/197:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/7![Icelandair logo]()
$537
This Justfly.com deal was found by Cheapflights users on 5/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Wed 6/177:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/7![Icelandair logo]()
$545
This Trip.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Sun 6/147:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/3![Icelandair logo]()
$550
This Gotogate deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Tue 9/223:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 5/3![ITA Airways logo]()
$561
This lol.travel deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:00 pm
LIN
- ORD
1 stop23h 10m
ITA Airways
Tue 9/223:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Deal found 5/4![ITA Airways logo]()
$562
This Gotogate deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Sun 6/147:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/4![Icelandair logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Mon 5/2510:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/3![Icelandair logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/74:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Mon 6/1510:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/7![Icelandair logo]()
$565
This Icelandair deal was found by Cheapflights users on 5/7. 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.
Mon 5/184:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Mon 6/110:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/7![Icelandair logo]()
$566
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 May 8, 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 May 8, 2026.
This Icelandair deal was found by Cheapflights users on 5/7. 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.
Fri 6/510:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Wed 6/177:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/7![Icelandair logo]()
$594
This British Airways deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:05 am
FCO
- ORD
Nonstop10h 30m
British Airways
Tue 9/224:55 pm
ORD
- FCO
Nonstop9h 15m
British Airways
Deal found 5/6![British Airways logo]()
$654
This FlightHub deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:20 am
VCE
- ORD
1 stop31h 20m
Turkish Airlines
Thu 7/98:10 pm
ORD
- VCE
1 stop33h 55m
Turkish Airlines
Deal found 5/3![Turkish Airlines logo]()
$659
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Thu 9/2410:30 pm
ORD
- FCO
1 stop12h 20m
United Airlines
Deal found 5/4![United Airlines logo]()
$694
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:35 am
FCO
- ORD
2 stops18h 15m
Delta
Sat 9/125:10 pm
ORD
- FCO
1 stop17h 20m
Delta
Deal found 5/5![Delta logo]()
$719
This Priceline deal was found by Cheapflights users on 5/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1812:20 pm
VCE
- ORD
1 stop14h 39m
Air Canada
Sun 6/218:35 am
ORD
- VCE
2 stops17h 55m
Air Canada
Deal found 5/7![Air Canada logo]()
$731
This JetBlue deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:00 am
MXP
- ORD
1 stop17h 53m
JetBlue
Mon 5/258:50 am
ORD
- MXP
1 stop16h 20m
JetBlue
Deal found 5/5![JetBlue logo]()
$739
This KLM deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:10 am
FCO
- ORD
1 stop14h 39m
KLM
Sat 6/65:41 pm
ORD
- FCO
1 stop11h 59m
KLM
Deal found 5/6![KLM logo]()
$741
This KLM deal was found by Cheapflights users on 5/7. 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 5/176:00 am
VCE
- ORD
1 stop15h 15m
Multiple Airlines
Sat 5/309:10 am
ORD
- VCE
1 stop16h 55m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$788
This ITA Airways deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Sun 6/213:00 pm
ORD
- LIN
1 stop23h 10m
ITA Airways
Deal found 5/3![ITA Airways logo]()
$811
This Icelandair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Mon 6/110:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/4![Icelandair logo]()
$629
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Thu 10/83:20 pm
FCO
- ORD
1 stop14h 55m
United Airlines
Mon 10/123:50 pm
ORD
- FCO
Nonstop9h 05m
United Airlines
Deal found 5/8![United Airlines logo]()
$697
This Delta deal was found by Cheapflights users on 5/8. 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.
Thu 10/81:10 pm
FCO
- MDW
1 stop15h 35m
Delta
Mon 10/121:05 pm
MDW
- FCO
2 stops14h 55m
Delta
Deal found 5/8![Delta logo]()
$721
This Icelandair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Mon 8/3110:25 pm
ORD
- FCO
1 stop33h 10m
Icelandair
Deal found 5/5![Icelandair logo]()
$661
This Air Canada deal was found by Cheapflights users on 5/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2211:20 am
MXP
- ORD
2 stops17h 45m
Air Canada
Mon 6/2911:05 am
ORD
- MXP
2 stops15h 45m
Air Canada
Deal found 5/8![Air Canada logo]()
$741
This British Airways deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:35 am
VCE
- ORD
1 stop17h 40m
British Airways
Mon 5/257:05 pm
ORD
- VCE
1 stop17h 55m
British Airways
Deal found 5/3![British Airways logo]()
$757
This KLM deal was found by Cheapflights users on 5/7. 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.
Sat 5/167:35 pm
LIN
- ORD
1 stop25h 40m
KLM
Mon 6/14:50 pm
ORD
- LIN
1 stop12h 10m
KLM
Deal found 5/7![KLM logo]()
$779
This Mytrip deal was found by Cheapflights users on 5/8. 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.
Mon 6/228:20 am
BGY
- ORD
2 stops32h 20m
Multiple Airlines
Thu 7/911:25 am
ORD
- BGY
2 stops29h 25m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$789
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:00 am
FCO
- MDW
1 stop16h 33m
Delta
Sun 9/65:59 pm
MDW
- FCO
2 stops13h 26m
Delta
Deal found 5/6![Delta logo]()
$725
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:20 am
MXP
- ORD
1 stop15h 35m
United Airlines
Wed 9/233:40 pm
ORD
- MXP
1 stop11h 40m
United Airlines
Deal found 5/4![United Airlines logo]()
$731
This ITA Airways deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:00 pm
LIN
- ORD
1 stop24h 10m
ITA Airways
Sun 6/213:00 pm
ORD
- LIN
1 stop23h 10m
ITA Airways
Deal found 5/3![ITA Airways logo]()
$811
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:50 am
MXP
- ORD
1 stop33h 50m
Turkish Airlines
Mon 6/2911:25 am
ORD
- MXP
1 stop14h 15m
Turkish Airlines
Deal found 5/8![Turkish Airlines logo]()
$854
This KLM deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:40 am
MXP
- MDW
1 stop16h 29m
KLM
Tue 5/2612:53 pm
MDW
- MXP
1 stop13h 32m
KLM
Deal found 5/8![KLM logo]()
$782
This Delta deal was found by Cheapflights users on 5/7. 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.
Sun 8/236:05 am
FCO
- ORD
2 stops17h 49m
Delta
Sun 9/65:45 pm
ORD
- FCO
2 stops15h 50m
Delta
Deal found 5/7![Delta logo]()
$728
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:00 pm
CIA
- ORD
1 stop26h 50m
Multiple Airlines
Sat 9/127:25 pm
ORD
- CIA
2 stops19h 30m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$802
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:00 am
MXP
- ORD
2 stops21h 15m
United Airlines
Sun 10/259:00 am
ORD
- MXP
2 stops16h 30m
United Airlines
Deal found 5/4![United Airlines logo]()
$733
This KLM deal was found by Cheapflights users on 5/7. 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.
Sat 5/166:40 am
LIN
- MDW
2 stops18h 16m
KLM
Mon 6/11:22 pm
MDW
- LIN
2 stops13h 43m
KLM
Deal found 5/7![KLM logo]()
$784
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:30 am
FCO
- ORD
2 stops17h 26m
Delta
Sat 6/202:35 pm
ORD
- FCO
1 stop13h 25m
Delta
Deal found 5/3![Delta logo]()
$735
This Mytrip deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:05 pm
BGY
- ORD
3 stops30h 11m
Multiple Airlines
Sun 6/149:55 am
ORD
- BGY
2 stops27h 35m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$855
This Icelandair deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/314:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Sun 6/77:25 pm
ORD
- MXP
1 stop12h 45m
Icelandair
Deal found 5/6![Icelandair logo]()
$861
Last-minute flights from Italy to ChicagoDiscover last-minute flight deals from Italy to Chicago. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Italy to Chicago. Data last updated May 8, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:00 am
FCO
- ORD
Nonstop10h 30m
British Airways
Mon 5/254:55 pm
ORD
- FCO
Nonstop9h 15m
British Airways
Deal found 5/4![British Airways logo]()
$645
This lol.travel deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:00 am
FCO
- ORD
Nonstop10h 30m
British Airways
Sun 5/174:55 pm
ORD
- FCO
Nonstop9h 15m
British Airways
Deal found 5/4![British Airways logo]()
$653
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Mon 5/253:00 pm
ORD
- LIN
1 stop12h 10m
ITA Airways
Deal found 5/7![ITA Airways logo]()
$626
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:25 am
LIN
- ORD
1 stop13h 25m
British Airways
Sat 5/235:00 pm
ORD
- LIN
1 stop13h 25m
British Airways
Deal found 5/7![British Airways logo]()
$634
This British Airways deal was found by Cheapflights users on 5/7. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:00 am
FCO
- ORD
Nonstop10h 30m
British Airways
Thu 5/289:15 pm
ORD
- FCO
1 stop30h 00m
British Airways
Deal found 5/7![British Airways logo]()
$648
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:05 am
LIN
- ORD
1 stop14h 10m
British Airways
Sun 5/249:15 pm
ORD
- LIN
1 stop13h 00m
British Airways
Deal found 5/7![British Airways logo]()
$651
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Mon 5/2510:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/3![Icelandair logo]()
$563
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:25 am
LIN
- ORD
1 stop13h 25m
British Airways
Sat 5/235:00 pm
ORD
- LIN
1 stop13h 25m
British Airways
Deal found 5/7![British Airways logo]()
$638
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:25 am
LIN
- ORD
1 stop13h 25m
British Airways
Sun 5/249:15 pm
ORD
- LIN
1 stop13h 00m
British Airways
Deal found 5/7![British Airways logo]()
$612
This deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Mon 5/253:00 pm
ORD
- LIN
1 stop12h 10m
ITA Airways
Deal found 5/7![ITA Airways logo]()
$627
This Icelandair deal was found by Cheapflights users on 5/7. 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.
Mon 5/184:20 pm
MXP
- ORD
1 stop12h 05m
Icelandair
Mon 6/110:25 pm
ORD
- MXP
1 stop16h 30m
Icelandair
Deal found 5/7![Icelandair logo]()
$566
This Mytrip deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:10 pm
VCE
- ORD
1 stop33h 05m
Icelandair
Sat 6/207:25 pm
ORD
- VCE
1 stop12h 35m
Icelandair
Deal found 5/3![Icelandair logo]()
$530
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 May 8, 2026.
Search for one-way flight options from Italy to Chicago. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:10 am
MXP
- ORD
2 stops40h 40m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 am
MXP
- ORD
2 stops40h 40m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$377
This Mytrip deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 5/4![Icelandair logo]()
$379
This Mytrip deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 5/4![Icelandair logo]()
$380
This Mytrip deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Deal found 5/7![Icelandair logo]()
$382
This Gotogate deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 5/6![Icelandair logo]()
$384
This oojo deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 5/6![Icelandair logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:55 pm
MXP
- ORD
3 stops24h 55m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$387
This oojo deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/134:20 pm
MXP
- ORD
1 stop32h 55m
Icelandair
Deal found 5/3![Icelandair logo]()
$388
This Justfly.com deal was found by Cheapflights users on 5/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:55 pm
MXP
- ORD
1 stop26h 20m
Icelandair
Deal found 5/7![Icelandair logo]()
$389
This Cheapflightsfares deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:15 pm
VCE
- ORD
1 stop13h 45m
British Airways
Deal found 5/4![British Airways logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:30 am
MXP
- MDW
3 stops45h 41m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$418
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $530 (Mytrip) |
One-way from | $368 (Kiwi.com) |
Popular in | January |
Cheapest in | September |
Average price | $712 |
Good round-trip deal | $665 or less |
Good one-way deal | $617 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 May 8, 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
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
Fri 6/5
10:55 pm-6:15 pm
1 stop26h 20m
Chicago O'Hare Intl
Wed 6/17
7:25 pm-3:10 pm
1 stop12h 45m
$594
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
Thu 5/21
4:20 pm-6:15 pm
1 stop32h 55m
Chicago O'Hare Intl
Mon 6/1
10:25 pm-9:55 pm
1 stop16h 30m
$629
Quickest round-trip
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Thu 9/17
11:05 am-2:35 pm
Nonstop10h 30m
Chicago O'Hare Intl
Tue 9/22
4:55 pm-9:10 am
Nonstop9h 15m
$654
VeniceChicago
VCE - ORD
VCEORD
Venice Marco Polo
Thu 6/18
9:20 am-9:40 am
1 stop31h 20m
Chicago O'Hare Intl
Thu 7/9
8:10 pm-1:05 pm
1 stop33h 55m
$659
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Fri 8/28
3:45 pm-9:25 pm
1 stop12h 40m
Chicago O'Hare Intl
Mon 8/31
10:25 pm-2:35 pm
1 stop33h 10m
$661
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Tue 9/15
9:45 am-1:10 pm
Nonstop10h 25m
Chicago O'Hare Intl
Thu 9/24
10:30 pm-5:50 pm
1 stop12h 20m
$694
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Thu 10/8
3:20 pm-11:15 pm
1 stop14h 55m
Chicago O'Hare Intl
Mon 10/12
3:50 pm-7:55 am
Nonstop9h 05m
$697
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Wed 8/26
10:35 am-9:50 pm
2 stops18h 15m
Chicago O'Hare Intl
Sat 9/12
5:10 pm-5:30 pm
1 stop17h 20m
$719
RomeChicago
FCO - MDW
FCOMDW
Rome Fiumicino
Thu 10/8
1:10 pm-9:45 pm
1 stop15h 35m
Chicago Midway
Mon 10/12
1:05 pm-11:00 am
2 stops14h 55m
$721
RomeChicago
FCO - MDW
FCOMDW
Rome Fiumicino
Sun 8/23
9:00 am-6:33 pm
1 stop16h 33m
Chicago Midway
Sun 9/6
5:59 pm-2:25 pm
2 stops13h 26m
$725
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.
MXP-ORD
VCE-ORD
MXP-MDW
LIN-ORD
BGY-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
MXP-ORD
VCE-ORD
MXP-MDW
LIN-ORD
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 77 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Italy to Chicago?
Currently, June is the cheapest month in which you can book a flight from Italy to Chicago (average of $264). Flying from Italy to Chicago in August is currently the most expensive (average of $1,412). 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 May 8, 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.
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 194 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 14% of flights being delayed.
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 May 8, 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.
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Crew
7.8
Overall
7.4
Boarding
7.3
Comfort
7.3
Entertainment
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
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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 May 8, 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 May 8, 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 5 airlines flying from Italy to Chicago
Discover the top 5 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$537 | Average$692 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$571 | Average$885 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$658 | Average$795 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$690 | Average$710 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$722 | Average$747 | FlexibilityNo cancel fee | On-time77% |