$261+ Cheap flights from Chicago (CHI) to Italy
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Jul 8 — Jul 151
Round-trip
1 adult, Economy
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Cheapest flights from Chicago to ItalyExplore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 8, 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 June 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sun 10/47:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Mon 10/127:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$590
This Justfly.com deal was found by Cheapflights users on 6/7. 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.
Thu 10/17:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/7![Scandinavian Airlines logo]()
$614
This FlightHub deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:15 pm
ORD
- FLR
2 stops30h 55m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/7![Scandinavian Airlines logo]()
$615
This FlightHub deal was found by Cheapflights users on 6/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:15 pm
ORD
- FLR
2 stops54h 55m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 9/307:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$620
This Scandinavian Airlines deal was found by Cheapflights users on 6/5. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/5![Scandinavian Airlines logo]()
$636
This Scandinavian Airlines deal was found by Cheapflights users on 6/3. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/3![Scandinavian Airlines logo]()
$637
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Sun 10/47:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
2 stops33h 09m
Scandinavian Airlines
Deal found 6/3![Scandinavian Airlines logo]()
$640
This Justfly.com deal was found by Cheapflights users on 6/4. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:15 pm
ORD
- FLR
1 stop16h 25m
Scandinavian Airlines
Mon 10/127:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$644
This FlightHub deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:15 pm
ORD
- FLR
2 stops38h 15m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/7![Scandinavian Airlines logo]()
$645
This Trip.com deal was found by Cheapflights users on 6/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:10 pm
ORD
- PMO
2 stops18h 40m
Multiple Airlines
Tue 11/1710:25 pm
PMO
- ORD
2 stops24h 05m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$714
This Cheapflightsfares deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
- PMO
1 stop16h 45m
SWISS
Thu 8/279:45 am
PMO
- ORD
1 stop13h 10m
SWISS
Deal found 6/7![SWISS logo]()
$765
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 June 8, 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 June 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:40 pm
ORD
- MXP
Nonstop8h 40m
United Airlines
Sun 8/309:00 am
MXP
- ORD
1 stop12h 55m
United Airlines
Deal found 6/6![United Airlines logo]()
$779
This Scandinavian Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:15 pm
ORD
- LIN
2 stops33h 55m
Scandinavian Airlines
Wed 8/261:00 pm
LIN
- ORD
2 stops34h 10m
Scandinavian Airlines
Deal found 6/7![Scandinavian Airlines logo]()
$781
This KLM deal was found by Cheapflights users on 6/5. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:05 am
MDW
- MXP
1 stop20h 20m
KLM
Wed 8/1911:40 am
MXP
- MDW
1 stop17h 56m
KLM
Deal found 6/5![KLM logo]()
$792
This Delta deal was found by Cheapflights users on 6/5. 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 8/129:24 am
MDW
- MXP
2 stops18h 01m
Delta
Wed 8/1911:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 6/5![Delta logo]()
$796
This Air Serbia deal was found by Cheapflights users on 6/6. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:20 pm
ORD
- MXP
1 stop26h 10m
Air Serbia
Sat 9/129:20 am
MXP
- ORD
1 stop18h 55m
Air Serbia
Deal found 6/6![Air Serbia logo]()
$842
This Mytrip deal was found by Cheapflights users on 6/7. 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 9/57:25 pm
ORD
- CIA
2 stops19h 30m
Multiple Airlines
Sun 9/137:40 am
CIA
- ORD
3 stops41h 35m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$867
This British Airways deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:00 pm
ORD
- FCO
Nonstop9h 10m
British Airways
Sun 8/1610:00 am
FCO
- ORD
Nonstop10h 40m
British Airways
Deal found 6/6![British Airways logo]()
$903
This Austrian Airlines deal was found by Cheapflights users on 6/8. 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:56 pm
ORD
- VCE
2 stops17h 59m
Austrian Airlines
Tue 9/87:00 am
VCE
- ORD
2 stops17h 00m
Austrian Airlines
Deal found 6/8![Austrian Airlines logo]()
$1,012
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/5. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 pm
ORD
- NAP
1 stop34h 40m
TAP AIR PORTUGAL
Mon 8/1011:20 am
NAP
- ORD
2 stops59h 40m
TAP AIR PORTUGAL
Deal found 6/5![TAP AIR PORTUGAL logo]()
$1,016
This ITA Airways deal was found by Cheapflights users on 6/8. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:00 pm
ORD
- LIN
1 stop13h 40m
ITA Airways
Thu 8/137:00 am
LIN
- ORD
1 stop13h 10m
ITA Airways
Deal found 6/8![ITA Airways logo]()
$1,070
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 8/36:00 pm
ORD
- LIN
1 stop11h 20m
United Airlines
Wed 8/196:50 am
LIN
- ORD
1 stop13h 05m
United Airlines
Deal found 6/8![United Airlines logo]()
$786
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 8/36:05 am
MDW
- MXP
2 stops17h 40m
Delta
Wed 8/199:00 am
MXP
- MDW
2 stops20h 36m
Delta
Deal found 6/8![Delta logo]()
$796
This Air Serbia deal was found by Cheapflights users on 6/3. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:40 pm
ORD
- FCO
1 stop32h 45m
Air Serbia
Sun 9/139:00 pm
FCO
- ORD
1 stop24h 30m
Air Serbia
Deal found 6/3![Air Serbia logo]()
$848
This KLM deal was found by Cheapflights users on 6/5. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:56 am
MDW
- FCO
1 stop13h 39m
KLM
Sat 8/221:10 pm
FCO
- MDW
1 stop16h 26m
KLM
Deal found 6/5![KLM logo]()
$857
This KAYAK deal was found by Cheapflights users on 6/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
ORD
- PMO
1 stop14h 30m
Scandinavian Airlines
Sun 9/205:35 pm
PMO
- ORD
1 stop29h 35m
Scandinavian Airlines
Deal found 6/3![Scandinavian Airlines logo]()
$866
This Mytrip deal was found by Cheapflights users on 6/7. 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.
Mon 11/236:30 pm
ORD
- CIA
2 stops16h 25m
Multiple Airlines
Sun 11/298:40 pm
CIA
- ORD
3 stops27h 40m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$870
This Delta deal was found by Cheapflights users on 6/3. 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 8/185:10 pm
ORD
- LIN
1 stop11h 10m
Delta
Wed 8/2611:00 am
LIN
- ORD
2 stops16h 27m
Delta
Deal found 6/3![Delta logo]()
$799
This Air Serbia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:40 pm
ORD
- FCO
1 stop32h 45m
Air Serbia
Sun 9/209:00 pm
FCO
- ORD
1 stop24h 30m
Air Serbia
Deal found 6/7![Air Serbia logo]()
$871
This Mytrip deal was found by Cheapflights users on 6/5. 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.
Wed 11/116:30 pm
ORD
- CIA
2 stops15h 15m
Multiple Airlines
Sat 11/2110:50 am
CIA
- ORD
3 stops40h 30m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$871
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:50 pm
ORD
- FCO
Nonstop9h 05m
United Airlines
Fri 10/306:55 am
FCO
- ORD
1 stop14h 15m
United Airlines
Deal found 6/6![United Airlines logo]()
$883
This Delta deal was found by Cheapflights users on 6/5. 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.
Tue 8/45:10 pm
ORD
- PMO
1 stop14h 50m
Delta
Tue 8/183:45 pm
PMO
- ORD
2 stops31h 39m
Delta
Deal found 6/5![Delta logo]()
$830
This KLM deal was found by Cheapflights users on 6/7. 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.
Wed 8/1210:54 am
MDW
- FCO
1 stop13h 41m
KLM
Mon 8/179:00 am
FCO
- MDW
1 stop16h 33m
KLM
Deal found 6/7![KLM logo]()
$917
This Scandinavian Airlines deal was found by Cheapflights users on 6/6. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:15 pm
ORD
- FLR
1 stop32h 50m
Scandinavian Airlines
Sat 9/197:30 pm
FLR
- ORD
1 stop27h 40m
Scandinavian Airlines
Deal found 6/6![Scandinavian Airlines logo]()
$941
This Mytrip deal was found by Cheapflights users on 6/6. 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 9/159:50 am
ORD
- CIA
2 stops28h 25m
Multiple Airlines
Tue 9/227:25 am
CIA
- ORD
3 stops44h 55m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$877
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:40 pm
ORD
- MXP
Nonstop8h 40m
United Airlines
Sun 8/309:00 am
MXP
- ORD
1 stop12h 55m
United Airlines
Deal found 6/5![United Airlines logo]()
$884
This ITA Airways deal was found by Cheapflights users on 6/6. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/303:00 pm
ORD
- NAP
1 stop12h 35m
ITA Airways
Wed 8/56:35 am
NAP
- ORD
1 stop13h 35m
ITA Airways
Deal found 6/6![ITA Airways logo]()
$1,085
This British Airways deal was found by Cheapflights users on 6/3. 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.
Wed 7/295:30 pm
ORD
- NAP
Nonstop9h 30m
British Airways
Mon 8/103:00 pm
NAP
- ORD
Nonstop10h 45m
British Airways
Deal found 6/3![British Airways logo]()
$1,098
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:24 am
MDW
- MXP
2 stops18h 01m
Delta
Sun 8/3011:40 am
MXP
- MDW
1 stop17h 56m
Delta
Deal found 6/7![Delta logo]()
$846
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:50 pm
ORD
- NAP
2 stops19h 50m
TAP AIR PORTUGAL
Thu 9/33:05 pm
NAP
- ORD
2 stops31h 55m
TAP AIR PORTUGAL
Deal found 6/6![TAP AIR PORTUGAL logo]()
$1,134
This Mytrip deal was found by Cheapflights users on 6/3. 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.
Wed 8/1911:05 am
ORD
- CIA
3 stops25h 45m
Multiple Airlines
Wed 8/268:35 pm
CIA
- ORD
2 stops23h 20m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$886
Last-minute flights from Chicago to ItalyDiscover last-minute flight deals from Chicago to Italy. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Italy. Data last updated June 8, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/610:25 pm
ORD
- MXP
1 stop16h 30m
Multiple Airlines
Wed 7/1510:00 am
MXP
- ORD
1 stop16h 15m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$795
This Priceline deal was found by Cheapflights users on 6/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:25 pm
ORD
- MXP
1 stop19h 30m
Multiple Airlines
Mon 7/1310:00 am
MXP
- ORD
1 stop31h 06m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$801
This Orbitz deal was found by Cheapflights users on 6/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:09 pm
ORD
- MXP
1 stop12h 01m
JetBlue
Tue 7/1410:00 am
MXP
- ORD
1 stop16h 15m
JetBlue
Deal found 6/7![JetBlue logo]()
$786
This Mytrip deal was found by Cheapflights users on 6/4. 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.
Wed 7/226:00 pm
ORD
- MXP
2 stops24h 00m
Multiple Airlines
Wed 7/2911:35 am
MXP
- ORD
2 stops32h 05m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$802
This oojo deal was found by Cheapflights users on 6/4. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 pm
ORD
- MXP
1 stop15h 25m
TAP AIR PORTUGAL
Wed 7/298:00 pm
MXP
- ORD
1 stop23h 40m
TAP AIR PORTUGAL
Deal found 6/4![TAP AIR PORTUGAL logo]()
$804
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:45 am
ORD
- MXP
1 stop18h 35m
United Airlines
Wed 8/1911:20 am
MXP
- ORD
1 stop15h 35m
United Airlines
Deal found 6/6![United Airlines logo]()
$783
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/309:40 pm
ORD
- MXP
Nonstop8h 40m
United Airlines
Thu 8/279:00 am
MXP
- ORD
1 stop12h 55m
United Airlines
Deal found 6/6![United Airlines logo]()
$779
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:15 am
ORD
- MXP
2 stops16h 05m
United Airlines
Wed 8/2611:20 am
MXP
- ORD
1 stop15h 35m
United Airlines
Deal found 6/6![United Airlines logo]()
$787
This Air Canada deal was found by Cheapflights users on 6/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/303:40 pm
ORD
- MXP
1 stop11h 40m
Air Canada
Wed 8/2610:40 am
MXP
- ORD
2 stops16h 25m
Air Canada
Deal found 6/6![Air Canada logo]()
$788
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 pm
ORD
- LIN
1 stop11h 20m
United Airlines
Wed 8/2612:40 pm
LIN
- ORD
1 stop14h 15m
United Airlines
Deal found 6/6![United Airlines logo]()
$791
This Gotogate deal was found by Cheapflights users on 6/6. 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 7/308:45 am
ORD
- LIN
2 stops18h 15m
Multiple Airlines
Thu 8/276:50 am
LIN
- ORD
2 stops20h 15m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$793
This Gotogate deal was found by Cheapflights users on 6/6. 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 7/3011:05 am
ORD
- LIN
2 stops17h 55m
Multiple Airlines
Wed 8/268:00 pm
LIN
- ORD
1 stop24h 20m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$805
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 June 8, 2026.
Search for one-way flight options from Chicago to Italy. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:25 pm
ORD
- MXP
2 stops36h 50m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$261
This Mytrip deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:25 pm
ORD
- MXP
2 stops18h 10m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
ORD
- MXP
2 stops21h 00m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:25 pm
ORD
- LIN
3 stops40h 30m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:25 pm
ORD
- MXP
3 stops30h 45m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Tue 7/2810:25 pm
ORD
- NAP
3 stops25h 50m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Mon 7/2710:25 pm
ORD
- NAP
3 stops27h 45m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
ORD
- NAP
3 stops34h 00m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sat 7/47:25 pm
ORD
- MXP
2 stops21h 40m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:25 am
MDW
- MXP
2 stops23h 40m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/197:25 pm
ORD
- MXP
2 stops21h 00m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$315
This Trip.com deal was found by Cheapflights users on 6/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:25 pm
ORD
- MXP
2 stops15h 40m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$316
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 June 8, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $714 (Trip.com) |
One-way from | $261 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $930 |
Good round-trip deal | $947 or less |
Good one-way deal | $567 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Italy that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 8, 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
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Mon 8/17
9:40 pm-1:20 pm
Nonstop8h 40m
Milan Malpensa
Sun 8/30
9:00 am-2:55 pm
1 stop12h 55m
$779
ChicagoMilan
ORD - LIN
ORDLIN
Chicago O'Hare Intl
Sun 8/23
7:15 pm-12:10 pm
2 stops33h 55m
Milan Linate
Wed 8/26
1:00 pm-4:10 pm
2 stops34h 10m
$781
ChicagoMilan
ORD - LIN
ORDLIN
Chicago O'Hare Intl
Mon 8/3
6:00 pm-12:20 pm
1 stop11h 20m
Milan Linate
Wed 8/19
6:50 am-12:55 pm
1 stop13h 05m
$786
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 8/12
6:05 am-9:25 am
1 stop20h 20m
Milan Malpensa
Wed 8/19
11:40 am-10:36 pm
1 stop17h 56m
$792
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Wed 8/12
9:24 am-10:25 am
2 stops18h 01m
Milan Malpensa
Wed 8/19
11:40 am-10:36 pm
1 stop17h 56m
$796
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 8/3
6:05 am-6:45 am
2 stops17h 40m
Milan Malpensa
Wed 8/19
9:00 am-10:36 pm
2 stops20h 36m
$796
ChicagoMilan
ORD - LIN
ORDLIN
Chicago O'Hare Intl
Tue 8/18
5:10 pm-11:20 am
1 stop11h 10m
Milan Linate
Wed 8/26
11:00 am-8:27 pm
2 stops16h 27m
$799
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Tue 8/4
5:10 pm-3:00 pm
1 stop14h 50m
Palermo Punta Raisi
Tue 8/18
3:45 pm-4:24 pm
2 stops31h 39m
$830
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Sat 9/5
11:20 pm-8:30 am
1 stop26h 10m
Milan Malpensa
Sat 9/12
9:20 am-9:15 pm
1 stop18h 55m
$842
ChicagoMilan
MDW - MXP
MDWMXP
Chicago Midway
Mon 8/17
9:24 am-10:25 am
2 stops18h 01m
Milan Malpensa
Sun 8/30
11:40 am-10:36 pm
1 stop17h 56m
$846
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-MXP
ORD-LIN
ORD-NAP
MDW-MXP
ORD-FLR
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Italy
CHI-IT0
ORD-MXP
ORD-LIN
ORD-NAP
MDW-MXP
What is the cheapest month to book a flight from Chicago to Italy?
Currently, November is the cheapest month in which you can book a flight from Chicago to Italy (average of $594). Flying from Chicago to Italy in July is currently the most expensive (average of $1,076). 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 June 8, 2026.
When flying from Chicago to Italy, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to Italy delayed?
About 31% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 164 minutes.
What is the most punctual flight time for Chicago to Italy flights?
Historically, flights departing in the early afternoon 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?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Italy flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 31% 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 1 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 June 8, 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.
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Crew
7.8
Overall
7.4
Comfort
7.3
Food
7.5
Boarding
7.3
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
MIA - IST
Related info for your journey
Find useful and relevant information for your journey from Chicago to Italy. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Italy
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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 June 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Italy flights
Consider these flights traveling from Chicago to Italy.
Fly to Italy regions
Consider these flights traveling to Italy regions.
Top 10 airlines flying from Chicago to Italy
Discover the top 10 airlines that operate flights from Chicago to Italy. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$337 | Average$524 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$375 | Average$669 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$384 | Average$914 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$395 | Average$693 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$414 | Average$590 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$455 | Average$793 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$455 | Average$860 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$489 | Average$1,019 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$491 | Average$964 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$496 | Average$1,008 | FlexibilityNo cancel fee | On-time69% |