
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 |
Fly from
Fly to
Route
Depart
Return
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
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
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
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
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
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
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
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
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
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
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.
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.
About 31% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 164 minutes.
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.
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.
Over the last year, American Airlines have had the lowest number of delays on this route, with just 31% of flights being delayed.
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.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Anonymous,May 2026
MIA - IST
| 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% |