
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $535 (Mytrip) |
One-way from | $373 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $771 |
Good round-trip deal | $655 or less |
Good one-way deal | $990 or less |
Fly from
Fly to
Route
Depart
Return
MilanChicago
LIN - ORD
LINORD
Milan Linate
dim. 5/10
7:25 am-5:04 pm
2 stops16h 39m
Chicago O'Hare Intl
lun. 5/25
7:05 pm-1:35 pm
1 stop11h 30m
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
mer. 5/20
9:00 am-9:09 pm
2 stops19h 09m
Chicago Midway
mer. 5/27
1:59 pm-2:45 pm
2 stops17h 46m
MilanChicago
MXP - MDW
MXPMDW
Milan Malpensa
jeu. 10/1
11:40 am-9:46 pm
1 stop17h 06m
Chicago Midway
jeu. 10/15
1:05 pm-12:05 pm
2 stops16h 00m
MilanChicago
LIN - MDW
LINMDW
Milan Linate
dim. 5/10
6:40 am-6:33 pm
2 stops18h 53m
Chicago Midway
mar. 5/26
7:13 pm-3:55 pm
2 stops13h 42m
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
sam. 5/16
6:45 am-5:20 pm
2 stops17h 35m
Chicago O'Hare Intl
mar. 5/26
6:07 am-6:45 am
1 stop17h 38m
MilanChicago
MXP - ORD
MXPORD
Milan Malpensa
dim. 5/10
6:45 am-5:49 pm
2 stops18h 04m
Chicago O'Hare Intl
lun. 5/25
6:07 am-6:45 am
1 stop17h 38m
MilanChicago
LIN - MDW
LINMDW
Milan Linate
sam. 5/16
6:40 am-6:33 pm
2 stops18h 53m
Chicago Midway
mar. 5/26
6:36 pm-3:55 pm
2 stops14h 19m
MilanChicago
LIN - MDW
LINMDW
Milan Linate
jeu. 10/8
6:40 am-6:37 pm
2 stops18h 57m
Chicago Midway
mar. 10/13
5:35 pm-3:55 pm
2 stops15h 20m
BergamoChicago
BGY - ORD
BGYORD
Bergamo Orio Al Serio
mar. 5/26
5:55 am-7:55 pm
2 stops21h 00m
Chicago O'Hare Intl
mar. 6/2
9:55 am-5:40 pm
2 stops24h 45m
BergamoChicago
BGY - ORD
BGYORD
Bergamo Orio Al Serio
lun. 6/8
10:05 pm-2:50 pm
3 stops23h 45m
Chicago O'Hare Intl
lun. 6/15
8:45 am-5:40 pm
2 stops25h 55m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
The price you pay for your flight from Milan to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $356). Flying from Milan to Chicago in July is currently the most expensive (average of $615). 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 Milan 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.
The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 on average).
About 22% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 208 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Friday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 21% of flights being delayed.
Food
Crew
Boarding
Comfort
Entertainment
Overall
Reviews
Anonymous,Apr 2026
DFW - EWR
Food
Crew
Boarding
Comfort
Entertainment
Overall
Reviews
Anonymous,Apr 2026
DFW - EWR
Food
Crew
Boarding
Comfort
Entertainment
Overall
Reviews
Anonymous,Apr 2026
DFW - EWR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$695 | Average$933 | FlexibilityNo cancel fee | On-time69% |