
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $761 (Mytrip) |
One-way from | $300 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $1,098 |
Good round-trip deal | $1,291 or less |
Good one-way deal | $794 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoMilan
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Fri 8/21
10:07 am-10:40 am
2 stops17h 33m
Milan Malpensa
Sun 8/30
9:20 am-4:10 pm
1 stop13h 50m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Fri 10/16
4:55 pm-11:35 am
1 stop11h 40m
Bergamo Orio Al Serio
Mon 10/19
7:30 am-5:50 pm
2 stops17h 20m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Mon 8/31
7:15 pm-1:15 am
2 stops23h 00m
Bergamo Orio Al Serio
Mon 9/7
1:35 pm-4:10 pm
2 stops33h 35m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Fri 8/21
9:30 pm-11:50 pm
1 stop19h 20m
Bergamo Orio Al Serio
Tue 8/25
6:00 am-5:50 pm
2 stops18h 50m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Wed 8/5
9:50 am-10:30 pm
2 stops29h 40m
Bergamo Orio Al Serio
Tue 8/18
9:15 pm-4:00 pm
2 stops25h 45m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Mon 9/7
7:25 pm-9:50 pm
2 stops19h 25m
Bergamo Orio Al Serio
Mon 9/14
8:40 am-6:15 pm
2 stops16h 35m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Sun 10/25
6:40 pm-1:50 pm
1 stop13h 10m
Bergamo Orio Al Serio
Thu 11/5
6:45 am-2:55 pm
1 stop15h 10m
ChicagoBergamo
ORD - BGY
ORDBGY
Chicago O'Hare Intl
Sun 9/6
3:45 pm-12:10 pm
1 stop13h 25m
Bergamo Orio Al Serio
Sun 9/13
10:50 pm-2:25 pm
1 stop22h 35m
ChicagoMilan
MDW - LIN
MDWLIN
Chicago Midway
Sun 7/19
1:18 pm-11:20 am
2 stops15h 02m
Milan Linate
Tue 8/4
6:40 am-6:33 pm
2 stops18h 53m
ChicagoMilan
ORD - LIN
ORDLIN
Chicago O'Hare Intl
Wed 8/19
3:00 pm-10:10 am
1 stop12h 10m
Milan Linate
Thu 8/27
7:00 am-1:10 pm
1 stop13h 10m
| 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star |
Currently, July is the cheapest month in which you can book a flight from Chicago to Milan (average of $187). Flying from Chicago to Milan in June is currently the most expensive (average of $671). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Milan as you normally would.
The most flights from CHI to MIL are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
Copenhagen (CPH) – chosen by Cheapflights users on 38% of 1-stop itineraries from Chicago to Milan on Cheapflights.
Montreal (YUL) is the most affordable 1-stop option, with an average round-trip price of $613.
Flights via Montreal (YUL) have the shortest average one-way travel time for 1-stop routes: 11h 20m.
Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 48m.
The price you pay for your flight from Chicago to Milan may vary depending on when you book. For the best chance of a lower fare, look to book 8 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
Overall
Boarding
Crew
Entertainment
Food
Comfort
Reviews
Henry,May 2026
PRG - CPH
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$401 | Average$629 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$410 | Average$572 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$493 | Average$799 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$534 | Average$653 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$627 | Average$828 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$644 | Average$968 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$739 | Average$1,237 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$840 | Average$1,235 | FlexibilityNo cancel fee | On-time76% |