Air Canada Chicago to Milan Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Air Canada flights from Chicago to Milan. Compare airline ticket prices and book air tickets starting from $505 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Air Canada, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Milan by Air Canada

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in february: one-way - $505, two-way – $866.

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Cheap Flights from Chicago to Milan by Air Canada

Look at the list of plane tickets for the most connecting flights by Air Canada, their prices start from $505. There’re no direct flights. The fastest connecting flight – 11h 45m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $545 Find flight	3:35 pm Chicago O'Hare International	10:20 am+1 день Milan Malpensa	11h 45m layover 1h 38m - Montreal	Air Canada	AC8962 AC894
from $545 Find flight	11:35 am Chicago O'Hare International	10:20 am+1 день Milan Malpensa	15h 45m layover 5h 38m - Montreal	Air Canada	AC8960 AC894
from $709 Find flight	2:01 pm Chicago O'Hare International	10:20 am+1 день Milan Malpensa	13h 19m layover 3h 6m - Montreal	Air Canada	AC3335 AC894
from $981 Find flight	5:58 pm Chicago O'Hare International	10:20 am+2 дня Milan Malpensa	33h 22m layover 23h 8m - Montreal	Air Canada	AC4048 AC894
from $505 Find flight	3:35 pm Chicago O'Hare International	2:50 pm+1 день Milan Malpensa	16h 15m layover 1h 33m - Montreal 3h 15m - Barcelona	Air Canada	AC8962 AC822 W46330
from $532 Find flight	11:35 am Chicago O'Hare International	2:50 pm+1 день Milan Malpensa	20h 15m layover 5h 33m - Montreal 3h 15m - Barcelona	Air Canada	AC8960 AC822 W46330
from $549 Find flight	11:35 am Chicago O'Hare International	2:10 pm+1 день Milan Malpensa	19h 35m layover 5h 33m - Montreal 2h 40m - Barcelona	Air Canada	AC8960 AC822 VY6338
from $565 Find flight	11:35 am Chicago O'Hare International	12:35 pm+1 день Milan Malpensa	18h 0m layover 5h 23m - Montreal 2h 5m - Munich	Air Canada	AC8960 AC9098 AC7376
from $565 Find flight	11:35 am Chicago O'Hare International	4:35 pm+1 день Milan Malpensa	22h 0m layover 5h 23m - Montreal 6h 5m - Munich	Air Canada	AC8960 AC9098 AC9216
from $565 Find flight	11:35 am Chicago O'Hare International	2:05 pm+1 день Milan Linate	19h 30m layover 3h 13m - Montreal 5h 25m - Frankfurt	Air Canada	AC8960 AC844 AC9114
from $565 Find flight	11:35 am Chicago O'Hare International	4:55 pm+1 день Milan Linate	22h 20m layover 3h 13m - Montreal 8h 15m - Frankfurt	Air Canada	AC8960 AC844 AC9545
from $569 Find flight	9:50 am Chicago O'Hare International	2:00 pm+1 день Milan Malpensa	21h 10m layover 8h 5m - Toronto 2h 40m - Zurich	Air Canada	AC8902 AC880 AC6786
from $570 Find flight	4:00 pm Chicago O'Hare International	4:35 pm+1 день Milan Malpensa	17h 35m layover 1h 4m - Toronto 5h 40m - Munich	Air Canada	AC506 AC836 AC9216
from $570 Find flight	2:05 pm Chicago O'Hare International	4:35 pm+1 день Milan Malpensa	19h 30m layover 2h 59m - Toronto 5h 40m - Munich	Air Canada	AC504 AC836 AC9216
from $570 Find flight	9:50 am Chicago O'Hare International	4:35 pm+1 день Milan Malpensa	23h 45m layover 7h 20m - Toronto 5h 40m - Munich	Air Canada	AC8902 AC836 AC9216
from $596 Find flight	7:20 am Chicago O'Hare International	10:00 am+1 день Milan Linate	19h 40m layover 7h 28m - Montreal 1h 20m - Frankfurt	Air Canada	AC8958 AC844 EN8800

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 01/31/2025

Air Canada Flight Schedule Chicago to Milan

Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
11:35 am — 10:20 am +1 day	11:35 am — 2:47 pm AC8960 Air Canada Chicago — Montreal 5h 38m stop 8:25 pm — 10:20 am AC894 Air Canada Montreal — Milan	15h 45m including layover	Find flight from$545
12:52 pm — 10:20 am +1 day	9:05 pm — 11:43 pm AC4899 Air Canada Chicago — Toronto 1h 15m stop 8:45 pm — 10:30 am AC894 Air Canada Toronto — Milan	14h 28m including layover	Find flight from$1451
3:35 pm — 10:20 am +1 day	3:35 pm — 6:47 pm AC8962 Air Canada Chicago — Montreal 1h 38m stop 8:25 pm — 10:20 am AC894 Air Canada Montreal — Milan	11h 45m including layover	Find flight from$545
6:39 pm — 10:20 am +2 days	6:38 pm — 9:25 pm AC4994 Air Canada Chicago — Toronto 19h 35m stop 5:00 pm — 10:20 am AC894 Air Canada Toronto — Milan	32h 41m including layover	Find flight from$4448
7:20 am — 10:20 am +1 day	7:20 am — 10:32 am AC8958 Air Canada Chicago — Montreal 9h 53m stop 8:25 pm — 10:20 am AC894 Air Canada Montreal — Milan	20h including layover	Find flight from$545
8:30 pm — 10:20 am +2 days	8:25 pm — 11:06 pm AC510 Air Canada Chicago — Toronto 17h 49m stop 5:00 pm — 10:20 am AC894 Air Canada Toronto — Milan	30h 50m including layover	Find flight from$4448
10:53 am — 2:05 pm +1 day	10:51 am — 1:42 pm AC4407 Air Canada Chicago — Toronto 2h 48m stop 4:30 pm — 6:30 am AC840 Air Canada Toronto — Frankfurt 6h 20m stop 1:05 pm — 2:20 pm AC9114 Air Canada Frankfurt — Milan	20h 12m including layover	Find flight from$571
10:53 am — 2:05 pm +1 day	10:51 am — 1:42 pm AC4407 Air Canada Chicago — Toronto 7h 43m stop 9:25 pm — 11:10 am AC842 Air Canada Toronto — Frankfurt 1h 40m stop 12:50 pm — 2:05 pm AC9114 Air Canada Frankfurt — Milan	20h 12m including layover	Find flight from$571
11:35 am — 2:50 pm +1 day	11:35 am — 2:47 pm AC8960 Air Canada Chicago — Montreal 5h 33m stop 8:25 pm — 9:50 am AC822 Air Canada Montreal — Barcelona 3h 15m stop 1:05 pm — 2:50 pm W46330 Aero Services Executive Barcelona — Milan	20h 15m including layover	Find flight from$532
1:04 pm — 4:55 pm +1 day	12:52 pm — 3:45 pm AC4899 Air Canada Chicago — Toronto 5h 40m stop 9:25 pm — 11:10 am AC842 Air Canada Toronto — Frankfurt 4h 30m stop 3:40 pm — 4:55 pm AC9545 Air Canada Frankfurt — Milan	20h 51m including layover	Find flight from$571
1:04 pm — 12:35 pm +1 day	12:51 pm — 3:45 pm AC4899 Air Canada Chicago — Toronto 4h stop 7:45 pm — 9:50 am AC836 Air Canada Toronto — Munich 1h 40m stop 11:30 am — 12:35 pm AC7376 Air Canada Munich — Milan	16h 31m including layover	Find flight from$734
2:05 pm — 4:35 pm +1 day	2:05 pm — 4:46 pm AC504 Air Canada Chicago — Toronto 2h 59m stop 7:45 pm — 9:50 am AC836 Air Canada Toronto — Munich 5h 40m stop 3:30 pm — 4:35 pm AC9216 Air Canada Munich — Milan	19h 30m including layover	Find flight from$570
2:05 pm — 2:05 pm +1 day	2:05 pm — 4:46 pm AC504 Air Canada Chicago — Toronto 1h 29m stop 6:15 pm — 7:50 am AC9104 Air Canada Toronto — Frankfurt 5h stop 1:05 pm — 2:20 pm AC9114 Air Canada Frankfurt — Milan	17h including layover	Find flight from$571
3:35 pm — 2:50 pm +1 day	3:35 pm — 6:47 pm AC8962 Air Canada Chicago — Montreal 1h 33m stop 8:25 pm — 9:50 am AC822 Air Canada Montreal — Barcelona 3h 15m stop 1:05 pm — 2:50 pm W46330 Aero Services Executive Barcelona — Milan	16h 15m including layover	Find flight from$505
4:00 pm — 4:35 pm +1 day	4:00 pm — 6:41 pm AC506 Air Canada Chicago — Toronto 1h 4m stop 7:45 pm — 9:50 am AC836 Air Canada Toronto — Munich 5h 40m stop 3:30 pm — 4:35 pm AC9216 Air Canada Munich — Milan	17h 35m including layover	Find flight from$570
4:00 pm — 2:05 pm +1 day	4:00 pm — 6:41 pm AC506 Air Canada Chicago — Toronto 2h 44m stop 9:30 pm — 11:10 am AC842 Air Canada Toronto — Frankfurt 1h 40m stop 1:05 pm — 2:20 pm AC9114 Air Canada Frankfurt — Milan	15h 5m including layover	Find flight from$571
5:01 pm — 4:55 pm +1 day	4:52 pm — 7:45 pm AC5014 Air Canada Chicago — Toronto 1h 40m stop 9:25 pm — 11:10 am AC842 Air Canada Toronto — Frankfurt 4h 30m stop 3:40 pm — 4:55 pm AC9545 Air Canada Frankfurt — Milan	16h 54m including layover	Find flight from$571
5:01 pm — 1:55 pm +1 day	4:52 pm — 7:45 pm AC5014 Air Canada Chicago — Toronto 1h 40m stop 9:30 pm — 11:10 am AC842 Air Canada Toronto — Frankfurt 1h 30m stop 12:35 pm — 1:50 pm EN8810 Air Dolomiti Frankfurt — Milan	13h 54m including layover	Find flight from$622
7:20 am — 12:35 pm +1 day	7:20 am — 10:32 am AC8958 Air Canada Chicago — Montreal 9h 38m stop 8:10 pm — 9:25 am AC9098 Air Canada Montreal — Munich 2h 5m stop 11:30 am — 12:35 pm AC7376 Air Canada Munich — Milan	22h 15m including layover	Find flight from$565
9:50 am — 2:00 pm +1 day	9:50 am — 12:30 pm AC8902 Air Canada Chicago — Toronto 8h 5m stop 8:30 pm — 10:25 am AC880 Air Canada Toronto — Zurich 2h 40m stop 1:05 pm — 2:00 pm AC6786 Air Canada Zurich — Milan	21h 10m including layover	Find flight from$569
9:50 am — 4:35 pm +1 day	9:50 am — 12:25 pm AC8902 Air Canada Chicago — Toronto 7h 20m stop 7:45 pm — 9:50 am AC836 Air Canada Toronto — Munich 5h 40m stop 3:30 pm — 4:35 pm AC9216 Air Canada Munich — Milan	23h 45m including layover	Find flight from$570

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 01/31/2025

Flight Information

There are 99 flights by Air Canada from Chicago to Milan every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate.

Departures start from 10:53 am to 9:50 am. Nonstop flight is 11h 45m. The time difference between Chicago and Milan is 7h.

The fastest flight 11h 45m
Average flight time 18h
The earliest flight 10:53 am
The latest flight 9:50 am
Distance 4530 ml

The cheapest months for traveling to Milan are november (from 447 $), december (from 451 $), january (from 495 $).

The most expensive and popular months are february (from 505 $), january (from 495 $), december (from 451 $).

The cheapest flight by Air Canada that our users were able to find is $505. This airfare is economy class on one-way AC8962 flight for February 21, 2025 leaving O'Hare International in Chicago at 3:35 pm, it includes all taxes and additional fees.

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Air Canada Airplanes on the Route

List of the most popular Air Canada airplanes flying from Chicago to Milan:

Boeing 737-800

from $1 451

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Embraer Lineage 1000

from $1 503

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Other Popular Airlines on the Route

Besides Air Canada there are other 17 airline carriers between Chicago and Milan. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Milan.

Nonstop flights

There’re no direct flights on this route. Try flights with stops.

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Connecting Flights

List of flights with layovers (1 and more stops):

UA - United Airlines

from $367

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FI - Icelandair

from $337

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LO - LOT

from $445

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OS - Austrian Airlines

from $551

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EI - Aer Lingus

from $732

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JU - Air Serbia

from $521

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LX - SWISS International Air Lines

from $386

Find
F9 - Frontier Airlines

from $543

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TK - Turkish Airlines

from $503

Find
AY - Finnair

from $571

Find
SK - SAS

from $600

Find

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