Alitalia Chicago to Milan Flights

Cheapflightsplus.com will find cheap Alitalia flights from Chicago to Milan. Compare airline ticket prices and book air tickets starting from $483 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Alitalia, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Milan by Alitalia

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 march: one-way - $483, two-way – $828.
Direct flights
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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 Arrival Flight Details Flight Time Price
10:45 am — 2:40 pm
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
7h 10m stop
9:15 pm — 11:45 am AZ611 Alitalia
New York — Rome
1h 45m stop
1:30 pm — 2:40 pm AZ2030 Alitalia
Rome — Milan
20h 55m
including layover
Find flight
from$483
10:45 am — 2:10 pm
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
2h 40m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
5h 55m stop
1:00 pm — 2:10 pm AZ2032 Alitalia
Rome — Milan
20h 25m
including layover
Find flight
from$496
10:45 am — 12:10 pm
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
2h 40m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
3h 55m stop
11:00 am — 12:10 pm AZ2068 Alitalia
Rome — Milan
18h 25m
including layover
Find flight
from$513
10:45 am — 10:30 am
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
2h 40m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
2h 5m stop
9:10 am — 10:30 am XZ2223 Ivoire Aero-Services
Rome — Milan
16h 45m
including layover
Find flight
from$522
10:45 am — 10:40 am
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
2h 40m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
2h 25m stop
9:30 am — 10:40 am AZ2022 Alitalia
Rome — Milan
16h 55m
including layover
Find flight
from$623
11:00 am — 10:10 am
+1 day
10:45 am — 2:05 pm AZ3507 Alitalia
Chicago — New York
2h 22m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
1h 55m stop
9:00 am — 10:10 am AZ2028 Alitalia
Rome — Milan
16h 10m
including layover
Find flight
from$487
11:00 am — 11:10 am
+1 day
11:00 am — 2:23 pm AZ3507 Alitalia
Chicago — New York
2h 22m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
2h 55m stop
10:00 am — 11:10 am AZ2036 Alitalia
Rome — Milan
17h 10m
including layover
Find flight
from$490
1:50 pm — 2:40 pm
+1 day
1:50 pm — 4:59 pm AZ5941 Alitalia
Chicago — New York
4h 16m stop
9:15 pm — 11:45 am AZ611 Alitalia
New York — Rome
1h 45m stop
1:30 pm — 2:40 pm AZ2030 Alitalia
Rome — Milan
17h 50m
including layover
Find flight
from$485
7:05 am — 2:10 pm
+1 day
7:05 am — 10:30 am AZ3522 Alitalia
Chicago — New York
6h 15m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
5h 55m stop
1:00 pm — 2:10 pm AZ2032 Alitalia
Rome — Milan
24h 5m
including layover
Find flight
from$487
7:05 am — 10:30 am
+1 day
7:05 am — 10:30 am AZ3522 Alitalia
Chicago — New York
6h 15m stop
4:45 pm — 7:05 am AZ609 Alitalia
New York — Rome
2h 5m stop
9:10 am — 10:30 am XZ2223 Ivoire Aero-Services
Rome — Milan
20h 25m
including layover
Find flight
from$528
*Departure and arrival times are local. Last updated on 02/24/2025

Flight Information

There are 11 flights by Alitalia 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 10:45 am to 7:05 am. Nonstop flight is 16h 10m. The time difference between Chicago and Milan is 7h.

  • The fastest flight 16h 10m
  • Average flight time 18h 8m
  • The earliest flight 10:45 am
  • The latest flight 7:05 am
  • Distance 4530 ml

The cheapest months for traveling to Milan are november (from 483 $), january (from 487 $).

The cheapest flight by Alitalia that our users were able to find is $483. This airfare is economy class on one-way AZ3507 flight for November 13, 2024 leaving O'Hare International in Chicago at 10:45 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Alitalia there are other 3 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):

  • from $367
    Find
  • TK - Turkish Airlines
    from $645
    Find
  • LX - SWISS International Air Lines
    from $386
    Find
See more connecting flights

How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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