Helping travelers to find the best flight offers
Below you will find a list of airlines operating flights on the Chicago — Milan route and the starting prices for flights of each specific airline on it.
Starting at $250
Starting at $277
Starting at $365
Starting at $405
Starting at $410
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Milan:
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Unable to find information about the schedule of direct flights from
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Milan. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Milan
A direct flight is the most convenient and comfortable way to fly from Chicago to Milan, despite the fact that sometimes flights with transfers can cost significantly less.
Chicago — Milan
05/19/2025
Departure date
Direct flight
UA416
Starting at $929
Chicago — Milan
05/22/2025
Departure date
Direct flight
UA416
Starting at $1,144
Chicago — Milan
08/07/2025
Departure date
Direct flight
UA416
Starting at $824
Chicago — Milan
08/08/2025
Departure date
Direct flight
UA416
Starting at $820
The cheapest flight ticket from Chicago to Milan according to data for the last 48 hours costs $250
Often the best time to buy tickets from Chicago to Milan is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Milan can be found flying in these months: April, June.
The fastest flights from Chicago to Milan start from 0 hours in the air.
The following airlines operate direct flights on the route Chicago — Milan: United Airlines
The cheapest one-way flight from Chicago to Milan departs on 08/06/2025, is operated by Spirit Airlines and costs $250
The cheapest roundtrip flight from Chicago to Milan departs on 09/09/2025, is operated by Scandinavian Airlines and costs $533
Fastest flight from Chicago to Milan takes 1d 0h
There are no direct flights on this route.
The distance between Chicago and Milan is 7288km (4519 miles). There are 8 direct flights from Chicago to Milan. The time difference between Chicago and Milan is 7h . Flights from Chicago begin at 9:35 PM. The latest flight from Chicago departs at 9:35 PM.
We couldn't find any special offers for flights from Chicago to Milan
