Cheap Flights from Milan to Chicago from $387

Frequently Asked Questions

• What are the cheapest flights from Milan to Chicago (MIL-CHI)?

  Based on Trip.com data, Wizz Air Malta offers one-way fares as low as $387 on Cheapest nonstop routes (e.g. MXP to ORD on Tue, Mar 17), while Scandinavian Airlines offers Cheapest nonstop round-trips from $561 departing on Thu, Mar 19 and returning on Sun, Mar 22.

• Which airlines offer flights from Milan to Chicago?

  At the moment, several airlines serve connecting flights from Milan to Chicago, including: TAP Air Portugal Scandinavian Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.

• When is the best time to book flights from Milan to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Milan to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How can I find the best deals on flights from Milan to Chicago?

  To find best deals on flights from Milan to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, Mar 17, with one-way flights priced at just $387.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Wizz Air Malta.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Milan (MIL) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Milan to Chicago is December, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Milan to Chicago on?

  After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Milan to Chicago on February 18, 2026 with Scandinavian Airlines, with prices starting at $530.

• Which airports can I fly to for Chicago from Milan?

  You can land at any one of the following hubs in Chicago, with Milan Malpensa Airport to O'Hare International Airport (MXP-ORD) is by far the most common option on this route: O'Hare International Airport (ORD) Midway International Airport (MDW) Chicago Rockford International Airport (RFD).

• Is there any time difference between Milan and Chicago?

  The time difference between Chicago and Milan is 7h.

• How do I change or cancel my ticket from Milan to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.