Cheap Flights from Chicago to Milan from $368

Frequently Asked Questions

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

  Based on Trip.com data, Air Serbia offers one-way fares as low as $368 on Cheapest nonstop routes (e.g. ORD to MXP on Fri, Oct 9), while Scandinavian Airlines offers Cheapest nonstop round-trips from $472 departing on Thu, Sep 17 and returning on Wed, Sep 23.

• Which airlines offer direct flights from Chicago to Milan?

  At the moment, you can catch a nonstop flight from Chicago to Milan with the following airlines, including: United Airlines Lufthansa Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Chicago (CHI) to Milan (MIL) and what is the distance?

  It takes around 8 hours 42 minutes to fly from Chicago (CHI) to Milan (MIL).

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

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Milan 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 many flights are there per week from Chicago to Milan?

  Based on Trip.com data in the past 4 weeks, there is 6 flight per week flying from Chicago to Milan. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA416 (23:14) Lufthansa: S/M/T/W/T/F/S -- LH8871 (23:14)

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

  To find best deals on flights from Chicago to Milan, 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 Fri, Oct 9, with one-way flights priced at just $368.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
  · 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 Milan travel is around January.
  · Get exclusive promo codes for Trip.com app users.

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

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

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

  After crunching the numbers on our August flight calendar, it's currently cheapest to fly from Chicago to Milan on August 30, 2026 with TAP Air Portugal, with prices starting at $592.

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

  You can land at any one of the following hubs in Milan, with O'Hare International Airport to Milan Malpensa Airport (ORD-MXP) is by far the most common option on this route: Milan Malpensa Airport (MXP) Milan Linate Airport (LIN) Il Caravaggio International Airport (BGY) Parma Airport (PMF).

• Is there any time difference between Chicago and Milan?

  The time difference between Milan and Chicago is 7h.

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

  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.

• What is the average cost of a one-way flight from Chicago to Milan?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Chicago to Milan is $862. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Chicago to Milan?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Chicago to Milan is $1,149. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Chicago to Milan on Trip.com?

  Enter Chicago and Milan, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.