Cheap flights from Chicago to Milan

Flight deals from Chicago to Milan

Below you can see the best deals on flights Chicago — Milan for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 29 August, from $263.

Top 10 cheap flights from Chicago to Milan

When is the best time to book a flight from Chicago to Milan?

The price of a flight from Chicago to Milan changes depending on how far ahead you book. For the best chance of a lower fare, book around 14 days before departure, when the average ticket costs about $516. Fares also tend to climb as the departure date gets closer.

About the Chicago — Milan flight

Looking for cheap flights from Chicago to Milan? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Milan ticket online at the best price.

The route has direct flights — around 14 flights per week, flights are operated by United Airlines, a nonstop flight takes about 8 h 40 min, the distance between the cities is around 7,308 km.

Planning your trip? You may find our Milan travel guide, how to get from the airport into town and Milan weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

from $263Min. price

AugustCheapest

DecemberPeak season

YesDirect flights

7,308 kmDistance

8 h 40 minTravel time

1Airlines

14 / wkFlights

Flight schedule from Chicago to Milan

The table shows direct flights from Chicago to Milan on the selected date. The flight takes approximately 8 h 40 min. Regular flights are operated by United Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Milano Malpensa Airport, Orio al Serio International Airport and Milano Linate Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today

Any time

Last update: 08 Aug 2026

Airline

Flight

Departure

Arrival

Duration

Days

Status

Below is a calendar of the lowest flight ticket prices for Chicago — Milan by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $263 in August, and the most expensive are around $483 in December. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

Prices by month

Average one-way fares from Chicago to Milan by month. Tickets are usually cheapest in February (around $397) and priciest in August (about $706) — use the table and chart below to pick the best time to fly.

Month	Average price	Level	Month	Average price	Level	Month	Average price	Level
Jan	$419	low	May	$530	medium	Sep	$574	medium
Feb	$397	low	Jun	$662	high	Oct	$485	medium
Mar	$441	medium	Jul	$684	high	Nov	$430	low
Apr	$463	medium	Aug	$706	high	Dec	$640	high

Some values are estimated based on seasonality.

When to fly

Weather in Milan: it is warmest in July (up to 30 °C on average) and coolest in December (around 8 °C). The driest month is February.

Tickets are usually cheapest in August and most expensive in December. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Milan

Dry and wet days · Milan

Wind speed and direction · Milan

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How to get the best deal on a Chicago — Milan ticket

Book ahead: fares for Chicago — Milan are usually lower 3–8 weeks before departure than at the last minute.
Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
Chicago is served by more than one airport — compare fares and travel time to each before you book.
The cheapest month to fly to Milan is usually August — plan your trip around it if your dates are flexible.
Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Flights on the Chicago — Milan route are operated by 1 airline; United Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

United AirlinesUA
5x/week
WebsiteFleet: 956165M pax/year
- Direct flight ORD → MXP5x/week
100.0%Open →

Cities and airports on the Chicago — Milan route

Flights Chicago — Milan depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Milano Malpensa Airport, Orio al Serio International Airport and Milano Linate Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI

United States

About the city How to get there Weather All about the country United States

Arrival

Milan

MIL

Italy

About the city How to get there Weather All about the country Italy

Departure airports

O'Hare International AirportORD
About the airport
Chicago Midway International AirportMDW
About the airport
Midway International AirportNOH
About the airport
Chicago Rockford International AirportRFD
About the airport

Arrival airports

Milano Malpensa AirportMXP
About the airport
Orio al Serio International AirportBGY
About the airport
Milano Linate AirportLIN
About the airport

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Frequently asked questions about the Chicago — Milan flight

How long is the flight from Chicago to Milan?

A nonstop Chicago — Milan flight takes about 8 h 40 min — the distance between the cities is around 7,308 km.

How far is it from Chicago to Milan?

The distance from Chicago to Milan is about 7,308 km, which a nonstop flight covers in around 8 h 40 min.

Are there direct flights from Chicago to Milan?

Yes, there are nonstop flights Chicago — Milan — around 14 flights per week.

Which airlines fly from Chicago to Milan?

Airlines operating Chicago — Milan include United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Milan flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Milano Malpensa Airport, Orio al Serio International Airport, Milano Linate Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Milan?

The price of a Chicago — Milan ticket depends on your travel date, season and demand: it is usually cheapest to fly in August, and most expensive in December. Tickets typically cost between $263 and $483. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Milan?

Flights Chicago — Milan are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is August. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Milan?

To catch a low fare Chicago — Milan, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually August.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.