Cheap flights from Chicago to Milan

7 nonstop flights a week, 1 of them today. Operated by United Airlines, about 8h 45m in the air, 4,529 mi (7,289 km). Tickets from $350, nonstop from $763.

Flights from Chicago to Milan

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Chicago to Milan

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Chicago to Milan

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Chicago to Milan at a glance

flight time, from 8h 40m to 8h 55m
8h 45m
straight-line distance
4,529 mi (7,289 km)
flights a week
7
flight today
1
departure time
21:35
lowest price, with a connection, 30 December
$350
lowest nonstop price
$763
airline
1

Chicago to Milan ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: December 2026, tickets from $350. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is January 2027: from $493. The average across months is $398.

Chicago to Milan flight schedule

7 flights a week, 1 today, 3 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
UA 416
United Airlines
21:35 , terminal 1
13:15 Milano Malpensa, terminal 1
8h 40m
Daily
Boeing 787-800

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 27 March.

FlightDepartsArrivesDurationDaysAircraft
UA 416
United Airlines
21:25 , terminal 1
13:20 Milano Malpensa, terminal 1
8h 55m
Seasonal
Boeing 787-800
UA 416
United Airlines
21:30 , terminal 1
13:20 Milano Malpensa, terminal 1
8h 50m
Seasonal
Boeing 787
UA 416
United Airlines
21:40 , terminal 1
13:20 Milano Malpensa, terminal 1
8h 40m
Seasonal
Boeing 787

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Milan is 7 hours ahead of Chicago. The search shows seat availability and the price for your date.

Airlines flying Chicago to Milan

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

Airports

Where flights from Chicago to Milan depart and land

Arrival in Milan

7 flights a week, terminal 1, 25 mi (41 km) from the city centre

When to visit Milan

Weather by month

Best time to visit: April, September and October, +18° to +25° by day. In November it is +12° by day and +5° at night, with 10 rainy days.

Jan
+8° 0° 9 days
Feb
+12° +3° 8 days
Mar
+15° +5° 8 days
Apr
+18° +8° 8 days
May
+22° +13° 17 days
Jun
+29° +19° 9 days
Jul
+30° +20° 12 days
Aug
+30° +20° 10 days
Sep
+25° +16° 12 days
Oct
+20° +12° 10 days
Nov
+12° +5° 10 days
Dec
+8° +2° 8 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from Chicago to Milan?
A nonstop flight takes 8 hours 45 minutes on average, from 8h 40m to 8h 55m depending on the flight.
How far is Milan from Chicago?
4,529 mi (7,289 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to Milan?
United Airlines (7 a week).
How many flights a day are there from Chicago to Milan?
1 flight today and 7 a week, about 1 a day on average.
When are the first and last flights from Chicago to Milan?
The flight departs at 21:35 (UA416). Local time.
What is the cheapest month to fly from Chicago to Milan?
December 2026: tickets from $350. The most expensive is January 2027, from $493.
What is the cheapest upcoming date to fly from Chicago to Milan?
30 December 2026 (Wednesday): from $350 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to Milan?
United Airlines: nonstop tickets from $763 on 30 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and Milan?
Milan is 7 hours ahead of Chicago. Schedule times on this page are local to each airport.