Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to Milan
The cheapest flights right now
Chicago – Milan
Outbound – Nov 9, 2026
direct
8h 40m Return – Nov 24, 2026
direct
10h 0m $808
3 days ago
Chicago – Milan
Outbound – Nov 9, 2026
direct
8h 40m Return – Nov 24, 2026
direct
10h 0m $857
2 days ago
Chicago – Milan
Outbound – Nov 9, 2026
direct
8h 40m Return – Nov 24, 2026
direct
10h 0m $856
yesterday
Chicago – Milan
Outbound – Nov 9, 2026
direct
8h 40m Return – Nov 24, 2026
1 stop
12h 55m ZRH
$851
2 days ago
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$556
Average price of a round trip
$731
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
8h40
A flight from Chicago to Milan takes on average 8h40.
Best time
October
According to user searches, the ideal month to go to Milan is October.
Tips for finding a cheap flight from Chicago to Milan
Check out our tips for booking your flight to Milan (Italy) from Chicago (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is November, with an average flight ticket price of $292 (calculation over the last two years). The most touristic season corresponds to the months of October, December and January.
For the cheapest flights, it is advisable to buy your ticket at least 39 days before the departure date.
The airline offering the cheapest flight tickets is TAP Air Portugal. A ticket from the airline TAP Air Portugal to Milan costs on average $590.
The airlines that offer the most flights are United Airlines and United Airlines.
Price of flight tickets from Chicago to Milan
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $556 to $1102
- The average price of a flight ticket is about $731
- Prices are lowest for stays in the month of November
- The month in which booking a ticket is cheaper is: October
info departure city :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is a city in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {fromLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
destination info :
Milan, Italy
airports :
Milan-Linate Airport (LIN)
Milan Malpensa International Airport (MXP)
local time :
Milan is in the country Italy, the time zone is [[timezone]]. In Milan, it is currently {toLocalTime}, the temperature is on average 19°C, with a minimum of 15°C and a maximum of 23°C.
The city of Milan (MIL) has 2 airport(s): Milan-Linate and Milan Malpensa
Useful info about Milan
What is the least touristic period to go to Milan?
If you want to visit Milan during the least touristic period, choose the month of October.
What is the most popular time to travel to Milan?
In Milan, the most popular month is October. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Chicago to Milan?
According to our data, it is recommended to book your flight 39 days before your departure. If you book your flight ticket 6 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Chicago to Milan is Monday.
What are the arrival and destination airports when traveling between Chicago and Milan?
When you leave, you can leave from Chicago-O'Hare, and you will arrive at Bergamo-Orio al Serio, Milan-Linate or Milan Malpensa.
How to reach Chicago airport from the city centre?
The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from Chicago to Milan?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Chicago and Milan?
In summer, the average temperature is 24°C in Milan and 22°C in Chicago. The average rainfall in summer is 129 mm in Milan and 145 mm in Chicago. In summer, it is warmer in Milan and it rains less in Milan. In winter, it is colder in Milan and it rains more in Milan.
