Cheap flights from Chicago to Milan from $269
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 7/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Milan
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Milan?
What is the cheapest month to fly to Milan?
The month of November is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $601. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $670.
What is the cheapest day to depart on your flight to Milan?
Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,186. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,580.
What is the cheapest time of day to depart on your flight to Milan?
In the morning is the cheapest time of day to fly from Chicago to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,364. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Milan flight route?
Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices
How far in advance should I book a flight to Milan?
You are more likely to see cheaper flights to Milan from Chicago when booking 25 weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $1,007 when searching 25 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $761 on momondo.
What cabin class options are available on Chicago to Milan flights?
There are 3 cabin classes available to choose from on Chicago to Milan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Milan?
TAP AIR PORTUGAL, Air Serbia, and Scandinavian Airlines are the most popular carriers operating from Chicago to Milan
What airlines fly to Milan?
United Airlines, Scandinavian Airlines and British Airways are the top three most popular airlines that fly to Milan from Chicago according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 13 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Milan on average per day?
As of April 2025, there are 5 flights per day flying from Chicago to Milan. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.
How many flights depart from Chicago to Milan on average per week?
As of April 2025, there are 35 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Chicago to Milan
Cheap Chicago to Milan (CHI to MIL) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan
How far is Chicago to Milan by plane?
There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 10h 45m.
When did momondo last update prices for flights from Chicago to Milan?
Prices for flights from Chicago to Milan are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Milan?
The number of operators available for flights from Chicago to Milan is 13 as of April 2025.
How old do you have to be to fly from Chicago to Milan?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.
What documentation or ID do you need to fly to Milan?
The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Milan?
Based on momondo bookings for flights between Chicago and Milan, the leading plane model is Boeing 787 Dreamliner, making up 50.83% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 44.87%, Boeing 787-9 Dreamliner with 1.66%, and Boeing 787-10 Dreamliner with 0.83%.
What is the most popular airline from Chicago to Milan?
momondo data reveals that the most frequently booked airline on the route from Chicago to Milan is United Airlines, representing 24% of all bookings. The subsequent popular airlines are Aer Lingus at 20%, Scandinavian Airlines at 17%, and ITA Airways at 8%.
Best airlines flying from Chicago to Milan
Compare and see reviews for airlines that fly from Chicago to Milan with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $443 | Free Cancellation | Rating 7.3 1,349 reviews | |||
| PriceFrom $485 | Free Cancellation | Rating 7.0 487 reviews | |||
| PriceFrom $499 | Free Cancellation | Rating 7.1 1,851 reviews | |||
| PriceFrom $518 | Free Cancellation | Rating 7.3 3,790 reviews | |||
| PriceFrom $550 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $558 | Free Cancellation | Rating 7.0 1,076 reviews | |||
| PriceFrom $567 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $575 | Free Cancellation | Rating 7.4 1,446 reviews | |||
| PriceFrom $584 | Free Cancellation | Rating 6.7 967 reviews | |||
| PriceFrom $619 | Free Cancellation | Rating 6.6 6,842 reviews |
SWISS Flights From Chicago to Milan
SWISS operates around 7 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,248, but momondo users have found SWISS deals from Chicago to Milan from as low as $1,113 round-trip. SWISS has been scored 7.5/10 in 1,588 reviews.
United Airlines Flights From Chicago to Milan
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Milan start from as low as $784 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $1,336. United Airlines operates 7 flights to Milan from Chicago in an average week. Users have rated it 7.4/10 across 8,696 reviews.
Traveling to a place near Milan?
Book flights to Milan if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Milan?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.
Can I find flights from Chicago to Milan with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.
How can momondo help me find flights from Chicago to Milan?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.
I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.