Cheap flights from Chicago to Milan from $253
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 7/20. 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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Air France flights from Chicago to Milan Malpensa Airport
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Scandinavian Airlines flights from Chicago to Milan Malpensa Airport
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How to get the cheapest flight ticket from Chicago to Milan Malpensa Airport
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 cheapest month to fly to Milan Malpensa Airport?
In general, February is the cheapest month to fly from Chicago to Milan Malpensa Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $593. If you don’t want to visit Milan Malpensa Airport in February, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $644.
What is the cheapest day to depart on your flight to Milan Malpensa Airport?
Our data shows that Tuesday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,183. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,495.
What is the cheapest time of day to depart on your flight to Milan Malpensa Airport?
According to our data, the cheapest time of day to fly to Milan Malpensa Airport is in the morning. momondo users have found flights departing from Chicago to Milan Malpensa Airport in the morning for as low as $796. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the evening are often more expensive with an average ticket price of $1,338.
What is the cheapest Chicago to Milan Malpensa flight route?
Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan Malpensa flight prices
How far in advance should I book a flight to Milan Malpensa Airport?
You are more likely to see cheaper flights to Milan Malpensa Airport from Chicago when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Milan Malpensa Airport for around $957 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan Malpensa Airport from Chicago for as low as $693 on momondo.
What cabin class options are available on Chicago to Milan Malpensa flights?
There are 3 cabin classes available to choose from on Chicago to Milan Malpensa 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 Malpensa?
TAP AIR PORTUGAL, Icelandair, and Scandinavian Airlines are the most popular carriers operating from Chicago to Milan Malpensa
What airlines fly to Milan Malpensa Airport?
United Airlines, Scandinavian Airlines and British Airways are the top three most popular airlines that fly to Milan Malpensa Airport from Chicago according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Milan Malpensa Airport. Keep in mind that there are 10 different airlines that fly to Milan Malpensa Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Milan Malpensa Airport on average per day?
As of June 2025, there are 5 flights per day flying from Chicago to Milan Malpensa Airport. 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 Malpensa Airport on average per week?
As of June 2025, there are 35 flights per week flying from Chicago to Milan Malpensa Airport. 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 Malpensa Airport
Cheap Chicago to Milan Malpensa Airport (CHI to MXP) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan Malpensa Airport
How far is Chicago to Milan Malpensa by plane?
There are 4501.5 mi between Chicago and Milan Malpensa. By plane, this route typically takes 11h 55m.
When did momondo last update prices for flights from Chicago to Milan Malpensa Airport?
Prices for flights from Chicago to Milan Malpensa Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Milan Malpensa Airport?
As of June 2025, there are 10 operators available to choose from for flights from Chicago to Milan Malpensa Airport.
How old do you have to be to fly from Chicago to Milan Malpensa Airport?
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 Malpensa Airport.
What documentation or ID do you need to fly to Milan Malpensa Airport?
The required travel and health documents for your Milan Malpensa Airport 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 Malpensa Airport. 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 Malpensa Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Milan Malpensa Airport is Boeing 787 Dreamliner (52.06% of total bookings). The next most popular plane models are Boeing 787-8 Dreamliner (43.97%), Boeing 787-9 Dreamliner (1.53%), and Boeing 787-10 Dreamliner (0.61%).
What is the most popular airline from Chicago to Milan Malpensa Airport?
momondo data reveals that the most frequently booked airline on the route from Chicago to Milan Malpensa Airport is United Airlines, representing 39% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 20%, American Airlines at 11%, and British Airways at 11%.
Best airlines flying from Chicago to Milan Malpensa Airport
Compare and see reviews for airlines that fly from Chicago to Milan Malpensa Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $419 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $423 | Free Cancellation | Rating 7.3 1,388 reviews | |||
| PriceFrom $484 | Free Cancellation | Rating 7.0 499 reviews | |||
| PriceFrom $499 | Free Cancellation | Rating 7.1 1,892 reviews | |||
| PriceFrom $518 | Free Cancellation | Rating 7.3 3,852 reviews | |||
| PriceFrom $536 | Free Cancellation | Rating 6.6 7,019 reviews | |||
| PriceFrom $550 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $575 | Free Cancellation | Rating 7.5 1,466 reviews | |||
| PriceFrom $756 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $806 | Free Cancellation | Rating 7.6 1,080 reviews |
United Airlines Flights From Chicago to Milan Malpensa Airport
United Airlines flies from Chicago to Milan Malpensa Airport around 7 times per week, with 8,801 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Milan Malpensa Airport in the last 72 hours was $756 (round-trip), much lower than the average airfare cost of $1,281 for United Airlines flights on this route.
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Why should I use momondo to find a flight deal from Chicago to Milan?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Milan for you.
Can I find flights from Chicago to Milan with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Milan flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Milan?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Milan from Chicago.
I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.