Cheap flights from Milan to Chicago from $374
This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 10/1. 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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TAP AIR PORTUGAL flights from Milan to Chicago
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How to get the cheapest flight ticket from Milan to Chicago
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 Milan and Chicago?
What is the cheapest month to fly to Chicago?
The month of November is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $471. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Milan to Chicago during February average around $570.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $858. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $1,009.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Milan to Chicago during this time can be as low as $561. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $915.
What is the cheapest Milan to Chicago flight route?
Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Milan when booking 19 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $712 when searching 19 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as $556 on momondo.
What cabin class options are available on Milan to Chicago flights?
There are 3 cabin classes available to choose from on Milan to Chicago 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 Milan to Chicago?
Icelandair, Air Serbia, and TAP AIR PORTUGAL are the most popular carriers operating from Milan to Chicago
What airlines fly to Chicago?
United Airlines, TAP AIR PORTUGAL and British Airways are the top three most popular airlines that fly to Chicago from Milan according to our data. United Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Milan to Chicago on average per day?
As of June 2025, 4 flights take off from Milan and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 100% of daily flights taking off in the afternoon.
How many flights depart from Milan to Chicago on average per week?
33 flights are operational weekly from Milan to Chicago as of June 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.
When to book flights from Milan to Chicago
Cheap Milan to Chicago (MIL to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago
How far is Milan to Chicago by plane?
The straight-line distance from Milan to Chicago is 4526.2 mi. In terms of flight time, this usually takes a little over 9h 50m.
When did momondo last update prices for flights from Milan to Chicago?
Prices for flights from Milan to Chicago are updated daily.
How many operators does momondo search for flights from Milan to Chicago?
As of June 2025, there are 3 operators available to choose from for flights from Milan to Chicago.
How old do you have to be to fly from Milan to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milan to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Milan to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Milan to Chicago is Boeing 787-8 Dreamliner (55.56% of total bookings). The next most popular plane models are Boeing 787 Dreamliner (28.03%), Boeing 787-9 Dreamliner (2.74%), and Boeing 767-400 (2.74%).
What is the most popular airline from Milan to Chicago?
momondo data reveals that the most frequently booked airline on the route from Milan to Chicago is United Airlines, representing 29% of all bookings. The subsequent popular airlines are Aer Lingus at 17%, TAP AIR PORTUGAL at 17%, and British Airways at 14%.
Best airlines flying from Milan to Chicago
Compare and see reviews for airlines that fly from Milan to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $525 | Free Cancellation | Rating 6.6 7,008 reviews | |||
| PriceFrom $537 | Free Cancellation | Rating 7.1 1,885 reviews | |||
| PriceFrom $626 | Free Cancellation | Rating 7.4 8,790 reviews |
United Airlines Flights From Milan to Chicago
Across 5 United Airlines flights from Milan to Chicago this week, the average price was $943, with the best United Airlines deals starting from $626 round-trip. 8,790 users have rated United Airlines on momondo, with an average score of 7.4/10.
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Milan to Chicago?
It is quick and easy to find Milan to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Milan to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Milan with this policy.
How can momondo help me find flights from Milan to Chicago?
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 Chicago from Milan.
I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Milan are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.