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 O'Hare Intl Airport
Our best TAP AIR PORTUGAL deals on Milan to Chicago O'Hare Intl Airport flight tickets
Scandinavian Airlines flights from Milan to Chicago O'Hare Intl Airport
Our best Scandinavian Airlines deals on Milan to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Milan to Chicago O'Hare Intl 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 typical price of a round-trip flight between Milan and Chicago O'Hare Intl Airport?
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Milan averaging around $526.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Sunday is the most expensive day to depart from Milan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,009.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Milan in the morning is the least expensive time of day to depart. momondo users have found prices as low as $586 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $915. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Milan to Chicago O'Hare Intl flight route?
Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Milan when booking 19 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport from Milan for as low as $556 on momondo.
What cabin class options are available on Milan to Chicago O'Hare Intl flights?
There are 3 cabin classes available to choose from on Milan to Chicago O'Hare Intl 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 O'Hare Intl?
Icelandair, Air Serbia, and TAP AIR PORTUGAL are the most popular carriers operating from Milan to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, TAP AIR PORTUGAL and British Airways are the top three most popular airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Milan to Chicago O'Hare Intl Airport on average per day?
The number of flights available between Milan and Chicago O'Hare Intl Airport is 4 per day as of June 2025. The most frequent departure time is 3:00PM, with 100% of daily flights leaving in the afternoon.
How many flights depart from Milan to Chicago O'Hare Intl Airport on average per week?
As of June 2025, 33 flights take off from Milan and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.
When to book flights from Milan to Chicago O'Hare Intl Airport
Cheap Milan to Chicago O'Hare Intl Airport (MIL to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago O'Hare Intl Airport
How far is Milan to Chicago O'Hare Intl by plane?
Milan and Chicago O'Hare Intl are 4532.4 mi apart from one another. Flights usually cover this in 9h 50m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Milan to Chicago O'Hare Intl Airport?
Prices for flights from Milan to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Milan to Chicago O'Hare Intl Airport?
The number of operators available for flights from Milan to Chicago O'Hare Intl Airport is 3 as of June 2025.
How old do you have to be to fly from Milan to Chicago O'Hare Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Milan to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked plane model on the route from Milan to Chicago O'Hare Intl Airport is Boeing 787-8 Dreamliner, representing 55.56% of all bookings. The subsequent popular models are Boeing 787 Dreamliner at 28.03%, Boeing 787-9 Dreamliner at 2.74%, and Boeing 767-400 at 2.74%.
What is the most popular airline from Milan to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Milan and Chicago O'Hare Intl Airport, the leading airline is United Airlines, making up 29% of the total bookings. Other popular airlines include Aer Lingus with 25%, British Airways with 16%, and Lufthansa with 15%.
Best airlines flying from Milan to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Milan to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport
United Airlines flies from Milan to Chicago O'Hare Intl Airport around 5 times per week, with 8,790 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Milan to Chicago O'Hare Intl Airport in the last 72 hours was $626 (round-trip), much lower than the average airfare cost of $943 for United Airlines flights on this route.
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Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Milan to Chicago?
Finding the right flight to Chicago from Milan is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Milan to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Milan on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Milan to Chicago?
momondo helps you find the best flight between Milan and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Milan to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.