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Cheap Flights from Chicago (ORD) to Milan (MXP)

View AU$630 flight on Sat, 6 Mar 2027Opens in a new window

Popular airlines from Chicago O'Hare International Airport (ORD) to Malpensa International Airport (MXP)

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Cheap Flights from Chicago (ORD) to Milan (MXP)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Turkish Airlines
Tue, 1 Dec - Sun, 13 Dec
ORD
Chicago
MXP
Milan
AU$1,008 Return, found 6 days ago
AU$1,008
Return
found 6 days ago
Select Turkish Airlines flight, departing Tue, 1 Dec from Chicago to Milan, returning Sun, 13 Dec, priced at AU$1,008 found 6 days ago
United
Tue, 1 Dec - Sun, 13 Dec
ORD
Chicago
MXP
Milan
AU$1,125 Return, found 6 days ago
AU$1,125
Return
found 6 days ago
Select United flight, departing Tue, 1 Dec from Chicago to Milan, returning Sun, 13 Dec, priced at AU$1,125 found 6 days ago
Delta
Wed, 24 Mar - Tue, 30 Mar
ORD
Chicago
MXP
Milan
AU$1,128 Return, found 6 days ago
AU$1,128
Return
found 6 days ago
Select Delta flight, departing Wed, 24 Mar from Chicago to Milan, returning Tue, 30 Mar, priced at AU$1,128 found 6 days ago
Lufthansa
Wed, 24 Mar - Tue, 30 Mar
ORD
Chicago
MXP
Milan
AU$1,134 Return, found 6 days ago
AU$1,134
Return
found 6 days ago
Select Lufthansa flight, departing Wed, 24 Mar from Chicago to Milan, returning Tue, 30 Mar, priced at AU$1,134 found 6 days ago
Swiss International Air Lines
Wed, 24 Mar - Tue, 30 Mar
ORD
Chicago
MXP
Milan
AU$1,139 Return, found 6 days ago
AU$1,139
Return
found 6 days ago
Select Swiss International Air Lines flight, departing Wed, 24 Mar from Chicago to Milan, returning Tue, 30 Mar, priced at AU$1,139 found 6 days ago
TAP Portugal
Fri, 28 Aug - Fri, 4 Sept
ORD
Chicago
MXP
Milan
AU$1,147 Return, found 5 days ago
AU$1,147
Return
found 5 days ago
Select TAP Portugal flight, departing Fri, 28 Aug from Chicago to Milan, returning Fri, 4 Sept, priced at AU$1,147 found 5 days ago
Air Canada
Tue, 1 Dec - Sun, 13 Dec
ORD
Chicago
MXP
Milan
AU$1,157 Return, found 6 days ago
AU$1,157
Return
found 6 days ago
Select Air Canada flight, departing Tue, 1 Dec from Chicago to Milan, returning Sun, 13 Dec, priced at AU$1,157 found 6 days ago
Scandinavian Airlines
Tue, 1 Dec - Sun, 13 Dec
ORD
Chicago
MXP
Milan
AU$1,172 Return, found 6 days ago
AU$1,172
Return
found 6 days ago
Select Scandinavian Airlines flight, departing Tue, 1 Dec from Chicago to Milan, returning Sun, 13 Dec, priced at AU$1,172 found 6 days ago
KLM
Wed, 24 Mar - Tue, 30 Mar
ORD
Chicago
MXP
Milan
AU$1,209 Return, found 6 days ago
AU$1,209
Return
found 6 days ago
Select KLM flight, departing Wed, 24 Mar from Chicago to Milan, returning Tue, 30 Mar, priced at AU$1,209 found 6 days ago
British Airways
Tue, 1 Dec - Sun, 13 Dec
ORD
Chicago
MXP
Milan
AU$1,258 Return, found 6 days ago
AU$1,258
Return
found 6 days ago
Select British Airways flight, departing Tue, 1 Dec from Chicago to Milan, returning Sun, 13 Dec, priced at AU$1,258 found 6 days ago

Find the cheapest month to fly from Chicago (ORD) to Milan (MXP)

April is typically the cheapest month to fly

From AU$575 - AU$1,117 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) cost?
You can find one-way and return flights from ORD to MXP with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to MXP ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD) to Milan (MXP)?
The cheapest months to fly from Chicago, IL (ORD) to Milan (MXP) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
Only one airline offers direct flights from Chicago O'Hare International Airport (ORD) to Milan Malpensa International Airport (MXP). United operates 7 direct flights from ORD to MXP every week.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
Icelandair offers one of the cheapest connecting return flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) starting from around AU$1997. United is one of the cheapest airlines offering nonstop return flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.), with tickets starting from around AU$2344 for flights that can be booked for departure within the next year. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. American Airlines offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD) to Milan (MXP)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
You'll find around 122 connecting flights per day from Chicago O'Hare International (ORD) to Milan Malpensa International (MXP). Some common connection points include John F. Kennedy International (JFK), Pearson International (YYZ), and Logan International (BOS).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) typically departs around 5:00 AM local time. This service is operated by American Airlines and is a seasonal offering, active in June. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
You'll generally find the most flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) on a Tuesday, with around 95 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, United, and Delta. Flight options are notably more abundant on Tuesdays compared to other days of the week, offering you a wider selection.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) are in the late evening, from 9pm to midnight. Many major carriers, including United, Lufthansa and American Airlines, offer flights during this window. Many travellers prefer these times because you can make the most of your day in Chicago before your evening flight, and you'll arrive in Milan in the morning, ready to start your day.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
A non-stop flight from Chicago O'Hare International Airport (ORD) to Milan Malpensa International Airport (MXP) typically takes around 8 hours 48 minutes, covering a distance of approximately 7,260 kilometers. If you opt for a flight with one stop, your journey will usually be longer, taking about 12 hours 30 minutes. Flights with two or more stops will extend your travel time even further, to around 17 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some flexibility in your travel plans.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
Yes, you can fly business class or first class between ORD and MXP. Airlines that offer business class service on this route include:
  • Lufthansa
  • Iberia
  • Air France
  • Swiss International Air Lines
  • TAP Portugal
  • British Airways
  • Air Serbia
  • Air Canada
  • JetBlue Airways
  • Icelandair
  • Turkish Airlines
  • SAS
  • Emirates
  • LOT-Polish Airlines
  • United
  • Royal Jordanian
  • Republic Airlines
  • Delta
  • Finnair
  • Ethiopian Airlines
  • American Airlines
First class cabins are available on Lufthansa, Swiss International Air Lines, and United.
How do I earn miles on a Chicago, IL (ORD) to Milan (MXP) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Milan (MXP) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Milan (MXP) from Chicago, IL (ORD)?
If you're planning to travel to Milan from O'Hare Intl. (ORD), you can fly directly into Malpensa Intl. (MXP). Some flights may connect through major hubs like Pearson Intl. (YYZ), Heathrow (LHR), or Logan Intl. (BOS) before reaching Milan. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD) to Milan (MXP) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to Milan (MXP) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD) to Milan (MXP) flight and hotel package?
Securing a Chicago, IL (ORD) to Milan (MXP) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Malpensa Intl.
Return price
AU$1,008
Distance
7216 km
Average flight time
8 hours 40 mins

Book with confidence

Your quick guide to flights from Chicago to Milan

Pick up great flights from Chicago to Milan

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Chicago to Milan. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to Milan that take around hours.

Find cheap flights from Chicago to Milan

From the great flight deals with prices currently ranging from AU$1,008 to AU$1,258, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to Milan around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Milan is normally in December.

Reasons to book your flight from Chicago to Milan with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to Milan across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Milan right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Chicago to Milan

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