$383 Cheap Flights from Chicago (ORD) to Milan (MXP)

View $383 flight on Wed, Sep 30, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Milan Malpensa Airport (MXP)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Milan (ORD-MXP)

Prices were available within the past 7 days and start at $383 for one-way flights and $561 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Sun, Feb 21 - Sun, Feb 28
ORD
Chicago
MXP
Milan
$561 Roundtrip, found 3 hours ago
$561
Roundtrip
found 3 hours ago
Select Scandinavian Airlines flight, departing Sun, Feb 21 from Chicago to Milan, returning Sun, Feb 28, priced at $561 found 3 hours ago
Turkish Airlines
Tue, Feb 16 - Wed, Feb 24
ORD
Chicago
MXP
Milan
$661 Roundtrip, found 6 days ago
$661
Roundtrip
found 6 days ago
Select Turkish Airlines flight, departing Tue, Feb 16 from Chicago to Milan, returning Wed, Feb 24, priced at $661 found 6 days ago
TAP Portugal
Wed, Oct 28 - Tue, Nov 10
ORD
Chicago
MXP
Milan
$684 Roundtrip, found 19 hours ago
$684
Roundtrip
found 19 hours ago
Select TAP Portugal flight, departing Wed, Oct 28 from Chicago to Milan, returning Tue, Nov 10, priced at $684 found 19 hours ago
Air Serbia
Mon, Aug 17 - Fri, Aug 28
ORD
Chicago
MXP
Milan
$709 Roundtrip, found 11 hours ago
$709
Roundtrip
found 11 hours ago
Select Air Serbia flight, departing Mon, Aug 17 from Chicago to Milan, returning Fri, Aug 28, priced at $709 found 11 hours ago
United
Thu, Aug 6 - Tue, Aug 18
ORD
Chicago
MXP
Milan
$832 Roundtrip, found 2 hours ago
$832
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Aug 6 from Chicago to Milan, returning Tue, Aug 18, priced at $832 found 2 hours ago
Air Canada
Mon, Aug 17 - Mon, Aug 24
ORD
Chicago
MXP
Milan
$834 Roundtrip, found 10 hours ago
$834
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Mon, Aug 17 from Chicago to Milan, returning Mon, Aug 24, priced at $834 found 10 hours ago
Lufthansa
Mon, Aug 17 - Mon, Aug 24
ORD
Chicago
MXP
Milan
$837 Roundtrip, found 10 hours ago
$837
Roundtrip
found 10 hours ago
Select Lufthansa flight, departing Mon, Aug 17 from Chicago to Milan, returning Mon, Aug 24, priced at $837 found 10 hours ago
Swiss International Air Lines
Fri, Feb 12 - Fri, Feb 19
ORD
Chicago
MXP
Milan
$841 Roundtrip, just found
$841
Roundtrip
just found
Select Swiss International Air Lines flight, departing Fri, Feb 12 from Chicago to Milan, returning Fri, Feb 19, priced at $841 just found
Delta
Mon, Sep 14 - Wed, Sep 16
ORD
Chicago
MXP
Milan
$885 Roundtrip, found 3 days ago
$885
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 14 from Chicago to Milan, returning Wed, Sep 16, priced at $885 found 3 days ago
JetBlue Airways
Thu, Sep 24 - Mon, Sep 28
ORD
Chicago
MXP
Milan
$890 Roundtrip, found 6 days ago
$890
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Sep 24 from Chicago to Milan, returning Mon, Sep 28, priced at $890 found 6 days ago

Alternative airports near Milan

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Linate LIN. Closest option available. Average driving time to city center is 11 minutes. Flights from $1,365
LIN
Linate
Closest
Average driving time to city center11 min
Flights from $1,365

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) cost?
You can find cheap one-way flights from $383 and cheap return flights from $561 Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) with Expedia. One-way flights usually range from $597 to $5538, and return flights typically cost between $980 and $6098. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
March is the cheapest month to fly from Chicago, IL (ORD) to Milan (MXP), with average return fares around $931. This is about 19% lower than the average price throughout the year, as demand tends to dip after the winter holiday season. Other budget-friendly months for this route include January and February.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
You can fly direct from ORD to MXP on United, with around 7 flights per week.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
United is one of the cheapest airlines offering nonstop flights from Chicago, IL (ORD) to Milan (MXP) starting from around $735. 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.*Prices based on flights available on Expedia in the last year.
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) to Milan (MXP) 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 ORD to MXP, 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-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
For flights from Chicago (ORD) to Milan (MXP), February and March are the best months to travel. Return flights average around $931 in February, making it a good time to find deals. These months are less busy, allowing you to enjoy Milan's attractions without the usual crowds.*Prices based on flights available on Expedia in the last year.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
You can find approximately 1 nonstop flights per day from O'Hare Intl. (ORD) to Malpensa Intl. (MXP). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
The earliest flight from O'Hare International Airport (ORD) to Malpensa International Airport (MXP) typically leaves at around 5:00 AM, operated by American Airlines. Departing early can help you make the most of your time in Milan. This service is seasonal and operates in June. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
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 O'Hare International Airport (ORD) to Milan Malpensa International Airport (MXP) are in the late evening, from 9pm to midnight. About 28% of passengers prefer this time window. Many major carriers, including United, Lufthansa, and Air Canada, offer flights during this window. This timing works well because it allows you to enjoy a full day in Chicago before heading to the airport.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
Flying nonstop from ORD to MXP takes around 8 hours 50 minutes, with the route covering approximately 4,511 miles. Flights with a layover typically take 3 hours 40 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.)?
Select the "Business class" and "First class" filters when looking for ORD to MXP flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) 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 from O'Hare Intl. (ORD)?
When traveling from O'Hare Intl. (ORD) to Milan, you can fly into Linate (LIN) and Malpensa Intl. (MXP). Some flights may connect through major hubs like Pearson Intl. (YYZ), John F. Kennedy Intl. (JFK), Pierre Elliott Trudeau Intl. (YUL) 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-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) 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-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Milan (MXP-Malpensa Intl.) Milan Vacation Packages 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.
Airlines serving
Aer Lingus, Air Canada, Air France, Air Serbia, American Airlines, British Airways, Brussels Airlines, Delta, Finnair, Iberia, Icelandair, JetBlue Airways, LOT-Polish Airlines, Lufthansa, Royal Jordanian, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$560
Distance
4510 mi
Average flight time
8 hours 50 mins

Book with confidence

Chicago to Milan Flights

The cheapest times to fly from Chicago to Milan

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Milan are during the month of February. You can find some of the cheapest flights from Chicago to Milan with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Milan

Sunday is one of the best days to book for cheap flights from Chicago to Milan: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Milan

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Milan in 2026. You can also book with separate airlines for your outbound and return journeys, from $383 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Milan flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Milan airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Milan Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia