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$428 Cheap Flights from Chicago (ORD) to Milan (MXP)

View $428 flight on Wed, Aug 5, 2026Opens in a new window

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

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Cheap Flights from Chicago to Milan (ORD-MXP)

Prices were available within the past 7 days and start at $428 for one-way flights and $591 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Sun, Mar 14 - Thu, Mar 18
ORD
Chicago
MXP
Milan
$591 Roundtrip, found 9 hours ago
$591
Roundtrip
found 9 hours ago
Select Scandinavian Airlines flight, departing Sun, Mar 14 from Chicago to Milan, returning Thu, Mar 18, priced at $591 found 9 hours ago
JetBlue Airways
Thu, Aug 13 - Tue, Aug 25
ORD
Chicago
MXP
Milan
$680 Roundtrip, found 21 hours ago
$680
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Chicago to Milan, returning Tue, Aug 25, priced at $680 found 21 hours ago
TAP Portugal
Wed, Apr 7 - Wed, Apr 21
ORD
Chicago
MXP
Milan
$764 Roundtrip, found 6 hours ago
$764
Roundtrip
found 6 hours ago
Select TAP Portugal flight, departing Wed, Apr 7 from Chicago to Milan, returning Wed, Apr 21, priced at $764 found 6 hours ago
Air Canada
Mon, Aug 3 - Wed, Aug 19
ORD
Chicago
MXP
Milan
$764 Roundtrip, found 5 hours ago
$764
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Mon, Aug 3 from Chicago to Milan, returning Wed, Aug 19, priced at $764 found 5 hours ago
United
Sun, Aug 9 - Wed, Aug 19
ORD
Chicago
MXP
Milan
$777 Roundtrip, found 6 hours ago
$777
Roundtrip
found 6 hours ago
Select United flight, departing Sun, Aug 9 from Chicago to Milan, returning Wed, Aug 19, priced at $777 found 6 hours ago
American Airlines
Wed, Nov 11 - Tue, Nov 24
ORD
Chicago
MXP
Milan
$781 Roundtrip, found 2 days ago
$781
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 11 from Chicago to Milan, returning Tue, Nov 24, priced at $781 found 2 days ago
British Airways
Wed, Nov 11 - Wed, Mar 3
ORD
Chicago
MXP
Milan
$785 Roundtrip, found 1 day ago
$785
Roundtrip
found 1 day ago
Select British Airways flight, departing Wed, Nov 11 from Chicago to Milan, returning Wed, Mar 3, priced at $785 found 1 day ago
Lufthansa
Mon, Aug 3 - Sun, Aug 30
ORD
Chicago
MXP
Milan
$787 Roundtrip, found 3 hours ago
$787
Roundtrip
found 3 hours ago
Select Lufthansa flight, departing Mon, Aug 3 from Chicago to Milan, returning Sun, Aug 30, priced at $787 found 3 hours ago
Finnair
Mon, Apr 19 - Fri, Apr 23
ORD
Chicago
MXP
Milan
$787 Roundtrip, found 2 days ago
$787
Roundtrip
found 2 days ago
Select Finnair flight, departing Mon, Apr 19 from Chicago to Milan, returning Fri, Apr 23, priced at $787 found 2 days ago
Iberia
Tue, Oct 27 - Thu, Nov 5
ORD
Chicago
MXP
Milan
$789 Roundtrip, found 2 hours ago
$789
Roundtrip
found 2 hours ago
Select Iberia flight, departing Tue, Oct 27 from Chicago to Milan, returning Thu, Nov 5, priced at $789 found 2 hours 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 $1,368
LIN
Linate
Closest
Average driving time to city center11 min
Flights from $1,368

What you need to know for your flight from O'Hare Intl. to Malpensa Intl.

Chicago (ORD) to Milan (MXP) at a glance

Embark on an international adventure with a range of options for Milan flights from Chicago O'Hare International Airport (ORD) to Malpensa International Airport (MXP). Whether you prefer full-service airlines or budget-friendly carriers, you can easily compare flights from ORD to MXP to find the schedule and price that best suit your travel plans. Prepare to explore the iconic sights and neighborhoods of Milan as you plan your journey.

  • Fastest flight duration: around 8h 45m non-stop
  • Route distance: roughly 4,500 miles (7,240 km)
  • Flights per week: around 11 departures on average
  • Typical fares (one-way): economy tickets often range from $235–$1030, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Malpensa International Airport (MXP)

Based on the latest traveler bookings, here are the top airlines favored for flights from Chicago to Milan, featuring both non-stop and one-stop options. Popular layover points include Kastrup Airport, CPH (approximately 3 hours), Humberto Delgado Airport, LIS (around 4 hours and 30 minutes), and Istanbul Airport, IST (about 1 hour and 15 minutes). This variety allows you to tailor your journey by balancing price, total travel time, and cabin class to secure the best itinerary.

  • United: As a comprehensive carrier, United provides both non-stop and one-stop flights, with one-way ticket prices generally ranging from $335 to $1205. It represents roughly 34% of departures on this route, with a standard non-stop flight duration of 8 hours and 45 minutes.
  • SAS: This full-service airline offers one-stop and multi-stop options, with one-way fares typically between $235 and $620. SAS accounts for about 19% of departures on this route, featuring an in-flight time of 10 hours and 30 minutes, culminating in a total travel time of approximately 14 hours and 15 minutes.
  • TAP Portugal: A full-service airline that provides one-stop journeys, TAP Portugal has one-way fares that usually fall between $235 and $705. It covers around 12% of departures for this route, with an in-flight duration of 10 hours and 30 minutes, and a combined journey time of about 14 hours and 15 minutes, including layover time.
  • Turkish Airlines: This full-service carrier offers one-stop flights, with one-way prices typically ranging from $275 to $1335. Turkish Airlines is responsible for about 9% of departures on this route, with an in-flight time of 10 hours and 30 minutes, leading to a total travel time of approximately 14 hours and 15 minutes, factoring in layovers.
  • American Airlines: Known for its one-stop services, American Airlines features one-way fares generally between $290 and $720. It accounts for roughly 5% of departures on this route, with an in-flight duration of 10 hours and 30 minutes, resulting in a total journey time of around 14 hours and 15 minutes when including layovers.

Travelers flying from Chicago to Milan have the option to upgrade their flights. Top airlines include SAS and United, both offering business class and premium economy service, while Turkish Airlines provides business class seating.

Best time to fly from Chicago (ORD) to Milan (MXP)

The most popular months for travelers flying from Chicago to Milan are March, April, and September, when peak temperatures in Milan reach up to 67.8°F in September. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 48.7°F. For better deals, January usually offers the lowest average one-way fare around $444. Flight availability peaks in March and May, with approximately 13 flights per week, making it easier to find convenient departure times. December has the fewest flights, with approximately 9 flights per week.

  • Cheapest time to fly: January usually offers good deals with average one-way fare around $444, roughly 22% cheaper than the yearly average.
  • More budget-friendly months to fly: February and March typically offer average one-way fares roughly ranging from $449 to $467.
  • Most flight options: March and May have the highest number of flights from Chicago to Milan, with approximately 13 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January38.7°F (3.7°C)Average10$444
February42.1°F (5.6°C)Average10$449
March48.9°F (9.4°C)Moderately High13$467
April56.1°F (13.4°C)Moderately High12$490
May63.3°F (17.4°C)Average13$704
June72.3°F (22.4°C)Average12$813
July76.6°F (24.8°C)Average12$620
August75.7°F (24.3°C)Average11$563
September67.8°F (19.9°C)Moderately High12$559
October58.8°F (14.9°C)Moderately Low10$517
November48.7°F (9.3°C)Moderately Low10$506
December39.9°F (4.4°C)Moderately Low9$704

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Chicago (ORD) to Milan (MXP)

  • Chicago to Milan (ORD-LIN): Linate Airport (LIN) is located approximately 30 miles from Malpensa International Airport (MXP). One-way economy ticket prices on this route generally fall between $275 and $840, influenced by the time of year and how far in advance you book. This route often features both one-stop and multi-stop flights, with common layover points at Dublin Airport (DUB) and Heathrow Airport (LHR). Major airlines operating on this path include Aer Lingus and British Airways. Additionally, business class service is offered for travelers seeking more comfort.

How to find the best prices for flights from Chicago (ORD) to Milan (MXP)

Getting some of the best deals on flights from Chicago to Milan is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, which aligns with when most travelers make their reservations. Evening departures between 6 PM and 12 AM tend to be less expensive and are also the most popular flight times. Additionally, flying on Wednesday often results in lower prices, although Friday is the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Malpensa International Airport from O'Hare International Airport

Milan welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Milan efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Milan, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Malpensa International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Malpensa International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Malpensa International Airport, travelers can easily access several transportation options. The Malpensa Airport Terminal 1 Station, a metro station, is located just 0.1 miles away on foot, while Ferno-Lonate Pozzolo Station, a train station, is about 4.8 miles from the airport by car. For those looking to reach the coast, Milan Malpensa Seaport, a seaport, is approximately 4.1 miles away by car.

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 $428 and cheap return flights from $591 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, Delta, Finnair, Iberia, Icelandair, JetBlue Airways, KLM, LOT-Polish Airlines, Lufthansa, Royal Jordanian, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$591
Distance
4510 mi
Average flight time
8 hours 40 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 March. 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 $428 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.

 

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