$328 Cheap Flights from Chicago (ORD) to Milan (MXP)

View $328 flight on Sat, Jan 31, 2026Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

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

    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 $328 for one-way flights and $399 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Icelandair
Fri, Apr 10 - Sat, Apr 18
ORD
Chicago
MXP
Milan
$399 Roundtrip, just found
$399
Roundtrip
just found
Select Icelandair flight, departing Fri, Apr 10 from Chicago to Milan, returning Sat, Apr 18, priced at $399 just found
TAP Portugal
Wed, Apr 15 - Sun, Apr 19
ORD
Chicago
MXP
Milan
$429 Roundtrip, found 7 hours ago
$429
Roundtrip
found 7 hours ago
Select TAP Portugal flight, departing Wed, Apr 15 from Chicago to Milan, returning Sun, Apr 19, priced at $429 found 7 hours ago
Scandinavian Airlines
Thu, Feb 26 - Wed, Mar 4
ORD
Chicago
MXP
Milan
$450 Roundtrip, just found
$450
Roundtrip
just found
Select Scandinavian Airlines flight, departing Thu, Feb 26 from Chicago to Milan, returning Wed, Mar 4, priced at $450 just found
Delta
Mon, Apr 27 - Wed, Apr 29
ORD
Chicago
MXP
Milan
$514 Roundtrip, found 3 days ago
$514
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Apr 27 from Chicago to Milan, returning Wed, Apr 29, priced at $514 found 3 days ago
Turkish Airlines
Mon, Feb 23 - Thu, Mar 5
ORD
Chicago
MXP
Milan
$586 Roundtrip, found 21 hours ago
$586
Roundtrip
found 21 hours ago
Select Turkish Airlines flight, departing Mon, Feb 23 from Chicago to Milan, returning Thu, Mar 5, priced at $586 found 21 hours ago
JetBlue Airways
Tue, Aug 18 - Tue, Aug 25
ORD
Chicago
MXP
Milan
$611 Roundtrip, found 12 hours ago
$611
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Chicago to Milan, returning Tue, Aug 25, priced at $611 found 12 hours ago
Air Serbia
Sat, Jan 24 - Thu, Jan 29
ORD
Chicago
MXP
Milan
$612 Roundtrip, found 6 days ago
$612
Roundtrip
found 6 days ago
Select Air Serbia flight, departing Sat, Jan 24 from Chicago to Milan, returning Thu, Jan 29, priced at $612 found 6 days ago
LOT-Polish Airlines
Fri, Feb 20 - Mon, Feb 23
ORD
Chicago
MXP
Milan
$787 Roundtrip, just found
$787
Roundtrip
just found
Select LOT-Polish Airlines flight, departing Fri, Feb 20 from Chicago to Milan, returning Mon, Feb 23, priced at $787 just found
United
Wed, Aug 5 - Wed, Aug 19
ORD
Chicago
MXP
Milan
$816 Roundtrip, found 2 days ago
$816
Roundtrip
found 2 days ago
Select United flight, departing Wed, Aug 5 from Chicago to Milan, returning Wed, Aug 19, priced at $816 found 2 days ago
Air Canada
Wed, Mar 11 - Wed, Mar 18
ORD
Chicago
MXP
Milan
$822 Roundtrip, found 9 hours ago
$822
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Wed, Mar 11 from Chicago to Milan, returning Wed, Mar 18, priced at $822 found 9 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 $1,474
LIN
Linate
Closest
Average driving time to city center11 min
Flights from $1,474
Flights from Chicago (ORD) to Milan (MXP)
Origin airport
O'Hare Intl.
Destination airport
Malpensa Intl.
Airlines serving
Air Canada, Air France, Air Serbia, American Airlines, British Airways, Brussels Airlines, 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
$399
Distance
4510 mi

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 April. 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 $328 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.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) cost?
Snag a cheap one-way flight from $328 or cheap return flight from $399 from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP)?
Planning your trip for April may help you find better deals, as it's the cheapest month for flights between ORD and MXP. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP)?
To find the cheapest airline that'll fly you from ORD to MXP, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP)?
There are no daily direct flights departing from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from ORD to MXP?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can change depending on a range of factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ORD to MXP?
Consider booking with United Airlines if you'd like to go straight from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) without any interruptions. This carrier has the strongest track record for punctuality, with an on-time score of 80%. Want real-time updates? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP)?
Book a flight from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) that leaves before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) last-minute?
Booking your flight from ORD to MXP right before your journey is generally more expensive. However, if there's some wiggle room with your departure dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book an ORD to MXP flight and hotel package?
Booking an ORD to MXP flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Pick from our wide range of hotels and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP)?
In most instances, you can modify or cancel your ORD to MXP flight. However, additional charges may apply, especially if you booked over 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you need further details, go to our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.