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

View AU$453 flight on Wed, 1 Oct. 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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.

TAP Portugal
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$923 Return, found 3 days ago
AU$923
Return
found 3 days ago
Select TAP Portugal flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$923 found 3 days ago
Turkish Airlines
Sun, 17 Aug. - Tue, 2 Sep.
ORD
Chicago
MXP
Milan
AU$956 Return, found 4 days ago
AU$956
Return
found 4 days ago
Select Turkish Airlines flight, departing Sun, 17 Aug. from Chicago to Milan, returning Tue, 2 Sep., priced at AU$956 found 4 days ago
TAP Portugal
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$969 Return, found 3 days ago
AU$969
Return
found 3 days ago
Select TAP Portugal flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$969 found 3 days ago
Turkish Airlines
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$985 Return, found 3 days ago
AU$985
Return
found 3 days ago
Select Turkish Airlines flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$985 found 3 days ago
United
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$1,230 Return, found 3 days ago
AU$1,230
Return
found 3 days ago
Select United flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$1,230 found 3 days ago
Air Canada
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$1,230 Return, found 3 days ago
AU$1,230
Return
found 3 days ago
Select Air Canada flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$1,230 found 3 days ago
Lufthansa
Wed, 1 Oct. - Mon, 6 Oct.
ORD
Chicago
MXP
Milan
AU$1,248 Return, found 3 days ago
AU$1,248
Return
found 3 days ago
Select Lufthansa flight, departing Wed, 1 Oct. from Chicago to Milan, returning Mon, 6 Oct., priced at AU$1,248 found 3 days ago
Swiss International Air Lines
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$1,312 Return, found 3 days ago
AU$1,312
Return
found 3 days ago
Select Swiss International Air Lines flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$1,312 found 3 days ago
British Airways
Wed, 1 Oct. - Mon, 6 Oct.
ORD
Chicago
MXP
Milan
AU$1,322 Return, found 3 days ago
AU$1,322
Return
found 3 days ago
Select British Airways flight, departing Wed, 1 Oct. from Chicago to Milan, returning Mon, 6 Oct., priced at AU$1,322 found 3 days ago
Austrian Airlines
Fri, 26 Sep. - Wed, 1 Oct.
ORD
Chicago
MXP
Milan
AU$1,330 Return, found 3 days ago
AU$1,330
Return
found 3 days ago
Select Austrian Airlines flight, departing Fri, 26 Sep. from Chicago to Milan, returning Wed, 1 Oct., priced at AU$1,330 found 3 days ago

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

February is typically the cheapest month to fly

From AU$635 - AU$1,738 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Milan route information
Origin airport
O'Hare Intl.
Destination airport
Malpensa Intl.
Return price
AU$923
Distance
7216 km
Average flight time
8 hours 45 mins

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$923 to AU$1,330, 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 September.

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.

Frequently asked questions

How much is a flight from ORD to Malpensa Intl. Airport (MXP)?
Pack your bags, because round-trip flights between O'Hare Intl. Airport (ORD) and Milan Malpensa Airport start from AU$923. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book now to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Milan Malpensa Airport?
This varies between air carriers, as each one has its own set of terms and conditions. Head to the Customer Service Portal, where there are easy-to-follow instructions on how to cancel online.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to Milan Malpensa Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Intl. Airport (ORD) to Malpensa Intl. Airport (MXP) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Milan Malpensa Airport?
With a flight distance of 7 300 kilometres between O'Hare Intl. Airport (ORD) and MXP, this is a long-haul trip. Remember to stay hydrated and get up to stretch your legs from time to time.
Which airlines fly direct from O'Hare Airport to MXP?
Unfortunately, there are no airlines that fly directly between O'Hare Intl. Airport (ORD) and Malpensa Intl. Airport (MXP). You'll need to book a flight with one or more stops.
Are O'Hare Intl. Airport (ORD) to Milan Malpensa Airport flight tickets cheaper when they're purchased at the last minute?
Flight tickets from O'Hare Airport to MXP are available up to 12 months before departure on Expedia. And although you may occasionally pick up a great last-minute deal, it's never a sure thing. Also, booking your flights ahead of time means you'll have more options — and you can avoid getting caught in the dreaded middle seat! We regularly update our fares to bring you the best bargains, so keep checking in for all the latest specials.

Explore a world of travel with Expedia

Milan Flight Deals

Milan

*Available to Expedia members.