S$511 Cheap Flights from Chicago to Milan

View S$511 flight on Sat, 16 Aug, 2025Opens 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 S$511 for one-way flights and S$938 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, 4 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$938 Return, found 5 hours ago
S$938
Return
found 5 hours ago
Select United flight, departing Mon, 4 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$938 found 5 hours ago
United
Mon, 4 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$938 Return, found 5 hours ago
S$938
Return
found 5 hours ago
Select United flight, departing Mon, 4 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$938 found 5 hours ago
Air Canada
Mon, 4 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$938 Return, found 5 hours ago
S$938
Return
found 5 hours ago
Select Air Canada flight, departing Mon, 4 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$938 found 5 hours ago
Delta
Mon, 18 Aug - Wed, 27 Aug
ORD
Chicago
MXP
Milan
S$944 Return, found 2 hours ago
S$944
Return
found 2 hours ago
Select Delta flight, departing Mon, 18 Aug from Chicago to Milan, returning Wed, 27 Aug, priced at S$944 found 2 hours ago
Air Canada
Mon, 4 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$947 Return, found 5 hours ago
S$947
Return
found 5 hours ago
Select Air Canada flight, departing Mon, 4 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$947 found 5 hours ago
United
Sat, 2 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$954 Return, found 4 days ago
S$954
Return
found 4 days ago
Select United flight, departing Sat, 2 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$954 found 4 days ago
Air Canada
Mon, 4 Aug - Thu, 21 Aug
ORD
Chicago
MXP
Milan
S$956 Return, found 5 hours ago
S$956
Return
found 5 hours ago
Select Air Canada flight, departing Mon, 4 Aug from Chicago to Milan, returning Thu, 21 Aug, priced at S$956 found 5 hours ago
Lufthansa
Mon, 18 Aug - Wed, 27 Aug
ORD
Chicago
MXP
Milan
S$1,008 Return, found 2 hours ago
S$1,008
Return
found 2 hours ago
Select Lufthansa flight, departing Mon, 18 Aug from Chicago to Milan, returning Wed, 27 Aug, priced at S$1,008 found 2 hours ago
KLM
Mon, 18 Aug - Wed, 27 Aug
ORD
Chicago
MXP
Milan
S$1,011 Return, found 2 hours ago
S$1,011
Return
found 2 hours ago
Select KLM flight, departing Mon, 18 Aug from Chicago to Milan, returning Wed, 27 Aug, priced at S$1,011 found 2 hours ago
Swiss International Air Lines
Mon, 18 Aug - Wed, 27 Aug
ORD
Chicago
MXP
Milan
S$1,014 Return, found 2 hours ago
S$1,014
Return
found 2 hours ago
Select Swiss International Air Lines flight, departing Mon, 18 Aug from Chicago to Milan, returning Wed, 27 Aug, priced at S$1,014 found 2 hours ago

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

February is typically the cheapest month to fly

From S$525 - S$1,492 per traveller.

Graph displaying average flight prices per month

Chicago to Milan route information
Origin airport
O'Hare Intl.
Destination airport
Malpensa Intl.
Airlines serving
Air Canada, American Airlines, Austrian Airlines, British Airways, Finnair, Iberia, LOT-Polish Airlines, Lufthansa, Swiss International Air Lines, Turkish Airlines, United
Return price
S$937
Distance
7216 km
Average flight time
8 hours 45 mins

Flights from Chicago to Milan

There are several airlines that operate frequent flights from Chicago (ORD) to Milan (MXP) including

The earliest flight leaves O'Hare Intl. Airport at 10:50 and arrives at Malpensa Intl. Airport at 07:00. The last flight of the day departs Chicago at 23:05 and arrives at Milan at 20:10.

The flight distance from Chicago to Milan is about 7694 km, the shortest flight is 10 hours 40 minutes with WestJet.

Expedia lets you search across the largest number of airlines and Milan flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Milan flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Milan trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Milan flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Milan with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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 S$938. 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.

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