S$577 Cheap Flights from Chicago to Milan

View S$577 flight on Sat, 29 Mar,2025Opens in a new window

Featured airlines

Singapore Airlines
AirAsia
Scoot
Philippine Airlines
Malaysia Airlines
Thai Airways International
Asiana Airlines
Qatar Airways
Air India

  • 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 40% 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 to Milan (ORD-MXP)

Prices were available within the past 7 days and start at S$577 for one-way flights and S$875 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Turkish Airlines
Wed, 2 Apr - Wed, 9 Apr
ORD
Chicago
MXP
Milan
S$875 Return, found 2 hours ago
S$875
Return
found 2 hours ago
Select Turkish Airlines flight, departing Wed, 2 Apr from Chicago to Milan, returning Wed, 9 Apr, priced at S$875 found 2 hours ago
Turkish Airlines
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$899 Return, found 3 days ago
S$899
Return
found 3 days ago
Select Turkish Airlines flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$899 found 3 days ago
British Airways
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$906 Return, found 3 days ago
S$906
Return
found 3 days ago
Select British Airways flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$906 found 3 days ago
British Airways
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$974 Return, found 3 days ago
S$974
Return
found 3 days ago
Select British Airways flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$974 found 3 days ago
Turkish Airlines
Mon, 31 Mar - Mon, 7 Apr
ORD
Chicago
MXP
Milan
S$1,130 Return, found 1 day ago
S$1,130
Return
found 1 day ago
Select Turkish Airlines flight, departing Mon, 31 Mar from Chicago to Milan, returning Mon, 7 Apr, priced at S$1,130 found 1 day ago
American Airlines
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$1,156 Return, found 3 days ago
S$1,156
Return
found 3 days ago
Select American Airlines flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$1,156 found 3 days ago
Air Serbia
Sat, 29 Mar - Sat, 5 Apr
ORD
Chicago
MXP
Milan
S$1,165 Return, found 3 days ago
S$1,165
Return
found 3 days ago
Select Air Serbia flight, departing Sat, 29 Mar from Chicago to Milan, returning Sat, 5 Apr, priced at S$1,165 found 3 days ago
LOT-Polish Airlines
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$1,166 Return, found 3 days ago
S$1,166
Return
found 3 days ago
Select LOT-Polish Airlines flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$1,166 found 3 days ago
Iberia
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$1,177 Return, found 3 days ago
S$1,177
Return
found 3 days ago
Select Iberia flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$1,177 found 3 days ago
American Airlines
Mon, 3 Mar - Mon, 10 Mar
ORD
Chicago
MXP
Milan
S$1,180 Return, found 3 days ago
S$1,180
Return
found 3 days ago
Select American Airlines flight, departing Mon, 3 Mar from Chicago to Milan, returning Mon, 10 Mar, priced at S$1,180 found 3 days ago
Chicago to Milan route information
Origin airport
O'Hare Intl.
Destination airport
Malpensa Intl.
Return price
S$874
Distance
7216 km

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$875. 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.
Milan Airports

Milan

*Available to Expedia members.