Which layover airport has the shortest travel time from Chicago to Milan?

Flights connecting via Paris (CDG) have the shortest average one-way travel time: 10h 55m.

How many flights depart from Chicago to Milan on average per day?

As of April 2026, there are 4 flights per day flying from Chicago to Milan. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

What is the cheapest airline that flies from Chicago to Milan?

United Airlines, Lufthansa, and ITA Airways are the most popular carriers operating from Chicago to Milan

Which layover airport offers the lowest fares from Chicago to Milan?

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $395.

Which airport is the most popular layover for flights between Chicago and Milan?

Copenhagen (CPH) was the most common stop: 29% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Chicago to Milan?

Rome (FCO) has the shortest average layover time for this route: 1h 25m.

How many flights depart from Chicago to Milan on average per week?

As of April 2026, there are 32 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

What airlines fly to Milan?

United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 9 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to Milan?

Prices for flights from Chicago to Milan are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Milan?

The number of operators available for flights from Chicago to Milan is 9 as of April 2026.

How old do you have to be to fly from Chicago to Milan?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.

What documentation or ID do you need to fly to Milan?

The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$332 Cheap Flights from Chicago to Milan in 2026

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Find the cheapest flights from Chicago to Milan

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:40 pm - 8:30 am

ORD

MXP

32h 50m

1 stop

8:30 pm - 4:45 pm

MXP

ORD

27h 15m

1 stop

$645Air Serbia

Mon, Aug 24 - Fri, Dec 18

4:40 pm - 8:30 am

ORD

MXP

32h 50m

1 stop

8:50 pm - 2:30 pm

MXP

ORD

24h 40m

1 stop

$650Air Serbia

Mon, Aug 17 - Sun, Aug 30

4:40 pm - 8:30 am

ORD

MXP

32h 50m

1 stop

8:50 pm - 2:30 pm

MXP

ORD

24h 40m

1 stop

$652Air Serbia

Mon, Aug 24 - Sun, Sep 6

8:10 pm - 11:45 pm

ORD

MXP

20h 35m

1 stop

6:50 am - 11:05 am

MXP

ORD

35h 15m

1 stop

$655Turkish Airlines

Sun, Oct 11 - Sat, Oct 24

8:10 pm - 5:45 pm

ORD

MXP

14h 35m

1 stop

6:35 pm - 11:05 am

MXP

ORD

22h 30m

1 stop

$659Turkish Airlines

Sun, Oct 18 - Sun, Oct 25

10:30 am - 10:35 am

ORD

MXP

17h 05m

2 stops

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$663Scandinavian Airlines

Tue, Oct 20 - Wed, Nov 4

7:15 pm - 7:10 pm

ORD

MXP

16h 55m

1 stop

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$667Scandinavian Airlines

Sun, Oct 18 - Sun, Nov 8

9:40 pm - 5:45 pm

ORD

LIN

13h 05m

1 stop

6:10 am - 1:10 pm

LIN

ORD

14h 00m

1 stop

$773Lufthansa

Tue, Oct 13 - Thu, Nov 12

9:40 pm - 5:45 pm

ORD

LIN

13h 05m

1 stop

2:50 pm - 8:05 pm

LIN

ORD

12h 15m

1 stop

$774Lufthansa

Tue, Oct 20 - Thu, Nov 12

9:15 pm - 5:15 pm

ORD

LIN

13h 00m

1 stop

11:05 am - 6:15 pm

LIN

ORD

14h 10m

1 stop

$785British Airways

Mon, Aug 10 - Thu, Aug 20

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KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets

KLM

Aug 17

MDW1:05 pmChicago Midway

13h 20m

1 stop

MXP9:25 amMilan Malpensa

Aug 28

MXP11:40 amMilan Malpensa

17h 06m

1 stop

MDW9:46 pmChicago Midway

$864

KLM

Aug 17

MDW1:05 pmChicago Midway

13h 20m

1 stop

MXP9:25 amMilan Malpensa

Aug 28

MXP11:40 amMilan Malpensa

17h 06m

1 stop

MDW9:46 pmChicago Midway

$885

KLM

Oct 20

MDW1:05 pmChicago Midway

13h 20m

1 stop

MXP9:25 amMilan Malpensa

Nov 3

MXP1:05 pmMilan Malpensa

15h 40m

1 stop

MDW9:45 pmChicago Midway

$1,126

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

Oct 20

ORD10:30 amChicago O'Hare Intl

17h 05m

2 stops

MXP10:35 amMilan Malpensa

Nov 4

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$663

Scandinavian Airlines

Oct 18

ORD7:15 pmChicago O'Hare Intl

16h 55m

1 stop

MXP7:10 pmMilan Malpensa

Nov 8

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$667

Scandinavian Airlines

Oct 15

ORD7:15 pmChicago O'Hare Intl

32h 25m

2 stops

MXP10:40 amMilan Malpensa

Nov 5

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$676

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/24

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Fri 12/18

8:30 pm-4:45 pm

1 stop27h 15m

$645

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/17

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Sun 8/30

8:50 pm-2:30 pm

1 stop24h 40m

$650

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/24

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Sun 9/6

8:50 pm-2:30 pm

1 stop24h 40m

$652

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 10/11

8:10 pm-11:45 pm

1 stop20h 35m

Milan Malpensa

Sat 10/24

6:50 am-11:05 am

1 stop35h 15m

$655

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 10/18

8:10 pm-5:45 pm

1 stop14h 35m

Milan Malpensa

Sun 10/25

6:35 pm-11:05 am

1 stop22h 30m

$659

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 10/20

10:30 am-10:35 am

2 stops17h 05m

Milan Malpensa

Wed 11/4

11:15 am-4:45 pm

1 stop12h 30m

$663

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 10/18

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sun 11/8

11:15 am-4:45 pm

1 stop12h 30m

$667

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 10/13

9:40 pm-5:45 pm

1 stop13h 05m

Milan Linate

Thu 11/12

6:10 am-1:10 pm

1 stop14h 00m

$773

Quickest round-trip

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 10/20

9:40 pm-5:45 pm

1 stop13h 05m

Milan Linate

Thu 11/12

2:50 pm-8:05 pm

1 stop12h 15m

$774

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 8/10

9:15 pm-5:15 pm

1 stop13h 00m

Milan Linate

Thu 8/20

11:05 am-6:15 pm

1 stop14h 10m

$785

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and Milan?

What is the cheapest month to fly to Milan?

The month of January is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $534. The month of February is another great option to travel to Milan, with average flight prices from Chicago averaging around $543.

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,220. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,344.

What is the cheapest Chicago to Milan flight route?

Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices

How far in advance should I book a flight from Chicago to Milan?

You are more likely to see cheaper flights to Milan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $842 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $517 on momondo.

What cabin class options are available on Chicago to Milan flights?

There are 3 cabin classes available to choose from on Chicago to Milan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 33% on your flight if you consider stops on a Chicago to Milan flight.

How have Chicago to Milan flight prices changed over time?

As of April 2026, prices for Chicago to Milan flights are approximately 77% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Milan according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Milan (CHI to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan

Best Price Found	$874
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Milan	2 airports

The best one-way flight to Milan from Chicago in the past 72 hours is $874. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,286.

The fastest flight from Chicago to Milan takes 8h 30m

Direct flights go from Chicago to Milan every day.

There are 2 airports in Milan. From Chicago there are direct flights to Milan Malpensa (MXP).

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Frequently asked questions about flying from Chicago to Milan

How far is Chicago to Milan by plane?
There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 8h 30m.
When did momondo last update prices for flights from Chicago to Milan?
Prices for flights from Chicago to Milan are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Milan?
The number of operators available for flights from Chicago to Milan is 9 as of April 2026.
How old do you have to be to fly from Chicago to Milan?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.
What documentation or ID do you need to fly to Milan?
The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Milan?
Based on momondo bookings for flights between Chicago and Milan, the leading plane model is Boeing 787 Dreamliner, making up 46.89% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 45.01%, Boeing 787-8 Dreamliner with 6.59%, and Boeing 737 MAX 8 with 0.19%.
What is the most popular airline from Chicago to Milan?
momondo data reveals that the most frequently booked airline on the route from Chicago to Milan is United Airlines, representing 32% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 30%, TAP AIR PORTUGAL at 9%, and Aer Lingus at 8%.

Best airlines flying from Chicago to Milan

Compare and see reviews for airlines that fly from Chicago to Milan with momondo

Airline	Rating	Free Cancellation	Price
TAP AIR PORTUGAL	PriceFrom $401	Free Cancellation	Rating 7.1 2,219 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $410	Free Cancellation	Rating 7.3 1,759 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $496	Free Cancellation	Rating 6.7 7,910 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.4 4,326 reviews	Search Turkish Airlines flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.1 11,664 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.3 1,527 reviews	Search Aer Lingus flights
ITA Airways	PriceFrom $644	Free Cancellation	Rating 6.7 1,195 reviews	Search ITA Airways flights
United Airlines	PriceFrom $764	Free Cancellation	Rating 7.4 9,644 reviews	Search United Airlines flights
Lufthansa	PriceFrom $889	Free Cancellation	Rating 6.8 7,944 reviews	Search Lufthansa flights

United Airlines Flights From Chicago to Milan
United Airlines operates around 7 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,232, but momondo users have found United Airlines deals from Chicago to Milan from as low as $764 round-trip. United Airlines has been scored 7.4/10 in 9,644 reviews.
Lufthansa Flights From Chicago to Milan
Lufthansa is also a popular choice for this route. Lufthansa flight deals for Chicago to Milan start from as low as $889 round-trip, depending on your selected dates, with average Lufthansa deals seen on momondo around $1,096. Lufthansa operates 7 flights to Milan from Chicago in an average week. Users have rated it 6.8/10 across 7,944 reviews.

Bellagio

Varenna

Menaggio

Stresa

Brescia

Livigno

Levanto

Bellano

Monza

Lecco

Assago

Crema

Domodossola

Cernobbio

Moltrasio

Bormio

Rho

Novara

Baveno

Iseo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Chicago to Milan from $332

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 10/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago to Milan

What is the typical price of a round-trip flight between Chicago and Milan?

What is the cheapest month to fly to Milan?

What is the cheapest day to depart on your flight to Milan?

What is the cheapest Chicago to Milan flight route?

How far in advance should I book a flight from Chicago to Milan?

What cabin class options are available on Chicago to Milan flights?

Can stopping save me money on Chicago to Milan flights?

How have Chicago to Milan flight prices changed over time?

What is the cheapest airline that flies from Chicago to Milan?

What airlines fly to Milan?

Which airport is the most popular layover for flights between Chicago and Milan?

Which layover airport offers the lowest fares from Chicago to Milan?

Which layover airport has the shortest travel time from Chicago to Milan?

Which layover airport has the shortest connection time from Chicago to Milan?

How many flights depart from Chicago to Milan on average per day?

How many flights depart from Chicago to Milan on average per week?

When to book flights from Chicago to Milan

Cheap Chicago to Milan (CHI to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan

Best Price Found

Fastest flight time

Direct flights

Airports in Milan

Frequently asked questions about flying from Chicago to Milan

Best airlines flying from Chicago to Milan

Compare and see reviews for airlines that fly from Chicago to Milan with momondo

United Airlines Flights From Chicago to Milan

Lufthansa Flights From Chicago to Milan

Traveling to a place near Milan?

Why use momondo?

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan

Fly your favorite airline to Milan

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Cabin classes currently available on flights to Milan

List of cabin classes available on flights landing in Milan. Availability may vary depending on flight origin and airline.

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