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

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $403.

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

Air Serbia, Iberia, and Aer Lingus are the most popular carriers operating from Chicago to Milan

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

Copenhagen (CPH) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

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 week?

As of July 2026, there are 35 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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.

What airlines fly to Milan?

Scandinavian Airlines, United Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan from Chicago according to our data. Scandinavian Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 8 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

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

As of July 2026, there are 5 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.

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 8 as of July 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.

$227 Cheap Flights from Chicago to Milan in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Milan

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 pm - 4:55 pm

ORD

MXP

13h 45m

1 stop

6:15 am - 3:30 pm

MXP

ORD

16h 15m

1 stop

$620TAP AIR PORTUGAL

Fri, Nov 13 - Sun, Nov 22

6:00 pm - 4:25 pm

ORD

MXP

15h 25m

1 stop

5:50 am - 4:00 pm

MXP

ORD

17h 10m

1 stop

$621TAP AIR PORTUGAL

Thu, Oct 8 - Fri, Oct 16

7:25 pm - 11:00 pm

ORD

MXP

20h 35m

2 stops

4:20 pm - 6:15 pm

MXP

ORD

32h 55m

1 stop

$622Multiple Airlines

Mon, Aug 31 - Tue, Sep 22

7:30 pm - 4:45 pm

ORD

MXP

15h 15m

1 stop

6:10 am - 5:20 pm

MXP

ORD

18h 10m

1 stop

$624Multiple Airlines

Sat, Oct 31 - Wed, Nov 4

3:00 pm - 11:40 am

ORD

LIN

13h 40m

1 stop

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

$633ITA Airways

Wed, Aug 5 - Wed, Aug 26

3:00 pm - 10:10 am

ORD

LIN

12h 10m

1 stop

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

$634ITA Airways

Wed, Aug 12 - Wed, Aug 19

10:54 am - 9:25 am

MDW

MXP

15h 31m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$780Air France

Mon, Aug 3 - Wed, Aug 19

10:54 am - 9:25 am

MDW

MXP

15h 31m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$781Air France

Mon, Aug 3 - Wed, Aug 19

1:19 pm - 12:05 pm

MDW

MXP

15h 46m

2 stops

11:40 am - 10:25 pm

MXP

MDW

17h 45m

1 stop

$785Delta

Sun, Sep 27 - Fri, Oct 16

10:54 am - 9:25 am

MDW

MXP

15h 31m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$786Delta

Mon, Aug 24 - Tue, Sep 1

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KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets

KLM

Aug 12

MDW12:46 pmChicago Midway

13h 39m

1 stop

MXP9:25 amMilan Malpensa

Aug 19

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$791

KLM

Aug 8

MDW6:11 amChicago Midway

20h 14m

1 stop

MXP9:25 amMilan Malpensa

Aug 21

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$832

KLM

Nov 30

MDW1:05 pmChicago Midway

15h 05m

1 stop

MXP11:10 amMilan Malpensa

Dec 5

MXP1:05 pmMilan Malpensa

16h 05m

1 stop

MDW10:10 pmChicago Midway

$834

Icelandair flights from Chicago to Milan

Our best Icelandair deals on Chicago to Milan flight tickets

Icelandair

Aug 26

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

Sep 1

MXP10:55 pmMilan Malpensa

29h 30m

1 stop

ORD9:25 pmChicago O'Hare Intl

$619

Icelandair

Aug 29

ORD10:25 pmChicago O'Hare Intl

33h 45m

1 stop

MXP3:10 pmMilan Malpensa

Sep 5

MXP4:20 pmMilan Malpensa

12h 05m

1 stop

ORD9:25 pmChicago O'Hare Intl

$633

Icelandair

Aug 23

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

Sep 1

MXP10:55 pmMilan Malpensa

26h 20m

1 stop

ORD6:15 pmChicago O'Hare Intl

$634

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 11/13

8:10 pm-4:55 pm

1 stop13h 45m

Milan Malpensa

Sun 11/22

6:15 am-3:30 pm

1 stop16h 15m

$620

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 10/8

6:00 pm-4:25 pm

1 stop15h 25m

Milan Malpensa

Fri 10/16

5:50 am-4:00 pm

1 stop17h 10m

$621

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/31

7:25 pm-11:00 pm

2 stops20h 35m

Milan Malpensa

Tue 9/22

4:20 pm-6:15 pm

1 stop32h 55m

$622

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 10/31

7:30 pm-4:45 pm

1 stop15h 15m

Milan Malpensa

Wed 11/4

6:10 am-5:20 pm

1 stop18h 10m

$624

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 8/5

3:00 pm-11:40 am

1 stop13h 40m

Milan Linate

Wed 8/26

9:00 pm-1:10 pm

1 stop23h 10m

$633

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 8/12

3:00 pm-10:10 am

1 stop12h 10m

Milan Linate

Wed 8/19

9:00 pm-1:10 pm

1 stop23h 10m

$634

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$780

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$781

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 9/27

1:19 pm-12:05 pm

2 stops15h 46m

Milan Malpensa

Fri 10/16

11:40 am-10:25 pm

1 stop17h 45m

$785

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/24

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Tue 9/1

11:40 am-10:36 pm

1 stop17h 56m

$786

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 July is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $187. The month of October is another great option to travel to Milan, with average flight prices from Chicago averaging around $266.

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 $1,332. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,526.

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 $849 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 $555 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 39% 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 July 2026, prices for Chicago to Milan flights are approximately 21% cheaper 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	$584
Fastest flight time	8h 40m
Direct flights	Every day
Airports in Milan	2 airports

The best one-way flight to Milan from Chicago in the past 72 hours is $584. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $985.

The fastest flight from Chicago to Milan takes 8h 40m

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).

Search flight deals

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 40m.
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 8 as of July 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 787-10 Dreamliner, making up 84.62% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 8.46%, Boeing 787 Dreamliner with 4.36%, and Boeing 787-9 Dreamliner with 0.90%.
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 Scandinavian Airlines, representing 33% of all bookings. The subsequent popular airlines are United Airlines at 28%, Lufthansa at 11%, and TAP AIR PORTUGAL at 7%.

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 7.2 2,338 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 1,885 reviews	Search Scandinavian Airlines flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.4 4,449 reviews	Search Turkish Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.3 1,671 reviews	Search Aer Lingus flights
British Airways	PriceFrom $644	Free Cancellation	Rating 6.7 8,122 reviews	Search British Airways flights
ITA Airways	PriceFrom $644	Free Cancellation	Rating 6.7 1,293 reviews	Search ITA Airways flights
United Airlines	PriceFrom $780	Free Cancellation	Rating 7.4 10,006 reviews	Search United Airlines flights
Lufthansa	PriceFrom $840	Free Cancellation	Rating 6.8 8,143 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 $1,249, but momondo users have found United Airlines deals from Chicago to Milan from as low as $780 round-trip. United Airlines has been scored 7.4/10 in 10,006 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 $840 round-trip, depending on your selected dates, with average Lufthansa deals seen on momondo around $1,193. Lufthansa operates 7 flights to Milan from Chicago in an average week. Users have rated it 6.8/10 across 8,143 reviews.

Bellagio

Varenna

Stresa

Brescia

Livigno

Monza

Lecco

Domodossola

Menaggio

Bellano

Assago

Crema

Cernobbio

Baveno

Levanto

Moltrasio

Rho

Bormio

Iseo

Novara

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 $227

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 10/6. 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

Icelandair flights from Chicago to Milan

Our best Icelandair 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

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

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

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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.

Popular cities in Italy

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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