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

Scandinavian Airlines, KLM, and Delta are the most popular carriers operating from Chicago to Milan

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

As of November 2025, there are 33 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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.

What airlines fly to Milan?

United Airlines, Scandinavian Airlines and British Airways 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 44% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 11 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

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

Madrid (MAD) has the shortest average layover time for this route: 1h 10m.

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

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $447.

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

Copenhagen (CPH) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

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

As of November 2025, 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.

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 11 as of November 2025.

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.

$236 Cheap Flights from Chicago to Milan in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $610 to $1,300. The lowest price recently found on this route was $454.

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6:30 pm - 7:40 pmORD-BGY

18h 10m2 stops

10:35 pm - 5:20 pmBGY-ORD

25h 45m2 stops

$454Multiple Airlines

Find Deal

Fri, Jan 23 - Thu, Jan 29

6:30 pm - 8:05 pmORD-BGY

18h 35m2 stops

5:45 am - 5:20 pmBGY-ORD

18h 35m2 stops

$462Multiple Airlines

Find Deal

Thu, Jan 8 - Thu, Jan 15

7:00 am - 7:10 pmORD-MXP

29h 10m2 stops

8:00 pm - 4:10 pmMXP-ORD

27h 10m1 stop

$496Scandinavian Airlines

Find Deal

Sat, Apr 4 - Sun, Apr 12

7:20 pm - 8:25 amORD-MXP

30h 05m1 stop

8:00 pm - 4:45 pmMXP-ORD

27h 45m1 stop

$497Scandinavian Airlines

Find Deal

Wed, Feb 4 - Sun, Mar 1

7:20 pm - 7:10 pmORD-MXP

16h 50m1 stop

8:00 pm - 10:29 pmMXP-ORD

33h 29m2 stops

$498Scandinavian Airlines

Find Deal

Thu, Jan 15 - Mon, Jan 19

7:20 pm - 7:10 pmORD-MXP

16h 50m1 stop

9:15 am - 9:48 pmMXP-ORD

19h 33m2 stops

$502Scandinavian Airlines

Find Deal

Wed, Feb 11 - Tue, Feb 17

5:00 pm - 3:05 pmORD-LIN

15h 05m1 stop

7:25 am - 1:50 pmLIN-ORD

13h 25m1 stop

$555British Airways

Find Deal

Wed, Apr 1 - Fri, Apr 10

12:46 pm - 9:05 amMDW-MXP

13h 19m1 stop

11:05 am - 10:44 pmMXP-MDW

18h 39m1 stop

$829KLM

Find Deal

Tue, Feb 24 - Wed, Mar 4

6:40 pm - 6:50 pmMDW-MXP

17h 10m2 stops

11:05 am - 10:42 pmMXP-MDW

18h 37m1 stop

$832Delta

Find Deal

Sun, Feb 22 - Wed, Mar 4

1:49 pm - 11:40 amMDW-MXP

14h 51m2 stops

11:05 am - 10:22 pmMXP-MDW

18h 17m1 stop

$833Delta

Find Deal

Wed, Jan 14 - Thu, Jan 22

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

May 8

ORD7:15 pmChicago O'Hare Intl

32h 20m

1 stop

MXP10:35 amMilan Malpensa

May 16

MXP11:30 amMilan Malpensa

35h 40m

2 stops

ORD4:10 pmChicago O'Hare Intl

$491

Find similar

Scandinavian Airlines

Apr 4

ORD7:00 amChicago O'Hare Intl

29h 10m

2 stops

MXP7:10 pmMilan Malpensa

Apr 12

MXP8:00 pmMilan Malpensa

27h 10m

1 stop

ORD4:10 pmChicago O'Hare Intl

$496

Find similar

Scandinavian Airlines

Feb 4

ORD7:20 pmChicago O'Hare Intl

30h 05m

1 stop

MXP8:25 amMilan Malpensa

Mar 2

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$497

Find similar

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets

TAP AIR PORTUGAL

Dec 5

ORD8:15 pmChicago O'Hare Intl

20h 20m

1 stop

MXP11:35 pmMilan Malpensa

Dec 9

MXP5:45 pmMilan Malpensa

28h 15m

1 stop

ORD3:00 pmChicago O'Hare Intl

$536

Find similar

TAP AIR PORTUGAL

Feb 1

ORD8:25 pmChicago O'Hare Intl

13h 30m

1 stop

MXP4:55 pmMilan Malpensa

Feb 27

MXP6:20 amMilan Malpensa

16h 05m

1 stop

ORD3:25 pmChicago O'Hare Intl

$549

Find similar

TAP AIR PORTUGAL

Feb 8

ORD8:25 pmChicago O'Hare Intl

20h 10m

1 stop

MXP11:35 pmMilan Malpensa

Feb 14

MXP5:45 pmMilan Malpensa

28h 00m

1 stop

ORD2:45 pmChicago O'Hare Intl

$558

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 1/23

6:30 pm-7:40 pm

2 stops18h 10m

Bergamo Orio Al Serio

Thu 1/29

10:35 pm-5:20 pm

2 stops25h 45m

$454

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Thu 1/8

6:30 pm-8:05 pm

2 stops18h 35m

Bergamo Orio Al Serio

Thu 1/15

5:45 am-5:20 pm

2 stops18h 35m

$462

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 4/4

7:00 am-7:10 pm

2 stops29h 10m

Milan Malpensa

Sun 4/12

8:00 pm-4:10 pm

1 stop27h 10m

$496

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/4

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Sun 3/1

8:00 pm-4:45 pm

1 stop27h 45m

$497

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 1/15

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Mon 1/19

8:00 pm-10:29 pm

2 stops33h 29m

$498

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/11

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Tue 2/17

9:15 am-9:48 pm

2 stops19h 33m

$502

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 4/1

5:00 pm-3:05 pm

1 stop15h 05m

Milan Linate

Fri 4/10

7:25 am-1:50 pm

1 stop13h 25m

$555

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 2/24

12:46 pm-9:05 am

1 stop13h 19m

Milan Malpensa

Wed 3/4

11:05 am-10:44 pm

1 stop18h 39m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/22

6:40 pm-6:50 pm

2 stops17h 10m

Milan Malpensa

Wed 3/4

11:05 am-10:42 pm

1 stop18h 37m

$832

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/14

1:49 pm-11:40 am

2 stops14h 51m

Milan Malpensa

Thu 1/22

11:05 am-10:22 pm

1 stop18h 17m

$833

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 $636. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $639.

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 $1,186. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,494.

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

In the morning is the cheapest time of day to fly from Chicago to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,350. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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 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 $930 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 $650 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 23% 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 November 2025, prices for Chicago to Milan flights are approximately 2% 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	$632
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Milan	1 airport

The best one-way flight to Milan from Chicago in the past 72 hours is $632. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,342.

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

Direct flights go from Chicago to Milan every day.

There is 1 airport near Milan: Milan Malpensa (MXP)

Search flight deals

How far is Chicago to Milan by plane?
There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 11h 35m.
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 11 as of November 2025.
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 51.62% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 45.95%, Boeing 787-10 Dreamliner with 1.89%, and Boeing 737 MAX 8 with 0.27%.
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 27% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 24%, Aer Lingus at 14%, and TAP AIR PORTUGAL 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 $398	Free Cancellation	Rating 7.1 2,074 reviews	Search TAP AIR PORTUGAL flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 7,999 reviews	Search Delta flights
Scandinavian Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 1,589 reviews	Search Scandinavian Airlines flights
Icelandair	PriceFrom $484	Free Cancellation	Rating 7.0 581 reviews	Search Icelandair flights
Turkish Airlines	PriceFrom $518	Free Cancellation	Rating 7.3 4,059 reviews	Search Turkish Airlines flights
British Airways	PriceFrom $536	Free Cancellation	Rating 6.7 7,539 reviews	Search British Airways flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,089 reviews	Search ITA Airways flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $626	Free Cancellation	Rating 7.2 1,381 reviews	Search Aer Lingus flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,034 reviews	Search Iberia flights

United Airlines Flights From Chicago to Milan
United Airlines operates around 6 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,288, but momondo users have found United Airlines deals from Chicago to Milan from as low as $789 round-trip. United Airlines has been scored 7.4/10 in 9,046 reviews.

Bellagio

Varenna

Menaggio

Brescia

Stresa

Monza

Assago

Levanto

Livigno

Domodossola

Bellano

Lecco

Rho

Bormio

Crema

Cernobbio

Moltrasio

Saronno

Novara

Baveno

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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Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Fly to other destinations from Chicago

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Cheap flights from Chicago to Milan from $236

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 12/3. 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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Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

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Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets

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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

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 $636. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $639.

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 $1,186. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,494.

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

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 to Milan?

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 23% 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 November 2025, prices for Chicago to Milan flights are approximately 2% cheaper when compared to flights at the same time last year.

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

Scandinavian Airlines, KLM, and Delta are the most popular carriers operating from Chicago to Milan

What airlines fly to Milan?

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

Copenhagen (CPH) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $447.

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.

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

Madrid (MAD) has the shortest average layover time for this route: 1h 10m.

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

As of November 2025, 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.

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

As of November 2025, there are 33 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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

How far is Chicago to Milan by plane?

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

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

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

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

What is the most popular plane model from Chicago to Milan?

What is the most popular airline 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

Traveling to a place near Milan?

Why use momondo?

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

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

How can momondo help me find flights 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?

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