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

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

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

Copenhagen (CPH) was the most common stop: 36% 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.

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.

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

Scandinavian Airlines and Air Serbia are the most popular carriers operating from Chicago to Milan

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 has the shortest travel time from Chicago to Milan?

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

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.

$213 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 $608 to $1,305. The lowest price recently found on this route was $455.

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One-way

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6:30 pm - 7:40 pmORD-BGY

18h 10m2 stops

10:35 pm - 5:20 pmBGY-ORD

25h 45m2 stops

$455Multiple Airlines

Find Deal

Fri, Jan 23 - Thu, Jan 29

6:30 pm - 7:40 pmORD-BGY

18h 10m2 stops

10:35 pm - 5:20 pmBGY-ORD

25h 45m2 stops

$456Multiple Airlines

Find Deal

Fri, Jan 23 - Thu, Jan 29

6:30 pm - 9:00 pmORD-BGY

19h 30m2 stops

5:45 am - 5:20 pmBGY-ORD

18h 35m2 stops

$469Multiple Airlines

Find Deal

Wed, Dec 10 - Tue, Dec 16

8:20 pm - 7:10 pmORD-MXP

16h 50m1 stop

6:25 pm - 5:45 pmMXP-ORD

29h 20m2 stops

$488Scandinavian Airlines

Find Deal

Sun, Mar 8 - Sat, Mar 14

7:20 pm - 8:00 pmORD-MXP

17h 40m2 stops

3:45 pm - 4:45 pmMXP-ORD

32h 00m2 stops

$489Scandinavian Airlines

Find Deal

Thu, Feb 12 - Tue, Feb 17

3:50 pm - 11:05 amORD-LIN

12h 15m1 stop

11:45 am - 5:55 pmLIN-ORD

13h 10m1 stop

$521Aer Lingus

Find Deal

Mon, Dec 1 - Tue, Dec 16

3:00 pm - 6:10 pmORD-LIN

20h 10m1 stop

7:00 am - 1:10 pmLIN-ORD

13h 10m1 stop

$523ITA Airways

Find Deal

Wed, Apr 1 - Fri, Apr 10

8:50 am - 11:40 amORD-LIN

19h 50m2 stops

11:30 am - 1:10 pmLIN-ORD

32h 40m1 stop

$550ITA Airways

Find Deal

Sun, Apr 26 - Tue, May 12

12:46 pm - 9:05 amMDW-MXP

13h 19m1 stop

10:05 am - 9:46 pmMXP-MDW

17h 41m1 stop

$829Delta

Find Deal

Tue, Feb 24 - Tue, Mar 10

1:49 pm - 11:40 amMDW-MXP

14h 51m2 stops

11:05 am - 10:44 pmMXP-MDW

18h 39m1 stop

$833Delta

Find Deal

Wed, Feb 18 - Wed, Feb 25

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

Mar 8

ORD8:20 pmChicago O'Hare Intl

16h 50m

1 stop

MXP7:10 pmMilan Malpensa

Mar 14

MXP6:25 pmMilan Malpensa

29h 20m

2 stops

ORD5:45 pmChicago O'Hare Intl

$488

Find similar

Scandinavian Airlines

Feb 12

ORD7:20 pmChicago O'Hare Intl

17h 40m

2 stops

MXP8:00 pmMilan Malpensa

Feb 17

MXP3:45 pmMilan Malpensa

32h 00m

2 stops

ORD4:45 pmChicago O'Hare Intl

$489

Find similar

Scandinavian Airlines

Feb 12

ORD7:20 pmChicago O'Hare Intl

16h 50m

1 stop

MXP7:10 pmMilan Malpensa

Feb 22

MXP8:00 pmMilan Malpensa

27h 45m

1 stop

ORD4:45 pmChicago O'Hare Intl

$492

Find similar

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

Delta

Feb 24

MDW12:46 pmChicago Midway

13h 19m

1 stop

MXP9:05 amMilan Malpensa

Mar 10

MXP10:05 amMilan Malpensa

17h 41m

1 stop

MDW9:46 pmChicago Midway

$829

Find similar

Delta

Feb 18

MDW1:49 pmChicago Midway

14h 51m

2 stops

MXP11:40 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

18h 39m

1 stop

MDW10:44 pmChicago Midway

$833

Find similar

Delta

Feb 11

MDW9:33 amChicago Midway

17h 12m

2 stops

MXP9:45 amMilan Malpensa

Feb 19

MXP1:20 pmMilan Malpensa

16h 24m

1 stop

MDW10:44 pmChicago Midway

$834

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

$455

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

$456

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 12/10

6:30 pm-9:00 pm

2 stops19h 30m

Bergamo Orio Al Serio

Tue 12/16

5:45 am-5:20 pm

2 stops18h 35m

$469

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 3/8

8:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Sat 3/14

6:25 pm-5:45 pm

2 stops29h 20m

$488

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 2/12

7:20 pm-8:00 pm

2 stops17h 40m

Milan Malpensa

Tue 2/17

3:45 pm-4:45 pm

2 stops32h 00m

$489

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 12/1

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Tue 12/16

11:45 am-5:55 pm

1 stop13h 10m

$521

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 4/1

3:00 pm-6:10 pm

1 stop20h 10m

Milan Linate

Fri 4/10

7:00 am-1:10 pm

1 stop13h 10m

$523

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 4/26

8:50 am-11:40 am

2 stops19h 50m

Milan Linate

Tue 5/12

11:30 am-1:10 pm

1 stop32h 40m

$550

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 2/24

12:46 pm-9:05 am

1 stop13h 19m

Milan Malpensa

Tue 3/10

10:05 am-9:46 pm

1 stop17h 41m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/18

1:49 pm-11:40 am

2 stops14h 51m

Milan Malpensa

Wed 2/25

11:05 am-10:44 pm

1 stop18h 39m

$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 $640.

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 $1,189. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,492.

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 $1,351. 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 $925 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 17% 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 $1,343.

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 25m.
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 23%, Aer Lingus at 14%, 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 $398	Free Cancellation	Rating 7.1 2,067 reviews	Search TAP AIR PORTUGAL flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Scandinavian Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 1,584 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 4,045 reviews	Search Turkish Airlines flights
British Airways	PriceFrom $536	Free Cancellation	Rating 6.7 7,534 reviews	Search British Airways flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,086 reviews	Search ITA Airways flights
Aer Lingus	PriceFrom $623	Free Cancellation	Rating 7.2 1,377 reviews	Search Aer Lingus flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,027 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 $1,281, 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 9,029 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 $246

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 1/10. 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 Delta 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 $640.

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 $1,189. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,492.

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 17% 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 and Air Serbia 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: 36% 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