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

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 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 49% 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.

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

Air Serbia and Scandinavian Airlines 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: 41% of momondo users choosing 1-stop flights on this route connected there.

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 January 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.

$239 Cheap Flights from Chicago to Milan in 2026

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 $498 to $700. The lowest price recently found on this route was $427.

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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.

7:20 pm - 7:10 pm

ORD

MXP

16h 50m

1 stop

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$427Scandinavian Airlines

Wed, Feb 25 - Mon, Mar 2

7:10 pm - 7:10 pm

ORD

MXP

17h 00m

1 stop

8:00 pm - 4:45 pm

MXP

ORD

27h 45m

1 stop

$428Scandinavian Airlines

Sun, Feb 22 - Sun, Mar 1

7:15 pm - 7:10 pm

ORD

MXP

16h 55m

1 stop

11:45 am - 4:10 pm

MXP

ORD

35h 25m

2 stops

$430Scandinavian Airlines

Wed, Apr 15 - Fri, Apr 24

6:30 pm - 12:10 am

ORD

BGY

22h 40m

2 stops

6:45 am - 5:20 pm

BGY

ORD

17h 35m

2 stops

$484Multiple Airlines

Wed, Feb 25 - Wed, Mar 4

6:30 pm - 9:35 pm

ORD

BGY

20h 05m

2 stops

10:10 pm - 6:20 pm

BGY

ORD

26h 10m

2 stops

$538Multiple Airlines

Tue, Mar 3 - Mon, Mar 9

1:06 pm - 3:10 pm

ORD

LIN

20h 04m

2 stops

9:00 pm - 6:39 pm

LIN

ORD

28h 39m

2 stops

$564ITA Airways

Tue, Mar 24 - Mon, Mar 30

12:47 pm - 8:05 am

MDW

MXP

13h 18m

1 stop

11:40 am - 10:31 pm

MXP

MDW

17h 51m

1 stop

$831Delta

Wed, Mar 18 - Tue, Mar 31

9:35 am - 8:05 am

MDW

MXP

16h 30m

2 stops

6:55 am - 5:54 pm

MXP

MDW

16h 59m

2 stops

$896Delta

Thu, Mar 19 - Thu, Mar 26

10:45 am - 8:05 am

MDW

MXP

15h 20m

1 stop

11:40 am - 10:31 pm

MXP

MDW

17h 51m

1 stop

$941KLM

Thu, Mar 19 - Tue, Mar 31

12:47 pm - 8:05 am

MDW

MXP

13h 18m

1 stop

11:40 am - 10:31 pm

MXP

MDW

17h 51m

1 stop

$1,063KLM

Thu, Mar 19 - Wed, Apr 1

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

Delta

Mar 18

MDW12:47 pmChicago Midway

13h 18m

1 stop

MXP8:05 amMilan Malpensa

Mar 31

MXP11:40 amMilan Malpensa

17h 51m

1 stop

MDW10:31 pmChicago Midway

$831

Delta

Mar 19

MDW9:35 amChicago Midway

16h 30m

2 stops

MXP8:05 amMilan Malpensa

Mar 26

MXP6:55 amMilan Malpensa

16h 59m

2 stops

MDW5:54 pmChicago Midway

$896

Delta

Mar 19

MDW9:35 amChicago Midway

16h 30m

2 stops

MXP8:05 amMilan Malpensa

Apr 1

MXP6:45 amMilan Malpensa

18h 55m

2 stops

MDW6:40 pmChicago Midway

$897

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets

KLM

Mar 19

MDW10:45 amChicago Midway

15h 20m

1 stop

MXP8:05 amMilan Malpensa

Mar 31

MXP11:40 amMilan Malpensa

17h 51m

1 stop

MDW10:31 pmChicago Midway

$941

KLM

Mar 19

MDW12:47 pmChicago Midway

13h 18m

1 stop

MXP8:05 amMilan Malpensa

Apr 1

MXP11:40 amMilan Malpensa

17h 51m

1 stop

MDW10:31 pmChicago Midway

$1,063

KLM

Apr 9

MDW12:47 pmChicago Midway

13h 38m

1 stop

MXP9:25 amMilan Malpensa

Apr 18

MXP11:40 amMilan Malpensa

17h 49m

1 stop

MDW10:29 pmChicago Midway

$1,086

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/25

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Mon 3/2

11:15 am-4:45 pm

1 stop12h 30m

$427

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 2/22

7:10 pm-7:10 pm

1 stop17h 00m

Milan Malpensa

Sun 3/1

8:00 pm-4:45 pm

1 stop27h 45m

$428

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/15

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Fri 4/24

11:45 am-4:10 pm

2 stops35h 25m

$430

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 2/25

6:30 pm-12:10 am

2 stops22h 40m

Bergamo Orio Al Serio

Wed 3/4

6:45 am-5:20 pm

2 stops17h 35m

$484

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 3/3

6:30 pm-9:35 pm

2 stops20h 05m

Bergamo Orio Al Serio

Mon 3/9

10:10 pm-6:20 pm

2 stops26h 10m

$538

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 3/24

1:06 pm-3:10 pm

2 stops20h 04m

Milan Linate

Mon 3/30

9:00 pm-6:39 pm

2 stops28h 39m

$564

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/18

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$831

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

9:35 am-8:05 am

2 stops16h 30m

Milan Malpensa

Thu 3/26

6:55 am-5:54 pm

2 stops16h 59m

$896

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$941

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Wed 4/1

11:40 am-10:31 pm

1 stop17h 51m

$1,063

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

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 $543. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $614.

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 $1,478.

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 $918 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 $711 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 5% 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 January 2026, prices for Chicago to Milan flights are approximately 11% 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	$764
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 $764. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,070.

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

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 9 as of January 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 50.43% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 28.70%, Boeing 787-8 Dreamliner with 18.70%, and Boeing 737 MAX 8 with 0.43%.
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 29% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 26%, Aer Lingus at 13%, 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 2,130 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $410	Free Cancellation	Rating 7.3 1,674 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $496	Free Cancellation	Rating 6.7 7,705 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $518	Free Cancellation	Rating 7.3 4,208 reviews	Search Turkish Airlines flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,137 reviews	Search ITA Airways flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $626	Free Cancellation	Rating 7.2 1,443 reviews	Search Aer Lingus flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,099 reviews	Search Iberia flights
United Airlines	PriceFrom $793	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights

Bellagio

Varenna

Menaggio

Brescia

Stresa

Livigno

Levanto

Monza

Assago

Bellano

Domodossola

Lecco

Crema

Rho

Cernobbio

Bormio

Moltrasio

Saronno

Baveno

Asti

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.

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.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Cheap flights from Chicago to Milan from $239

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 3/28. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

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Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets

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Use the filters below to find and compare flights from Chicago to Milan that are best for you.

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?

The month of January is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $543. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $614.

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 $1,478.

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 5% 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 January 2026, prices for Chicago to Milan flights are approximately 11% cheaper when compared to flights at the same time last year.

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

Air Serbia and Scandinavian Airlines 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: 41% 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 Reykjavik (KEF) offer the lowest average round-trip price of $395.

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.

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

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

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