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 offers the lowest fares from Chicago to Milan?

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

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 45% 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 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 is the cheapest airline that flies from Chicago to Milan?

Aer Lingus, TAP AIR PORTUGAL, and KLM are the most popular carriers operating from Chicago to Milan

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 March 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.

$217 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 $533 to $834. The lowest price recently found on this route was $434.

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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.

7:15 pm - 7:10 pm

ORD

MXP

16h 55m

1 stop

9:20 am - 4:10 pm

MXP

ORD

13h 50m

1 stop

$434Scandinavian Airlines

Wed, Apr 29 - Sat, May 9

7:15 pm - 3:05 pm

ORD

MXP

12h 50m

1 stop

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$441Scandinavian Airlines

Mon, Apr 27 - Tue, May 5

7:15 pm - 7:10 pm

ORD

MXP

16h 55m

1 stop

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$443Scandinavian Airlines

Wed, Apr 29 - Sun, May 10

7:15 pm - 7:50 pm

ORD

MXP

17h 35m

2 stops

3:00 pm - 4:10 pm

MXP

ORD

32h 10m

1 stop

$444Scandinavian Airlines

Mon, Apr 27 - Sun, May 10

7:25 pm - 12:25 am

ORD

BGY

22h 00m

2 stops

6:00 am - 6:15 pm

BGY

ORD

19h 15m

2 stops

$539Multiple Airlines

Tue, Apr 21 - Tue, Apr 28

7:25 pm - 11:20 pm

ORD

BGY

20h 55m

2 stops

6:00 am - 5:50 pm

BGY

ORD

18h 50m

2 stops

$567Multiple Airlines

Sun, Apr 26 - Tue, May 12

6:38 pm - 3:55 pm

MDW

LIN

14h 17m

2 stops

6:40 am - 6:33 pm

LIN

MDW

18h 53m

2 stops

$1,014Delta

Sun, Apr 26 - Tue, May 12

1:00 pm - 11:20 am

MDW

LIN

15h 20m

2 stops

6:25 am - 6:31 pm

LIN

MDW

19h 06m

2 stops

$1,019Delta

Sat, Aug 15 - Sat, Aug 22

6:38 pm - 3:55 pm

MDW

LIN

14h 17m

2 stops

11:00 am - 6:33 pm

LIN

MDW

14h 33m

2 stops

$1,061KLM

Sun, Apr 26 - Tue, May 12

12:52 pm - 9:25 am

MDW

MXP

13h 33m

1 stop

11:40 am - 9:09 pm

MXP

MDW

16h 29m

1 stop

$1,094KLM

Sun, Apr 26 - Tue, May 12

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Turkish Airlines

Mar 14

ORD12:50 pmChicago O'Hare Intl

21h 45m

1 stop

MXP4:35 pmMilan Malpensa

Mar 23

MXP6:55 amMilan Malpensa

34h 10m

1 stop

ORD11:05 amChicago O'Hare Intl

$618

Turkish Airlines

Mar 17

ORD12:50 pmChicago O'Hare Intl

18h 40m

1 stop

MXP1:30 pmMilan Malpensa

Mar 29

MXP7:45 pmMilan Malpensa

20h 55m

1 stop

ORD9:40 amChicago O'Hare Intl

$755

Turkish Airlines

Mar 9

ORD12:50 pmChicago O'Hare Intl

14h 50m

1 stop

MXP9:40 amMilan Malpensa

Mar 24

MXP6:35 pmMilan Malpensa

22h 30m

1 stop

ORD11:05 amChicago O'Hare Intl

$758

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

Delta

Apr 26

MDW6:38 pmChicago Midway

14h 17m

2 stops

LIN3:55 pmMilan Linate

May 12

LIN6:40 amMilan Linate

18h 53m

2 stops

MDW6:33 pmChicago Midway

$1,014

Delta

Aug 15

MDW1:00 pmChicago Midway

15h 20m

2 stops

LIN11:20 amMilan Linate

Aug 22

LIN6:25 amMilan Linate

19h 06m

2 stops

MDW6:31 pmChicago Midway

$1,019

Delta

Apr 26

MDW1:24 pmChicago Midway

15h 41m

2 stops

MXP12:05 pmMilan Malpensa

May 12

MXP9:00 amMilan Malpensa

19h 09m

2 stops

MDW9:09 pmChicago Midway

$1,050

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/29

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sat 5/9

9:20 am-4:10 pm

1 stop13h 50m

$434

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/27

7:15 pm-3:05 pm

1 stop12h 50m

Milan Malpensa

Tue 5/5

8:00 pm-4:10 pm

1 stop27h 10m

$441

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/29

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sun 5/10

8:00 pm-4:10 pm

1 stop27h 10m

$443

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/27

7:15 pm-7:50 pm

2 stops17h 35m

Milan Malpensa

Sun 5/10

3:00 pm-4:10 pm

1 stop32h 10m

$444

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 4/21

7:25 pm-12:25 am

2 stops22h 00m

Bergamo Orio Al Serio

Tue 4/28

6:00 am-6:15 pm

2 stops19h 15m

$539

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 4/26

7:25 pm-11:20 pm

2 stops20h 55m

Bergamo Orio Al Serio

Tue 5/12

6:00 am-5:50 pm

2 stops18h 50m

$567

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 4/26

6:38 pm-3:55 pm

2 stops14h 17m

Milan Linate

Tue 5/12

6:40 am-6:33 pm

2 stops18h 53m

$1,014

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sat 8/15

1:00 pm-11:20 am

2 stops15h 20m

Milan Linate

Sat 8/22

6:25 am-6:31 pm

2 stops19h 06m

$1,019

Quickest round-trip

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 4/26

6:38 pm-3:55 pm

2 stops14h 17m

Milan Linate

Tue 5/12

11:00 am-6:33 pm

2 stops14h 33m

$1,061

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 4/26

12:52 pm-9:25 am

1 stop13h 33m

Milan Malpensa

Tue 5/12

11:40 am-9:09 pm

1 stop16h 29m

$1,094

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 February is another great option to travel to Milan, with average flight prices from Chicago averaging around $600.

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 $1,184. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,366.

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 $858 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 $553 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 3% 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 March 2026, prices for Chicago to Milan flights are approximately 15% 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 $1,226.

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 11 as of March 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 51.47% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 37.33%, Boeing 787-8 Dreamliner with 9.87%, 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 30% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 29%, Aer Lingus at 12%, 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 2,163 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $410	Free Cancellation	Rating 7.3 1,705 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $496	Free Cancellation	Rating 6.7 7,779 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.3 4,249 reviews	Search Turkish Airlines flights
Aer Lingus	PriceFrom $564	Free Cancellation	Rating 7.2 1,471 reviews	Search Aer Lingus flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,159 reviews	Search ITA Airways flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.1 11,398 reviews	Search American Airlines flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,135 reviews	Search Iberia flights
SWISS	PriceFrom $759	Free Cancellation	Rating 7.6 1,889 reviews	Search SWISS flights
United Airlines	PriceFrom $789	Free Cancellation	Rating 7.4 9,405 reviews	Search United Airlines flights

Bellagio

Varenna

Menaggio

Brescia

Stresa

Livigno

Levanto

Monza

Assago

Bellano

Lecco

Crema

Domodossola

Rho

Cernobbio

Moltrasio

Saronno

Bormio

Baveno

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.

An easier way to manage your Milan trip

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Cheap flights from Chicago to Milan from $217

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 4/14. 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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Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Delta flights from Chicago to Milan

Our best Delta 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?

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 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?

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

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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