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 is the cheapest airline that flies from Chicago to Milan?

Air Serbia, Turkish Airlines, 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 April 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.

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 43% 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.

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

Copenhagen (CPH) was the most common stop: 27% 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.

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.

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 April 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.

$318 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 $1,022 to $537. The lowest price recently found on this route was $595.

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Round-trip

One-way

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Cheap round-trip flights

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7:15 pm - 8:30 am

ORD

MXP

30h 15m

1 stop

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$595Scandinavian Airlines

Mon, Apr 27 - Thu, May 7

7:15 pm - 11:25 am

ORD

MXP

33h 10m

2 stops

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$610Scandinavian Airlines

Mon, Apr 27 - Thu, May 7

7:15 pm - 7:10 pm

ORD

MXP

16h 55m

1 stop

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$615Scandinavian Airlines

Mon, Aug 31 - Sun, Dec 13

11:25 am - 1:20 pm

ORD

MXP

18h 55m

1 stop

3:15 pm - 9:40 am

MXP

ORD

25h 25m

1 stop

$617Turkish Airlines

Sat, Sep 26 - Wed, Oct 7

11:25 am - 8:40 am

ORD

MXP

14h 15m

1 stop

6:50 am - 9:40 am

MXP

ORD

33h 50m

1 stop

$618Turkish Airlines

Tue, Apr 28 - Wed, May 20

3:45 pm - 10:40 am

ORD

LIN

11h 55m

1 stop

11:20 am - 7:15 pm

LIN

ORD

14h 55m

1 stop

$726Aer Lingus

Tue, Sep 8 - Mon, Oct 12

7:25 pm - 6:20 pm

ORD

BGY

15h 55m

2 stops

12:55 pm - 4:00 pm

BGY

ORD

34h 05m

2 stops

$731Multiple Airlines

Mon, Apr 27 - Thu, May 7

7:25 pm - 7:30 pm

ORD

BGY

17h 05m

3 stops

6:45 am - 6:15 pm

BGY

ORD

18h 30m

2 stops

$739Multiple Airlines

Mon, Apr 27 - Thu, May 7

1:00 pm - 11:20 am

MDW

LIN

15h 20m

2 stops

6:30 am - 4:22 pm

LIN

MDW

16h 52m

2 stops

$1,324Delta

Sat, Aug 22 - Wed, Dec 23

1:00 pm - 10:05 am

MDW

LIN

14h 05m

2 stops

6:40 am - 6:31 pm

LIN

MDW

18h 51m

2 stops

$1,527Delta

Fri, Aug 28 - Sun, Sep 13

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

Apr 27

ORD7:15 pmChicago O'Hare Intl

30h 15m

1 stop

MXP8:30 amMilan Malpensa

May 7

MXP8:00 pmMilan Malpensa

27h 10m

1 stop

ORD4:10 pmChicago O'Hare Intl

$595

Scandinavian Airlines

Apr 27

ORD7:15 pmChicago O'Hare Intl

33h 10m

2 stops

MXP11:25 amMilan Malpensa

May 7

MXP8:00 pmMilan Malpensa

27h 10m

1 stop

ORD4:10 pmChicago O'Hare Intl

$610

Scandinavian Airlines

Aug 31

ORD7:15 pmChicago O'Hare Intl

16h 55m

1 stop

MXP7:10 pmMilan Malpensa

Dec 13

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$615

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Turkish Airlines

Sep 26

ORD8:10 pmChicago O'Hare Intl

20h 35m

1 stop

MXP11:45 pmMilan Malpensa

Oct 8

MXP2:55 pmMilan Malpensa

25h 45m

1 stop

ORD9:40 amChicago O'Hare Intl

$617

Turkish Airlines

Apr 28

ORD11:25 amChicago O'Hare Intl

14h 15m

1 stop

MXP8:40 amMilan Malpensa

May 20

MXP6:50 amMilan Malpensa

33h 50m

1 stop

ORD9:40 amChicago O'Hare Intl

$618

Turkish Airlines

Sep 29

ORD11:25 amChicago O'Hare Intl

29h 20m

1 stop

MXP11:45 pmMilan Malpensa

Oct 12

MXP10:40 amMilan Malpensa

30h 00m

1 stop

ORD9:40 amChicago O'Hare Intl

$627

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/27

7:15 pm-8:30 am

1 stop30h 15m

Milan Malpensa

Thu 5/7

8:00 pm-4:10 pm

1 stop27h 10m

$595

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/27

7:15 pm-11:25 am

2 stops33h 10m

Milan Malpensa

Thu 5/7

8:00 pm-4:10 pm

1 stop27h 10m

$610

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/31

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sun 12/13

11:15 am-4:45 pm

1 stop12h 30m

$615

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 9/26

11:25 am-1:20 pm

1 stop18h 55m

Milan Malpensa

Wed 10/7

3:15 pm-9:40 am

1 stop25h 25m

$617

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 4/28

11:25 am-8:40 am

1 stop14h 15m

Milan Malpensa

Wed 5/20

6:50 am-9:40 am

1 stop33h 50m

$618

Quickest round-trip

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 9/8

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Mon 10/12

11:20 am-7:15 pm

1 stop14h 55m

$726

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 4/27

7:25 pm-6:20 pm

2 stops15h 55m

Bergamo Orio Al Serio

Thu 5/7

12:55 pm-4:00 pm

2 stops34h 05m

$731

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 4/27

7:25 pm-7:30 pm

3 stops17h 05m

Bergamo Orio Al Serio

Thu 5/7

6:45 am-6:15 pm

2 stops18h 30m

$739

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sat 8/22

1:00 pm-11:20 am

2 stops15h 20m

Milan Linate

Wed 12/23

6:30 am-4:22 pm

2 stops16h 52m

$1,324

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Fri 8/28

1:00 pm-10:05 am

2 stops14h 05m

Milan Linate

Sun 9/13

6:40 am-6:31 pm

2 stops18h 51m

$1,527

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 $534. The month of February is another great option to travel to Milan, with average flight prices from Chicago averaging around $543.

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 $1,213. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,361.

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 $860 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 $517 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 April 2026, prices for Chicago to Milan flights are approximately 77% more expensive 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	$848
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Milan	2 airports

The best one-way flight to Milan from Chicago in the past 72 hours is $848. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,236.

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

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 30m.
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 April 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 55.66% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 36.98%, Boeing 787-8 Dreamliner with 6.04%, and Boeing 737 MAX 8 with 0.19%.
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 30%, Aer Lingus at 12%, and TAP AIR PORTUGAL at 9%.

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 7.1 2,196 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $403	Free Cancellation	Rating 7.3 1,748 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $496	Free Cancellation	Rating 6.7 7,867 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.3 4,305 reviews	Search Turkish Airlines flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.1 11,561 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.2 1,500 reviews	Search Aer Lingus flights
ITA Airways	PriceFrom $644	Free Cancellation	Rating 6.7 1,182 reviews	Search ITA Airways flights
United Airlines	PriceFrom $764	Free Cancellation	Rating 7.4 9,561 reviews	Search United Airlines flights
Lufthansa	PriceFrom $840	Free Cancellation	Rating 6.8 7,901 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 $1,231, but momondo users have found United Airlines deals from Chicago to Milan from as low as $764 round-trip. United Airlines has been scored 7.4/10 in 9,561 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 $1,096. Lufthansa operates 7 flights to Milan from Chicago in an average week. Users have rated it 6.8/10 across 7,901 reviews.

Bellagio

Varenna

Menaggio

Stresa

Brescia

Livigno

Levanto

Assago

Monza

Bellano

Lecco

Crema

Rho

Domodossola

Cernobbio

Moltrasio

Bormio

Novara

Baveno

Saronno

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 $318

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 4/25. 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

Turkish Airlines flights from Chicago to Milan

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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 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 week?

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

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

United Airlines Flights From Chicago to Milan

Lufthansa Flights From Chicago to Milan

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.

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

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