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.

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

Air Serbia, KLM, and Delta are the most popular carriers operating from Chicago to Milan

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 46% 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 offers the lowest fares from Chicago to Milan?

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

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

Copenhagen (CPH) was the most common stop: 31% 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 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.

$245 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 $519 to $858. The lowest price recently found on this route was $508.

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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 - 7:50 pm

ORD

MXP

17h 35m

2 stops

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$508Scandinavian Airlines

Fri, Aug 21 - Sat, Dec 12

7:15 pm - 11:20 am

ORD

MXP

33h 05m

2 stops

9:20 am - 4:10 pm

MXP

ORD

13h 50m

1 stop

$528Scandinavian Airlines

Sat, Apr 18 - Wed, Apr 22

7:15 pm - 8:30 am

ORD

MXP

30h 15m

1 stop

3:55 pm - 4:10 pm

MXP

ORD

31h 15m

1 stop

$531Scandinavian Airlines

Sat, Apr 18 - Tue, Apr 21

7:15 pm - 6:00 pm

ORD

MXP

15h 45m

2 stops

3:55 pm - 4:10 pm

MXP

ORD

31h 15m

1 stop

$532Scandinavian Airlines

Sat, Apr 18 - Tue, Apr 21

7:15 pm - 11:25 am

ORD

MXP

33h 10m

2 stops

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$534Scandinavian Airlines

Sun, Aug 30 - Thu, Sep 10

6:23 pm - 7:10 pm

ORD

MXP

41h 47m

2 stops

8:00 pm - 4:10 pm

MXP

ORD

27h 10m

1 stop

$543Scandinavian Airlines

Sat, May 2 - Fri, May 15

4:05 pm - 9:40 pm

ORD

BGY

22h 35m

2 stops

10:50 am - 1:20 pm

BGY

ORD

33h 30m

2 stops

$595Multiple Airlines

Mon, Apr 13 - Mon, Apr 20

10:35 am - 9:25 am

MDW

MXP

15h 50m

1 stop

6:45 am - 4:27 pm

MXP

MDW

16h 42m

2 stops

$1,012Delta

Sat, Aug 8 - Wed, Aug 19

9:30 am - 9:25 am

MDW

MXP

16h 55m

2 stops

6:45 am - 4:27 pm

MXP

MDW

16h 42m

2 stops

$1,016Delta

Sat, Aug 8 - Wed, Aug 19

12:51 pm - 12:00 pm

MDW

LIN

16h 09m

2 stops

6:40 am - 6:05 pm

LIN

MDW

18h 25m

2 stops

$1,237Delta

Thu, May 21 - Wed, Aug 19

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

Aug 21

ORD7:15 pmChicago O'Hare Intl

17h 35m

2 stops

MXP7:50 pmMilan Malpensa

Dec 12

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

$508

Scandinavian Airlines

Apr 18

ORD7:15 pmChicago O'Hare Intl

33h 05m

2 stops

MXP11:20 amMilan Malpensa

Apr 22

MXP9:20 amMilan Malpensa

13h 50m

1 stop

ORD4:10 pmChicago O'Hare Intl

$528

Scandinavian Airlines

Apr 18

ORD7:15 pmChicago O'Hare Intl

30h 15m

1 stop

MXP8:30 amMilan Malpensa

Apr 21

MXP3:55 pmMilan Malpensa

31h 15m

1 stop

ORD4:10 pmChicago O'Hare Intl

$531

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Turkish Airlines

Apr 28

ORD11:25 amChicago O'Hare Intl

23h 35m

1 stop

MXP6:00 pmMilan Malpensa

May 26

MXP6:50 amMilan Malpensa

33h 50m

1 stop

ORD9:40 amChicago O'Hare Intl

$553

Turkish Airlines

Apr 14

ORD8:10 pmChicago O'Hare Intl

34h 10m

1 stop

MXP1:20 pmMilan Malpensa

Apr 22

MXP8:10 pmMilan Malpensa

20h 30m

1 stop

ORD9:40 amChicago O'Hare Intl

$565

Turkish Airlines

Sep 6

ORD8:10 pmChicago O'Hare Intl

20h 35m

1 stop

MXP11:45 pmMilan Malpensa

Sep 17

MXP10:40 amMilan Malpensa

30h 00m

1 stop

ORD9:40 amChicago O'Hare Intl

$572

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 8/21

7:15 pm-7:50 pm

2 stops17h 35m

Milan Malpensa

Sat 12/12

11:15 am-4:45 pm

1 stop12h 30m

$508

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 4/18

7:15 pm-11:20 am

2 stops33h 05m

Milan Malpensa

Wed 4/22

9:20 am-4:10 pm

1 stop13h 50m

$528

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 4/18

7:15 pm-8:30 am

1 stop30h 15m

Milan Malpensa

Tue 4/21

3:55 pm-4:10 pm

1 stop31h 15m

$531

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 4/18

7:15 pm-6:00 pm

2 stops15h 45m

Milan Malpensa

Tue 4/21

3:55 pm-4:10 pm

1 stop31h 15m

$532

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 8/30

7:15 pm-11:25 am

2 stops33h 10m

Milan Malpensa

Thu 9/10

8:00 pm-4:10 pm

1 stop27h 10m

$534

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 5/2

6:23 pm-7:10 pm

2 stops41h 47m

Milan Malpensa

Fri 5/15

8:00 pm-4:10 pm

1 stop27h 10m

$543

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 4/13

4:05 pm-9:40 pm

2 stops22h 35m

Bergamo Orio Al Serio

Mon 4/20

10:50 am-1:20 pm

2 stops33h 30m

$595

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 8/8

10:35 am-9:25 am

1 stop15h 50m

Milan Malpensa

Wed 8/19

6:45 am-4:27 pm

2 stops16h 42m

$1,012

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 8/8

9:30 am-9:25 am

2 stops16h 55m

Milan Malpensa

Wed 8/19

6:45 am-4:27 pm

2 stops16h 42m

$1,016

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Thu 5/21

12:51 pm-12:00 pm

2 stops16h 09m

Milan Linate

Wed 8/19

6:40 am-6:05 pm

2 stops18h 25m

$1,237

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 $539. The month of February is another great option to travel to Milan, with average flight prices from Chicago averaging around $594.

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

Our data shows that Sunday 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 Thursday, with ticket prices averaging around $1,365.

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 $859 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 4% 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	$774
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 $774. 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 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 54.64% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 35.65%, Boeing 787-8 Dreamliner with 8.65%, and Boeing 737 MAX 8 with 0.21%.
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 31% 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 $401	Free Cancellation	Rating 7.1 2,166 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $403	Free Cancellation	Rating 7.3 1,715 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $496	Free Cancellation	Rating 6.7 7,794 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.3 4,256 reviews	Search Turkish Airlines flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,170 reviews	Search ITA Airways flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.1 11,466 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.2 1,477 reviews	Search Aer Lingus flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,136 reviews	Search Iberia flights
SWISS	PriceFrom $759	Free Cancellation	Rating 7.5 1,897 reviews	Search SWISS flights
United Airlines	PriceFrom $789	Free Cancellation	Rating 7.4 9,428 reviews	Search United Airlines flights

Bellagio

Varenna

Menaggio

Brescia

Stresa

Livigno

Levanto

Monza

Assago

Bellano

Lecco

Crema

Rho

Domodossola

Cernobbio

Moltrasio

Bormio

Saronno

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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Milan Linate Airport

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Cheap flights from Chicago to Milan from $245

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 4/21. 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 Turkish Airlines deals on Chicago to Milan flight tickets

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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?

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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