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.

How many flights depart from Chicago to Milan on average per day?

As of July 2026, there are 5 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 is the cheapest airline that flies from Chicago to Milan?

Air Serbia, JetBlue, and Aer Lingus 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 38% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 8 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Milan on average per week?

As of July 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.

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

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $403.

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

Copenhagen (CPH) was the most common stop: 33% 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 8 as of July 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.

$256 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 $934 to $1,526. The lowest price recently found on this route was $641.

Discover deals from 900+ travel sites with momondo.

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.

7:25 pm - 12:25 am

ORD

BGY

22h 00m

2 stops

6:00 am - 6:15 pm

BGY

ORD

19h 15m

2 stops

$641Multiple Airlines

Tue, Aug 18 - Tue, Aug 25

7:15 pm - 7:50 pm

ORD

MXP

17h 35m

2 stops

8:40 pm - 4:10 pm

MXP

ORD

26h 30m

2 stops

$650Scandinavian Airlines

Mon, Aug 24 - Mon, Aug 31

3:00 pm - 9:10 pm

ORD

LIN

23h 10m

1 stop

7:00 pm - 1:10 pm

LIN

ORD

25h 10m

1 stop

$654ITA Airways

Tue, Aug 18 - Tue, Aug 25

3:00 pm - 11:40 am

ORD

LIN

13h 40m

1 stop

1:00 pm - 1:10 pm

LIN

ORD

31h 10m

1 stop

$655ITA Airways

Wed, Aug 19 - Wed, Aug 26

1:05 pm - 10:55 am

MDW

MXP

14h 50m

1 stop

1:05 pm - 10:10 pm

MXP

MDW

16h 05m

1 stop

$784KLM

Mon, Dec 7 - Tue, Dec 22

12:41 pm - 9:25 am

MDW

MXP

13h 44m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$791Delta

Wed, Jul 29 - Fri, Aug 21

12:46 pm - 10:25 am

MDW

MXP

14h 39m

2 stops

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$795Delta

Wed, Aug 19 - Wed, Aug 26

4:39 pm - 9:25 am

MDW

MXP

33h 46m

1 stop

11:40 am - 10:36 pm

MXP

MDW

17h 56m

1 stop

$797KLM

Sat, Aug 8 - Fri, Aug 21

4:39 pm - 9:25 am

MDW

MXP

33h 46m

1 stop

11:25 am - 10:36 pm

MXP

MDW

18h 11m

2 stops

$808Air France

Sat, Aug 8 - Fri, Aug 21

1:51 pm - 11:20 am

MDW

LIN

14h 29m

2 stops

6:25 am - 4:15 pm

LIN

MDW

16h 50m

2 stops

$846Air France

Mon, Aug 3 - Wed, Aug 19

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Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Scandinavian Airlines

Aug 24

ORD7:15 pmChicago O'Hare Intl

12h 50m

1 stop

MXP3:05 pmMilan Malpensa

Aug 31

MXP8:40 pmMilan Malpensa

26h 30m

2 stops

ORD4:10 pmChicago O'Hare Intl

$639

Scandinavian Airlines

Aug 24

ORD7:15 pmChicago O'Hare Intl

17h 35m

2 stops

MXP7:50 pmMilan Malpensa

Aug 31

MXP8:40 pmMilan Malpensa

26h 30m

2 stops

ORD4:10 pmChicago O'Hare Intl

$650

Scandinavian Airlines

Sep 17

ORD7:15 pmChicago O'Hare Intl

16h 45m

2 stops

MXP7:00 pmMilan Malpensa

Sep 26

MXP11:30 amMilan Malpensa

35h 40m

2 stops

ORD4:10 pmChicago O'Hare Intl

$652

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

Delta

Jul 29

MDW12:41 pmChicago Midway

13h 44m

1 stop

MXP9:25 amMilan Malpensa

Aug 26

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$791

Delta

Aug 19

MDW12:46 pmChicago Midway

14h 39m

2 stops

MXP10:25 amMilan Malpensa

Aug 26

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$795

Delta

Aug 3

MDW1:25 pmChicago Midway

15h 40m

2 stops

MXP12:05 pmMilan Malpensa

Aug 20

MXP11:40 amMilan Malpensa

17h 56m

1 stop

MDW10:36 pmChicago Midway

$796

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 8/18

7:25 pm-12:25 am

2 stops22h 00m

Bergamo Orio Al Serio

Tue 8/25

6:00 am-6:15 pm

2 stops19h 15m

$641

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/24

7:15 pm-7:50 pm

2 stops17h 35m

Milan Malpensa

Mon 8/31

8:40 pm-4:10 pm

2 stops26h 30m

$650

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 8/18

3:00 pm-9:10 pm

1 stop23h 10m

Milan Linate

Tue 8/25

7:00 pm-1:10 pm

1 stop25h 10m

$654

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 8/19

3:00 pm-11:40 am

1 stop13h 40m

Milan Linate

Wed 8/26

1:00 pm-1:10 pm

1 stop31h 10m

$655

Quickest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 12/7

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Tue 12/22

1:05 pm-10:10 pm

1 stop16h 05m

$784

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 7/29

12:41 pm-9:25 am

1 stop13h 44m

Milan Malpensa

Fri 8/21

11:40 am-10:36 pm

1 stop17h 56m

$791

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/19

12:46 pm-10:25 am

2 stops14h 39m

Milan Malpensa

Wed 8/26

11:40 am-10:36 pm

1 stop17h 56m

$795

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 8/8

4:39 pm-9:25 am

1 stop33h 46m

Milan Malpensa

Fri 8/21

11:40 am-10:36 pm

1 stop17h 56m

$797

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 8/8

4:39 pm-9:25 am

1 stop33h 46m

Milan Malpensa

Fri 8/21

11:25 am-10:36 pm

2 stops18h 11m

$808

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 8/3

1:51 pm-11:20 am

2 stops14h 29m

Milan Linate

Wed 8/19

6:25 am-4:15 pm

2 stops16h 50m

$846

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 July is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $187. The month of October is another great option to travel to Milan, with average flight prices from Chicago averaging around $266.

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

Our data shows that Friday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,337. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,526.

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 from Chicago 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 $851 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 $555 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 39% 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 July 2026, prices for Chicago to Milan flights are approximately 21% 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	$873
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 $873. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $894.

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

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 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 8 as of July 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 787-10 Dreamliner, making up 84.61% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 8.02%, Boeing 787 Dreamliner with 4.83%, and Boeing 787-9 Dreamliner with 0.89%.
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 Scandinavian Airlines, representing 32% of all bookings. The subsequent popular airlines are United Airlines at 28%, Lufthansa at 11%, 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 7.2 2,324 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 1,871 reviews	Search Scandinavian Airlines flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.4 4,439 reviews	Search Turkish Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.3 1,648 reviews	Search Aer Lingus flights
British Airways	PriceFrom $644	Free Cancellation	Rating 6.7 8,103 reviews	Search British Airways flights
ITA Airways	PriceFrom $644	Free Cancellation	Rating 6.7 1,282 reviews	Search ITA Airways flights
United Airlines	PriceFrom $774	Free Cancellation	Rating 7.4 9,945 reviews	Search United Airlines flights
Lufthansa	PriceFrom $840	Free Cancellation	Rating 6.8 8,124 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 $1,236, but momondo users have found United Airlines deals from Chicago to Milan from as low as $774 round-trip. United Airlines has been scored 7.4/10 in 9,945 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 $1,193. Lufthansa operates 7 flights to Milan from Chicago in an average week. Users have rated it 6.8/10 across 8,124 reviews.

Bellagio

Varenna

Stresa

Brescia

Livigno

Lecco

Monza

Domodossola

Menaggio

Bellano

Assago

Crema

Cernobbio

Levanto

Moltrasio

Baveno

Bormio

Rho

Iseo

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.

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Cheap flights from Chicago to Milan from $256

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 7/26. 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

Delta flights from Chicago to Milan

Our best Delta 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 from Chicago 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 day?

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

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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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