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

Copenhagen (CPH) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

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

Scandinavian Airlines and Delta are the most popular carriers operating from Chicago to Milan

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 Lisbon (LIS) offer the lowest average round-trip price of $493.

What airlines fly to Milan?

United Airlines, Scandinavian Airlines and British Airways 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 travel time from Chicago to Milan?

Flights connecting via Paris (CDG) have the shortest average one-way travel time: 10h 55m.

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 December 2025.

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.

$248 Cheap Flights from Chicago to Milan in 2025/26

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 $670 to $1,684. The lowest price recently found on this route was $452.

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One-way

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Cheap round-trip flights

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6:30 pm - 12:10 amORD-BGY

22h 40m2 stops

6:45 am - 5:20 pmBGY-ORD

17h 35m2 stops

$452Multiple Airlines

Find Deal

Wed, Jan 14 - Wed, Jan 21

6:30 pm - 9:00 pmORD-BGY

19h 30m2 stops

10:10 pm - 5:20 pmBGY-ORD

26h 10m2 stops

$462Multiple Airlines

Find Deal

Wed, Jan 14 - Mon, Jan 19

6:30 pm - 8:05 pmORD-BGY

18h 35m2 stops

5:45 am - 5:20 pmBGY-ORD

18h 35m2 stops

$486Multiple Airlines

Find Deal

Thu, Jan 15 - Thu, Jan 22

7:15 pm - 7:50 pmORD-MXP

17h 35m2 stops

8:40 pm - 4:10 pmMXP-ORD

50h 30m2 stops

$491Scandinavian Airlines

Find Deal

Mon, Apr 13 - Sat, Apr 25

10:29 am - 10:25 amORD-MXP

16h 56m2 stops

8:00 pm - 10:29 pmMXP-ORD

33h 29m2 stops

$492Scandinavian Airlines

Find Deal

Thu, Feb 5 - Mon, Feb 9

7:05 pm - 3:00 pmORD-LIN

12h 55m1 stop

11:10 am - 6:15 pmLIN-ORD

14h 05m1 stop

$551British Airways

Find Deal

Sun, Apr 26 - Tue, May 5

10:46 am - 9:05 amMDW-MXP

15h 19m1 stop

11:05 am - 10:22 pmMXP-MDW

18h 17m1 stop

$829KLM

Find Deal

Wed, Jan 21 - Fri, Jan 30

12:48 pm - 11:40 amMDW-MXP

15h 52m2 stops

11:05 am - 10:22 pmMXP-MDW

18h 17m1 stop

$833Delta

Find Deal

Wed, Jan 21 - Fri, Jan 30

12:47 pm - 8:05 amMDW-MXP

13h 18m1 stop

11:00 am - 10:29 pmMXP-MDW

17h 29m2 stops

$834Delta

Find Deal

Tue, Mar 10 - Tue, Mar 17

12:48 pm - 9:05 amMDW-MXP

13h 17m1 stop

11:05 am - 10:22 pmMXP-MDW

18h 17m1 stop

$879KLM

Find Deal

Fri, Jan 23 - Fri, Jan 30

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets

TAP AIR PORTUGAL

Apr 3

ORD6:00 pmChicago O'Hare Intl

15h 55m

1 stop

MXP4:55 pmMilan Malpensa

Apr 11

MXP8:00 pmMilan Malpensa

27h 00m

1 stop

ORD4:00 pmChicago O'Hare Intl

$508

Find similar

TAP AIR PORTUGAL

Dec 5

ORD8:15 pmChicago O'Hare Intl

20h 20m

1 stop

MXP11:35 pmMilan Malpensa

Dec 7

MXP6:20 amMilan Malpensa

15h 25m

1 stop

ORD2:45 pmChicago O'Hare Intl

$513

Find similar

TAP AIR PORTUGAL

Mar 4

ORD7:10 pmChicago O'Hare Intl

14h 45m

1 stop

MXP4:55 pmMilan Malpensa

Mar 14

MXP5:45 pmMilan Malpensa

28h 00m

1 stop

ORD3:45 pmChicago O'Hare Intl

$520

Find similar

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets

Delta

Jan 21

MDW12:48 pmChicago Midway

15h 52m

2 stops

MXP11:40 amMilan Malpensa

Jan 30

MXP11:05 amMilan Malpensa

18h 17m

1 stop

MDW10:22 pmChicago Midway

$833

Find similar

Delta

Mar 10

MDW9:32 amChicago Midway

16h 33m

2 stops

MXP8:05 amMilan Malpensa

Mar 17

MXP11:00 amMilan Malpensa

17h 29m

2 stops

MDW10:29 pmChicago Midway

$834

Find similar

Delta

Feb 9

MDW1:26 pmChicago Midway

14h 09m

2 stops

MXP10:35 amMilan Malpensa

Feb 16

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$883

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 1/14

6:30 pm-12:10 am

2 stops22h 40m

Bergamo Orio Al Serio

Wed 1/21

6:45 am-5:20 pm

2 stops17h 35m

$452

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 1/14

6:30 pm-9:00 pm

2 stops19h 30m

Bergamo Orio Al Serio

Mon 1/19

10:10 pm-5:20 pm

2 stops26h 10m

$462

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Thu 1/15

6:30 pm-8:05 pm

2 stops18h 35m

Bergamo Orio Al Serio

Thu 1/22

5:45 am-5:20 pm

2 stops18h 35m

$486

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/13

7:15 pm-7:50 pm

2 stops17h 35m

Milan Malpensa

Sat 4/25

8:40 pm-4:10 pm

2 stops50h 30m

$491

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 2/5

10:29 am-10:25 am

2 stops16h 56m

Milan Malpensa

Mon 2/9

8:00 pm-10:29 pm

2 stops33h 29m

$492

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 4/26

7:05 pm-3:00 pm

1 stop12h 55m

Milan Linate

Tue 5/5

11:10 am-6:15 pm

1 stop14h 05m

$551

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/21

10:46 am-9:05 am

1 stop15h 19m

Milan Malpensa

Fri 1/30

11:05 am-10:22 pm

1 stop18h 17m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/21

12:48 pm-11:40 am

2 stops15h 52m

Milan Malpensa

Fri 1/30

11:05 am-10:22 pm

1 stop18h 17m

$833

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 3/10

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 3/17

11:00 am-10:29 pm

2 stops17h 29m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 1/23

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Fri 1/30

11:05 am-10:22 pm

1 stop18h 17m

$879

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 March is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $627. The month of January is another great option to travel to Milan, with average flight prices from Chicago averaging around $636.

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 $1,186. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,492.

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

In the morning is the cheapest time of day to fly from Chicago to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,350. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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 $916 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 $650 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 23% 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 December 2025, prices for Chicago to Milan flights are approximately 39% 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	$765
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Milan	1 airport

The best one-way flight to Milan from Chicago in the past 72 hours is $765. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,224.

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

Direct flights go from Chicago to Milan every day.

There is 1 airport near Milan: 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 11h 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 11 as of December 2025.
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 47.04% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 45.06%, Boeing 787-10 Dreamliner with 6.72%, and Boeing 737 MAX 8 with 0.40%.
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 27% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 24%, Aer Lingus at 14%, 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 2,079 reviews	Search TAP AIR PORTUGAL flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 8,013 reviews	Search Delta flights
Scandinavian Airlines	PriceFrom $420	Free Cancellation	Rating 7.4 1,591 reviews	Search Scandinavian Airlines flights
Icelandair	PriceFrom $484	Free Cancellation	Rating 7.0 584 reviews	Search Icelandair flights
Turkish Airlines	PriceFrom $518	Free Cancellation	Rating 7.3 4,072 reviews	Search Turkish Airlines flights
British Airways	PriceFrom $536	Free Cancellation	Rating 6.7 7,550 reviews	Search British Airways flights
ITA Airways	PriceFrom $584	Free Cancellation	Rating 6.7 1,094 reviews	Search ITA Airways flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $626	Free Cancellation	Rating 7.2 1,384 reviews	Search Aer Lingus flights
Iberia	PriceFrom $639	Free Cancellation	Rating 7.0 3,039 reviews	Search Iberia flights

Bellagio

Varenna

Menaggio

Brescia

Stresa

Assago

Levanto

Monza

Livigno

Domodossola

Bellano

Lecco

Bormio

Crema

Rho

Cernobbio

Moltrasio

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

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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Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Fly to other destinations from Chicago

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Flights from Chicago O'Hare Intl to Minneapolis St Paul

Cheap flights from Chicago to Milan from $248

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 12/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

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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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TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL 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

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

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 March is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $627. The month of January is another great option to travel to Milan, with average flight prices from Chicago averaging around $636.

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 $1,186. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,492.

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

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 23% 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 December 2025, prices for Chicago to Milan flights are approximately 39% cheaper when compared to flights at the same time last year.

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

Scandinavian Airlines and Delta 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: 35% 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 Lisbon (LIS) offer the lowest average round-trip price of $493.

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