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

Dublin (DUB) was the most common stop: 36% of momondo users choosing 1-stop flights on this route connected there.

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

TAP AIR PORTUGAL is the most popular carrier operating from Milan to Chicago

How long does it take to fly to Chicago?

Average flight duration from Milan to Chicago depends on which airport you fly into and out of. Flying from Milan to Chicago O'Hare Intl Airport is 11h 20m on average, while flying from Bergamo to Chicago O'Hare Intl Airport is 13h 45m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

Flights via Lisbon (LIS) offer the lowest average round-trip price of $400.

Which layover airport has the shortest travel time from Milan to Chicago?

Flights connecting via London (LHR) have the shortest average one-way travel time: 12h 40m.

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

As of August 2025, 5 flights take off from Milan and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 100% of daily flights taking off in the afternoon.

Which layover airport has the shortest connection time from Milan to Chicago?

Rome (FCO) has the shortest average layover time for this route: 1h 10m.

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

35 flights are operational weekly from Milan to Chicago as of August 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

When did momondo last update prices for flights from Milan to Chicago?

Prices for flights from Milan to Chicago are updated daily.

How many operators does momondo search for flights from Milan to Chicago?

As of August 2025, there are 2 operators available to choose from for flights from Milan to Chicago.

How old do you have to be to fly from Milan to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milan to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$306 Cheap Flights from Milan to Chicago in 2025

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Find the cheapest flights from Milan to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:20 am - 3:15 pmMXP-ORD

15h 55m1 stop

8:15 pm - 4:55 pmORD-MXP

13h 40m1 stop

$445TAP AIR PORTUGAL

Find Deal

Fri, Nov 7 - Fri, Nov 14

8:15 pm - 12:35 pmMXP-ORD

23h 20m1 stop

8:15 pm - 11:35 pmORD-MXP

20h 20m1 stop

$448TAP AIR PORTUGAL

Find Deal

Wed, Oct 22 - Fri, Nov 7

6:20 am - 3:00 pmMXP-ORD

15h 40m1 stop

8:25 pm - 4:55 pmORD-MXP

13h 30m1 stop

$449TAP AIR PORTUGAL

Find Deal

Wed, Nov 26 - Sun, Nov 30

9:10 am - 2:55 pmMXP-ORD

12h 45m1 stop

3:35 pm - 10:00 amORD-MXP

11h 25m1 stop

$548United Airlines

Find Deal

Mon, Sep 22 - Tue, Sep 30

9:10 am - 2:55 pmMXP-ORD

12h 45m1 stop

10:30 pm - 6:00 pmORD-MXP

12h 30m1 stop

$554United Airlines

Find Deal

Tue, Sep 16 - Tue, Sep 23

11:20 am - 7:00 pmLIN-ORD

14h 40m1 stop

3:45 pm - 10:40 amORD-LIN

11h 55m1 stop

$568Aer Lingus

Find Deal

Fri, Sep 26 - Fri, Oct 3

11:45 am - 5:55 pmLIN-ORD

13h 10m1 stop

3:55 pm - 11:05 amORD-LIN

12h 10m1 stop

$601Aer Lingus

Find Deal

Sat, Nov 8 - Fri, Nov 14

7:05 am - 12:55 pmLIN-ORD

12h 50m1 stop

4:00 pm - 10:00 amORD-LIN

11h 00m1 stop

$603Lufthansa

Find Deal

Thu, Sep 18 - Sun, Sep 21

11:10 am - 5:00 pmLIN-ORD

12h 50m1 stop

9:15 pm - 5:15 pmORD-LIN

13h 00m1 stop

$608British Airways

Find Deal

Fri, Aug 29 - Sun, Sep 14

6:00 am - 11:10 amLIN-ORD

12h 10m1 stop

6:25 pm - 12:35 pmORD-LIN

11h 10m1 stop

$611Lufthansa

Find Deal

Thu, Nov 6 - Thu, Nov 13

Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets

Icelandair

Oct 2

MXP3:10 pmMilan Malpensa

34h 05m

1 stop

ORD6:15 pmChicago O'Hare Intl

Oct 17

ORD10:15 pmChicago O'Hare Intl

33h 15m

1 stop

MXP2:30 pmMilan Malpensa

$483

Find similar

Icelandair

Aug 29

MXP11:00 pmMilan Malpensa

26h 15m

1 stop

ORD6:15 pmChicago O'Hare Intl

Sep 14

ORD7:25 pmChicago O'Hare Intl

11h 45m

1 stop

MXP2:10 pmMilan Malpensa

$486

Find similar

Icelandair

Aug 28

MXP3:10 pmMilan Malpensa

13h 05m

1 stop

ORD9:15 pmChicago O'Hare Intl

Sep 1

ORD10:15 pmChicago O'Hare Intl

16h 45m

1 stop

MXP10:00 pmMilan Malpensa

$494

Find similar

Austrian Airlines flights from Milan to Chicago

Our best Austrian Airlines deals on Milan to Chicago flight tickets

Austrian Airlines

Nov 6

LIN10:00 amMilan Linate

35h 00m

1 stop

ORD2:00 pmChicago O'Hare Intl

Nov 14

ORD1:00 pmChicago O'Hare Intl

23h 55m

2 stops

LIN7:55 pmMilan Linate

$621

Find similar

Austrian Airlines

Dec 19

LIN7:20 amMilan Linate

13h 40m

1 stop

ORD2:00 pmChicago O'Hare Intl

Jan 29

ORD9:05 pmChicago O'Hare Intl

29h 10m

2 stops

LIN9:15 amMilan Linate

$643

Find similar

Austrian Airlines

Aug 28

MXP8:30 pmMilan Malpensa

24h 40m

2 stops

ORD2:10 pmChicago O'Hare Intl

Sep 1

ORD9:25 pmChicago O'Hare Intl

17h 35m

2 stops

MXP10:00 pmMilan Malpensa

$998

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/7

6:20 am-3:15 pm

1 stop15h 55m

Chicago O'Hare Intl

Fri 11/14

8:15 pm-4:55 pm

1 stop13h 40m

$445

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 10/22

8:15 pm-12:35 pm

1 stop23h 20m

Chicago O'Hare Intl

Fri 11/7

8:15 pm-11:35 pm

1 stop20h 20m

$448

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 11/26

6:20 am-3:00 pm

1 stop15h 40m

Chicago O'Hare Intl

Sun 11/30

8:25 pm-4:55 pm

1 stop13h 30m

$449

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/22

9:10 am-2:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Tue 9/30

3:35 pm-10:00 am

1 stop11h 25m

$548

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/16

9:10 am-2:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Tue 9/23

10:30 pm-6:00 pm

1 stop12h 30m

$554

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 9/26

11:20 am-7:00 pm

1 stop14h 40m

Chicago O'Hare Intl

Fri 10/3

3:45 pm-10:40 am

1 stop11h 55m

$568

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sat 11/8

11:45 am-5:55 pm

1 stop13h 10m

Chicago O'Hare Intl

Fri 11/14

3:55 pm-11:05 am

1 stop12h 10m

$601

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 9/18

7:05 am-12:55 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 9/21

4:00 pm-10:00 am

1 stop11h 00m

$603

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 8/29

11:10 am-5:00 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 9/14

9:15 pm-5:15 pm

1 stop13h 00m

$608

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 11/6

6:00 am-11:10 am

1 stop12h 10m

Chicago O'Hare Intl

Thu 11/13

6:25 pm-12:35 pm

1 stop11h 10m

$611

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 Milan to Chicago

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 Milan and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $523. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Milan to Chicago during February average around $570.

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

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $783. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $1,213.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Milan to Chicago during this time can be as low as $561. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $892.

What is the cheapest Milan to Chicago flight route?

Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Milan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $725 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as $556 on momondo.

What cabin class options are available on Milan to Chicago flights?

There are 3 cabin classes available to choose from on Milan to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Milan to Chicago flight prices changed over time?

As of August 2025, prices for Milan to Chicago flights are approximately 36% more expensive when compared to flights at the same time last year.

When to book flights from Milan to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Milan to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Milan to Chicago (MIL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago

Best Price Found	$306
Fastest flight time	9h 50m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Milan in the past 72 hours is $306. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $445.

The fastest flight from Milan to Chicago takes 9h 50m

Direct flights go from Milan to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Milan to Chicago by plane?
The straight-line distance from Milan to Chicago is 4526.2 mi. In terms of flight time, this usually takes a little over 9h 50m.
When did momondo last update prices for flights from Milan to Chicago?
Prices for flights from Milan to Chicago are updated daily.
How many operators does momondo search for flights from Milan to Chicago?
As of August 2025, there are 2 operators available to choose from for flights from Milan to Chicago.
How old do you have to be to fly from Milan to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milan to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Milan to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Milan to Chicago is Boeing 787-8 Dreamliner (44.79% of total bookings). The next most popular plane models are Boeing 787 Dreamliner (33.48%), Boeing 777-200/200ER (5.36%), and Airbus A330-300 (4.02%).
What is the most popular airline from Milan to Chicago?
momondo data reveals that the most frequently booked airline on the route from Milan to Chicago is United Airlines, representing 36% of all bookings. The subsequent popular airlines are Aer Lingus at 16%, Lufthansa at 16%, and TAP AIR PORTUGAL at 12%.

Best airlines flying from Milan to Chicago

Compare and see reviews for airlines that fly from Milan to Chicago with momondo

Airline	Rating	Free Cancellation	Price
British Airways	PriceFrom $525	Free Cancellation	Rating 6.6 7,266 reviews		Search British Airways flights
United Airlines	PriceFrom $626	Free Cancellation	Rating 7.4 8,916 reviews		Search United Airlines flights

United Airlines Flights From Milan to Chicago
Across 7 United Airlines flights from Milan to Chicago this week, the average price was $943, with the best United Airlines deals starting from $626 round-trip. 8,916 users have rated United Airlines on momondo, with an average score of 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Milan to Chicago?

It is quick and easy to find Milan to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Milan to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Milan with this policy.

How can momondo help me find flights from Milan to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Milan.

I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Milan are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Washington, D.C.from $58

Flights to Bostonfrom $76

Flights to Atlantafrom $48

Flights to Dallasfrom $57

Flights to Seattlefrom $71

Flights to Denverfrom $65

Cheap flights from Milan to Chicago from $306

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 9/4. 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

Price Alerts

Find the cheapest flights from Milan to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets

Austrian Airlines flights from Milan to Chicago

Our best Austrian Airlines deals on Milan to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Milan to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Milan to Chicago

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 Milan and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $523. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Milan to Chicago during February average around $570.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Milan to Chicago during this time can be as low as $561. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $892.

What is the cheapest Milan to Chicago flight route?

Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Milan to Chicago flights?

There are 3 cabin classes available to choose from on Milan to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Milan to Chicago flight prices changed over time?

As of August 2025, prices for Milan to Chicago flights are approximately 36% more expensive when compared to flights at the same time last year.

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

TAP AIR PORTUGAL is the most popular carrier operating from Milan to Chicago

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

Dublin (DUB) was the most common stop: 36% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Lisbon (LIS) offer the lowest average round-trip price of $400.

Which layover airport has the shortest travel time from Milan to Chicago?

Flights connecting via London (LHR) have the shortest average one-way travel time: 12h 40m.

Which layover airport has the shortest connection time from Milan to Chicago?

Rome (FCO) has the shortest average layover time for this route: 1h 10m.

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

As of August 2025, 5 flights take off from Milan and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 100% of daily flights taking off in the afternoon.

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

35 flights are operational weekly from Milan to Chicago as of August 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Milan to Chicago

Cheap Milan to Chicago (MIL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Milan to Chicago by plane?

When did momondo last update prices for flights from Milan to Chicago?

How many operators does momondo search for flights from Milan to Chicago?

How old do you have to be to fly from Milan to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Milan to Chicago?

What is the most popular airline from Milan to Chicago?

Best airlines flying from Milan to Chicago

Compare and see reviews for airlines that fly from Milan to Chicago with momondo

United Airlines Flights From Milan to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Milan to Chicago?

Can I find flights from Milan to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Milan to Chicago?

I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago 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 the United States