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

The number of flights available between Milan and Chicago is 35 per week as of August 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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

5 flights are operational daily from Milan to Chicago as of August 2025. The most popular departure time for this route is 15:00, with 100% of flights per day taking off in the afternoon.

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

TAP AIR PORTUGAL, United Airlines, and Lufthansa are the most popular carriers operating from Milan to Chicago

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

Prices for flights from Milan to Chicago are updated daily.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago.

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

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

£352 Cheap Flights from Milan to Chicago in 2025

Q: What is the typical price of a round-trip flight between Milan and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from £496 to £802. The lowest price recently found on this route was £352.

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Find the cheapest flights from Milan to Chicago

Round-trip

One-way

Last minute

Direct

Cheap return flights

17:30 - 10:55MXP-ORD

24h 25m1 stop

18:00 - 00:45ORD-MXP

23h 45m1 stop

£352TAP AIR PORTUGAL

Find Deal

Wed, 17 Sep - Sun, 21 Sep

06:20 - 15:15MXP-ORD

15h 55m1 stop

20:15 - 23:35ORD-MXP

20h 20m1 stop

£374TAP AIR PORTUGAL

Find Deal

Fri, 7 Nov - Fri, 14 Nov

20:00 - 16:45MXP-ORD

27h 45m1 stop

19:20 - 08:25ORD-MXP

30h 05m1 stop

£378Scandinavian Airlines

Find Deal

Tue, 25 Nov - Mon, 1 Dec

13:00 - 16:45MXP-ORD

34h 45m2 stops

19:20 - 08:25ORD-MXP

30h 05m1 stop

£385Scandinavian Airlines

Find Deal

Wed, 26 Nov - Mon, 1 Dec

20:00 - 16:45MXP-ORD

27h 45m1 stop

19:20 - 19:10ORD-MXP

16h 50m1 stop

£395Scandinavian Airlines

Find Deal

Fri, 26 Dec - Sun, 28 Dec

11:15 - 16:45MXP-ORD

12h 30m1 stop

19:20 - 19:10ORD-MXP

16h 50m1 stop

£400Scandinavian Airlines

Find Deal

Thu, 11 Dec - Fri, 13 Feb

15:10 - 18:15MXP-ORD

34h 05m1 stop

19:25 - 14:10ORD-MXP

11h 45m1 stop

£425Icelandair

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Mon, 15 Sep - Sun, 28 Sep

09:10 - 15:20MXP-ORD

13h 10m1 stop

21:35 - 13:05ORD-MXP

8h 30mdirect

£437United Airlines

Find Deal

Fri, 7 Nov - Sun, 16 Nov

11:15 - 20:11MXP-ORD

15h 56m2 stops

14:08 - 10:00ORD-MXP

12h 52m1 stop

£438Air Canada

Find Deal

Wed, 17 Sep - Sun, 21 Sep

09:10 - 20:05MXP-ORD

17h 55m1 stop

12:50 - 09:55ORD-MXP

14h 05m1 stop

£439United Airlines

Find Deal

Mon, 15 Dec - Wed, 11 Feb

Austrian Airlines flights from Milan to Chicago

Our best Austrian Airlines deals on Milan to Chicago flight tickets

Austrian Airlines

21 Sept

MXP14:45Milan Malpensa

29h 35m

1 stop

ORD13:20Chicago O'Hare Intl

6 Oct

ORD12:55Chicago O'Hare Intl

18h 05m

2 stops

MXP14:00Milan Malpensa

£457

Find similar

Austrian Airlines

6 Nov

LIN17:15Milan Linate

27h 45m

1 stop

ORD14:00Chicago O'Hare Intl

14 Nov

ORD13:00Chicago O'Hare Intl

37h 15m

2 stops

LIN09:15Milan Linate

£458

Find similar

Austrian Airlines

21 Sept

MXP07:00Milan Malpensa

18h 25m

2 stops

ORD18:25Chicago O'Hare Intl

6 Oct

ORD12:55Chicago O'Hare Intl

18h 05m

2 stops

MXP14:00Milan Malpensa

£461

Find similar

United Airlines flights from Milan to Chicago

Our best United Airlines deals on Milan to Chicago flight tickets

United Airlines

7 Nov

MXP09:10Milan Malpensa

13h 10m

1 stop

ORD15:20Chicago O'Hare Intl

16 Nov

ORD21:35Chicago O'Hare Intl

8h 30m

MXP13:05Milan Malpensa

£437

Find similar

United Airlines

15 Dec

MXP09:10Milan Malpensa

17h 55m

1 stop

ORD20:05Chicago O'Hare Intl

11 Feb

ORD12:50Chicago O'Hare Intl

14h 05m

1 stop

MXP09:55Milan Malpensa

£439

Find similar

United Airlines

18 Sept

MXP09:10Milan Malpensa

17h 45m

1 stop

ORD19:55Chicago O'Hare Intl

21 Sept

ORD08:50Chicago O'Hare Intl

18h 10m

2 stops

MXP10:00Milan Malpensa

£440

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 17/9

17:30-10:55

1 stop24h 25m

Chicago O'Hare Intl

Sun 21/9

18:00-00:45

1 stop23h 45m

£352

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 7/11

06:20-15:15

1 stop15h 55m

Chicago O'Hare Intl

Fri 14/11

20:15-23:35

1 stop20h 20m

£374

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 25/11

20:00-16:45

1 stop27h 45m

Chicago O'Hare Intl

Mon 1/12

19:20-08:25

1 stop30h 05m

£378

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 26/11

13:00-16:45

2 stops34h 45m

Chicago O'Hare Intl

Mon 1/12

19:20-08:25

1 stop30h 05m

£385

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 26/12

20:00-16:45

1 stop27h 45m

Chicago O'Hare Intl

Sun 28/12

19:20-19:10

1 stop16h 50m

£395

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 11/12

11:15-16:45

1 stop12h 30m

Chicago O'Hare Intl

Fri 13/2

19:20-19:10

1 stop16h 50m

£400

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 15/9

15:10-18:15

1 stop34h 05m

Chicago O'Hare Intl

Sun 28/9

19:25-14:10

1 stop11h 45m

£425

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 7/11

09:10-15:20

1 stop13h 10m

Chicago O'Hare Intl

Sun 16/11

21:35-13:05

Nonstop8h 30m

£437

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 17/9

11:15-20:11

2 stops15h 56m

Chicago O'Hare Intl

Sun 21/9

14:08-10:00

1 stop12h 52m

£438

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 15/12

09:10-20:05

1 stop17h 55m

Chicago O'Hare Intl

Wed 11/2

12:50-09:55

1 stop14h 05m

£439

Flights are sorted by cheapest return 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

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 cheapest month to fly to Chicago from Milan is in November. Flight prices, which tend to average around £386, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Chicago from Milan during February instead. Flights to Chicago in February, while not as cheap as those in November, still average around £420.

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 Saturday when prices can be found for as low as £547. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Monday, with ticket prices averaging around £1,009.

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

Flying to Chicago from Milan in the morning is the least expensive time of day to depart. momondo users have found prices as low as £592 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £620.

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 £535 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as £410 on momondo.

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

There are 2 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.

Can stopping save me money on Milan to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Milan to Chicago flight.

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 return 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	£658
Fastest flight time	9h 50m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Milan in the past 72 hours is £658. The best return flight deal from Milan to Chicago found on momondo in the last 72 hours is £352.

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

Direct flights go from Milan to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Milan to Chicago by plane?
There are 4526.2 mi between Milan and Chicago. By plane, this route typically takes 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 old do you have to be to fly from Milan to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Milan to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Milan to Chicago is Boeing 787-8 Dreamliner, representing 44.79% of all bookings. The subsequent popular models are Boeing 787 Dreamliner at 33.48%, Boeing 777-200/200ER at 5.36%, and Airbus A330-300 at 4.02%.

Why use momondo?

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

Finding the right flight to Chicago from Milan is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Flights from Milan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Milan to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Milan to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

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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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Cheap flights from Milan to Chicago from £352

This is the cheapest return flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 17/9. 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, great deals

Big names, great 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 return flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Austrian Airlines flights from Milan to Chicago

Our best Austrian Airlines deals on Milan to Chicago flight tickets

United Airlines flights from Milan to Chicago

Our best United 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?

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?

Flying to Chicago from Milan in the morning is the least expensive time of day to depart. momondo users have found prices as low as £592 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £620.

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 2 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.

Can stopping save me money on Milan to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Milan to Chicago flight.

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, United Airlines, and Lufthansa are the most popular carriers operating from Milan to Chicago

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

5 flights are operational daily from Milan to Chicago as of August 2025. The most popular departure time for this route is 15:00, with 100% of flights per day taking off in the afternoon.

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

The number of flights available between Milan and Chicago is 35 per week as of August 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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 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?

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, organise 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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago