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 connection time from Milan to Chicago?

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

How often are flights from Milan to Chicago delayed?

Historically, on average around 18% of flights between Milan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 196 minutes.

What day of the week experiences the fewest flight delays on this route?

Friday is statistically the day of the week which experiences the fewest number of delays on this flight route. Tuesday has historically seen more delays on average compared to the rest of the week.

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

Reykjavik (KEF) was the most common stop: 42% of momondo users choosing 1-stop flights on this route connected there.

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 22m on average, while flying from Bergamo to Chicago O'Hare Intl Airport is 13h 30m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

TAP AIR PORTUGAL and British Airways are the most popular carriers operating from Milan to Chicago

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

As of November 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 travel time from Milan to Chicago?

Flights connecting via Frankfurt am Main (FRA) have the shortest average one-way travel time: 12h 00m.

Which airline has the best punctuality record on Milan to Chicago flights?

According to our data, Qatar Airways have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

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

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

What is the most punctual flight time for Milan to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

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 November 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.

$291 Cheap Flights from Milan to Chicago in 2025/26

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 $611 to $880. The lowest price recently found on this route was $430.

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Find the cheapest flights from Milan to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:45 pm - 3:25 pmMXP-ORD

28h 40m1 stop

7:10 pm - 4:55 pmORD-MXP

14h 45m1 stop

$430TAP AIR PORTUGAL

Find Deal

Thu, Jan 15 - Wed, Jan 28

5:45 pm - 3:25 pmMXP-ORD

28h 40m1 stop

7:10 pm - 11:35 pmORD-MXP

21h 25m1 stop

$432TAP AIR PORTUGAL

Find Deal

Thu, Jan 15 - Wed, Jan 28

5:45 pm - 3:25 pmMXP-ORD

28h 40m1 stop

7:10 pm - 11:05 amORD-MXP

32h 55m1 stop

$435TAP AIR PORTUGAL

Find Deal

Thu, Jan 15 - Wed, Jan 28

11:15 am - 4:45 pmMXP-ORD

12h 30m1 stop

7:20 pm - 10:25 amORD-MXP

32h 05m1 stop

$492Scandinavian Airlines

Find Deal

Thu, Jan 15 - Wed, Jan 28

5:45 pm - 3:25 pmMXP-ORD

28h 40m1 stop

7:10 pm - 11:35 pmORD-MXP

21h 25m1 stop

$493TAP AIR PORTUGAL

Find Deal

Thu, Jan 15 - Wed, Jan 28

8:00 pm - 4:45 pmMXP-ORD

27h 45m1 stop

7:10 pm - 8:25 amORD-MXP

30h 15m1 stop

$495Scandinavian Airlines

Find Deal

Fri, Jan 16 - Sun, Feb 1

5:45 am - 5:20 pmBGY-ORD

18h 35m2 stops

6:30 pm - 8:05 pmORD-BGY

18h 35m2 stops

$532Multiple Airlines

Find Deal

Thu, Jan 8 - Thu, Jan 15

5:45 am - 5:20 pmBGY-ORD

18h 35m2 stops

6:30 pm - 9:00 pmORD-BGY

19h 30m2 stops

$572Multiple Airlines

Find Deal

Thu, Jan 15 - Wed, Jan 28

6:00 am - 3:20 pmLIN-ORD

16h 20m1 stop

9:50 pm - 6:50 pmORD-LIN

14h 00m1 stop

$628Lufthansa

Find Deal

Thu, Feb 12 - Fri, Feb 27

6:00 am - 3:20 pmLIN-ORD

16h 20m1 stop

6:25 pm - 2:05 pmORD-LIN

12h 40m1 stop

$630United Airlines

Find Deal

Thu, Jan 15 - Wed, Jan 28

Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets

Icelandair

Apr 18

MXP4:20 pmMilan Malpensa

32h 55m

1 stop

ORD6:15 pmChicago O'Hare Intl

Apr 24

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$553

Find similar

Icelandair

May 21

MXP4:20 pmMilan Malpensa

32h 50m

1 stop

ORD6:10 pmChicago O'Hare Intl

Jun 1

ORD7:20 pmChicago O'Hare Intl

19h 40m

1 stop

MXP10:00 pmMilan Malpensa

$567

Find similar

ITA Airways flights from Milan to Chicago

Our best ITA Airways deals on Milan to Chicago flight tickets

ITA Airways

Apr 1

LIN7:00 amMilan Linate

13h 10m

1 stop

ORD1:10 pmChicago O'Hare Intl

Apr 12

ORD3:00 pmChicago O'Hare Intl

20h 10m

1 stop

LIN6:10 pmMilan Linate

$611

Find similar

ITA Airways

May 16

LIN7:00 pmMilan Linate

25h 10m

1 stop

ORD1:10 pmChicago O'Hare Intl

May 26

ORD11:15 amChicago O'Hare Intl

15h 55m

2 stops

LIN10:10 amMilan Linate

$632

Find similar

ITA Airways

May 16

LIN7:00 pmMilan Linate

25h 10m

1 stop

ORD1:10 pmChicago O'Hare Intl

May 26

ORD11:15 amChicago O'Hare Intl

15h 55m

2 stops

LIN10:10 amMilan Linate

$633

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 1/28

7:10 pm-4:55 pm

1 stop14h 45m

$430

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 1/28

7:10 pm-11:35 pm

1 stop21h 25m

$432

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 1/28

7:10 pm-11:05 am

1 stop32h 55m

$435

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Wed 1/28

7:20 pm-10:25 am

1 stop32h 05m

$492

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 1/28

7:10 pm-11:35 pm

1 stop21h 25m

$493

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 1/16

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Sun 2/1

7:10 pm-8:25 am

1 stop30h 15m

$495

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 1/8

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Thu 1/15

6:30 pm-8:05 pm

2 stops18h 35m

$532

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 1/15

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Wed 1/28

6:30 pm-9:00 pm

2 stops19h 30m

$572

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 2/12

6:00 am-3:20 pm

1 stop16h 20m

Chicago O'Hare Intl

Fri 2/27

9:50 pm-6:50 pm

1 stop14h 00m

$628

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 1/15

6:00 am-3:20 pm

1 stop16h 20m

Chicago O'Hare Intl

Wed 1/28

6:25 pm-2:05 pm

1 stop12h 40m

$630

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

Delays

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 February is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $570. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Milan to Chicago during March average around $574.

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 $820. 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 $883.

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

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 November 2025, prices for Milan to Chicago flights are approximately 2% cheaper 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	$816
Fastest flight time	9h 40m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Milan in the past 72 hours is $816. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $645.

The fastest flight from Milan to Chicago takes 9h 40m

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?
The straight-line distance from Milan to Chicago is 4526.2 mi. In terms of flight time, this usually takes a little over 11h 55m.
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 November 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 (39.78% of total bookings). The next most popular plane models are Boeing 787 Dreamliner (38.22%), Airbus A330-300 (4.89%), and Boeing 767-400 (2.44%).
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 55% of all bookings. The subsequent popular airlines are Lufthansa at 27% and British Airways at 17%.

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 6.7 7,539 reviews		Search British Airways flights
United Airlines	PriceFrom $672	Free Cancellation	Rating 7.4 9,046 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 $1,110, with the best United Airlines deals starting from $672 round-trip. 9,046 users have rated United Airlines on momondo, with an average score of 7.4/10.

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Hammond

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Saint Joseph

Portage

Lansing

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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 San Franciscofrom $57

Flights to Washington, D.C.from $38

Flights to Bostonfrom $59

Flights to Atlantafrom $48

Flights to Dallasfrom $54

Flights to Seattlefrom $58

Flights to Denverfrom $57

Cheap flights from Milan to Chicago from $291

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 2/10. 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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Big names and deals

Filter for what you want

Filter for what you want

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Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets

ITA Airways flights from Milan to Chicago

Our best ITA Airways deals on Milan to Chicago flight tickets

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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 February is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $570. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Milan to Chicago during March average around $574.

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 $883.

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

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 November 2025, prices for Milan to Chicago flights are approximately 2% cheaper when compared to flights at the same time last year.

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

TAP AIR PORTUGAL and British Airways are the most popular carriers operating from Milan to Chicago

How often are flights from Milan to Chicago delayed?

Historically, on average around 18% of flights between Milan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 196 minutes.

What is the most punctual flight time for Milan to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Friday is statistically the day of the week which experiences the fewest number of delays on this flight route. Tuesday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Milan to Chicago flights?

According to our data, Qatar Airways have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

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

Reykjavik (KEF) was the most common stop: 42% 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 Frankfurt am Main (FRA) have the shortest average one-way travel time: 12h 00m.

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 November 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 November 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?