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

Lisbon (LIS) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

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

Frankfurt am Main (FRA) has the shortest average layover time for this route: 1h 43m.

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

35 flights are operational weekly from Milan to Chicago as of June 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

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 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 08m.

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

As of June 2026, 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 often are flights from Milan to Chicago delayed?

Historically, on average around 23% 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 205 minutes.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 22% of their flights experiencing any sort of delay.

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

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

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.

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 30m on average, while flying from Bergamo to Chicago O'Hare Intl Airport is 13h 25m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 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.

$316 Cheap Flights from Milan to Chicago in 2026

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 $1,081 to $687. The lowest price recently found on this route was $529.

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Find the cheapest flights from Milan to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:20 pm - 9:25 pm

MXP

ORD

12h 05m

1 stop

7:25 pm - 3:10 pm

ORD

MXP

12h 45m

1 stop

$529Icelandair

Sat, Sep 5 - Sat, Sep 19

10:55 pm - 9:25 pm

MXP

ORD

29h 30m

1 stop

7:25 pm - 3:10 pm

ORD

MXP

12h 45m

1 stop

$531Icelandair

Tue, Sep 8 - Sat, Sep 26

10:55 pm - 9:25 pm

MXP

ORD

29h 30m

1 stop

7:25 pm - 3:10 pm

ORD

MXP

12h 45m

1 stop

$532Icelandair

Tue, Sep 8 - Sat, Sep 12

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

3:00 pm - 10:10 am

ORD

LIN

12h 10m

1 stop

$547ITA Airways

Mon, Sep 21 - Sun, Oct 4

7:00 am - 1:10 pm

LIN

ORD

13h 10m

1 stop

3:00 pm - 3:10 pm

ORD

LIN

17h 10m

1 stop

$553ITA Airways

Thu, Sep 10 - Tue, Sep 15

7:55 am - 3:10 pm

LIN

ORD

14h 15m

1 stop

9:45 pm - 11:30 am

ORD

LIN

30h 45m

1 stop

$697American Airlines

Wed, Nov 4 - Sun, Nov 8

8:50 am - 5:50 pm

BGY

ORD

40h 00m

2 stops

9:30 pm - 1:10 am

ORD

BGY

20h 40m

1 stop

$712Multiple Airlines

Tue, Sep 1 - Tue, Sep 29

8:40 am - 7:50 pm

BGY

ORD

18h 10m

1 stop

9:50 pm - 8:05 pm

ORD

BGY

15h 15m

1 stop

$737Multiple Airlines

Tue, Sep 1 - Mon, Sep 14

6:30 am - 6:37 pm

LIN

MDW

18h 07m

2 stops

1:00 pm - 11:15 am

MDW

LIN

15h 15m

2 stops

$772Delta

Thu, Oct 29 - Tue, Nov 3

1:05 pm - 9:45 pm

MXP

MDW

14h 40m

1 stop

1:00 pm - 11:40 am

MDW

MXP

15h 40m

2 stops

$772Delta

Wed, Oct 28 - Mon, Nov 2

Scandinavian Airlines flights from Milan to Chicago

Our best Scandinavian Airlines deals on Milan to Chicago flight tickets

Scandinavian Airlines

Nov 30

MXP8:05 pmMilan Malpensa

27h 40m

1 stop

ORD4:45 pmChicago O'Hare Intl

Dec 7

ORD7:15 pmChicago O'Hare Intl

32h 15m

1 stop

MXP10:30 amMilan Malpensa

$603

Scandinavian Airlines

Oct 22

MXP8:00 pmMilan Malpensa

27h 10m

1 stop

ORD4:10 pmChicago O'Hare Intl

Nov 8

ORD7:15 pmChicago O'Hare Intl

32h 15m

1 stop

MXP10:30 amMilan Malpensa

$609

Scandinavian Airlines

Aug 24

MXP8:40 pmMilan Malpensa

26h 30m

2 stops

ORD4:10 pmChicago O'Hare Intl

Aug 29

ORD7:15 pmChicago O'Hare Intl

15h 45m

2 stops

MXP6:00 pmMilan Malpensa

$616

Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets

Icelandair

Sep 5

MXP4:20 pmMilan Malpensa

12h 05m

1 stop

ORD9:25 pmChicago O'Hare Intl

Sep 19

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$529

Icelandair

Sep 8

MXP10:55 pmMilan Malpensa

29h 30m

1 stop

ORD9:25 pmChicago O'Hare Intl

Sep 26

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$531

Icelandair

Sep 8

MXP10:55 pmMilan Malpensa

29h 30m

1 stop

ORD9:25 pmChicago O'Hare Intl

Sep 12

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$532

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 9/5

4:20 pm-9:25 pm

1 stop12h 05m

Chicago O'Hare Intl

Sat 9/19

7:25 pm-3:10 pm

1 stop12h 45m

$529

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/8

10:55 pm-9:25 pm

1 stop29h 30m

Chicago O'Hare Intl

Sat 9/26

7:25 pm-3:10 pm

1 stop12h 45m

$531

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/8

10:55 pm-9:25 pm

1 stop29h 30m

Chicago O'Hare Intl

Sat 9/12

7:25 pm-3:10 pm

1 stop12h 45m

$532

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 9/21

9:00 pm-1:10 pm

1 stop23h 10m

Chicago O'Hare Intl

Sun 10/4

3:00 pm-10:10 am

1 stop12h 10m

$547

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 9/10

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Tue 9/15

3:00 pm-3:10 pm

1 stop17h 10m

$553

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 11/4

7:55 am-3:10 pm

1 stop14h 15m

Chicago O'Hare Intl

Sun 11/8

9:45 pm-11:30 am

1 stop30h 45m

$697

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Tue 9/1

8:50 am-5:50 pm

2 stops40h 00m

Chicago O'Hare Intl

Tue 9/29

9:30 pm-1:10 am

1 stop20h 40m

$712

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Tue 9/1

8:40 am-7:50 pm

1 stop18h 10m

Chicago O'Hare Intl

Mon 9/14

9:50 pm-8:05 pm

1 stop15h 15m

$737

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 10/29

6:30 am-6:37 pm

2 stops18h 07m

Chicago Midway

Tue 11/3

1:00 pm-11:15 am

2 stops15h 15m

$772

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 10/28

1:05 pm-9:45 pm

1 stop14h 40m

Chicago Midway

Mon 11/2

1:00 pm-11:40 am

2 stops15h 40m

$772

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

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Delays

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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 September is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $356. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Milan to Chicago during August average around $400.

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 $760. 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 $1,039.

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 June 2026, prices for Milan to Chicago flights are approximately 16% 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	$842
Fastest flight time	9h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Milan in the past 72 hours is $842. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $658.

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

Direct flights go from Milan to Chicago every day.

There are 3 airports in Chicago. From Milan there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Milan to Chicago

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 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 787-10 Dreamliner (47.46% of total bookings). The next most popular plane models are Boeing 787 Dreamliner (20.76%), Boeing 787-8 Dreamliner (9.32%), and Boeing 787-9 Dreamliner (3.81%).
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 60% of all bookings. The subsequent popular airline is Lufthansa at 40%.

Merrillville

New Buffalo

Hammond

Saint Joseph

Portage

Benton Harbor

Lansing

Valparaiso

Schererville

Munster

Crown Point

Monticello

Chesterton

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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Cheap flights from Milan to Chicago from $316

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 7/7. 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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How to get the cheapest flight ticket from Milan to Chicago

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 Milan to Chicago flight route?

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

How have Milan to Chicago flight prices changed over time?

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

How often are flights from Milan to Chicago delayed?

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

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

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

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

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

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

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

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

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

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

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Frequently asked questions about flying from Milan to Chicago

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An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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